Editing Hugh Roe O'Donnell

{{short description|Irish clan chief and military leader (1572–1602)}}
{{for|the earlier ruler of Tyrconnell|Hugh Roe O'Donnell (died 1505)}}
{{Use dmy dates|date=November 2024}}{{Use Hiberno-English|date=July 2024}}
{{Infobox royalty
| name         = Hugh Roe O'Donnell II
| title        = 
| image        = Hugh Roe O'Donnell, depiction in stained-glass window by Richard King (cropped).png
| caption      = 1934 depiction of O'Donnell by [[Richard King (artist)|Richard King]]
| succession   = [[Kings of Tír Chonaill|Lord of Tyrconnell]]
| reign        = {{Nowrap|23 April 1592 – 30 August 1602}}
| coronation   = 23 April 1592
| cor-type     = Inauguration
| predecessor  = [[Sir Hugh O'Donnell|Hugh MacManus O'Donnell]]
| successor    = [[Rory O'Donnell, 1st Earl of Tyrconnell|Rory O'Donnell]]
| suc-type     = 
| spouse       = {{marriage|[[Rose O'Neill (Irish noblewoman)|Rose O'Neill]]|1592|1597|end=div}}
| issue        = None
| house        = [[O'Donnell dynasty]]
| father       = [[Sir Hugh O'Donnell|Hugh MacManus O'Donnell]]
| mother       = [[Iníon Dubh]]
| signature    = Підпис ОДонелла.jpg
| birth_date   = {{circa}} 20 October 1572
| birth_place  = [[Tyrconnell]], Ireland
| death_date   = {{death date and age|1602|8|30|1572|10|20|df=y}}
| death_place  = [[Castle of Simancas|Simancas Castle]], [[Crown of Castile]]
| burial_date  = 1 September 1602
| place of burial = [[Convent of St. Francis, Valladolid]]
}}

'''Hugh Roe O'Donnell II'''{{efn|His [[Hugh Roe O'Donnell (died 1505)|great-grandfather, also named Hugh Roe O'Donnell]], was clan chief from 1461 to 1505; historian [[Francis Martin O'Donnell]] thus distinguishes them using [[regnal number]]s I and II.<ref name="2020c">{{Citation |last=O'Donnell |first=Francis Martin |author-link= |url=https://www.academia.edu/43816384 |title=What did they really look like? An Iconography of the O'Donnells of Tyrconnell: myth, allegory, prejudice, and evidence |date=10 August 2020c|publisher=Tyrconnell-Fyngal Publishing |pages=1–12}}</ref>}} ({{langx|ga|Aodh Ruadh Ó Domhnaill}}; {{Circa}} 20 October 1572 – 30 August 1602),{{efn|<nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] {{Circa}} 30 October 1572 – 9<!-- Do not change to 10 September; see the note under "Death and burial"--> September 1602<nowiki>]</nowiki>}}{{efn|Unless otherwise stated, all dates before 1752 are given in the [[Julian calendar]], which was used in the [[Kingdom of Ireland]] throughout O'Donnell's lifetime. The [[Gregorian calendar]] was used by the Irish confederates and chroniclers throughout O'Donnell's lifetime, as well as in Spain where he died.<ref>{{Cite book|last=Morgan |first=Hiram |author-link= |url=https://celt.ucc.ie/Calender_Rome.pdf |title='The Pope's new invention': the introduction of the Gregorian calendar in Ireland, 1583-1782 |date=1 April 2006 |archive-url=https://web.archive.org/web/20240104222623/https://celt.ucc.ie/Calender_Rome.pdf |archive-date=4 January 2024}}</ref>}} also known as '''Red Hugh O'Donnell''', was an Irish [[Chief of the Name|clan chief]] and senior leader of the Irish confederacy during the [[Nine Years' War (Ireland)|Nine Years' War]]. He was Lord<!-- Do not change to "King of Tyrconnell" {{Harvnb|O'Donnell|2006|p=31}}. "...the title of king was no longer used in their annalist obits by the end of the reign of Aodh Dubh (reign 1505-37)"--> of [[Tyrconnell]] from 1592 until his death in 1602.

He was born into the powerful [[O'Donnell dynasty|O'Donnell clan]] of Tyrconnell (present-day [[County Donegal]]). By the age of fourteen, he was recognised as his clan's [[Tanistry|tanist]] and engaged to the daughter of the prominent [[Hugh O'Neill, Earl of Tyrone|Earl of Tyrone]]. The [[Dublin Castle administration|English-led Irish government]] feared that an alliance between Tyrone and the O'Donnell clan would threaten [[the Crown]]'s control over [[Ulster]], so in 1587 [[Lord Deputy of Ireland|Lord Deputy]] [[John Perrot]] arranged Hugh Roe's kidnapping. The government subsequently backed [[regime change]] in Tyrconnell. After four years' imprisonment in [[Dublin Castle]], Hugh Roe escaped circa January 1592 with the help of Tyrone's bribery. At nineteen years old, he was inaugurated as clan chief at [[Kilmacrennan]] on 23 April <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 3 May<nowiki>]</nowiki> 1592.

Along with his father-in-law Tyrone, Hugh Roe O'Donnell led a confederacy of [[Irish clan]]s in the Nine Years' War, motivated to prevent [[Tudor conquest of Ireland|English incursions into their territory]] and to end [[Catholic Church in Ireland|Catholic]] [[religious persecution|persecution]] under [[Elizabeth I]]. Throughout the war, O'Donnell expanded his territory into [[Connacht]] by launching raids against successive Lord Presidents [[Richard Bingham (soldier)|Richard Bingham]] and [[Conyers Clifford]]. O'Donnell led the confederacy to victory at the [[Battle of Curlew Pass]]. In 1600, he suffered various military and personal losses.{{efn|Such as the death of commander [[Hugh Maguire (Lord of Fermanagh)|Hugh Maguire]],<ref name="barryhugh"/> the establishment of [[Henry Docwra, 1st Baron Docwra of Culmore|Henry Docwra]]'s garrison at Derry,{{sfnm|1a1=Connolly|1y=2007|1p=423|2a1=Morgan|2y=2009|2ps=, 5th paragraph.}} the defection of his cousin [[Niall Garve O'Donnell|Niall Garve]],<ref>{{harvnb|Clavin|2009|ps=, 5th paragraph.}}</ref> and the successive deaths of his brother [[Manus O'Donnell (died 1600)|Manus]] and father [[Sir Hugh O'Donnell|Hugh MacManus]].{{sfn|Concannon|1920|p=232}}}} His cousin [[Niall Garve O'Donnell|Niall Garve]] defected to the English, which greatly emboldened commander [[Henry Docwra, 1st Baron Docwra of Culmore|Henry Docwra]]'s troops and forced O'Donnell out of Tyrconnell.

After a crushing defeat at the [[Siege of Kinsale]], O'Donnell travelled to [[Habsburg Spain]] to acquire reinforcements from [[Philip III of Spain|King Philip III]]. The promised reinforcements were continually postponed, and whilst preparing for a follow-up meeting with the king, O'Donnell died of a sudden illness at the [[Castle of Simancas]], aged 29. His body was buried inside the Chapel of Wonders at the [[Convent of St. Francis, Valladolid|Convent of St. Francis]] in [[Valladolid]]. O'Donnell's premature death disheartened an already withering Irish resistance; Tyrone ended the Nine Years' War in 1603 with the [[Treaty of Mellifont]].

Fiercely patriotic and militarily aggressive, O'Donnell is considered a [[folk hero]] and a symbol of [[Irish nationalism]]. He has drawn comparisons to [[El Cid]] and [[William Wallace]].<ref name="HI">{{Cite web |last=Murray |first=Eavan |date=2022-09-14 |title=How an Italian clue could solve the mystery of Irish hero Red Hugh O'Donnell's final burial place |url=https://www.independent.ie/irish-news/how-an-italian-clue-could-solve-the-mystery-of-irish-hero-red-hugh-odonnells-final-burial-place/41985868.html |archive-url=https://web.archive.org/web/20231227050114/https://www.independent.ie/irish-news/how-an-italian-clue-could-solve-the-mystery-of-irish-hero-red-hugh-odonnells-final-burial-place/41985868.html |archive-date=27 December 2023 |access-date=2025-01-02 |website=Irish Independent |language=en}}</ref> In 2020, an unsuccessful [[Archaeological excavation|archaeological dig]] for his remains drew international media attention. Since 2022, the city has annually reenacted his 1602 [[funeral procession]] in period costumes.

== Early life ==

=== Family background ===
Hugh Roe O'Donnell was born {{Circa}} 20 October <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] {{Circa}} 30 October<nowiki>]</nowiki> 1572,{{efn|His biographer [[Lughaidh Ó Cléirigh]] does not give an exact birthdate, but notes that Hugh Roe O'Donnell was not yet fifteen years old when he was kidnapped shortly before 25 September 1587.{{Sfn|O'Clery|O'Clery|Murphy|1895|pp=xxxi, xxxiii}} Ó Cléirigh also stated that he was under thirty when he died.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=xxxi, 327|2a1=Walsh|2y=1939|2pp=235–236}} The ''[[Short Annals of Tirconaill]]'' state that O'Donnell was 29 years old when he set out for Kinsale on 19 October <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 29 October<nowiki>]</nowiki> 1601.<ref name="age29">[[Paul Walsh (priest)|Walsh, Paul]], ed. (2004). [https://web.archive.org/web/20181231213144/https://celt.ucc.ie/published/G100019/note033.html Short Annals of Tirconaill]. Electronic edition compiled by Benjamin Hazard, Eoin P. Kelleher. CELT: Corpus of Electronic Texts. Note 33. Archived from [https://celt.ucc.ie/published/G100019/note033.html the original] on 31 December 2018.</ref> [[Paul Walsh (priest)|Paul Walsh]] notes that therefore O'Donnell was born towards the end of October 1572, per New Style dating.{{sfn|Walsh|1939|pp=235–236}} John J. Silke estimates that O'Donnell was born on or about 20 October.<ref>{{harvnb|Silke|2004|ps=, 1st paragraph.}}</ref>}} the eldest son of Irish lord [[Sir Hugh O'Donnell|Hugh MacManus O'Donnell]] and his second wife, Scottish aristocrat [[Iníon Dubh|Fiona "Iníon Dubh" MacDonald]]. He was born into the ruling branch of the [[O'Donnell dynasty|O'Donnell clan]], a [[Gaelic Ireland|Gaelic Irish]] noble dynasty based in [[Tyrconnell]],<ref>{{Harvnb|Silke|2004|ps=, 1st paragraph}}; {{Harvnb|Morgan|2009|ps=, 1st paragraph}}.</ref> a kingdom geographically associated with present-day [[County Donegal]].<ref>{{Cite EB1911|wstitle=Tyrconnell|volume=27|page=549}}</ref> He had three younger brothers, [[Rory O'Donnell, 1st Earl of Tyrconnell|Rory]], [[Manus O'Donnell (died 1600)|Manus]] and [[Cathbarr O'Donnell|Cathbarr]] (ordered oldest to youngest),{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=3|2a1=McGettigan|2y=2005|2p=36}} and several sisters, [[Nuala O'Donnell|Nuala]], Margaret and [[Mary O'Donnell (sister of Hugh Roe)|Mary]]. He also had older half-siblings from his father's previous relationships,{{Sfnm|1a1=McGettigan|1y=2005|1p=36|2a1=Walsh|2y=1922|2pp=359–361}} including [[Donnell O'Donnell|Donal]] and [[Siobhán O'Donnell|Siobhán]].{{sfnm|1a1=Morgan|1y=1993|1p=123|1ps=: Donal was an elder half-brother of Hugh Roe|2a1=Walsh|2y=1930|2pp=17–18|2ps=: Siobhán was an elder half-sister of Hugh Roe.}}

Paternally Hugh Roe claimed descent, via the lineage of [[Conall Gulban]] of the [[Branches of the Cenél Conaill|Cenél Conaill]], from the semi-legendary [[High King of Ireland|High King]] [[Niall of the Nine Hostages]].{{Sfn|O'Clery|O'Clery|Murphy|1895|p=xii}} Through his mother, Hugh Roe was a descendant of the first six [[Scottish clan chief|Scottish Chief]]s of [[Clan MacDonald of Dunnyveg]] and from [[Somerled]], the first [[Lord of the Isles]]. He was also descended from [[King of Scots]] [[Robert the Bruce]] and his grandson [[Robert II of Scotland|Robert II]], the first [[House of Stuart|Stuart]] king of Scotland.{{Sfn|O'Clery|O'Clery|Murphy|1895|p=xxx}}<ref>{{Citation |last=O'Donnell |first=Francis Martin |author-link=Francis Martin O'Donnell |url=https://www.academia.edu/43237024 |title=The Holy Cross and the restoration of Donegal Abbey as a mausoleum for the return of the remains of Red Hugh O'Donnell, Sovereign of Tír Chonaill |work=The O'Donnells of Tyrconnell - A Hidden Legacy |date=2019 |pages=1–4|postscript=. fn. 8.}}</ref>

Hugh Roe's father, Hugh MacManus, had ruled as [[Chief of the Name|clan chief]] and Lord<ref>{{Harvnb|O'Donnell|2006|p=31}}. "...the title of king was no longer used in their annalist obits by the end of the reign of Aodh Dubh (reign 1505-37)"</ref> of Tyrconnell since 1566.{{sfnm|1a1=Dunlop|1y=1894|1p=436|2a1=Morgan|2y=2009|2ps=, 1st paragraph.}} He was a wary politician who alternated between alliances with the [[O'Neill dynasty|O'Neill clan]], his long-established rivals in [[Ulster]], and the English government, which controlled the area around Dublin ([[the Pale]]).{{Sfn|Dunlop|1894|p=436}}<ref>The Editors of Encyclopaedia Britannica (29 March 2024). [https://web.archive.org/web/20240701045142/https://www.britannica.com/biography/Hugh-ODonnell "Hugh O'Donnell"]. ''[[Encyclopedia Britannica]]''. Archived from [https://www.britannica.com/biography/Hugh-ODonnell the original] on 1 July 2024.</ref> In 1569 Hugh MacManus married Iníon Dubh{{sfnm|1a1=Walsh|1y=1922|1p=362|2a1=Morgan|2y=1993|2p=124}} of [[Clan MacDonald of Dunnyveg]], as part of a marriage alliance,<ref name="ob1">{{harvnb|O'Byrne|2009a|ps=, 1st paragraph}}.</ref> which gave the O'Donnell clan access to the formidable Scottish mercenary forces known as [[Redshank (soldier)|Redshanks]].{{sfnm|1a1=Morgan|1y=1993|1p=124|2a1=Morgan|2y=2009|2ps=, 1st paragraph.}} Iníon Dubh pushed the O'Donnell clan further into opposition with the English,{{sfnm|1a1=Dunlop|1y=1894|1p=436|2a1=O'Byrne|2y=2009a|2ps=, 2nd paragraph.}} and in 1574 the clan established an alliance with ascendant O'Neill clansman [[Hugh O'Neill, Earl of Tyrone|Hugh O'Neill]] (future [[Earl of Tyrone]]) via his marriage to Siobhán.{{Sfnm|1a1=Walsh|1y=1930|2a1=Casway|2y=2016|1pp=17–18|2p=71}}

=== Education and fosterage ===
{{Chart top|Family tree|width=auto|collapsed=no|align=right|clear=right}}
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{{Tree chart|Txt|Txt=Hugh Roe O'Donnell and selected relatives|boxstyle_Txt=border: 0 solid white; text-align: left;}}
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{{Tree chart||||||||Duff|Duff=[[Hugh Duff O'Donnell|'''Hugh Dubh<br />O'Donnell''']]<br />d. 1537|boxstyle_Duff=border-width: 1px; border-radius: 0.5em; background: lavender;}}
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{{Tree chart||!|||||||||||Calvagh|boxstyle=border-width: 1px; border-radius: 0.5em;|ShnON=[[Shane O'Neill (Irish chieftain)|'''Shane<br />O'Neill''']]<br />{{circa|1530}}–1567|boxstyle_ShnON=border-width: 1px; border-radius: 0.5em; background: wheat;|Calvagh=[[Calvagh O'Donnell|'''Calvagh<br />O'Donnell''']]<br />{{circa|1515}}–1566|boxstyle_Calvagh=border-width: 1px; border-radius: 0.5em; background: lavender;}}
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{{Tree chart|McManus|~|~|y|iniondubh||Gallagher||Conn|boxstyle=border-width: 1px; border-radius: 0.5em;|McManus=[[Sir Hugh O'Donnell|'''Hugh<br />MacManus<br />O'Donnell''']]<br />{{circa|1520}}–1600|boxstyle_McManus=border-width: 1px; border-radius: 0.5em; background: lavender;|Conn='''[[Conn O'Donnell|Conn<br />O'Donnell]]'''<br />d. 1583|boxstyle_Conn=border: 2px solid blue; border-radius: 0.5em; background: wheat;|Rose='''Rose<br />O'Neill'''|iniondubh=[[Iníon Dubh|'''Fiona<br />"Iníon Dubh"<br />MacDonald''']]|Gallagher='''[[Hugh MacEdegany|Hugh<br />MacEdegany]]'''<br />d. 1588<br />illegitimate|boxstyle_Gallagher=border-width: 1px; border-radius: 0.5em; background: wheat;}}
{{Tree chart||!||||)|-|-|-|.||||||!|}}
{{Tree chart|Donal||ArtON||BrnD2|~|~|~|Sbjct|boxstyle=border-width: 1px; border-radius: 0.5em;|Rory='''[[Rory O'Donnell, 1st Earl of Tyrconnell|Rory<br />O'Donnell]]'''<br />1575–1608|ArtON='''Hugh Roe<br />O'Donnell'''<br />1572–1602|boxstyle_ArtON=border: 2px solid red; border-radius: 0.5em; background: lavender;|BrnD2=[[Nuala O'Donnell|'''Nuala<br />O'Donnell''']]<br />{{circa|1575}}–{{circa|1630}}|Sbjct=[[Niall Garve O'Donnell|'''Niall Garve<br />O'Donnell''']]<br />{{circa|1569}}–1626|boxstyle_Sbjct=border-width: 1px; border-radius: 0.5em; background: wheat;|Donal=[[Donnell O'Donnell|'''Donal<br />O'Donnell''']]<br />d. 1590|boxstyle_Donal=border-width: 1px; border-radius: 0.5em; background: wheat;}}
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The [[Franciscans|Franciscan]] friars at [[Donegal Abbey]] were the spiritual counselors of the ruling O'Donnells, and were also the educators of the dynasty's children.<ref name="dddd">{{Citation |last=O'Donnell |first=Francis Martin |date=14 June 2020b |url=https://www.academia.edu/43323694 |title=The O'Donnell Dynasty and Donegal Abbey |publisher=Tyrconnell-Fyngal Publishing |pages=1–8}}</ref> In medieval Ireland, the sons of Irish clan chiefs were typically trained from the age of seven in horse-riding and weaponry.{{Sfn|McGettigan|2005|p=38}}

Children of the [[Gaelic nobility of Ireland|Gaelic Irish nobility]] were traditionally [[Fosterage|fostered]] to fellow clans in the hopes of developing political alliances.<ref>{{Cite journal |last=Chonaill |first=Bronagh Ní |date=1997 |title=Fosterage: Child-Rearing in Medieval Ireland |url=https://www.jstor.org/stable/27724427 |journal=[[History Ireland]] |volume=5 |issue=1 |pages=28–31 |issn=0791-8224 |jstor=27724427}}</ref>{{Sfn|Morgan|1993|p=95}} As such, Hugh Roe was fostered by four families of differing political alignments: Clans [[Clan Sweeney|Sweeney]] [[Doe Castle|na dTuath]] and [[O'Cahan]], as well as two rival O'Donnell branches led by [[Hugh Dubh O'Donnell|Hugh McHugh Dubh O'Donnell]] and [[Conn O'Donnell]].{{sfn|Morgan|1993|p=124}}{{efn|It is also possible that O'Donnell was fostered by his father's advisor [[Eoin O'Gallagher]].<ref>{{Harvnb|Breatnach|1986|p=201}}. fn. 15.</ref>}} Conn had a strong claim to the lordship as his father [[Calvagh O'Donnell|Calvagh]] was a prior ruler of Tyrconnell.{{Sfnm|1a1=Morgan|1y=1993|1pp=126–127|2a1=Clavin|2y=2009|2ps=, 1st paragraph.}} In 1581 Conn turned hostile towards the ruling O'Donnells and Hugh Roe was removed from his care.{{Sfn|McGettigan|2005|p=37}} Conn died in 1583 and Hugh Roe's succession seemed assured.{{sfnm|1a1=Morgan|1y=2002|1p=2|2a1=Morgan|2y=1993|2p=127}} Nevertheless, Conn's sons, particularly [[Niall Garve O'Donnell|Niall Garve]], looked to the English government as a means of restoring their branch of the family to power.<ref>{{harvnb|Clavin|2009|ps=, 1st paragraph}}.</ref> By 1587, Hugh Roe was in the care of Owen Óg MacSweeney na dTuath, his final foster-father. According to historian Darren McGettigan, MacSweeney na dTuath "appears to have given [Hugh Roe] much freedom".{{Sfn|McGettigan|2005|pp=37–38}}

Ultimately Hugh Roe's fosterage did not engender much loyalty in his foster-families. Hugh McHugh Dubh antagonised the ruling O'Donnells into the 1590s, and the sons of MacSweeney na dTuath and Conn eventually opposed Hugh Roe by defecting to the English.{{Sfn|McGettigan|2005|p=38}}

=== Rise to prominence ===
Hugh Roe saw his first military action in 1584, with his father's chief advisor [[Eoin O'Gallagher]], against Clan [[O'Rourke]] of [[West Breifne]].{{sfnm|1a1=Morgan|1y=1993|1p=127|2a1=Morgan|2y=2009|2ps=, 1st paragraph.}} Even before reaching the age of fifteen, Hugh Roe had become well known across Ireland.{{Sfn|McGettigan|2005|p=38}}{{Sfn|O'Clery|O'Clery|Murphy|1895|p=3}} Biographer [[Lughaidh Ó Cléirigh]] praised the young noble: "He continued to grow and increase in comeliness and urbanity, tact and eloquence, wisdom and knowledge, goodly size and noble deeds".{{Sfn|O'Clery|O'Clery|Murphy|1895|p=3}} Hugh Roe began to be associated with [[Aodh Eangach]], a prophesied high king.{{Sfn|McGettigan|2005|pp=38–39}} It was foretold that if two men named Hugh succeeded each other as O'Donnell chief, the last Hugh shall "be a monarch in Ireland and quite banish thence all foreign nations and conquerors".{{Sfn|Morgan|1993|pp=124–125}}

By 1587, Hugh Roe was betrothed to the Earl of Tyrone's daughter [[Rose O'Neill (Irish noblewoman)|Rose]].{{sfnm|1a1=Walsh|1y=1930|1p=36|2a1=Morgan|2y=1993|2pp=96, 124, 128}} In addition to Tyrone's marriage to Siobhán, this betrothal would further cement a growing alliance between two clans who had traditionally been mortal enemies for centuries.{{sfnm|1a1=Morgan|1y=1993|1pp=124, 135|2a1=Walsh|2y=1930|2p=37}} Hugh Roe had become a focus of authority within Tyrconnell, and Tyrone described him as "the stay that his father had for the quieting of his inhabitance".{{Sfn|Morgan|1993|p=128}} As [[Tanistry|tanist]] of the O'Donnell clan, Hugh Roe was widely considered to be his father's most likely successor.<ref name="HM">{{Harvnb|Morgan|2009|ps=, 1st paragraph}}.</ref>

== Imprisonment and escape ==

=== Capture at Rathmullan ===
The English government feared that the emergence of a powerful O'Neill-O'Donnell alliance, which would be cemented by Hugh Roe's marriage to Rose,{{sfnm|1a1=Morgan|1y=2002|1p=3|2a1=Connolly|2y=2007|2p=423}} would threaten English control over Ulster.{{Sfnm|1a1=Morgan|1y=1993|1pp=128, 135|2a1=McGinty|2y=2013a|2p=21}} Though Tyrone professed loyalty to the Crown, he was attracting suspicion from the government due to his growing power.{{Sfnm|1a1=Annals of the Four Masters|1y=2008|1p=1859|2a1=McGettigan|2y=2005|2pp=41–42|3a1=McGinty|3y=2013a|3p=21}} Hugh Roe's familial links to various [[Scottish clan|Scottish Highland clans]] were also a cause for concern;{{Sfn|Dunlop|1894|p=436}} English officials often pejoratively referred to him as "Scottish".<ref name="HM" /> Additionally Hugh Roe's father had failed to pay annual rents promised to the government,{{Sfnm|1a1=Morgan|1y=1993|1p=128|2a1=McGettigan|2y=2005|2p=41}} and at the time the English government kept hostages for policy reasons.{{sfnm|2a1=Morgan|2y=2009|1a1=Webb|1y=1878|1p=391|2ps=, 4th paragraph.}} Ultimately the government decided that Hugh Roe must not be allowed to succeed as O'Donnell clan chief,{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=3–5|2a1=Morgan|2y=1993|2p=128|3a1=McGettigan|3y=2005|3p=42}}{{efn|[[Hugh Dubh O'Donnell|Hugh McHugh Dubh]] was a prominent contender for clan chief, and the government suggested him as a preferred successor.{{sfn|Morgan|1993|p=128}}}} and so the [[Lord Deputy of Ireland]], Welsh statesman [[John Perrot]], hatched a plan to kidnap the young noble.<ref name="fghfgh"/> In May 1587, Perrot proposed to [[William Cecil, 1st Baron Burghley|Lord Burghley]] that he could capture "[Hugh MacManus], his wife (who is a great bringer in of Scots), and perhaps his son [Hugh Roe], by sending thither a boat with wines".<ref>{{Cite book |url=https://archive.org/details/calendarofstatep3158grea |title=Calendar of the State Papers Relating to Ireland, of the Reign of Elizabeth, 1586 – 1588, July. |publisher=George E. Eyre and W. Spottiswoode |year=1877 |editor-last=Hamilton |editor-first=Hans Claude |page=338}}</ref>
[[File:John Perrot.png|thumb|Lord Deputy [[John Perrot]] authorised Hugh Roe's kidnapping.]]In September, Hugh MacManus was summoned to a conference with Perrot.<ref name="fghfgh">{{harvnb|Morgan|2009|ps=, 2nd paragraph.}}</ref> Meanwhile the ship ''Matthew'', captained by Dublin merchant Nicholas Barnes{{sfnm|1a1=McGettigan|1y=2005|1p=42|2a1=Morgan|2y=2009|2ps=, 2nd paragraph.}} (alias Nicholas Skipper)<ref name="source"/> was dispatched to [[Rathmullan]] on [[Lough Swilly]],{{Sfnm|1a1=Morgan|1y=1993|1p=128|2a1=McGettigan|2y=2005|2p=42}} where fourteen-year-old{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=9|2a1=O'Sullivan Beare|2y=1903|2p=42}} Hugh Roe was sojourning with his foster-father MacSweeney na dTuath.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=9|2a1=Webb|2y=1878|2p=391}}{{efn|Though MacSweeney na dTuath was Hugh Roe's foster-father,{{Sfnm|1a1=Dunlop|1y=1894|1pp=436–437|2a1=McGettigan|2y=2005|2pp=37–38}} Rathmullan was the stronghold of Clan MacSweeney [[Fanad]], a related but distinct branch of Clan MacSweeney.<ref>{{Cite book |url=https://archive.org/details/leabharchlainnes00walsuoft |title=Leabhar Chlainne Suibhne: An Account of the MacSweeney Families in Ireland, with Pedigrees |publisher=Dollard Printinghouse |year=1920 |editor-last=Walsh |editor-first=Paul |editor-link=Paul Walsh (priest) |location=Dublin|page=xxx|others=Digitized by the [[Internet Archive]] in 2007 with funding from Microsoft Corporation}}</ref>}} The ship was anchored and the crew went on shore under the guise of ordinary merchants selling wine. Hugh Roe heard of the merchant ship and arrived with several young companions. Barnes claimed that he had no wine left unsold except for what was left on the ship, and invited Hugh Roe aboard.{{Sfnm|1a1=O'Clery|1y=1895|1p=9|2a1=McGettigan|2y=2005|2p=42|1a2=O'Clery|1a3=Murphy}} Chief Donnell MacSweeney Fanad (Hugh Roe's host) was ashamed that the young noble had missed out on the wine and unwittingly encouraged him to take a small boat to the ''Matthew''.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=9–11|2a1=Walsh|2y=1939|2p=236}}

Chief MacSweeney Fanad, Chief MacSweeney na dTuath and Eoin O'Gallagher accompanied Hugh Roe onto the ''Matthew''.{{efn|[[Philip O'Sullivan Beare]] clarified that Chief MacSweeney Fanad, Chief MacSweeney na dTuath and Eoin O'Gallagher accompanied Hugh Roe onto the ''Matthew'', and were later exchanged for younger hostages once captured.{{Sfn|O'Sullivan Beare|1903|p=42}} Lughaidh Ó Cléirigh describes Hugh Roe's party as "thoughtless forward persons who were with him though they were older in years".{{Sfn|O'Clery|O'Clery|Murphy|1895|pp=9–11}} That the older men were exchanged for younger hostages is corroborated by an English report which states that Hugh Roe arrived in Dublin with three fellow hostages: the eldest sons of MacSweeneys na dTuath and Fanad and "the best pledge" of O'Gallagher.<ref name="source"/>}} Once on board, Hugh Roe and his compatriots were conducted into a secured cabin and plied with food and wine. Whilst they were enjoying themselves, the hatches were fastened and their weapons were removed.{{sfn|O'Clery|O'Clery|Murphy|1895|pp=9–11}} MacSweeney Fanad was released in exchange for his eldest son Donnell Gorm MacSweeney Fanad. O'Gallagher likewise gave his nephew Hugh O'Gallagher. MacSweeney na dTuath was also released upon giving "his eldest son" (actually a young peasant dressed in his son's clothes) as a hostage.{{Sfn|O'Sullivan Beare|1903|p=42}} Hostages were offered in Hugh Roe's stead to no avail, and the ship set sail for Dublin.{{sfn|O'Clery|O'Clery|Murphy|1895|pp=9–11}}

=== Imprisonment ===
Hugh Roe arrived in Dublin on 25 September; Queen [[Elizabeth I]] was informed the next day.<ref name="source">{{Cite book |url=https://archive.org/details/calendarofmanusc03grea_1 |title=Calendar of the manuscripts of the Most Honourable the Marquess of Salisbury |date=1889 |publisher=[[Eyre & Spottiswoode]] |others=Digitized by the [[Internet Archive]] |location=London |pages=285–286}}</ref>{{Sfn|McGettigan|2005|p=42}} Perrot ascertained that the peasant was not MacSweeney na dTuath's son and dismissed him.{{Sfn|O'Sullivan Beare|1903|p=42}} Hugh Roe and his fellow hostages were imprisoned in [[Dublin Castle]], most likely one of the gate towers.<ref name=":2">{{harvnb|Silke|2004|ps=, 2nd paragraph}}.</ref>

{{Quote box
| quote = "It was anguish and sickness of mind and great pain to [Hugh Roe] to be as he was, and it was not on his own account but because of the great helplessness in which his friends and kinsmen, his chieftains and leaders, his clerics and holy ecclesiastics, his poets and learned men, his subjects and whole people were, owing to their expulsion and banishment to other territories throughout Erin. He was always meditating and searching how to find a way of escape."{{sfn|O'Clery|O'Clery|Murphy|1895|p=13}}
| source = —[[Lughaidh Ó Cléirigh]] on Hugh Roe's imprisonment
| width = 25%
| quoted =
}}

Within three months, Tyrone was lobbying the queen for Hugh Roe's release.{{Sfnm|1a1=Walsh|1y=1930|1pp=36–37|2a1=McGettigan|2y=2005|2p=44}} In 1588, he offered a bribe of £1000 to [[William FitzWilliam (Lord Deputy)|William FitzWilliam]] (Perrot's successor as Lord Deputy) plus £300 to newly-appointed officials. Tyrone was later accused of offering a further £1000 to Dublin Castle's constable.{{sfnm|2a1=Morgan|2p=55|2y=1993|1a1=McGettigan|1y=2005|1p=49|2ps=: FitzWilliam succeeded Perrot as Lord Deputy.|1ps=: Tyrone's bribery}} In spring 1588, Iníon Dubh offered Perrot a bribe of £2000, plus sureties and hostages, for her son's release.{{Sfn|Morgan|1993|p=131}} After the [[Spanish Armada]]'s September 1588 shipwreck in [[Inishowen]], Hugh MacManus offered the government thirty captured Spanish officers in exchange for his son.{{sfn|McGettigan|2005|p=44}} FitzWilliam refused due to "the dangers that might grow unto this miserable realm by letting loose the reins unto so harebrain and ungracious an imp". In 1590 he indicated a willingness to release Hugh Roe, but this came to naught.{{Sfn|Morgan|1993|p=131}}

The English attempted to convert Hugh Roe and his fellow [[Catholic Church|Catholic]] hostages to [[Protestantism]] by bringing them to a Protestant service, but the boys shouted over the hymns and music so the service could not be heard. They did not desist even when carried out of the church and sent back to their cell, and were never again summoned.{{Sfn|Starke|1984|p=9}}

During his time in Dublin Castle, Hugh Roe had little interaction with the outside world beyond conversations with fellow political prisoners (particularly the Anglo-Irish [[Munster]] lords imprisoned from the [[Desmond Rebellions]]).{{sfn|Morgan|2002|p=10}} In witnessing first-hand the brutality inflicted by the Dublin government on Irish rebels, he became embittered and resentful of English authority.{{Sfnm|1a1=McGettigan|1y=2005|1p=43|2a1=McGinty|2y=2013a|2p=23|3a1=McGinty|3y=2013b|3p=5}} Ó Cléirigh stated that "[O'Donnell] had been listening to [stories about the English] during the four years and three months he was in the prison in Dublin, and that was the tale which he remembered best from the captives cast into prison with him... he said that the promises of the English were always vain and deceitful, and that it was by false promises they had stolen their patrimony from the Irish of the province of [[Leinster]] and of the province of [Munster]...  The English tell you lies now, and they will attack you when they find you unprepared".{{Sfn|O'Clery|O'Clery|Murphy|1895|p=125}} Ironically, Hugh Roe learnt to speak English during his imprisonment.{{sfn|Morgan|2002|p=11}} This period in Dublin is seen as the defining event of his short life.{{Sfn|McGettigan|2005|p=43}}

=== Chaos in Tyrconnell ===

Hugh MacManus became prematurely senile,{{sfnm|1a1=Morgan|1y=2009|1ps=, 3rd paragraph|2a1=O'Byrne|2y=2009b|2ps=, 3rd paragraph.}} and Hugh Roe's imprisonment exacerbated a long-running succession dispute which had consumed Tyrconnell since October 1580.{{Sfn|Morgan|1993|pp=123, 126–127, 129}} The dispute was bloody; three of Conn's sons were violently killed in the conflict.<ref>{{harvnb|Clavin|2009|ps=, 2nd paragraph}}.</ref> Iníon Dubh effectively took over Tyrconnell and ruled in her husband's name.<ref>{{harvnb|O'Byrne|2009b|ps=, 3rd paragraph.}}</ref> She pushed successfully for Hugh Roe to become her husband's successor by spreading the Aodh Eangach prophecy and by directing her Redshanks to kill any challengers.{{sfnm|1a1=Morgan|1y=1993|1pp=124–125|2a1=O'Byrne|2y=2009a|2ps=, 2nd paragraph.}} [[Hugh MacEdegany]], an illegitimate son of Calvagh O'Donnell,{{sfnm|1a1=Annals of the Four Masters|1y=2008|1p=1873|2a1=Dunlop|2y=1894|2p=436|3a1=Silke|3y=2004|3ps=, 2nd paragraph.}} was the first major challenger.{{Sfnm|1a1=Morgan|1y=1993|1p=129|2a1=O'Byrne|2y=2009a|2ps=, 2nd paragraph.}} He was assassinated on Iníon Dubh's orders during a visit to her residence, [[Mongavlin Castle]], in May 1588,<ref>{{harvnb|O'Byrne|2009a|ps=, 2nd paragraph}}.</ref><ref>{{Cite web |last=Newmann |first=Kate |author-link=Kate Newmann |title=Finola MacDonald (c.1500 - ) |url=https://www.newulsterbiography.co.uk/index.php/home/viewPerson/967 |archive-url=https://web.archive.org/web/20241204185724/https://www.newulsterbiography.co.uk/index.php/home/viewPerson/967 |archive-date=4 December 2024 |access-date=13 November 2024 |website=The Dictionary of Ulster Biography}}</ref> leaving Niall Garve as head of the "MacCalvagh" branch.{{sfn|Finnegan|2007|p=61}}[[File:Ulster Early 16th Century.png|left|thumb|Map of Ulster's [[List of Irish kingdoms|Gaelic kingdoms]] in the 16th century]]

Further disruptions developed as the government appointed various administrators in Tyrconnell who ransacked and pillaged the kingdom. Perrot appointed [[William Mostian]] as Sheriff of Tyrconnell—he quickly carried out eight [[Cattle raiding|cattle raids]], ransacking Donegal Abbey and murdering its guardian. Later the same year, FitzWilliam gave Captain [[John Connill]] charge of Tyrconnell{{sfn|Morgan|1993|p=122}} after being bribed with two Spanish gold chains.{{Sfnm|1a1=Meehan|1y=1870|1p=12|2a1=McGettigan|2y=2005|2p=46}} Connill assisted the opponents of the ruling O'Donnells. He was later joined by Captain [[Humphrey Willis]] and two hundred soldiers.{{sfn|Morgan|1993|p=122}} At one point Connill befriended then captured Hugh MacManus, but he was freed by Niall Garve.{{Sfnm|1a1=Morgan|1y=1993|1p=123|2a1=McGettigan|2y=2005|2pp=46–47}} Another brutal administrator was Captain Bowen, a notorious torturer who fried the soles of his victims' feet. This chaos created mass resentment towards the English government.{{Sfn|McGinty|2013a|p=27}}

Hugh Roe's elder half-brother Donal became the Crown's favored candidate for the chiefdom, and shortly after the Armada's shipwreck, FitzWilliam knighted and appointed Donal as Sheriff.{{Sfn|Morgan|1993|p=130}} FitzWilliam also imprisoned important Tyrconnell nobles Sean O'Doherty (Lord of Inishowen) and Eoin O'Gallagher, believing them to possess Spanish treasure from the Armada.{{Sfn|McGinty|2013a|p=26}} O'Gallagher's imprisonment also had political motivations as he was a major adherent of Hugh Roe during the succession dispute.{{Sfn|Morgan|1993|pp=124, 130}} Donal made an effort to depose his father, backed by Connill's troops. Iníon Dubh, backed by her Redshanks and the clans of the [[Branches of the Cenél Conaill|Cenél Conaill]] who remained loyal to her husband, crushed Donal at the [[Battle of Doire Leathan]] on 3 September <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 14 September<nowiki>]</nowiki> 1590.<ref>{{harvnb|Annals of the Four Masters|2008|pp=1891–1893|ps=}}; {{harvnb|Morgan|1993|p=130|ps=}}; {{harvnb|O'Byrne|2009a|ps=, 2nd paragraph}}.</ref>

Willis (who replaced Donal as Sheriff) and Connill exploited the ensuing chaos. They took control of western Tyrconnell and began raiding into the east,{{Sfn|Morgan|1993|p=130}} accompanied by a Captain Fuller.<ref>{{harvnb|Walsh|1939|p=238|ps=. fn. 1.}}</ref> Their forces also ransacked southern Tyrconnell and forced many of the population to flee to the mountains.{{Sfn|McGinty|2013a|p=27}}

Iníon Dubh bought off Niall Garve with a political marriage to her daughter [[Nuala O'Donnell|Nuala]], in an attempt to temper his hostility.{{Sfnm|1a1=Concannon|1y=1920|1p=229|1ps=: Nuala and Niall Garve married "perhaps about 1591"|2a1=Walsh|2y=1922|2p=362|2ps=: Nuala and Niall Garve married prior to Hugh Roe's inauguration|3a1=Walsh|3y=1929|3p=569|3ps=: Nuala and Niall Garve married prior to the latter's submission to Hugh Roe in 1592.}} By 1592, Niall Garve was in a strong position to claim Tyrconnell's lordship.{{sfn|Finnegan|2007|p=62}} Despite the continual presence of freebooting government troops, Tyrconnell's nobility remained obsessed with their succession conflict.{{sfn|Morgan|1993|p=135}}

=== First escape attempt ===
[[File:Bermingham Tower, Dublin Castle.jpg|thumb|Hugh Roe was imprisoned in [[Dublin Castle]]'s Bermingham Tower.<ref>{{harvnb|Silke|2004|ps=, 2nd paragraph: Hugh Roe O'Donnell was imprisoned in the Record Tower of Dublin Castle}}; {{harvnb|Manning|2017|pp=145, 147|ps=: Diagrams showing the position of Bermingham Tower (the record tower) within Dublin Castle}}.</ref>]]
After three years and three months in captivity,{{Sfn|O'Clery|O'Clery|Murphy|1895|p=13}} Hugh Roe made his first escape attempt in January 1591,{{Sfnm|1a1=Walsh|1y=1922|1p=360|2a1=Morgan|2y=2009|2ps=, 4th paragraph.}} in the company of fellow Ulster hostages Donnell Gorm MacSweeney Fanad and Hugh O'Gallagher.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1p=66|2a1=Dunlop|2y=1894|2p=437}} It is possible that the escape was incentivised by news of Donal's death.{{sfn|Breatnach|1986|p=202}} Before Hugh Roe and his companions were put in their cells one night, they escaped through a nearby window and climbed down a rope onto the drawbridge. They jammed a block of timber into the door, preventing the guards from pursuing them.{{efn|According to Ó Cléirigh, a young Tyrconnell man awaited outside Dublin Castle and gave Hugh Roe two swords; Hugh Roe gave one to Leinster warrior Art Kavanagh.{{sfn|O'Clery|O'Clery|Murphy|1895|p=15}}}} By the time the guards noticed Hugh Roe's absence and gave chase, the fugitives had already escaped past the open city gates.{{Sfn|O'Clery|O'Clery|Murphy|1895|p=15}}{{Sfn|McGettigan|2005|p=|pp=47–49}}

Hugh Roe's shoes fell apart and he was left behind by his companions in the thick woods beyond [[Three Rock Mountain]]. He sent word to Castlekevin in [[County Wicklow]], the territory of Chief Felim O'Toole, who had visited him in Dublin Castle. O'Toole wanted to assist Hugh Roe but faced pressure from his clan, who feared the consequences of aiding a high profile fugitive.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=17|2a1=McGettigan|2y=2005|2p=49}} O'Toole's sister Rose quickly planned for her husband [[Fiach McHugh O'Byrne]], of [[O'Byrne clan|Clan O'Byrne]], to take Hugh Roe to his house in [[Glenmalure]].{{Sfn|McGettigan|2005|p=49}} According to O'Sullivan Beare, O'Byrne and his clansmen immediately set out to rescue Hugh Roe, but their inability to cross a flooded river prevented them from reaching Castlekevin in time.{{Sfn|O'Sullivan Beare|1903|p=66}} English officer [[George Carew, 1st Earl of Totnes|George Carew]] was dispatched to Castlekevin on 15 January <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 25 January<nowiki>]</nowiki><ref>{{harvnb|Walsh|1939|p=236}}: New Style date; {{harvnb|McGettigan|2005|p=49}}: Old Style date.</ref> and Hugh Roe was surrendered and returned to Dublin Castle in chains.{{Sfn|McGettigan|2005|p=49}} Ó Cléirigh states the [[Privy Council of Ireland|Privy Council]] were pleased with Hugh Roe's recapture: "they made little or no account of all the hostages and pledges who escaped from them, and they were thankful for the visit which restored him to them again".{{Sfn|O'Clery|O'Clery|Murphy|1895|p=19}} Hugh Roe was lodged in Dublin Castle's record tower (the Bermingham Tower),<ref name=":2"/> shackled more heavily than before,<ref name="mor4">{{harvnb|Morgan|2009|ps=, 4th paragraph}}.</ref> and checked by the chief gaoler twice a day.{{Sfn|McGettigan|2005|p=49}}

=== Second escape attempt ===
{{Further|Art O'Neill Challenge}}
Around January 1592,{{efn|Ó Cléirigh stated that the successful escape occurred on the eve of the [[Epiphany (holiday)|Epiphany]] (6 January) in 1592—this would be 5 January. O'Sullivan Beare put the date as a few days before Christmas 1591.{{sfn|Walsh|1922|p=361}} This means a difference in time of about a fortnight.{{sfn|Walsh|1939|p=237}} The ''Annals of the Four Masters'', which is partially adapted from Ó Cléirigh's biography,<ref name="beathaadapted"/><ref name="oclery"/> stated that Hugh Roe "remained in Dublin, in prison and in chains, after his first escape, to the winter of this year [1592]."{{sfn|Annals of the Four Masters|2008|pp=1913–1914}} Historians Denis Murphy, [[Helena Concannon]]{{sfn|Walsh|1922|p=361}} and [[Robert Dunlop (historian)|Robert Dunlop]] stated that O'Donnell escaped on Christmas Eve 1591.{{sfn|Dunlop|1894|p=437}} Historians [[Emmett O'Byrne]], Darren McGettigan, Anthony McCormack and Terry Clavin stated the escape was on 6 January 1592.{{sfnm|1a1=O'Byrne|1y=2009b|1ps=, 3rd paragraph|2a1=McGettigan|2y=2005|2p=50|3a1=McCormack|3a2=Clavin|3y=2009|3ps=, 2nd paragraph.}} John J. Silke stated that the escape was on 5 January.<ref name=":2"/>}} Hugh Roe made a successful escape attempt with his fellow prisoners [[Henry MacShane O'Neill]] and Art MacShane O'Neill.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1p=66|2a1=Webb|2y=1878|2p=391|3a1=Morgan|3y=2009|3ps=, 4th paragraph.}} After years of lobbying and bribery,{{sfnm|1a1=McGettigan|1y=2005|1p=49|2a1=Morgan|2y=2014|2ps=, 9th paragraph.}} Tyrone had finally succeeded in bribing officials to help facilitate Hugh Roe's escape.<ref name="mor4" /> FitzWilliam, considered one of [[Kingdom of Ireland|Tudor Ireland]]'s most corrupt Lord Deputies,{{sfnm|1a1=McGinty|1y=2013a|1pp=23–24|2a1=O'Neill|2y=2017|3p=44|3y=2005|3a1=McGettigan|2pp=24, 85}} was most likely the recipient of this bribe, though this has never been conclusively proven.{{sfn|Morgan|1993|pp=132–133}} A 17th-century account by Donegal priests alleged that Tyrone successfully bribed FitzWilliam with £1,000 (equivalent to £287,000 in March 2024).{{Sfn|Meehan|1870|p=11–12}} In summer 1590, [[Conn MacShane O'Neill]] alleged that Tyrone "did lay down a plot and practised the escape of Hugh Roe" from prison—the plot apparently involved a silk rope and prepared horses. This is obviously a reference to some previous attempt, but is an accurate forecast of Hugh Roe's eventually successful escape.{{Sfn|Morgan|1993|p=132}}[[File:Hugh_O'Neill,_1608.jpg|left|thumb|Hugh Roe O'Donnell's father-in-law, [[Hugh O'Neill, Earl of Tyrone]], bribed officials to ensure the successful prison escape.]]This escape plan was far more prepared than Hugh Roe's prior attempt.{{sfn|McGettigan|2005|p=50}} The constable of Dublin Castle John Maplesden was on his deathbed{{sfnm|1a1=Hamilton|1y=1974|1pp=518–519|2a1=McGettigan|2y=2005|2p=50}} which distracted the chief gaoler from his duties, making it the perfect time to mount an escape.{{sfn|McGettigan|2005|p=50}} A gaoler's servant named Edward Eustace promised four horses which would be saddled in a nearby stable for three days prior.<ref>{{harvnb|O'Clery|O'Clery|Murphy|1895|ps=. "There was a certain faithful servant who visited them in the castle, a horseboy, to whom they imparted their secret, so that he met them face to face when they wanted him to be their guide."|p=21}}; {{harvnb|O'Sullivan Beare|1903|pp=66–67|ps=. "This plan he also communicated to a youth—Edward Eustace a friend of his... The lad Edward promised to supply him for his flight with four horses... saddled in stable the three previous days..."}}; {{harvnb|McGettigan|2005|p=50|ps=. "Red Hugh certainly had the outside assistance of a guide, Edward Eustace, who agreed to provide him with horses and take him to Feagh McHugh O'Byrne in Glenmalure."}}; {{harvnb|Morgan|1993|p=132|ps=. "A servant who had visited them as a horseboy in the castle was waiting to act as a guide."}}; {{harvnb|Morgan|2009|ps=, 4th paragraph. "...a servant of one of the gaolers acted as their guide."}}</ref> Fiach McHugh O'Byrne promised shelter for the fugitives at Glenmalure.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1pp=66–67|2a1=McGettigan|2y=2005|2p=50}} Richard Weston, a servant of Tyrone, managed to supply Hugh Roe with a silk rope,{{sfnm|1a1=Morgan|1y=1993|1p=132|2a1=Morgan|2y=2009|2ps=, 4th paragraph}} and [[Winter clothing|winter clothes]] were acquired for the long journey.{{sfn|McGettigan|2005|p=50}}

When the three prisoners were unshackled to eat, they took advantage of the gaolers.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=19|1ps=. "...he and some of his companions found an opportunity on the part of the guards in the very beginning of the night before they were taken to the refectory, and they took off their fetters."|2a1=Annals of the Four Masters|2y=2008|2pp=1913–1914|2ps=. "...before they had been brought into the refection house, took an advantage of the keepers, and knocked off their fetters."|3a1=Morgan|3y=2009|3ps=, 4th paragraph. "...after being unshackled to eat..."}}{{efn|O'Sullivan Beare claimed that Hugh Roe himself "procured a file with which he cut the fastenings of his, Henry's and Art's chains".{{sfn|O'Sullivan Beare|1903|p=67}}}} The prisoners made their way to the [[wikt:privy house|privy house]]. They tied one end of the rope there, and fed the other end down the privy hole which led outside the castle.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1p=67|2a1=Annals of the Four Masters|2y=2008|2pp=1913–1915|3a1=Morgan|3y=1993|3p=132}} Henry became separated from the others. According to Ó Cléirigh, "the darkness of the night and the hurry of the flight separated [Henry] who was the oldest of the party... [The others] were not pleased at the separation".{{Sfn|O'Clery|O'Clery|Murphy|1895|p=21}} According to O'Sullivan Beare, Henry made his way down the rope first, and without waiting for the others, escaped safely back to Ulster. Hugh Roe followed, but Art MacShane was badly injured by a falling stone whilst sliding down the rope. Although Eustace had promised horses, on that day they had been removed without his knowledge.{{Sfn|O'Sullivan Beare|1903|p=67}} Once outside the castle, Hugh Roe and Art MacShane met with Eustace{{efn|Lughaidh Ó Cléirigh and the ''Annals of the Four Masters'' imply that the gaoler's servant (i.e. Eustace) was the guide who escorted Hugh Roe from Dublin to Glenmalure.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=21|2a1=Annals of the Four Masters|2y=2008|2pp=1915–1917}} Hiram Morgan, Darren McGettigan and Ken Cowley agree with these accounts.{{sfnm|1a1=Morgan|1y=2009|1ps=, 4th paragraph|2a1=McGettigan|2y=2005|2pp=50–51|3a1=Cowley|3y=2015|3p=6}} In contrast, O'Sullivan Beare implies that the guide, who was "sent by Fiach [O'Byrne]", was not Eustace.{{sfn|O'Sullivan Beare|1903|p=67}} [[Alfred Webb]] claims that Turlough O'Hagan (one of Tyrone's men) was the guide who escorted Hugh Roe from Dublin to Glenmalure,{{sfn|Webb|1878|p=391}} but Morgan and McGettigan clarify that though O'Hagan escorted O'Donnell back to Ulster, he was distinct from the guide that escorted the prisoners to Glenmalure.<ref name="mor4"/>{{sfn|McGettigan|2005|pp=50–51}}}} who guided them through Dublin.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1p=67|2a1=Annals of the Four Masters|2y=2008|2pp=1915–1917}} The trio proceeded through the dark streets, mixing with the crowds, and safely escaped the city.{{sfn|O'Clery|O'Clery|Murphy|1895|p=21}}

The escape plan went awry. The fugitives had left their winter clothes in prison and Hugh Roe's shoes became worn out, exposing him to the elements. Art MacShane had to be carried by the others, either because he had grown fat and unfit in prison,{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=21|2a1=McGettigan|2y=2005|2p=50}} or because of his injury from the falling stone.{{Sfn|O'Sullivan Beare|1903|p=67}} The trio made it into the [[Wicklow Mountains]] at which point they sought shelter in a cave,{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=21–23|2a1=McGettigan|2y=2005|2p=50|3a1=McCormack|3a2=Clavin|3y=2009|3ps=, 2nd paragraph.}} traditionally said to be along the slopes of [[Conavalla]].<ref name="irishexaminer.com">{{Cite web |last=O'Dwyer |first=John G. |date=3 September 2023 |title=Missing horses, amputated toes and a lonesome Wicklow bog — the story behind Art's Cross |url=https://www.irishexaminer.com/lifestyle/outdoors/arid-41211193.html |url-status=live |archive-url=https://web.archive.org/web/20230905012050/https://www.irishexaminer.com/lifestyle/outdoors/arid-41211193.html |archive-date=5 September 2023 |access-date=2 July 2024 |website=Irish Examiner |language=en}}</ref> Hugh Roe and Art MacShane were too weak to reach Glenmalure, so Eustace left them in the cave and went on ahead to get help.{{sfnm|1a1=O'Sullivan Beare|1y=1903|1p=67|2a1=Webb|2y=1878|2p=391|3a1=Morgan|3y=2009|3ps=, 4th paragraph.}} According to O'Sullivan Beare, Hugh Roe managed to survive by eating leaves and bark, but despite his pleas, Art MacShane could not eat. After three nights,{{Sfn|O'Sullivan Beare|1903|pp=67–68}} when O'Byrne's men arrived to rescue them, Hugh Roe and Art MacShane were found covered in snow.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=23|2a1=Webb|2y=1878|2p=391}} Art MacShane died of [[hypothermia]].{{sfnm|1a1=McGettigan|1y=2005|1p=50|2a1=McCormack|2a2=Clavin|2y=2009|2ps=, 2nd paragraph.}} O'Sullivan Beare claimed that Hugh Roe refused to eat due to his grief over Art MacShane's death, but was compelled to do so by O'Byrne's men.{{Sfn|O'Sullivan Beare|1903|p=68}} He was taken to Glenmalure where he was revived with difficulty, tended to and recovered.{{Sfnm|1a1=O'Sullivan Beare|1y=1903|1pp=67–68|2a1=Webb|2y=1878|2p=391|3a1=Morgan|3y=2009|3ps=, 4th paragraph.}} Art MacShane's family were rivals to Tyrone, so it was speculated that Tyrone had O'Byrne's party kill him, though it is more likely he died of exposure. He was buried on the mountainside.{{sfn|McGettigan|2005|pp=50–51}}

[[File:Art's Cross, Wicklow.jpg|thumb|A cross marks the spot where Art MacShane O'Neill is said to have died.]]Unusually, the state papers do not reference Hugh Roe's escape until his return to Ulster. This could point to corruption or embarrassment on the part of government officials.{{sfn|Morgan|1993|p=132}} In a letter to Lord Burghley, FitzWilliam attempted to vindicate himself by declaring he had sacked Maplesden (who died mere days after the escape) and imprisoned the chief gaoler.{{sfnm|1a1=Hamilton|1y=1974|1pp=518–519|2a1=Morgan|2y=1993|2pp=132–133}} An outraged Queen Elizabeth I wrote to statesman [[Thomas Burgh, 3rd Baron Burgh|Thomas Burgh]] in May 1592 and decreed that "O'Donnell escaped by the practice of money bestowed on somebody. Call to you the Chancellor, [[Lord Chief Justice of Ireland|Chief Justice]] [[Robert Gardiner (Chief Justice)|Gardiner]], and the Treasurer, and inquire who they are that have been touched by it".{{sfn|O'Clery|O'Clery|Murphy|1895|p=xli}}

== Accession as clan chief ==

=== Return to Ulster ===
For a few days after his rescue, Hugh Roe was tended to in a hidden cabin in Glenmalure.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=25|2a1=Webb|2y=1878|2p=391|3a1=McGettigan|3y=2005|3p=51}} Hugh Roe and O'Byrne swore oaths to mutually assist each other if they came under English attack, and Hugh Roe promised to make Tyrone and Chief [[Hugh Maguire (Lord of Fermanagh)|Hugh Maguire]] of [[Fermanagh]] swear similar oaths.{{sfn|Morgan|2002|p=10}} Turlough Boye O'Hagan, a trusted emissary of Tyrone, arrived to escort Hugh Roe back to Ulster; they set out immediately.{{sfn|McGettigan|2005|p=51}} Hugh Roe's feet were [[Frostbite|frostbitten]] so he had to be lifted up and off of his horse.{{sfn|O'Clery|O'Clery|p=25|Murphy|1895}} He was escorted across the [[River Liffey|Liffey]] by a band of horsemen (which included Felim O'Toole). He proceeded northwards under O'Hagan's guidance and crossed [[River Boyne|the Boyne]] on a small ferry kept by a "poor little fisherman", whilst his attendant led their horses through [[Drogheda]].{{sfn|Webb|1878|p=391}} At [[Mellifont]], he rested one night at the house of English ally [[Garret Moore, 1st Viscount Moore|Garret Moore]],{{sfnm|1a1=Webb|1y=1878|1p=391|2a1=Morgan|2y=2009|2ps=, 4th paragraph.}} travelled through [[Dundalk]] and [[the Fews]], and on the third day reached [[Armagh]]. The next day Hugh Roe arrived at [[Dungannon]], Tyrone's residence,{{sfn|Webb|1878|p=391}} where the two men presumably discussed their plans to retake Tyrconnell's lordship. It is also here that they may have planned their future attack on [[Turlough Lynagh O'Neill|Turlough Luineach O'Neill]], Tyrone's rival in [[Tír Eoghain]]. Hugh Roe remained at Tyrone's residence for four days, hidden in a secret chamber to avoid corrupting Tyrone's loyalist public image.{{sfn|McGettigan|2005|p=51}} Afterwards, Hugh Roe was received by Maguire in Fermanagh. Maguire conveyed Hugh Roe across [[Lough Erne]] and brought him to the border of Tyrconnell where a party of supporters welcomed him. Hugh Roe then arrived at his father's castle in [[Ballyshannon]].{{sfnm|1a1=Annals of the Four Masters|1y=2008|1p=1925|2a1=Webb|2y=1878|2p=391–392|3a1=McGettigan|3y=2005|3p=51}}

=== Attack on English occupation ===
Tyrconnell had suffered much repression and turmoil in Hugh Roe's absence.{{sfnm|1a1=McGettigan|1y=2005|1p=52|2a1=McGinty|2y=2013a|2p=26}}{{efn|In 1594, Hugh Roe O'Donnell estimated that Tyrconnell had suffered from £20,000 worth of damages.{{sfn|Morgan|2002|p=10}}}} Not long before his return, Willis and Connill's forces raided [[Donegal (town)|Donegal]] in the dead of night and occupied Donegal Abbey as a [[garrison]].<ref>{{harvnb|Meehan|1870|p=12}}: primary source by the 17th-century clergy of Donegal Abbey; {{harvnb|Breatnach|1986|p=203}}: [[Paul Walsh (priest)|Paul Walsh]] suggested that Willis had not been "long in Tír Conaill when Aodh Ruadh arrived home".</ref> [[Ballyshannon Castle]] and [[Donegal Castle]] were the two major strongholds in Tyrconnell not yet deprived by the Crown.{{sfnm|1a1=Annals of the Four Masters|1y=2008|1p=1925|2a1=McGettigan|2y=2005|2p=52}} Even nobles in Tyrconnell who previously favoured the Crown had become resentful by this time.{{Sfnm|1a1=Morgan|1y=1993|1p=135|2a1=McGettigan|2y=2005|2p=52}} Hugh Roe made expelling the English forces his first order of business,{{sfnm|1a1=McGettigan|1y=2005|1p=52|2a1=McGinty|2y=2013a|2p=27}} and he rallied his family's followers to Ballyshannon.{{sfnm|1a1=Annals of the Four Masters|1y=2008|1pp=1925–1927|2a1=McGettigan|2y=2005|2p=52}} [[File:Donegalcastle.jpg|thumb|[[Donegal Castle]] and [[Ballyshannon Castle]] were Hugh Roe O'Donnell's two major strongholds. The former (pictured) was restored in the 1990s; the latter was demolished in 1720.]]
As soon as Chief Donough MacSweeney Banagh heard of Hugh Roe's safe return, he attacked Willis, forcing him and his soldiers into their garrison in Donegal Abbey.<ref>{{Harvnb|O'Clery|O'Clery|Murphy|1895|p=33}}. fn 7. "MacSwiny Banagh attacked [Willis] as soon as Hugh O'Donnell reached Donegal."; {{harvnb|O'Sullivan Beare|1903|pp=68–69}}. "[Willis] was levying tribute in Tyrconnell, and was attacked by MacSweeny, as soon as ever the latter had heard of Roe's safe arrival. Willis betook himself to the monastery..." O'Sullivan Beare subsequently names Donough MacSweeny as "Chief of Banagh".</ref> Hugh Roe's forces killed a number of English troops, forcing them to abandon plunder.{{sfn|McGettigan|2005|p=52}} Hugh Roe travelled to Donegal to face Willis and forced the English troops to depart Tyrconnell. Sources conflict on the exact circumstances. According to Ó Cléirigh, Hugh Roe informed Willis that if he and his men left, they would not be harmed.{{Sfn|O'Clery|O'Clery|Murphy|1895|p=37}} According to a 17th-century account written by the clergy of Donegal Abbey, Willis threatened to [[Church arson|set the church on fire]], but Hugh Roe was "anxious to preserve the sacred edifice" and allowed Willis to depart unharmed.{{Sfn|Meehan|1870|p=13}} According to Captain [[Thomas Lee (army captain)|Thomas Lee]], O'Donnell intended to slaughter Willis's men but was held back by Tyrone.{{Sfn|McGinty|2013b|p=7}} According to O'Sullivan Beare, Willis surrendered to Hugh Roe, who dismissed the English forces in safety with an injunction that Tyrconnell would neither give tribute or allegiance to the Crown.{{Sfn|O'Sullivan Beare|1903|p=68}} Afterwards the clergy returned to the abbey.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=39|2a1=Meehan|2y=1870|2p=13}}

After expelling Willis's forces in February,{{Sfnm|1a1=Silke|1y=2004|2a1=O'Neill|2y=2016|2p=43|1ps=, 3rd paragraph}} Hugh Roe returned to Ballyshannon where his big toes were amputated due to frostbite.{{efn|O'Sullivan Beare believed that that Hugh Roe's big toes were amputated in Glenmalure.{{sfn|O'Sullivan Beare|1903|p=68}} Ó Cléirigh stated that the amputation occurred in Tyrconnell, and notes that Hugh Roe wasn't inaugurated until May because he was recovering from his amputation.{{sfn|O'Clery|O'Clery|Murphy|1895|pp=25, 39}} This is supported by Dunlop and Morgan.{{sfn|Dunlop|1894|p=437}}<ref name="mor4"/>}} He remained ill and in recovery for a year.{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=39|2a1=Silke|2y=2004|2ps=, 3rd paragraph.}}

=== Inauguration ===
[[File:RedHughInauguration 1885 Reigh.jpg|thumb|1885 illustration of O'Donnell's inauguration by [[John Dooley Reigh]]]]On 23 April <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 3 May<nowiki>]</nowiki> 1592{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=43|2a1=McGettigan|2y=2005|2p=54|3a1=Walsh|3y=1939|3p=237|3ps=: Walsh notes that this is 23 April in Old Style dating.}} at [[Kilmacrennan]] Friary, 19-year-old Hugh Roe O'Donnell was inaugurated as O'Donnell clan chief{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=41|2a1=O'Donovan|2a2=Herity|2y=2000|2pp=45–46|3a1=McGettigan|3y=2005|3p=54}} before an audience of his family and their supporters.{{sfn|Morgan|1993|p=133}} The inauguration ceremony was part-religious and part-secular,{{efn|For detail on the customs of the ceremony, see {{harvnb|O'Clery|O'Clery|Murphy|1895|pp=xliii, 41–43}}, {{harvnb|Ó Canann|2007|pp=101–116}} and {{harvnb|O'Donnell|2001|pages=48–49}}.}} and involved the O'Donnell clan's ornamental inauguration stone.{{sfn|McGettigan|2005|p=54}}{{efn|The inauguration stone ("Rock of Doon") was traditionally located at the [[Termon#Rock of Doon|Hill of Doon]], though by 1592 it had been moved to Kilmacrennan.{{sfn|O'Donovan|Herity|2000|pp=45–46}}}} Hugh MacManus's apparently voluntary abdication was "stage-managed" by Iníon Dubh, who remained the "head of advice and counsel" in Tyrconnell.{{sfn|Morgan|1993|p=133}} Following his abdication, Hugh MacManus spent his final years living in retirement among the Franciscans at Donegal Abbey and doing [[penance]] for his sins.{{Sfnm|1a1=Meehan|1y=1870|1p=13|2a1=O'Sullivan Beare|2y=1903|2p=69}} Hugh Roe's younger brother Rory was appointed as tanist.<ref name="RO" />

[[File:Kilmacrenan Friary W 2012 09 19.jpg|thumb|250x250px|Hugh Roe O'Donnell was inaugurated at Kilmacrennan Friary.]]The major surviving opponents to Hugh Roe's succession—including Niall Garve, Hugh McHugh Dubh and Sean O'Doherty—did not attend the inauguration out of protest.{{Sfnm|1a1=Morgan|1y=1993|1p=133|2a1=McGettigan|2y=2005|2p=55}} At the time, Niall Garve was in Dublin unsuccessfully seeking support from authorities.{{Sfnm|1a1=Morgan|1y=1993|1p=133|2a1=Clavin|2y=2009|2ps=, 2nd paragraph.}} Tomás G. Ó Canann noted that, as Hugh Roe O'Donnell failed to secure the attendance of such a significant chunk of the Cenél Conaill, his inauguration was arguably illegitimate.{{sfn|Ó Canann|2007|p=105}} With the exception of Niall Garve in 1603, Hugh Roe was the last O'Donnell clansman to be traditionally inaugurated as clan chief.<ref>{{harvnb|O'Donnell|2006|p=31|ps=. Niall Garbh was the last inaugurated head of the O'Donnell family in 1603}}; {{harvnb|Ó Canann|2007|pp=104–105|ps=. Rory was never inaugurated}}.</ref>

=== Rise in power ===
Immediately after his inauguration, Hugh Roe O'Donnell and Tyrone mounted raids against Turlough Luineach, who had provided assistance to O'Donnell's rivals{{Sfn|Morgan|1993|p=134}} such as Niall Garve.{{Sfnm|1a1=Finnegan|2ps=, 2nd paragraph.|2a1=Clavin|2y=2009|1p=62|1y=2007}} O'Donnell desired revenge and sought to assist his new ally Tyrone,{{Sfn|Morgan|1993|p=134}} whose alliance with O'Donnell was primarily founded on using the latter's military power to take control of Tír Eoghain.{{Sfnm|1a1=McGettigan|1y=2005|1pp=52–53, 122|2a1=McGinty|2y=2013a|2p=26}}

In June 1592, O'Donnell renewed his clan's interest in north [[Connacht]] by supporting a revolt among the lower MacWilliam Bourkes,{{sfn|Morgan|1993|p=134}} to the chagrin of Lord President [[Richard Bingham (soldier)|Richard Bingham]].<ref name=":3" /> O'Donnell imposed his control over Tyrconnell. He dispelled bandits from [[Barnesmore Gap]], established an execution site at Mullaghnashee beside Ballyshannon Castle, and took pledges from all nobles wealthy enough to maintain four horsemen.{{sfn|McGettigan|2005|p=56}}[[File:2052_O'Neill_1574.jpg|thumb|[[Turlough Lynagh O'Neill|Turlough Luineach O'Neill]] supported O'Donnell's opponents.]]

O'Donnell dispatched letters to the state informing of his inauguration and justifying his attack on Turlough Luineach. He offered to submit to FitzWilliam in person if he was lent £800. FitzWilliam, who recognised the necessity of conciliating with O'Donnell, reprimanded him for his arrogance but promised to pardon him and lend him £200 if they met at Dundalk by July. Tyrone was anxious to improve his own standing with the government,{{sfn|Dunlop|1894|p=437}} and at FitzWilliam's request, he travelled to Donegal to confer with O'Donnell. After some convincing, O'Donnell accompanied Tyrone to Dundalk to submit to FitzWilliam.{{sfnm|1a1=Dunlop|1y=1894|1p=437|2a1=McGettigan|2y=2005|2p=54}} Bribery was probably involved in the meeting, which took place in a church{{sfn|McGettigan|2005|p=54}} on 2 August 1592. According to Thomas Lee, O'Donnell bribed FitzWilliam with £500 to ensure favourable negotiations.{{sfn|Morgan|1993|p=134}} O'Donnell made various agreements with FitzWilliam: he pledged his loyalty to Elizabeth I, agreed to receive a Sheriff in Tyrconnell, promised to pay his father's covenanted rents,{{sfn|McGettigan|2005|p=54}} to treat his rivals (O'Doherty, Niall Garve and Hugh McHugh Dubh) fairly,{{sfn|Morgan|1993|p=134}} to banish Catholic clergy from Tyrconnell, and to avoid supporting the MacWilliam Bourkes in Connacht.<ref name=":3">{{Harvnb|Morgan|2009|ps=, 5th paragraph}}.</ref> O'Donnell successfully negotiated to retain about 100 redshanks in Tyrconnell for use as his mother's bodyguards, ostensibly because he was concerned for her safety. After the meeting, the two Hughs feasted at Dungannon where they further discussed their developing alliance.{{sfn|McGettigan|2005|p=54}}

Tyrone's daughter [[Rose O'Neill (Irish noblewoman)|Rose]] was escorted to Tyrconnell in expectation of her marriage to O'Donnell.{{Sfnm|1a1=Walsh|1y=1930|1p=37|2a1=Morgan|2y=2002|2p=8}} The couple were formally married during Christmas-time 1592 at O'Donnell's house.{{Sfnm|1a1=McGettigan|1y=2005|1pp=54–55|2a1=Casway|2y=2016|2p=71}} According to McGettigan, the marriage started out as a success with Rose having some measure of influence over O'Donnell.{{Sfn|McGettigan|2005|p=55}}

Despite his promises to FitzWilliam, O'Donnell subjugated his rivals. Sean O'Doherty was captured at a parley and imprisoned; only then did he acknowledge O'Donnell's lordship. In early 1593, O'Donnell obtained Hugh McHugh Dubh's submission by taking his last stronghold at [[Belleek, County Fermanagh|Belleek]] and beheading sixteen of his followers "by train of a feigned treaty of friendship, mediated by Maguire".{{sfn|Morgan|1993|pp=133–134}} This sufficiently intimidated Niall Garve that he submitted to his younger cousin through fear. He was forced to turn over control of [[Lifford]]'s castle, though he did not give up his ambitions to seize the lordship.{{sfnm|1a1=McGettigan|1y=2005|2a1=Finnegan|2y=2007|2p=63|1pp=55–56}} With the Tyrone-O'Donnell alliance against him, Turlough Luineach surrendered his lordship in May 1593.<ref>{{Cite journal |last=Brady |first=Ciaran |date=October 2009 |title=O'Neill, Turlough Luineach |url=https://www.dib.ie/biography/oneill-turlough-luineach-a6967 |url-status=live |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.006967.v1 |archive-url=https://web.archive.org/web/20240222003717/https://www.dib.ie/biography/oneill-turlough-luineach-a6967 |archive-date=22 February 2024 |access-date=12 August 2024|url-access=subscription }}</ref> Tyrone took control of Tír Eoghain, making both O'Donnell and his father-in-law the rulers of the two major kingdoms of Gaelic Ulster.{{sfn|McGinty|2013a|pp=28–30}}

== Initial rebellion ==

=== Conference of bishops ===
[[File:Portrait of Philip II of Spain by Sofonisba Anguissola - 002b.jpg|left|thumb|O'Donnell sought military aid from King [[Philip II of Spain]].]]
By late 1592 the Crown's continual advances into Ireland, as well as the recent executions of chieftains [[Hugh Roe McMahon|Hugh Roe MacMahon]] (1590) and [[Brian O'Rourke]] (1591) had created a fierce resentment in the Gaelic nobility and Irish Catholic clergy.<ref>{{harvnb|McGettigan|2005|pp=51–52, 59}}; {{harvnb|McGinty|2013a|pp=24–25}}; {{harvnb|Morgan|2013|p=5}}.</ref> Catholic priests were suffering harassment and imprisonment from English authorities, and Spain had been a refuge to the Irish Catholic clergy since the 1570s.{{sfn|McGettigan|2005|p=59}} Archbishop [[Edmund MacGauran]] returned from Spain having met with [[Philip II of Spain|King Philip II]] in September 1592.{{sfnm|1a1=Walsh|1y=1990|1p=68|2a1=McGettigan|2y=2005|2p=59}} MacGauran was eager to obtain Spanish military aid to combat English forces in Ireland.{{sfn|McGettigan|2005|p=59}} Philip II wanted Ireland as an ally in the [[Anglo-Spanish War (1585–1604)|Anglo-Spanish War]], but would only promise support if Ireland proved itself by launching prior military action.{{sfn|Morgan|2013|p=5}} MacGauran sought Irish lords willing to openly defy the Crown,{{sfn|O'Neill|2016|p=44}} and in December a conference of seven Catholic bishops met in Tyrconnell.<ref>{{harvnb|McGettigan|2005|p=59|ps=. "Seven Catholic bishops met in Ulster in late 1592, led by Archbishop Maguaran of Armagh and Archbishop James O'Hely of Tuam."}}; {{harvnb|Morgan|2009|ps=. "...in December a conference of northern bishops met in Tyrconnell."}}</ref> The bishops saw O'Donnell as their main hope,{{sfn|Morgan|1993|p=142}} and declared he was "fittest for the part" and thus to be "their leader or general".{{sfn|McGettigan|2005|pp=59–60}} On 29 March [<nowiki/>[[Old Style and New Style dates|N.S.]] 8 April] 1593, O'Donnell addressed Irish nobles living in Spain: "I and the other chiefs who have united with me and are striving to defend ourselves, cannot hold out long against the power of the Crown of England without the aid of his Grace the Catholic King.... We have thought it well to send the [[Roman Catholic Archdiocese of Tuam|Archbishop of Tuam]] [<nowiki/>[[Seamus Ó hÉilidhe|James O'Hely]]] to treat of this matter with his Majesty".{{sfn|O'Clery|O'Clery|pp=|Murphy|1895|p=l}}

=== Maguire's revolt ===
Captain Willis was appointed by FitzWilliam as Sheriff of Fermanagh against Maguire's will. In early April 1593,{{Sfnm|1a1=Morgan|1y=1993|1p=143|2a1=Barry|2y=2009b|2ps=, 2nd paragraph.}} Willis entered Fermanagh with at least 100 men and began violently pillaging and raiding.{{sfnm|1a1=O'Neill|1y=2016|1pp=42–44|2a1=O'Neill|2y=2017|2p=99}} This exacerbated resentment towards the Crown, and after Willis' first offensive,{{sfn|Morgan|1993|p=143}} O'Donnell met with MacGauran, Maguire, [[Brian Oge O'Rourke]]{{Sfn|O'Neill|2016|p=44}} and [[Tibbot na Long Bourke, 1st Viscount Mayo|Theobald]], Richard and John Bourke at [[Enniskillen Castle]] on 28 April [<nowiki/>[[Old Style and New Style dates|N.S.]] 8 May]. MacGauran advised that the noblemen sign a letter addressed to Philip II which emphasised their oppression and which requested urgent reinforcements from the Spanish army. Archbishop O'Hely was tasked with delivering the confederates' messages: two letters from O'Donnell, one letter from MacGauran, and the 28 April letter signed by the confederates.{{Sfn|Walsh|1990|pp=74–76}}{{efn|The other signatories of the 28 April letter were clergymen [[Redmond O'Gallagher]] ([[Bishop of Derry]]), [[Richard Brady]] ([[Bishop of Kilmore]]), [[Cornelius O'Devany]] ([[Bishop of Down and Connor]]), Patrick MacCaul ([[Bishop of Dromore]]) and Niall O'Boyle ([[Bishop of Raphoe]]).<ref>{{harvnb|Walsh|1990|p=76}}. fn. 28.</ref>}}[[File:Enniskillen_Castle_05.jpg|thumb|The Irish confederacy formed following a meeting at [[Hugh Maguire (Lord of Fermanagh)|Hugh Maguire]]'s stronghold, [[Enniskillen Castle]].]]Maguire obtained reinforcements from Tyrone's brother and foster-brothers,{{Sfnm|1a1=Morgan|1y=1993|1pp=143–144|2a1=O'Neill|2y=2016|2pp=43–44}} who were likely involved on Tyrone's behalf,<ref>{{harvnb|Morgan|2014|ps=, 11th paragraph.}}</ref> and forced Willis and his men from Fermanagh.{{sfnm|1a1=Webb|1y=1878|1p=324|2a1=O'Neill|2y=2016|2p=44}} Maguire's revolt marked the start of the [[Nine Years' War (Ireland)|Nine Years' War]].{{sfnm|1a1=Morgan|1y=1993|1p=143|2a1=McGinty|2y=2013b|2p=8|3a1=O'Neill|3y=2015|3p=14}}

Historians have debated on O'Donnell's position within the confederacy.{{efn|name=debate|Hiram Morgan and Darren McGettigan notably have polarising viewpoints on O'Donnell's role.<ref>{{Harvnb|McGettigan|2005|p=60}}. "Although the evidence for this is clear, the historian Hiram Morgan has recently disputed it. Morgan has attempted to lessen the importance of the roles played in the developing confederacy by Archbishop Maguaran and Red Hugh, emphasizing instead the importance of Hugh O'Neill."</ref><ref>{{Harvnb|Morgan|2007a|p=823}}. "Even though McGettigan acknowledges the key role played by O'Neill in springing O'Donnell from gaol in Dublin Castle, he is rather naïvely unwilling to give O'Neill the lead role in the conspiracies at the outset of the war".</ref>{{sfn|Kelly|2004|pp=160–161}} See {{harvnb|McGinty|2013a}} for further discussion of O'Donnell's relationship with his father-in-law.}} Historians [[Nicholas Canny]], Michael Finnegan, John J. Silke and Darren McGettigan credit O'Donnell as the confederacy's driving force until Tyrone's break into open rebellion.<ref>{{Harvnb|O'Neill|2017|p=25}}. "Canny suggests that Tyrone was unwillingly pushed into rebellion to prevent his followers defecting to his brother, Cormac MacBaron".; {{Harvnb|McGinty|2013a|p=40}}. "Michael Finnegan in his examination of the outbreak of the war concurs with Silke's assertion that O'Neill may not have been able to manage O'Donnell. Finnegan argues that the actions of O'Donnell and the other confederates actually undermined Tyrone who in 1593 at least, genuinely wanted to prevent a war and only engaged in an open rebellion in order to survive because his position as a loyal servant to the crown became unattainable due to him being associated with O'Donnell and Maguire's military undertakings."; {{Harvnb|McGettigan|2005|p=17}}. "...while the role played by Hugh O'Neill was crucial to the confederacy, he did not build it, and may have been carried along by events and his own success, much more than some historians realize."; p. 60. "...the near-contemporary accounts of Lughaidh Ó Cléirigh, Philip O'Sullivan Beare and Archbishop Lombard all agree that at this time O'Donnell was playing a lead role".</ref> Historians [[Hiram Morgan]] and James O'Neill have disputed this by emphasising that Tyrone was a more important figure who hid his allegiance to the confederacy for strategic reasons.<ref>{{Harvnb|Morgan|2007a|p=823}}. "Conspiracies are by their nature clandestine and the Ulster lords' messenger to Spain told Madrid that O'Neill was a secret member of the conspiracy. If we combine this with the fact that O'Neill only consented to a treaty of equality with O'Donnell in 1599 or 1600, it is hard not to say that the older O'Neill was the leader in 1592/3."; {{Harvnb|O'Neill|2016|p=43}}. "Reappraisal of the evidence suggests that not only was Tyrone the guiding force behind Maguire's revolt, the conflict in Fermanagh was an essential diversion of English forces, allowing Tyrone to suppress English clients in east Ulster and bring his military power to the point where the earl could realistically challenge crown authority in Ireland at the start of 1595."</ref> The [[High Sheriff of Monaghan|Sheriff of Monaghan]] alleged that Tyrone attended the meeting at Enniskillen Castle,{{sfnm|1a1=Morgan|1y=1993|1p=142|2a1=O'Neill|2y=2017|2p=43}} though Tyrone did not sign MacGauran's letter.{{Sfn|Walsh|1990|pp=74–76}} Around August 1593, Maguire stated to a spy that Tyrone had pushed him into rebellion and "promised to assist him and bear him out in his war".<ref>{{Cite book |url=https://archive.org/details/calendarofstatep5159grea |title=Calendar of the state papers, relating to Ireland, of the reign of Elizabeth, 1592, October—1596, June |publisher=Eyre and Spottiswoode |others=Digitized by the [[Internet Archive]] in 2015 |editor-last=Hamilton |editor-first=Hans Claude |publication-date=1890 |pages=182}}</ref> O'Hely reached the Spanish court by September 1593{{Sfn|Walsh|1990|p=76}} where he met with [[Juan de Idiáquez y Olazábal|Juan de Idiáquez]], the royal secretary. In Idiáquez's notes to Philip II, he notes that the early confederates wanted Tyrone to join them in open rebellion, though it appears Tyrone refused to publicly defy the Crown without reassurance that Spanish reinforcements would arrive.<ref>{{Cite journal |last=García Hernán |first=Enrique |author-link=Enrique García Hernán |date=2004 |editor-last=Morgan |editor-first=Hiram |editor-link=Hiram Morgan |title=Philip II's forgotten armada |url=http://www.irishinspain.es/archivos/philip_eghernan.pdf |journal=The Battle of Kinsale |location=Dublin |publisher=Wordwell Ltd |pages=45–58 |isbn=1-869857-70-4 |archive-url=https://web.archive.org/web/20130621004137/http://www.irishinspain.es/archivos/philip_eghernan.pdf |archive-date=21 June 2013 |access-date=26 May 2024 |postscript=. Idiáquez wrote to Philip II: "...it will be of great importance for the success of the confederacy of Irish Catholics that Your Majesty should write very affectionately to the earl of Tyrone, whose name is O'Neill, to induce him to enter into the confederacy openly. He already belongs to it secretly, and he should be assured that Your Majesty's aid shall not fail them. The archbishop begs Your Majesty to order a letter to be written to the earl to that effect."}}</ref>

=== Secret rebellion ===

Catholic bishops began to spread the Aodh Eangach prophecy to advance the Irish rebellion.{{sfn|Morgan|1993|pp=142–143}} Maguire and O'Rourke continued to rebel by attacking English forces. O'Donnell aided the growing rebellion by sending MacSweeney [[gallowglass]],{{Sfn|McGettigan|2005|p=60}} but publicly he feigned neutrality.<ref name="mor6"/> This was because he lacked sufficient forces to combat a direct assault from English forces; he also faced pressure from his father-in-law to likewise appear publicly loyal to the Crown.{{Sfn|McGinty|2013b|p=8}} Bingham put Maguire and O'Rourke under heavy pressure, and O'Donnell used their chiefdoms as a buffer between Bingham's forces and Tyrconnell. O'Donnell had some influence over Maguire, giving him advice and sheltering his creaghts on Tyrconnell's borders.{{Sfn|McGettigan|2005|pp=60–61}} MacGauran was killed on 23 June <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 3 July<nowiki>]</nowiki> 1593 whilst accompanying Maguire on a raid.{{Sfn|Walsh|1990|p=77}} In September, O'Donnell sent his mother to Scotland to secure further Scottish troops.{{Sfn|McGettigan|2005|p=62}}[[File:IrishConfederacySignatures8May1593.png|left|thumb|Signatures of the founding members of the Irish confederacy. Left column, top to bottom (clergymen): [[Edmund MacGauran]], [[Redmond O'Gallagher]], [[Richard Brady]], [[Cornelius O'Devany]], Patrick MacCaul, Niall O'Boyle. Right column, top to bottom (noblemen): [[Hugh Maguire (Lord of Fermanagh)|Hugh Maguire]], [[Tibbot na Long Bourke, 1st Viscount Mayo|Theobald Bourke]], Richard Bourke, John Bourke, [[Brian Oge O'Rourke]]. ]]

Maguire's rebellious activity provoked a large-scale military expedition led by Marshal [[Henry Bagenal]], which culminated at the [[Battle of Belleek]] in October.{{Sfn|O'Neill|2017|pp=29, 33–34}} Tyrone fought on Bagenal's side ostensibly to prove his loyalty to the Crown.{{Sfnm|1a1=McGinty|1y=2013b|1p=8|2a1=Morgan|2y=2014|2ps=, 10th paragraph.}} O'Donnell was in nearby Ballyshannon when the battle was taking place, but he was ordered by Tyrone not to reinforce Maguire. The battle was a ploy to make the confederacy seem weaker than it actually was, thus diverting English attention away from Ireland. O'Donnell partially disobeyed Tyrone's order and sent 60 horsemen, 60 swordsmen and 100 [[gallowglass]] under the command of Niall Garve. Historian James O'Neill has theorised that O'Donnell intentionally dispatched Niall Garve to [[Belleek, County Fermanagh|Belleek]] with the hope that he would die in the slaughter, thus easily eliminating a potential enemy. Bagenal's forces won the battle.{{Sfn|O'Neill|2017|pp=33–34}} Despite the successful ploy, the battle was damaging to O'Donnell. Many of the gallowglass were killed and Niall Garve survived. To placate the Crown's victorious army, O'Donnell sent 115 cattle to the English camp as a gift.{{Sfn|McGettigan|2005|pp=61, 119}} A letter from O'Donnell was later found on the corpse of a Redshank captain killed in the battle.{{Sfn|Morgan|1993|pp=157}}

By November 1593, Bingham had received intelligence that O'Donnell was secretly assisting Maguire and O'Rourke.{{Sfn|McGettigan|2005|p=60}} The Crown demanded that Tyrone discipline O'Donnell and bring him under control,<ref name="mor6" /> and in March 1594, Tyrone and O'Donnell met with government commissioners near Dundalk.{{Sfnm|1a1=McGettigan|1y=2005|1p=64|2a1=Morgan|2y=2014|2ps=, 10th paragraph.}} O'Donnell professed that "his ancestors had always been loyal to her majesty, and so he would continue but stood in danger of his life and feared practices would be used against him". Tyrone submitted a list of his and O'Donnell's grievances, but the talks ended in confusion when O'Donnell threatened to kill some of Tyrone's English friends.{{Sfn|McGettigan|2005|p=64}} Afterwards government commissioners surmised that a confederacy had been established between the Ulster lords.<ref>{{harvnb|Morgan|2014|ps=, 10th paragraph.}}</ref> In March 1594, Philip II sent a Spanish ship—containing O'Hely, Spanish experts and Irish émigrés—to Ireland on a reconnaissance mission, but the crew died when it was shipwrecked off the coast of [[Santander, Spain|Santander]].{{sfn|Morgan|2013|p=6}}

=== Open rebellion ===
[[File:Russell Sir William of Thornhaugh1.jpg|left|thumb|[[William Russell, 1st Baron Russell of Thornhaugh|William Russell]] served as Lord Deputy from 1594 to 1597.{{sfn|O'Neill|2017|p=330}}]]
O'Donnell was aware that Tyrconnell would become an easy target if Maguire and O'Rourke's territories were occupied by the English.{{Sfn|McGettigan|2005|pp=60, 63}} In February 1594, O'Donnell demolished castles in Belleek and Bundrowes to prevent English forces from taking them, and he concentrated his forces at Ballyshannon on his mother's advice.{{Sfn|McGettigan|2005|pp=63–64}} That same month, Captain John Dowdall captured Enniskillen Castle, Maguire's stronghold, after a [[Siege of Enniskillen (1594)|nine-day siege]].{{Sfn|O'Neill|2017|p=36}} O'Donnell rushed to Maguire's aid, assembling an army and joining Maguire to retake the castle. O'Donnell stated he "would not leave that siege until he had eaten the last cow in his country".{{Sfn|McGettigan|2005|pp=63–64}} The castle was blockaded by 11 June, and by late July the English soldiers were suffering from food shortages.{{Sfn|O'Neill|2017|p=37}} O'Donnell's decision to join the siege of Enniskillen brought his rebellion into the open.{{Sfnm|1a1=Morgan|1y=2009|2a1=O'Neill|2y=2017|2p=37|1ps=, 6th paragraph}}

O'Donnell encountered resistance from his family, with both his brother Rory and his father Hugh MacManus opposing his choice to go to war.{{Sfn|McGettigan|2005|p=64}} Frustrated with Tyrone's [[Loyalism|loyalist]] facade, O'Donnell warned Tyrone that he "must consider [him] his enemy, unless he came to his aid in such a pinch". Tyrone subsequently sent reinforcements under his brother [[Cormac MacBaron O'Neill]] to the [[Battle of the Ford of the Biscuits]].{{Sfn|McGinty|2013b|p=12}} O'Donnell continued to negotiate through his father-in-law; in August, Tyrone presented the new Lord Deputy, [[William Russell, 1st Baron Russell of Thornhaugh|William Russell]], with a lengthy document of O'Donnell's grievances and demands, titled "A note of such oppressions and indirect courses as hath been held in Tirconnell and other places".{{Sfnm|1a1=McGettigan|1y=2005|1p=65|2a1=Morgan|2y=2009|2ps=, 6th paragraph.}} O'Donnell requested a general pardon for himself and his followers, as well as "good security" for Maguire, O'Rourke and rebels in [[County Monaghan]]. Russell ignored these demands and resupplied Enniskillen castle with 1,200 [[Irish Army (1661–1801)|Irish Army]] soldiers—comprising most of the troops at his disposal.{{Sfn|McGettigan|2005|p=65}} The English relief mission was successful but ominously peaceful—Russell lost communication with his spies as they had all been captured by confederate soldiers.{{sfnm|1a1=McGettigan|1y=2005|1p=65|2a1=O'Neill|2y=2015|2p=17}} By early 1595, Tyrone had finally joined O'Donnell in open rebellion with an [[assault on the Blackwater Fort]].{{sfn|O'Neill|2015|p=17}}

=== Expansion into Connacht ===
[[File:Sir Richard Bingham from NPG.jpg|thumb|O'Donnell launched raids against [[Richard Bingham (soldier)|Richard Bingham]], Lord President of Connacht, who had persecuted Connacht's Gaelic population.]]
In 1595, O'Donnell began to expand his rebellion into Connacht. His ancestors (particularly his grandfather [[Manus O'Donnell]]) had ruled over Lower Connacht, and Hugh Roe O'Donnell increasingly demanded the restoration of these lands.{{Sfnm|1a1=McGettigan|1y=2005|1p=67|2a1=Morgan|2y=2009|2ps=, 5–6th paragraphs.}} Richard Bingham had persecuted Connacht's Gaelic population since the mid-1580s, causing many refugees to flee to Tyrconnell. O'Donnell aided the refugees and recruited many of them as swordsmen. O'Donnell resented Bingham and was "easily tempted" by the refugees, who urged him to attack Bingham's administration. O'Donnell invaded Connacht on 3 March 1595 with 400 men. From [[Rathcroghan]], the province's ancient royal capital,{{Sfn|McGettigan|2005|p=|pp=67–69}} he launched large raids into Longford and [[Roscommon]]. In June 1595, the castle of [[Sligo]], which was key to securing control over the province, was betrayed to O'Donnell "in a stroke of luck"; Bingham's government collapsed. O'Donnell reestablished [[brehon law]] and asserted suzerainty over north Connacht.<ref name="mor6">{{Harvnb|Morgan|2009|ps=, 6th paragraph}}.</ref> According to Ó Cléirigh, O'Donnell "spared no one over fifteen years of age who could not speak Irish".{{Sfn|Dunlop|1894|p=438}}

By 1595, O'Donnell and his wife were facing difficulties; Rose had not born him children. In order to increase his influence in southern Connacht,{{Sfn|McGettigan|2005|p=81}} O'Donnell had hopes of a marriage alliance with Lady Margaret Burke, daughter of the neutral [[Ulick Burke, 3rd Earl of Clanricarde|3rd Earl of Clanricarde]]. With Tyrone's consent, Rose and O'Donnell separated,<ref>{{harvnb|Walsh|1930|p=37|ps=. "About 1595 O'Donnell and Rose seem to have separated. There was question of his carrying away Lady Margaret Burke, daughter of the Earl of Clanricard, in December..."}}; {{harvnb|Morgan|2009|ps=, 10th paragraph. "...with [Tyrone]'s consent, he had separated from Rose... in the hope of marrying or even kidnapping Lady Margaret Burke, daughter of the earl of Clanrickard, who had refused to join in the revolt."}}</ref> purportedly over her "barrenness".{{Sfnm|1a1=Walsh|1y=1930|1p=37|2a1=McGinty|2y=2013a|2pp=43–44}} However the government became aware of his plan to reportedly "rob her from her parents by surprise or force", and in December Margaret was placed in protective custody.{{Sfn|Morgan|2002|p=8}} Additionally Clanricarde stated that he would "rather see [Margaret's] burial than her marriage to [O'Donnell] were he a good subject". Tyrone sent his trusted secretary [[Henry Hovenden]] to Tyrconnell to advise O'Donnell,{{Sfn|McGettigan|2005|p=81}} and O'Donnell eventually took Rose back.<ref name="OA" /> His choice to remain in a barren marriage is representative of his dependence on Tyrone.{{Sfn|Morgan|1993|p=216}}

== Peace talks ==

=== Negotiations with the Crown ===
[[File:Darnley stage 3.jpg|thumb|O'Donnell lived under the reign of English monarch [[Elizabeth I]] (1558–1603), who asserted herself as "Queen of Ireland".{{Sfnm|1p=96|2ps=: Queen of Ireland.|1a1=Connolly|2a1=Morgan|2y=2004|1y=2007|1ps=: Elizabeth I's reign|2p=297}}|left]]
Tyrone and O'Donnell sought to delay the war in order to buy time for the arrival of Spanish troops,{{Sfnm|1a1=Dunlop|1y=1894|1p=438|2a1=O'Neill|2y=2017|2pp=60–61}} and in September 1595, Tyrone sent overtures of submission to the Crown.{{Sfn|O'Neill|2017|p=56}} Tyrone convinced O'Donnell to submit to the authorities and agree to a ceasefire whilst the settlement could be negotiated.{{Sfn|McGettigan|2005|p=70}} He tendered his submission in October, expressing his "inward sorrow and most harty repentance".{{Sfn|Morgan|2002|p=11}} A cessation of arms was signed on 27 October 1595.{{Sfn|O'Neill|2017|p=56}} O'Donnell took advantage of the truce to intervene in Connacht politics. Accompanied by Cormac MacBaron and Tyrone's son [[Conn O'Neill (died 1601)|Conn]], he led a large force of troops into Mayo in December.{{Sfn|McGettigan|2005|p=70}} During Christmas-time, O'Donnell stage-managed the election of Connacht exile [[Tibbot MacWalter Kittagh Bourke|Tibbot MacWalter Kittagh]] as the Lower MacWilliam Bourke.<ref name="mor6"/> Further elections organised by O'Donnell, spanning four counties, were indicative of his growing power in Connacht.{{Sfn|McGettigan|2005|p=|pp=70–71}}{{efn|O'Donnell appointed Conor McDermot as Lord of Moylurg, Ferdorcha O'Kelly as Lord of Uí Maine, an O'Dowd of Tireragh, two McDonagh chieftains (of Tirerrill and of Corran) and an O'Hara Reagh.{{sfnm|1a1=McGettigan|1y=2005|1p=70|2a1=McGinty|2y=2013a|2p=43}}}}

In January 1596, O'Donnell and Tyrone entered into face-to-face negotiations with government commissioners.{{Sfn|McGettigan|2005|p=71}} The two confederates refused to meet the commissioners anywhere except in the open fields,{{Sfnm|1a1=Dunlop|1y=1894|1p=438|2a1=Dunlop|2y=1895|2p=191|3a1=Walsh|3y=1939|3p=247}} thus negotiations were conducted in the countryside near Dundalk.{{Sfnm|1a1=Dunlop|1y=1894|1p=438|2a1=McGettigan|2y=2005|2p=71}} O'Donnell demanded his ancestral claims of lands in Sligo, exemption from the jurisdiction of a sheriff, and a pardon for Connacht men including O'Rourke and MacWilliam Bourke. Similarly to Tyrone he demanded religious [[liberty of conscience]].{{Sfnm|1a1=Dunlop|1y=1894|1p=438|2a1=McGettigan|2y=2005|2pp=71–72|3a1=Morgan|3y=2009|3ps=, 7th paragraph.}} The queen warily accepted O'Donnell's claims to lands in Connacht. On 28 January, the commissioners presented O'Donnell with a list of twelve articles. These urged him to disperse his forces, to [[shire]] Tyrconnell, to stop aiding O'Rourke and Maguire, to re-edify Sligo Castle, to pay annual rents to the Crown as his father had done, and to confess the extent of his dealings with Spain. O'Donnell agreed to most articles, with some exceptions.{{Sfn|McGettigan|2005|p=72}} He refused to give hostages or make a personal submission. A compromise was created,<ref>{{Harvnb|Morgan|2009|ps=, 7th paragraph}}.</ref> and O'Donnell agreed to terms on 30 January.{{Sfn|McGettigan|2005|p=72}} A hollow peace was signed on 24 April 1596,{{Sfn|Dunlop|1895|p=191}} and further negotiations to develop a peace treaty were almost complete by May.{{Sfn|O'Neill|2017|p=62}}

=== Relations with Spain ===
In May, three Spanish ships arrived at Tyrconnell with the aim of encouraging the confederates and assessing Ireland's military situation.{{sfn|Morgan|1993|p=208}} Spanish captain Alonso Cobos arrived in [[Killybegs]] and was invited by O'Donnell to Lifford, where he was staying.{{Sfn|McGettigan|2005|p=73}} O'Donnell refused to go further into conversation without Tyrone present "because there was one above him naming [Tyrone], which if he would consent unto it he would do the same".{{Sfn|Morgan|2002|p=4}} O'Donnell called the confederates to Lifford and in the meantime, he entertained Cobos and his men for three nights. When the confederates arrived at Lifford, a subsequent dinner took place. The confederates upheld their allegiance to Spain and pleaded for Philip II to re-establish Catholicism across Ireland.{{Sfn|McGettigan|2005|pp=73–74}}[[File:Rubens - arquiduquealbertoVII01.jpg|thumb|O'Donnell sought to make [[Albert VII, Archduke of Austria|Albert VII]] Ireland's new Catholic sovereign.]]

Later on, a secret talk between Cobos and O'Donnell, Tyrone, and Cormac MacBaron occurred in a small house beside Lifford's castle.{{Sfnm|1a1=McGettigan|1y=2005|1p=74|2a1=Morgan|2y=2009|2ps=, 7th paragraph.}} [[Hugh Boy MacDavitt|Hugh Boye MacDavitt]] of Inishowen, a war veteran who had served in the Low Countries, served as their interpreter.{{Sfn|Morgan|2002|p=14}} After the meeting, the confederates jointly agreed to abandon the peace treaty and become [[vassals]] of Philip II. Tyrone and O'Donnell also petitioned Philip II to make [[Albert VII, Archduke of Austria]], the new Catholic monarch of Ireland.{{Sfn|Morgan|1993|pp=208–210}} O'Donnell and his father-in-law began to deliberately derail peace negotiations and provoke war in previously peaceful parts of the country.{{sfnm|1a1=Morgan|1y=1993|1p=212|2a1=O'Neill|2y=2017|2p=62}} They developed a sophisticated [[Good cop, bad cop|"good cop, bad cop"]] routine which they used to stall peace talks.{{sfn|Morgan|2007a|pp=823–824}} Additionally, O'Donnell was ashamed at the sparse nature of his residence and set about purchasing "linen and pewter and all other necessaries fit to entertain the Spaniards".{{Sfnm|1a1=Morgan|1y=2002|1p=14|2a1=McGettigan|2y=2005|2p=76}}

The confederate lords of Connacht refused to discuss peace talks with government commissioners until the arrival of O'Donnell, who was apparently delayed by dealings with Redshanks. When O'Donnell arrived that June, he refused to hand over English hostages until his terms were met. Tyrone sent Hovenden to ostensibly aid O'Donnell in pacifying Connacht,{{sfn|Morgan|1993|p=212}} but the government intercepted a letter revealing that Hovenden was intentionally stalling negotiations so that Tyrone would have to be brought in as an arbitrator; this he eventually was.{{Sfn|McGinty|2013a|p=44}}{{Sfn|Morgan|2002|p=5}} The commissioners were in a weak position due to Elizabeth I's health issues.{{Sfnm|1a1=Morgan|1y=1993|1p=213|2a1=McGettigan|2y=2005|2p=71}} Soon after, O'Donnell met with Tyrone, O'Rourke and MacWilliam Bourke at [[Strabane]]. Together, they issued a letter to Munster's population demanding they adhere to Catholicism and join the confederacy.{{Sfn|Morgan|2002|p=5}} In October, Cobos was sent back to Ireland to brief the confederates on the impending [[2nd Spanish Armada]]. Cobos's briefing motivated O'Donnell to make extensive preparations for the arrival of Spanish troops in Tyrconnell.{{Sfn|McGettigan|2005|pp=76–77}} After much delay, the Armada sailed from [[Lisbon]] in late October 1596, though it ended in disaster when a sudden storm claimed over 3,000 lives.{{Sfn|O'Neill|2017|p=65}}

Elizabeth I reopened negotiations in Dundalk. Ó Cléirigh states that Elizabeth offered to forfeit Ulster to the confederates (with the exception of land from Dundalk to [[the Boyne]]). O'Donnell was apparently instrumental in the confederacy's rejection of this offer—he was possibly motivated by Philip II's recently renewed interest in Ireland.{{Sfn|McGettigan|2005|p=|pp=77, 126}} O'Donnell's relationships to Spain and England were complicated by the fact that aging monarchs Philip II and Elizabeth I were both in ill health at the time.{{Sfn|McGettigan|2005|pp=71, 78}}

== Renewal of hostilities ==

=== Clifford's presidency ===
[[File:Sir Conyers Clifford.jpg|thumb|[[Conyers Clifford]] succeeded Bingham as Connacht's Lord President. After his death at the Battle of Curlew Pass, his severed head was carried by O'Donnell as a trophy.<ref name=":0" />]]Elizabeth I suspended Bingham from the presidency of Connacht. [[Conyers Clifford]], a distinguished soldier favoured by the Irish, was made Connacht's chief commissioner in December 1596.<ref name="CC">{{Cite encyclopedia |title=Clifford, Sir Conyers |encyclopedia=[[Dictionary of Irish Biography]] |url=https://www.dib.ie/biography/clifford-sir-conyers-a1747 |access-date=25 August 2024 |last=Hawkins |first=Richard |date=October 2009 |doi=10.3318/dib.001747.v1 |archive-url=https://web.archive.org/web/20211208162942/https://www.dib.ie/biography/clifford-sir-conyers-a1747 |archive-date=8 December 2021|url-access=subscription }}</ref>{{Sfn|McGettigan|2005|p=79}} O'Donnell again raided into Connacht in January 1597, sacking [[Athenry]] and plundering the suburbs of [[Galway|Galway city]].{{Sfn|McGettigan|2005|p=79}} He was supported by competitors to the Clanricarde title.<ref name=":0">{{Harvnb|Morgan|2009|ps=, 9th paragraph}}.</ref> Clifford responded by forcing MacWilliam Bourke from Mayo. O'Donnell reinstalled MacWilliam Bourke, but Clifford forced him out again in June.{{Sfn|McGettigan|2005|p=79}}

[[Thomas Burgh, 3rd Baron Burgh|Thomas Burgh]] took over as Lord Deputy in May 1597. Burgh refused to entertain the confederates' excuses and ordered prompt military attacks on both Tyrone and O'Donnell.{{Sfn|O'Neill|2017|p=66}} In July, the English launched a two-pronged assault in Ulster; Clifford assembled 1,500 men at [[Boyle, County Roscommon|Boyle]] and led them into Tyrconnell as the western arm of the assault. Clifford's army besieged Ballyshannon castle for five days, but it was successfully defended by O'Donnell's garrison of eighty men, which included Spaniards. Once O'Donnell himself arrived, Clifford's army, which had exhausted its supplies, retreated to Sligo, abandoning three pieces of ordnance and losing many men.{{Sfn|McGettigan|2005|p=79}}{{Sfn|Webb|1878|p=392}} On 4 September 1597, Clifford was appointed as Connacht's new Lord President.<ref name="CC" />

Lord Deputy Burgh died from illness in October. Despite the confederacy's advantageous position, Tyrone renewed peace negotiations.{{Sfn|O'Neill|2017|p=|pp=68–69}} He submitted to authorities on 22 December and promised to renounce his Gaelic titles and rebellious activities.{{Sfn|Dunlop|1895|p=192}} O'Donnell heavily criticised Tyrone for agreeing to a cessation, pointing out that the confederate forces were strong across Leinster, Connacht and Ulster. O'Donnell declared that he would break the cessation, though he never did.{{Sfn|McGinty|2013b|p=9}}

Clifford changed tactics following the defeat at Ballyshannon. He encouraged confederates to change sides by promising them royal grants. In February 1598, founding confederacy member O'Rourke submitted at Boyle.<ref name="BO"/> By April, Clifford had lured further confederates Conor McDermot, O'Connor Don and Shane MacManus Oge (O'Donnell's cousin). In response, O'Donnell executed six of McDermot and O'Connor Don's pledges. He detained Shane MacManus Oge upon the latter's secret return to Tyrconnell. O'Donnell also killed sixteen of Mulmurry MacSweeney na dTuath's men when MacSweeney na dTuath was linked to Shane MacManus Oge.{{Sfn|McGettigan|2005|pp=79–80}} O'Donnell's younger brother Rory was also engaged by Clifford, and he resolved to serve against his brother. When this news reached O'Donnell, he had Rory clamped in chains—the brothers' relationship eventually improved and by 1600 Rory was once again fighting alongside his older brother.<ref name="RO">{{Cite journal |last=O'Byrne |first=Emmett |date=October 2009c |title=O'Donnell (Ó Domhnall), Ruaidhrí |url=https://www.dib.ie/biography/odonnell-o-domhnall-ruaidhri-a6701 |journal=[[Dictionary of Irish Biography]] |language=en |doi=10.3318/dib.006701.v1 |archive-url=https://web.archive.org/web/20210623030003/https://www.dib.ie/biography/odonnell-o-domhnall-ruaidhri-a6701 |archive-date=23 June 2021 |access-date=2024-04-15|url-access=subscription }}</ref>{{Sfn|McGettigan|2005|pp=79–80}} O'Donnell captured O'Rourke's brother [[Teigue O'Rourke|Teigue]] and forced him to marry his sister [[Mary O'Donnell (sister of Hugh Roe)|Mary]], in order to formalise an alliance and antagonise O'Rourke.<ref name="BO">{{Cite journal |last=O'Byrne |first=Emmett |author-link=Emmett O'Byrne |date=October 2009d |title=O'Rourke (Ó Ruairc), Brian Óg |url=https://www.dib.ie/biography/orourke-o-ruairc-brian-og-a7028 |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.007028.v1 |access-date=11 November 2024|url-access=subscription }}</ref> By June 1598, O'Rourke had rejoined the confederacy in fear.{{Sfn|McGettigan|2005|p=80}}<ref name="BO" />

=== Battle of the Yellow Ford ===
{{Main|Battle of the Yellow Ford}}
Government commissioners abandoned negotiations by spring 1598, recognising that O'Donnell and Tyrone were intentionally impeding the [[peace process]].{{sfn|Morgan|2002|p=7}} Tyrone was granted a pardon in April 1598. However he felt that the Crown would eventually supersede his authority in Ulster. When the truce expired in June, Tyrone besieged the Blackwater Fort.{{Sfn|Dunlop|1895|p=192}}{{Sfn|Lennon|2005|p=298}} Bagenal encouraged for a relief exercise to be sent to the fort.{{Sfn|Lennon|2005|p=298}}[[File:BattleoftheYellowFord.jpg|thumb|The [[Battle of the Yellow Ford]] was the greatest confederate victory during the Nine Years' War.]]
Tyrone called O'Donnell and Maguire to assemble their combined forces, numbering 5,000 men. The confederates made extensive plans to obstruct Bagenal's army, preparing deep trenches in the ground outside [[Armagh]]. Prior to the attack, the confederates made a speech "to incite their people to acts of valour". On 14 August, Bagenal's army was attacked by O'Donnell, Tyrone and Maguire's combined forces. O'Donnell attacked from the left and Tyrone from the right simultaneously.{{Sfn|McGettigan|2005|p=|pp=82–83}} Bagenal was killed and roughly 2,000 men (half his army) were lost.{{Sfn|Walsh|1996|p=23}} O'Donnell's men ran out of ammunition and the English survivors fled to Armagh. More than 300 English soldiers deserted to the confederacy.{{sfn|McGettigan|2005|p=|pp=84–85}}

The battle was the greatest victory by Irish forces against England,{{Sfn|Morgan|2004|p=306}} and it sparked a general revolt throughout the country, particularly in Munster.{{Sfn|Dunlop|1895|p=192}} News of the battle spread across [[western Europe]], prompting Philip II to send a congratulatory letters to O'Donnell and Tyrone. Unfortunately for the confederacy,{{Sfn|McGettigan|2005|p=85}} Philip II died in September and was succeeded by his son [[Philip III of Spain|Philip III]].<ref>{{cite EB9 |wstitle = Philip II. of Spain |volume= XVIII |last= |first= |author-link= |pages=743–746 |short= 1}}</ref> Following the battle, O'Donnell purchased [[Ballymote Castle]] from [[McDonagh|Clan MacDonagh]] and made it his primary residence.{{Sfnm|1a1=Webb|1y=1878|1p=392|2a1=McGettigan|2y=2005|2p=85}} He sent Sean O'Doherty, Donough MacSweeney Banagh and MacWilliam Bourke to successfully attack the [[Kings of Umhaill|O'Malleys]] in [[County Mayo]]. In December, O'Donnell led another successful raid into Clanricarde.{{Sfn|McGettigan|2005|pp=85–86}}

The confederates' victory unravelled much of Clifford's success in Connacht, leaving loyalist Donough O'Connor Sligo (lord of Lower Connacht) as his only Gaelic Irish ally.<ref>{{Harvnb|O'Neill|2017|p=90|ps=}}; {{Harvnb|McGettigan|2005|p=86|ps=: O'Connor Sligo's forename and title.}}</ref> The Irish victory at the Yellow Ford was highly distressing to the [[Privy Council of England|English Privy Council]], and after much hesitation Elizabeth I appointed her [[Favourite|royal favourite]] [[Robert Devereux, 2nd Earl of Essex]], as the new Lord Deputy. He arrived at Dublin in April 1599. Despite the generous resources afforded to him, [[Essex in Ireland|Essex's campaign]] was a major failure on account of his poor generalship.{{Sfn|O'Neill|2017|p=|pp=85–87, 95, 98}}

=== Battle of Curlew Pass ===
{{Main|Battle of Curlew Pass}}[[File:Gaelic Chieftain.jpg|thumb|''The Gaelic Chieftain'' (1999) by [[Maurice Harron]], located near [[Boyle, County Roscommon|Boyle]], commemorates the [[Battle of Curlew Pass]].]]In July 1599, Essex sent O'Connor Sligo to confront O'Donnell. In response, O'Donnell quickly laid siege to O'Connor Sligo's stronghold, Collooney Castle. Essex then ordered Clifford to relieve O'Connor Sligo,{{Sfn|McGettigan|2005|p=|pp=86–88}} and Clifford subsequently led an expedition of 1,400 men towards Collooney Castle.{{Sfn|O'Neill|2017|pp=90–92}} O'Donnell left Niall Garve to continue the siege and he took up a position in the [[Curlew Mountains]], where he remained for two months, deliberately provoking Clifford. In August, Clifford finally gave in and marched his troops into the Curlew Mountains. O'Donnell made a dramatic speech and prepared his men.{{Sfn|McGettigan|2005|p=88}}

Once O'Donnell's brothers had lured Clifford's army into a prepared position, O'Donnell and O'Rourke (who was camped nearby) ambushed Clifford's forces in a swift battle.{{Sfn|McGettigan|2005|pp=88–89}} The English panicked and were routed back to [[Boyle Abbey]]. 240 English soldiers were killed, including Clifford who was stabbed by a pike. After the battle, O'Rourke decapitated Clifford and gave the head to O'Donnell. When O'Donnell presented Clifford's severed head to O'Connor Sligo, the latter surrendered Collooney Castle.{{Sfn|O'Neill|2017|pp=90–92}} The queen and her [[Secretary of State (England)|secretary of state]] [[Robert Cecil, 1st Earl of Salisbury|Robert Cecil]] were shocked by the Irish victory.{{Sfn|McGettigan|2005|p=89}} The victory is viewed as a highlight of O'Donnell's career, though contemporary sources credit O'Rourke and Conor McDermot with the battle's success.{{sfnm|1a1=Morgan|1y=2007a|1p=823|2a1=Morgan|2y=2020}}

O'Donnell forced O'Connor Sligo to join the confederacy, and he gave O'Connor Sligo "large numbers" of oxen, horses, cattle and corn to re-establish himself in lower Connacht. However he threatened O'Connor Sligo with imprisonment on an island in [[Lough Eske]] if he did not cooperate. By this time Iníon Dubh had been in Scotland for two months gathering redshanks—as Clifford's forces had been easily defeated, O'Donnell notified his mother that the redshanks were unnecessary, and she returned to Tyrconnell in January 1600 with gunpowder instead. O'Donnell followed the victory at Curlew Pass with a successful battle at the Ballaghboy Pass.{{Sfn|McGettigan|2005|p=|pp=89–90}}

=== Quarrels with Tyrone ===
[[File:Hugh O'Neill from La spada d'Orione.png|thumb|O"Donnell's partnership with Tyrone became strained over the former's divorce, their differing military approaches, and the division of resources from Spain.]]
By the late 1590s, O'Donnell's relationship with his father-in-law was coming under strain,<ref name="OA">{{Harvnb|Morgan|2009|ps=, 10th paragraph}}.</ref> not least because of the breakdown of O'Donnell's marriage to Rose.{{Sfnm|1a1=Morgan|1y=2002|1p=8|2a1=McGinty|2y=2013a|2pp=43–44}} It was reported in April 1597 that O'Donnell had recently renewed his alliance with Tyrone, and that "their league of friendship is more apparently confirmed... by O'Donnell's receiving of the earl's base daughter" in marriage.{{sfnm|1a1=Atkinson|1y=1974|1p=260|2a1=Morgan|2y=2002|2p=8|1ps=: primary source|2ps=: secondary source.}} By 1598, it was reported O'Donnell had divorced Rose,<ref name="HW">{{harvnb|Walsh|1939|p=237|ps=. fn. 5.}}</ref> most likely against Tyrone's wishes.{{sfn|McGinty|2013a|p=44}} She remarried to Tyrone's principal vassal [[Donnell Ballagh O'Cahan]] by 1599.<ref name="Donnell">{{Cite journal |last=Clavin |first=Terry |date=October 2009b |title=O'Cahan, Sir Donnell Ballach |url=https://www.dib.ie/biography/ocahan-sir-donnell-ballach-a6536 |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.006536.v1 |archive-url=https://web.archive.org/web/20210715165334/https://www.dib.ie/biography/ocahan-sir-donnell-ballach-a6536 |archive-date=15 July 2021|url-access=subscription }}</ref> O'Donnell reportedly divorced Rose due to her "barronness",<ref name="HW" /> though the historian Morwenna Donnelly has questioned this truthfulness of this explanation, considering that O'Donnell did not immediately remarry to ensure an heir.{{Sfn|Donnelly|1986|p=|pp=49–50}}

The confederacy leaders argued over the division of money and munitions sent from Spain. Tyrone typically demanded the superior portion; when munitions arrived in 1596, Tyrone took twenty [[Firkin (unit)|firkins]] of gunpowder compared to O'Donnell receiving fifteen. This came to a head in mid-1599, when O'Donnell debated over the division of a delivery brought by Barrionuevo. O'Donnell felt he was owed more resources in view of his recent victories, as well as his riskier approach to warfare. According to a spy's report, "Tyrone and O'Donnell fell into some contention about receiving of the said munition and treasure, Tyrone challenging the disposal of the whole, as chief and general of the common service, and O'Donnell claiming as great a right in it as he, as he affirmed, as deeply engaged therein as he. In the end the assembly there (by mediation of an Irish bishop from Rome with them) overruled the disposition of the whole for Tyrone". A treaty of equality was established between the two men, which decreed that "one had no pre-eminence over the other and that in walking and travelling together whichever was the elder should be on the right hand".{{sfn|Morgan|2002|pp=8–9}}

Tyrone refused to fight Essex's dwindling forces; instead the two men parleyed on 7 September 1599 and a six-week truce was organised.{{sfn|O'Neill|2017|p=94}} O'Donnell was furious at Tyrone's decision to negotiate with Essex, as he wanted to avoid any association with English officials in favour of soliciting aid from the Spanish. He declared that he would travel into Connacht, but Tyrone forbid him on account of the truce. O'Donnell admitted that he would burn the entire Pale if not for Tyrone preventing him.{{Sfn|McGinty|2013b|p=9}} Essex left Ireland on 24 September and was shortly afterwards removed from his post.{{sfnm|1a1=McGettigan|1y=2005|1pp=90–91|2a1=O'Neill|2y=2017|2pp=94–95}} His downfall briefly put the confederacy in a strong position.{{Sfnm|1a1=Lennon|1y=2005|1p=300|2a1=McGettigan|2y=2005|2p=91}} In February 1600, [[Charles Blount, 8th Baron Mountjoy]], arrived in Ireland as the new Lord Deputy. Mountjoy posed a major threat to the confederacy as he immediately began revitalising and restoring confidence in the royal army.{{Sfnm|1a1=Walsh|1y=1996|1p=30|2a1=O'Neill|2y=2017|2p=123}}

On 1 March [<nowiki/>[[Old Style and New Style dates|N.S.]] 11 March] 1600,<ref>{{Harvnb|Brewer|Bullen|1869|pp=|p=366}}: primary source; {{Harvnb|Dunlop|1895|pp=193–194}}: secondary source.</ref> Hugh Maguire was shot and killed whilst on reconnaissance near [[Cork (city)|Cork]].<ref name="barryhugh">{{harvnb|Barry|2009b|ps=, 7th paragraph.}}</ref> His lordship was contested by rival claimants Cúconnacht Maguire (his younger half-brother) and [[Connor Roe Maguire (died 1625)|Connor Roe Maguire]] (his loyalist-leaning cousin). Tyrone favoured Connor Roe's accession, perhaps to ensure Connor Roe's loyalism was kept in check. O'Donnell favoured Cúconnacht, and a debate ensued on how to resolve the succession crisis. At a banquet at Tyrone's house in [[Dungannon]], with Tyrone and both claimants present, O'Donnell addressed Cúconnacht as the new Maguire clan chief. O'Donnell's [[fait accompli]] affronted Tyrone and created further tension between the confederates.{{sfn|Morgan|2002|p=9}}<ref>{{Cite journal |last=Morley |first=Vincent |date=October 2009 |title=Mág Uidhir (Maguire), Cú Chonnacht Óg ('an Comharba') |url=https://www.dib.ie/biography/mag-uidhir-maguire-cu-chonnacht-og-comharba-a5370 |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.005370.v1 |access-date=2 February 2025|url-access=subscription }}</ref>

In April 1600, a Spanish ship arrived in Ireland bearing considerable supplies of money and ammunition for the confederacy, as well as letters from Philip III.{{Sfn|Dunlop|1895|p=194}}{{Sfn|McGettigan|2005|p=92}} Tyrone and O'Donnell stimulated the Irish-Spanish alliance by sending pledges to Spain; Tyrone sent his son [[Henry O'Neill (soldier)|Henry]], and O'Donnell sent the sons of O'Doherty and O'Gallagher.{{sfn|Morgan|2002|p=14}}

== Forced from Tyrconnell ==

=== Defection of Niall Garve ===
[[File:Derry_Guildhall_Tercentenary_Window_of_The_Honourable_The_Irish_Society_Detail_Sir_Henry_Docwra_landed_at_Culmore_16th_April_1600_A.D._2019_08_29.jpg|thumb|Commander [[Henry Docwra, 1st Baron Docwra of Culmore|Henry Docwra]] enticed Niall Garve to defect from the confederacy, which greatly weakened O'Donnell's power in Tyrconnell.]]In May 1600, English commander Henry Docwra established an English garrison in [[Derry]].{{Sfnm|1a1=McGettigan|1y=2005|1p=93|2a1=O'Neill|2y=2017|2p=128}} O'Donnell made a substantial attempt to weaken Docwra's forces on 29 July. O'Donnell captured at least 60 horses and Docwra was nearly killed by Hugh McHugh Dubh. O'Donnell later made a failed night attack on the garrison. Despite the poor conditions at the Derry garrison—desertion and disease was rife—Docwra managed to maintain his position,{{sfn|McGurk|2006|pp=70–82}} which led to further tension between O'Donnell and Tyrone.{{sfnm|1a1=McGurk|1y=2006|1pp=70, 73|2a1=Morgan|2y=2009|2ps=, 11th paragraph.}}

The prospects of Docwra's mission depended on winning over disaffected confederates, Niall Garve being the most important.{{sfnm|1a1=Morgan|1y=2002|1p=2|2a1=O'Neill|2y=2017|2p=131}} Niall Garve's grievances were well-known to the government on account of his overtures,{{sfn|Finnegan|2007|p=63}} and Docwra began secretly communicating with him. By August, Niall Garve had sent through his list of demands, the principal of which was to rule Tyrconnell in the same manner as his grandfather [[Calvagh O'Donnell|Calvagh]]. Docwra promised to obtain him a royal grant of Tyrconnell if he defected and served against his cousin.{{sfn|McGettigan|2005|pp=93–95}}

In September O'Donnell left Ulster for a raid in [[Thomond]], entrusting Niall Garve to besiege Derry.{{Sfnm|2a1=Clavin|2y=2009|1a1=McGurk|1y=2006|1p=94|2ps=, 4th paragraph.}}{{efn|O'Donnell had previously entrusted Niall Garve to besiege Derry in June 1600, when he left Ulster to plunder south Connacht and north Munster.{{sfn|McGettigan|2005|p=93}}}} Whilst O'Donnell was in [[Ballymote]], Niall Garve and his followers murdered Niall Garve's uncle Neachtan in a drunken rage. Neachtan was "a man of great authority with [O'Donnell] and all his country". Fearing O'Donnell's revenge,{{Sfn|McGettigan|2005|p=95}} Niall Garve—alongside his three brothers and about 100 soldiers—quickly defected to the English. They joined Docwra on 3 October.{{Sfn|McGurk|2006|p=83}} O'Donnell was in Thomond when he received the news,{{sfnm|1a1=Meehan|1y=1870|1p=14|2a1=McGettigan|2y=2005|2p=95|3a1=McGurk|3y=2006|3p=94}} and he immediately hurried to secure Lifford Castle to retain control over [[Lough Foyle]].{{sfn|Morgan|2002|p=2}} According to Willis, O'Donnell was "dumb-stricken" to hear of Niall Garve's betrayal and could not drink or sleep for three days.{{sfnm|1a1=Atkinson|1y=1903|1p=535|2a1=Morgan|2y=2002|2p=2|1ps=: primary source|2ps=: secondary source.}} Niall Garve and an English force stormed Lifford Castle on 9 October, taking it from O'Donnell's brother Rory.<ref name=":1"/><ref name="RO"/> O'Donnell wrote angrily to Tyrone, "charging him with many oversights, that he lay too long at the Moyry, that he spent his munition, lost his best men, and wasted his victuals there to no purpose".{{sfn|Morgan|2002|p=9}}

{{Quote box
| quote = "O'Donnell hath of late hanged many of good account . . . he dasht owt the brains of Neil Garve's childe (of [four] yeares olde) againste a post, beinge in the mother's custody, his owne naturall sister."{{sfnm|1a1=Morgan|1y=2002|1p=3|2a1=McGurk|2y=2008|2p=7}}
| source = —Report by Henry Docwra, February 1601
| align = left
| width = 25%
| quoted =
}}

O'Donnell's sister [[Nuala O'Donnell|Nuala]] separated from Niall Garve due to his defection.{{sfnm|1a1=O'Sullivan Beare|1y=1903|1p=136|2a1=Casway|2y=2003|2p=57|3a1=McGurk|3y=2006|3p=95}} According to a February 1601{{sfnm|1a1=Morgan|1y=2002|1p=3|2a1=McGettigan|2y=2005|2p=97}} report by Docwra, O'Donnell was so outraged by his brother-in-law's defection that he ordered mass hangings of Niall Garve's followers, and personally killed Niall Garve and Nuala's four-year-old son (his own nephew) by bashing the child's brains out against a post.{{sfn|McGurk|2006|p=95}} This accusation is considered contentious among historians.<ref>{{harvnb|Morgan|2007a|p=824|ps=. "...it fails to mention that Red Hugh, when he heard of the revolt and defection of his brother-in-law, Niall Garbh, to the English, bashed out the brains of the latter's four-year-old child in a frustrated rage. Maybe the author believes this to be English black propaganda..."}}; {{harvnb|McGurk|2008|pp=7–8|ps=. "...I would not like to be cast in the role of ''advocatus diaboli'' for the canonisation cause of Red Hugh O'Donnell... I have had much reason in the past in writing his biography to question the veracity of some of Docwra's reports..."}}; {{harvnb|O'Donnell|2020a|ps=. "...the complex character, and indeed weaknesses, of that O'Donnell prince, whilst politely ignoring the accusation of Sir Henry Docwra... it would be too simple to glorify or repudiate the character of Red Hugh on the basis of Franciscan hagiographies or the English "intelligence" of the era".}}</ref> Docwra's biographer John McGurk acknowledges the uncertainty of the report's truthfulness, and notes that it is unclear where Docwra received this intelligence. He points out that Docwra's "blunt" personality indicates that he reported current affairs accurately, and also admits that [[infanticide]] was a feature of warfare in the [[early modern period]].{{sfn|McGurk|2008|pp=7–8}} Morgan notes that since this is a contemporary account, it should not be dismissed out of hand.{{sfn|Morgan|2007a|p=824}}

=== Battle of Lifford ===
{{Main|Battle of Lifford}}[[File:The Somerset House Conference, 1604 from NPG (cropped) (cropped).png|thumb|The confederacy suffered—and eventually surrendered—under the deputyship of [[Charles Blount, 8th Baron Mountjoy]].]]O'Donnell tried in vain to retake Lifford from Niall Garve, with minor skirmishes occurring around the castle.{{sfn|McGurk|2006|p=84}} He lost about 20 men on 17 October 1600. He attacked again on 24 October,{{sfn|Morgan|2002|p=2}} but Niall Garve retaliated by leading a cavalry charge of mixed Irish and English forces out to battle.{{sfnm|1a1=Morgan|1y=2002|1p=2|2a1=McGurk|2y=2006|2pp=84–85}} During the battle, Niall Garve speared O'Donnell's brother [[Manus O'Donnell (died 1600)|Manus]] in the shoulder.{{sfnm|1a1=O'Clery|1a2=O'Clery|1p=257|1a3=Murphy|1y=1895|2a1=O'Sullivan Beare|2y=1903|3a1=Morgan|3p=2|3y=2002|2pp=136–137|4a1=McGurk|4y=2006|4p=85}} Manus was taken to Donegal where he died from his wounds.{{Efn|Ó Cléirigh confirms that Manus died from injuries sustained in the Battle of Lifford, but incorrectly states that Manus died on 12 October <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 22 October<nowiki>]</nowiki> 1600, which would be before the battle.{{sfn|O'Clery|O'Clery|Murphy|1895|p=261}}}} O'Donnell's father Hugh MacManus died shortly afterwards, apparently from grief, on 27 November [<nowiki/>[[Old Style and New Style dates|N.S.]] 7 December]. They were buried beside each other at Donegal Abbey,{{Sfn|O'Clery|O'Clery|Murphy|1895|pp=261–263}} as was customary for the ruling O'Donnell branch.<ref name="dddd"/>

Docwra was pleased that the outcome of the battle had exacerbated the feud between O'Donnell and Niall Garve: "I think there needeth no better hostages for his fidelity, for he hath slain with his own hands (in fight and open view of our men that saw him) O'Donnell's second brother... His love and credit with the people is little inferior to O'Donnell's and may easily be more, if he be backed and strengthened by Her Majesty..."{{sfn|Morgan|2002|pp=2–3}} By December 1600, O'Donnell had put a price of £300 on Niall Garve's head.{{Sfn|McGettigan|2005|pp=98, 158}} It appears Niall Garve made later efforts to rejoin the confederacy, but his murder of Manus made this near-impossible.<ref name=":1">{{harvnb|Clavin|2009|ps=, 4th paragraph}}.</ref>{{efn|According to O'Sullivan Beare, Conn O'Gallagher, a defector who assisted Niall Garve in Manus's killing,{{sfn|O'Clery|O'Clery|Murphy|1895|p=256}} was captured by O'Donnell and hanged.{{Sfn|O'Sullivan Beare|1903|pp=136–137}}}} His defection allowed Docwra to mobilise the Crown's forces beyond Lough Foyle into Tyrconnell, [[Inishowen]] and even Tír Eoghain.{{sfn|McGurk|2006|p=96}} In addition to his skill as a guide across Tyrconnell, Niall Garve informed Docwra of his cousin's tactics.{{sfnm|1a1=McGettigan|1y=2005|2a1=Clavin|2y=2009|1pp=95–96|2ps=, 5th paragraph.}}

=== Political alliances collapse ===
O'Donnell made further plans to cement his alliances beyond Ulster. In November 1600, he schemed to marry Joan FitzGerald (step-daughter to O'Connor Sligo and sister of the loyalist [[James FitzGerald, 1st Earl of Desmond|1st Earl of Desmond]]). A servant met with Joan in [[Limerick]] "alleging that O'Donnell was a great Lord, and very rich, and that if he would prove good, he were a fit marriage for the best lady in the country". Joan rejected the match; additionally [[Lord President of Munster]] George Carew placed her under house arrest as a precaution.{{Sfnm|1a1=Morgan|1y=2002|1p=8|2a1=McGettigan|2y=2005|2p=90|2ps=. notes the relationship between O'Connor Sligo and Joan.}}

O'Donnell became frustrated by the Spanish government's failure to send the military resources he desired. When a Spanish ship arrived around the time of the new year, O'Donnell was "like a madman when he saw no kind of news, neither of men nor money to come: presently swore he would go himself to Spain and would have gone indeed, if the Captain of the Spaniards had suffered him".{{sfn|Morgan|2002|p=|pp=14–15}}

Sean O'Doherty, Lord of Inishowen, died on 27 January 1601, leading to a succession dispute. The O'Doherty clan preferred Sean's eldest son [[Cahir O'Doherty|Cahir]] (then aged about 14) as the successor, but O'Donnell was bribed into inaugurating Sean's half-brother (and his own first cousin) Phelim Og O'Doherty. This decision outraged Cahir's foster family and they opened negotiations with Docwra to secure the lordship.{{sfn|McGettigan|2005|p=|pp=96–97}}<ref name="dib">{{cite journal |last1=McGettigan |first1=Darren |date=October 2009 |title=O'Doherty (Ó Dochartaigh), Cahir |url=https://www.dib.ie/biography/odoherty-o-dochartaigh-cahir-a6684 |url-status=live |journal=Dictionary of Irish Biography |publisher=Royal Irish Academy |doi=10.3318/dib.006684.v1 |archive-url=https://web.archive.org/web/20221029201840/https://www.dib.ie/biography/odoherty-o-dochartaigh-cahir-a6684 |archive-date=29 October 2022 |accessdate=2 December 2022|url-access=subscription }}</ref> O'Donnell attempted revenge by invading Inishowen with 1,500 men, but 40 of his men were killed and he retreated.{{sfn|McGettigan|2005|p=97}}

Both Docwra and O'Donnell's [[conduct of war]] was vicious; soldiers and civilians on either side were [[Summary execution|summarily executed]] (including Bishop [[Réamonn Ó Gallchobhair|Redmond O'Gallagher]]). In February 1601, Docwra noted that O'Donnell was regularly hanging individuals of otherwise good standing at the slightest cause for suspicion.{{sfnm|1a1=Morgan|1y=2002|1p=3|2a1=McGettigan|2y=2005|2p=97}} When O'Donnell discovered that O'Connor Sligo was plotting with Mountjoy in early 1601, he imprisoned O'Connor Sligo in Lough Eske Castle's prison.{{sfnm|1a1=Morgan|1y=2002|1p=12|2a1=McGettigan|2y=2005|2p=100}} Docwra plundered and garrisoned Rathmullan. By April, the list of O'Donnell's allies preparing to submit to Docwra included Tadhg Og O'Boyle, Owen Og MacSweeney (son of O'Donnell's late foster-father), Chief Donough MacSweeney Banagh, Chief Donnell MacSweeney Fanad and his son Donnell Gorm MacSweeney Fanad. By the end of 1601, only the immediate families of O'Donnell and Hugh McHugh Dubh remained loyal to the confederacy. Ballyshannon Castle became a safe haven to masses of women and children. Others took refuge in Lower Connacht.{{sfn|McGettigan|2005|p=98}} In late October 1601, O'Donnell's mother Iníon Dubh, plus one of his sisters, were taken prisoner in Collooney Castle.{{Sfn|Mahaffy|1912|p=140}}

=== Siege of Donegal ===
{{Main|Siege of Donegal}}[[File:Donegal Friary Choir 2009 09 23.jpg|thumb|300px|The ruins of [[Donegal Abbey]] in 2009|left]]On 18 March 1601, the government recognised Niall Garve as the rightful chief of the O'Donnell clan. Hugh Roe O'Donnell marched on Lifford in April 1601, forcing Niall Garve and his forces to temporarily retreat to Derry.<ref>{{harvnb|Clavin|2009|ps=, 5–6th paragraph.}}</ref> Following the Earl of Clanricarde's death in May, O'Donnell concentrated his forces at Ballymote in anticipation of an attack from Clanricarde's successor. This allowed Niall Garve to take Donegal Abbey{{sfn|Dunlop|1894|p=439}} in August and occupy it as a garrison, installing 500 English troops.{{sfnm|1a1=McGettigan|1y=2005|1p=96|2a1=O'Neill|2y=2017|2p=242}} His hold over Donegal was his greatest blow against O'Donnell; it virtually prevented O'Donnell from entering Tyrconnell and led to a month-long siege.<ref name="clavin6">{{harvnb|Clavin|2009|ps=, 6th paragraph.}}</ref> The siege climaxed on 26 September{{sfnm|1a1=Mahaffy|1y=1912|1pp=97–99|1ps=: primary source|2a1=Clavin|2y=2009|2ps=, 6th paragraph: secondary source.}} when a fire in the garrison's store detonated several barrels of gunpowder and caused the abbey to collapse.{{sfn|O'Neill|2017|p=242–243}} O'Donnell hurriedly ordered his men to attack, leading to a chaotic engagement amidst the burning abbey. Niall Garve's defeat seemed certain, but the loyalist forces held out until a relief force arrived and forced O'Donnell to call off the attack. 330 of Niall Garve's troops were killed during the battle, including his brother [[Conn Oge O'Donnell|Conn Oge]].{{sfnm|1a1=McGettigan|1y=2005|1p=100|2a1=Clavin|2y=2009|2p=|2ps=, 6th paragraph.}}

Niall Garve was so unsettled by his losses at the siege that, with Docwra's permission, he began negotiating with O'Donnell to became his tanist. Niall Garve's conditions (which included "that [Hugh Roe O'Donnell] and [Niall Garve] should be bound and sworn never to come in sight of one another") were so numerous that O'Donnell discarded negotiations.{{sfn|McGettigan|2005|p=100}}

=== Siege of Kinsale ===
{{Further|4th Spanish Armada|Siege of Kinsale}}[[File:Juan del Aguila y Arellano.jpg|thumb|Spanish general [[Juan del Águila]] fought with O'Donnell at Kinsale.]]Throughout 1601, Philip III was focused on dispatching an armed expedition to Ireland to improve his position in the Anglo-Spanish War.{{Sfn|Lennon|2005|p=302}} Under the command of General [[Juan del Águila]], the [[4th Spanish Armada]] finally landed and was besieged by English forces inside the port town of [[Kinsale]]—virtually the opposite end of Ireland from Ulster—on 21 September <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 1 October] 1601.{{sfnm|1a1=McGurk|1y=2001|1pp=16–17|2a1=McGettigan|2y=2005|2p=101}} O'Donnell was energised by the news of the Spanish expedition's long-awaited arrival and he called his forces to abandon their sieging of Niall Garve's forces.{{sfn|McGettigan|2005|p=101}} He set out for Kinsale from Ballymote{{sfnm|1a1=McGurk|1y=2001|1p=17|2ps=, 9th paragraph.|2a1=Silke|2y=2004}} in late October{{efn|Sources differ on the exact date; either 23 October <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 2 November]{{sfn|O'Clery|O'Clery|Murphy|1895|p=303}}{{sfn|McGurk|2001|p=17}}<ref>{{harvnb|Silke|2004|ps=, 9th paragraph.}}</ref> or 19 October <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 29 October].<ref name="age29" />{{sfn|McGettigan|2005|p=102}}}} with about 2,000 men.{{sfnm|1a1=Webb|1y=1878|1p=393|2a1=McGettigan|2y=2005|2p=102|3a1=Morgan|3y=2009|3ps=, 12th paragraph.}} Tyrone's forces began their separate march a week after O'Donnell.{{sfnm|1a1=McGurk|1y=2001|2a1=McGettigan|2y=2005|2pp=103–104|1pp=17–18}}

O'Donnell's army marched through Connacht to Ath Croch near [[Shannon Harbour]], where they were joined by Chief John Og McCoughlan{{sfn|McGettigan|2005|p=102}} and Captain [[Richard Tyrrell]].{{sfn|Ekin|2015|p=174}} O'Donnell's men carried two [[garron]]s loaded with Spanish silver on their march; this was to impress his wealth and wisdom upon locals he encountered.{{sfnm|1a1=Morgan|1y=2002|2a1=McGettigan|2y=2005|1p=15|2pp=102–103}} Marching onwards they reached Druim-Saileach in [[County Tipperary]], where the troops stopped for twenty days to plunder the neighbouring territories.{{sfn|McGettigan|2005|p=102}} O'Donnell visited [[Holy Cross Abbey]] on [[Saint Andrew's Day]] where he venerated its relic of the [[True Cross]]. He also dispatched an expedition to [[Ardfert]], which included his nephew [[Donal Oge O'Donnell|Donal Oge]] (son of his late half-brother [[Donnell O'Donnell|Donal]]), to recover the territory of confederacy ally [[Thomas Fitzmaurice, 18th Baron Kerry|Thomas Fitzmaurice]].{{Sfn|O'Clery|O'Clery|Murphy|1895|pp=303–307}}<ref>{{Cite book |last=O'Donnell |first=Francis Martin |author-link=Francis Martin O'Donnell |url=https://books.google.com/books?id=odnQugEACAAJ |title=The O'Donnells of Tyrconnell: A Hidden Legacy |date=2018 |publisher=Academica Press |isbn=978-1-68053-474-0 |language=en}}</ref> Carew attempted to intercept O'Donnell on 7 November but O'Donnell eluded him by passing through a defile in the [[Slieve Felim Mountains]]. O'Donnell's forces regrouped in Connelloe, [[County Limerick]], and finally united with Tyrone at [[Bandon, County Cork|Bandon]] on 15 December.{{sfn|McGurk|2001|p=18}}[[File:Kinsale-1601-02.jpg|left|thumb|Map of the Siege of Kinsale]]The Crown's army was trapped in Kinsale between the Irish and the Spaniards.{{sfn|McGurk|2001|p=18}} It appears Tyrone and O'Donnell had previously agreed to starve out the English,{{sfnm|1a1=Dunlop|1y=1894|1pp=439–440|2a1=Dunlop|2y=1895|2p=194}} but Juan del Águila urged for a prompt combined attack.{{sfnm|1a1=Dunlop|1y=1895|1p=194|2a1=McGinty|2y=2013b|2p=10}} Near-contemporary writers Ó Cléirigh and O'Sullivan Beare allege that O'Donnell was convinced by Juan del Águila and naively urged Tyrone to attack. This account is not unanimously accepted by historians. McGurk, Silke, McGettigan and [[Cyril Falls]] concur; Morgan and [[Gerard Anthony Hayes-McCoy|G. A. Hayes-McCoy]] disagree. O'Donnell had previously induced Tyrone into a full frontal assault during a campaign in 1598, so this narrative is not out of the question.{{sfn|McGinty|2013b|p=11}} Morgan claims that the pressure from the beleaguered Spaniards that wore down Tyrone,<ref>{{Citation |last=Morgan |first=Hiram |title=O'Faoláin's Great O'Neill |date=25 February 2000 |url=https://celt.ucc.ie/OFaolain.pdf |archive-url=https://web.archive.org/web/20240917092603/https://celt.ucc.ie/OFaolain.pdf |archive-date=17 September 2024 |quote=In fact none of the Irish leaders at Kinsale were particularly anxious to fight the battle but had little choice having answered the call of the beleaguered Spaniards.}}</ref> and that both O'Donnell and Tyrone had their reputations at stake.<ref name="morganoneill17">{{harvnb|Morgan|2014|ps=, 17th paragraph.}}</ref> Whatever the cause, Tyrone uncharacteristically agreed to a combined attack on both English camps.{{sfn|McGurk|2001|pp=18–19}}

At dawn on 24 December <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 3 January 1602] 1601, Tyrone's forces of 4,000 men took their position. Mountjoy spotted the soldiers and ordered an immediate attack.{{sfn|McGurk|2001|pp=18–19}} Tyrone retreated but Mountjoy's cavalry charge routed the confederate soldiers; 1,200 were killed and 800 were wounded.<ref name="morganoneill17"/> O'Donnell was too far off to aid Tyrone. The sight of butchered Irish forces demoralised O'Donnell's soldiers, and many fled despite O'Donnell's commands to stay and fight. O'Donnell's forces were lightly engaged but Tyrone's forces suffered the greatest losses.{{sfn|McGurk|2001|pp=18–19}} The defeat at Kinsale was a fatal blow for the confederacy{{sfn|O'Neill|2017|p=169}} and destroyed what remained of O'Donnell's military strength. Niall Garve was left as the de facto ruler of Tyrconnell.<ref>{{harvnb|Clavin|2009|ps=, 7th paragraph.}}</ref>

== Travel to Spain ==

=== Meeting with Philip III ===
The defeated confederates gathered at [[Innishannon]].{{sfn|McGettigan|2005|p=108}} Tyrone was strongly in favour of attempting another siege, but was unable to convince O'Donnell,{{sfnm|1a1=O'Sullivan Beare|1y=1903|1p=147|2a1=McGettigan|2y=2005|2pp=108–109}} who was in a state of [[nervous breakdown]].{{sfnm|1a1=McGettigan|1y=2005|1p=109|2a1=Ekin|2y=2015|2p=16}} According to Ó Cléirigh, his followers "were greatly afraid that he would bring on his death, through the suffering which seized him, so that he did not sleep nor eat in comfort for three days and three nights after". He became determined to travel to Spain to secure reinforcements from Philip III.{{Sfn|McGettigan|2005|p=109}} A factor in his decision was that, having been forced from Tyrconnell, O'Donnell had no property in Ulster to return to.{{sfn|Morgan|2002|p=3}} Tyrone disagreed with O'Donnell's plan but could not stop him. Before the confederate commanders returned to Ulster, O'Donnell appointed Rory as commander of his forces.{{Sfn|McGettigan|2005|p=109}}

O'Donnell left [[Castlehaven]] on 27 December <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 6 January 1602] 1601 with General [[Pedro de Zubiaur]]. He was accompanied by Archbishop [[Florence Conroy]], [[Muiris mac Donnchadh Ulltach Ó Duinnshléibhe|Maurice MacDonough Ultach]], [[Redmond Burke, Baron Leitrim|Redmond Burke]] and Captain Hugh Mostian. They arrived in [[Luarca]] on 3 January <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 13 January] after travelling through a stormy passage. As Philip III was in the province of [[Province of León|Leon]] at the time, the group headed to [[A Coruña]].{{sfn|Walsh|1996|pp=25–26}} They were welcomed to A Coruña by Luis de Carillo, the governor of Galicia and Conde de Caracena, who was a political supporter of the confederacy's cause. He offered the group the hospitality of his seaside house.{{sfn|Walsh|1996|p=|pp=26, 139}} O'Donnell was also taken to sightsee the [[Tower of Hercules|Farum Brigantium]], where the legendary sons of [[Milesius]] left for Ireland.{{sfnm|1a1=Purcell|1p=255|1y=1966|2a1=Morgan|2y=2002|2p=15}}
[[File:Pourbus, Frans II workshop - Philipp III of Spain - The Phoebus Foundation.jpg|thumb|O'Donnell travelled to Spain to seek assistance from King [[Philip III of Spain|Philip III]].]]
Philip III agreed to meet with O'Donnell on the recommendation of his advisors, and O'Donnell was escorted to [[Zamora, Spain|Zamora]] with a dozen Irishmen to meet the Spanish king.{{sfn|Walsh|1996|p=26}} When he arrived in the king's presence, O'Donnell knelt before him and vowed not to rise until three requests were granted:

{{Blockquote|text=1. To send a Spanish army (with O'Donnell) to Ireland;<br />2. To make O'Donnell the most powerful noble in Ireland, once it had been conquered by Spain;<br />3. To protect the rights of his clan and his successors.}}

Philip III agreed and bade O'Donnell to rise.{{sfnm|1a1=O'Clery|1y=1895|2a1=Ekin|2y=2015|2p=315|1p=323|1a2=O'Clery|1a3=Murphy}} During O'Donnell's time at the Spanish court, he met with Tyrone's son Henry (also his own nephew){{Sfn|Walsh|1996|p=27}} and was treated for a [[bubo|bubonic plague sore]] by Tyrconnell physician [[Niall Ó Glacáin|Nial O'Glacan]].<ref>{{Cite journal |last=Simms |first=Samuel |date=July 1935 |title=Nial O'Glacan of Donegal, An Irish Physician of the Sixteenth Century |journal=[[Ulster Medical Journal]] |volume=4 |issue=3 |pages=186–189 |pmc=2479006 |pmid=20476054}}</ref> He also spent much of his time working with Archbishop [[Mateo de Oviedo]] to assemble a case against Juan del Águila. The [[Spanish Council of State]] reported to the King that "[O'Donnell's] zeal and loyalty should be highly praised... He should be assured that His Majesty regards the Irish Catholics as his subjects." Philip III granted O'Donnell a generous pension and ordered him to return to A Coruña to supervise the planned naval reinforcements.{{sfn|Ekin|2015|p=315}}

=== Cancelled naval expedition ===
O'Donnell returned to A Coruña on 16 February [<nowiki/>[[Old Style and New Style dates|N.S.]] 26 February], by which time he received news of Juan del Águila's surrender, which was not unexpected. O'Donnell wrote to the King two days later, begging him to focus his attention on sending the discussed naval expedition to Ireland. Although O'Donnell would have been content with a small-scale expedition sent to Tyrconnell, Philip III wanted to send a large fleet—three times the size of the 4th Armada—to ensure military success and restore his damaged reputation. Due to the time it would take to assemble a force of this size, O'Donnell was left anxiously waiting in Spain.{{Sfn|Walsh|1996|pp=27–30}} Meanwhile, the confederacy disintegrated as English forces travelled across Ulster destroying crops and livestock. In June 1602 Tyrone [[Burning of Dungannon|burned Dungannon]] and retreated into [[Glenconkeyne]].{{Sfn|O'Neill|2017|pp=169–175}} O'Donnell kept in contact with Ireland during this time—he wrote to one confederate "if there is anything bad it may be concealed from the Spaniard, but not from me".{{sfn|McGettigan|2005|p=|pp=113–114}}

Throughout 1602 O'Donnell was placated with promises that the Spanish fleet was being gradually assembled.{{sfn|Ekin|2015|p=316}} He insistently asked to return to court to discuss the military situation.{{Sfn|Walsh|1996|p=32}} In March, O'Donnell was alarmed by the [[Duke of Lerma]]'s suggestion that O'Donnell could be sent back to Ireland with only one ship and 50,000 [[ducat]]s. On 10 June <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 20 June] O'Donnell wrote to Philip III: "I am weary of seeing how I am wasting my time here, and I fear that things are going on badly at home".{{Sfn|McGettigan|2005|p=111}} By July it became clear that, due to delays, the envisioned fleet would not be ready until the next year.{{Sfn|Walsh|1996|p=32}} On 23 July <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 2 August], the ships already prepared at A Coruña were sent to the [[New World]] on unrelated missions.{{sfnm|1a1=Walsh|1y=1996|1p=32|2a1=McGettigan|2y=2005|2p=114}} O'Donnell's companions reported that he was gripped "by an extreme melancholia and disgust which took hold of him when buoyed up by hope as a result of the promises and letters he had received... he saw the whole [Spanish] army suddenly diverted... without even a mention being made of Ireland".{{sfnm|1a1=Jones|1y=1951|1p=33|2a1=McGettigan|2y=2005|2p=115}} Philip III permitted O'Donnell to meet with him, and O'Donnell left A Coruña on 26 July <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 5 August] to go to [[Simancas]].{{sfnm|1a1=Walsh|1y=1996|1p=32|2a1=McGettigan|2y=2005|2p=115}}

=== Death and burial ===
[[File:Castillo de Simancas.jpg|thumb|O'Donnell died at the [[Castle of Simancas]] on 30 August 1602.]]
O'Donnell arrived at the [[Castle of Simancas]] on around 31 July <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 10 August<nowiki>]</nowiki>.{{sfn|Walsh|1996|p=32}} Within weeks he had developed a fever,{{sfn|Purcell|1966|p=257}} and by 14 August <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 24 August<nowiki>]</nowiki> he was extremely ill.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=325|1ps=: O'Donnell suffered for sixteen days before his death|2a1=Annals of the Four Masters|2y=2008|2p=2297|2ps=: O'Donnell suffered for seventeen days before his death.}} He was attended by Irish doctor John Noonan; the guilty king also sent his own physician, Álvarez, to the castle.{{sfnm|2a1=Silke|2y=1988|2p=51|2ps=: for Noonan's forename.|1a1=Purcell|1y=1966|1p=257}} O'Donnell was aware he was dying, and indicated that he was "fearful of death, as is natural to my creaturely condition".{{sfn|McGettigan|2005|pp=115–116}} He received the [[last rites]]{{sfn|O'Clery|O'Clery|Murphy|1895|p=325}} and was attended by Archbishop Conroy and two Franciscans, Maurice MacDonough Ultach and [[Muiris mac Seaán Ulltach Ó Duinnshléibhe|Maurice MacSean Ultach]].{{Sfn|Silke|1988|p=51}}

O'Donnell made his will on 28 August <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 7 September<nowiki>]</nowiki>, whilst on his deathbed.{{sfn|McGettigan|2005|pp=115–116}} He dictated his will in Irish, but Conroy translated it into [[Castilian Spanish]] for the notary.{{sfn|Silke|1988|p=60}}{{efn|Other individuals present during the creation of O'Donnell's will include his secretary Matthew Tully, notary Diego de Albiz, witness Pedro de Monsalvo, and Philip III's servants Juan de Albiz and Juan Fernandez de Camara.{{sfn|Silke|1988|pp=51, 60}}}} O'Donnell was in an extremely weak physical condition and could only blot the page when attempting to sign his signature.{{sfnm|1a1=Silke|1y=1988|1p=60|2a1=McGettigan|2y=2005|2p=116}} He warned against news of his death reaching Ireland before Spanish reinforcements arrived, as he believed the news would demotivate the confederacy and lead to a peace treaty with England. O'Donnell was content to be a vassal of the Spanish king if the Gaelic chiefs could keep their power over Ireland, which would effectively make Ireland a Spanish colony.{{sfn|McGettigan|2005|pp=115–116}}<ref name="NA">{{Cite web |last=Siggins |first=Lorna |date=21 January 2024 |title=New analysis reveals secrets in the will of Red Hugh O'Donnell |url=https://www.independent.ie/irish-news/new-analysis-reveals-secrets-in-the-will-of-red-hugh-odonnell/a2094455255.html |archive-url=https://web.archive.org/web/20250313013210/https://www.independent.ie/irish-news/new-analysis-reveals-secrets-in-the-will-of-red-hugh-odonnell/a2094455255.html |archive-date=13 March 2025 |access-date=3 October 2024 |website=Irish Independent |language=en}}</ref> O'Donnell bequeathed "all [his] estates, lands, lordships and vassals" to his younger brother Rory.{{sfnm|2a1=McGettigan|2y=2005|2p=115|3a1=Ó Canann|3y=2007|3p=104|1a1=Silke|1y=2004|1ps=, 12th paragraph}}

After over two weeks of bedridden suffering,{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1p=325|1ps=: O'Donnell suffered for sixteen days before his death|2a1=Annals of the Four Masters|2y=2008|2p=2297|2ps=: O'Donnell suffered for seventeen days before his death.}} Hugh Roe O'Donnell died at the Castle of Simancas{{sfnm|1a1=Silke|1y=1988|1p=51|2a1=Morgan|2y=2002|2p=15}} on 30 August <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 9 September<nowiki>]</nowiki> 1602.{{efn|Fr. Ludovico Mansoni, who was in Valladolid during O'Donnell's last weeks, wrote on 11 September ([[Old Style and New Style dates|N.S.]]) that O'Donnell had died "the day before yesterday, which was the 9th."<ref>{{harvnb|Jones|1951|p=32|ps=. On 11 September ([[Old Style and New Style dates|N.S.]]), Mansoni wrote: "Although I reported to Your Excellency by the last courier some improvement in Count O'Donnell, his illness grew more serious and the day before yesterday, which was the 9th, he died in Simancas."}}</ref> Both the State Papers and Ó Cléirigh's biography assert that O'Donnell instead died on the 10th.{{sfn|Mahaffy|1912|pp=483–484, 499|ps=. On 28 September ([[Old Style and New Style dates|N.S.]]), statesman Thomas Goold wrote from Lisbon that "O'Donnell departed this world the tenth day of this month and was very honourably buried in Vallodelite..."}}<ref>{{harvnb|O'Clery|O'Clery|Murphy|1895|p=325}}. Around the 1620s, Ó Cléirigh wrote that "At last he died at the end of that time, the tenth day of September exactly..."</ref><ref>{{harvnb|Jones|1951|p=32}}. fn. 4.</ref> The historian Frederick M. Jones notes that, because Mansoni was ten miles from Simancas and writing only days after O'Donnell's death, he would be better informed than these other sources.{{Sfn|Jones|1951|pp=32–33}} Modern historians corroborate 9 September/30 August as O'Donnell's deathdate.{{sfnm|1a1=Silke|1y=2004|1ps=, 12th paragraph|2a1=McGettigan|2y=2005|2p=116|3a1=Morgan|3y=2009|3ps=, 13th paragraph.}}<ref name="brit">{{cite journal |date=29 March 2024 |title=Hugh Roe O'Donnell |url=https://www.britannica.com/biography/Hugh-Roe-ODonnell |journal=[[Encyclopedia Britannica]] |archive-url=https://web.archive.org/web/20240701051706/https://www.britannica.com/biography/Hugh-Roe-ODonnell |archive-date=1 July 2024 |access-date=1 July 2024}}</ref>}} He was 29 years of age,{{Sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=xxxi, 327|2a1=Walsh|2y=1939|2pp=235–236}} and left no children.{{sfnm|1a1=Jones|1y=1951|1p=33|2a1=Webb|2y=1878|2p=393}} The same evening, his body was taken to [[Valladolid]] in a four-wheeled hearse "with blazing torches and bright flambeaux of beautiful waxlights blazing all round on each side of it". The elaborate procession was attended by Philip III, state officers and council members.{{sfnm|1a1=O'Clery|1a2=O'Clery|1a3=Murphy|1y=1895|1pp=325–327|1ps=: description of the funeral|2a1=Purcell|2y=1966|2ps=: procession occurred the same evening as O'Donnell's death, and was attended by Philip III.|2p=257}} His [[funeral rites]] were performed in Valladolid on the morning of 1 September <nowiki>[</nowiki>[[Old Style and New Style dates|N.S.]] 11 September<nowiki>]</nowiki>.{{Sfn|Jones|1951|pp=32–33}} Per his will, O'Donnell was buried in the [[Convent of St. Francis, Valladolid|Convent of St. Francis]],{{efn|The Italian explorer [[Christopher Columbus]] was buried in the same convent almost 100 years earlier,<ref name="flanagan2020"/> and [[Tibbot MacWalter Kittagh Bourke|MacWilliam Bourke]] was buried there in November 1604.{{sfn|Morgan|2020}}}} in the Chapel of Wonders.{{Sfn|O'Neill|2020|p=7}}{{efn|''{{langx|es|La Capilla de las Maravillas}}'';<ref>{{Cite web |last=O'Connor |first=Rachael |date=29 May 2020 |title=Skull found in dig for 16th century Irish lord who almost freed Ireland from the British |url=https://www.irishpost.com/uncategorized/skull-found-in-dig-for-16th-century-irish-lord-who-almost-freed-ireland-from-the-british-185847 |access-date=2025-05-15 |website=The Irish Post}}</ref> also translated as the Chapel of Marvels.<ref name="recover">{{cite news |last=McGreevy |first=Ronan |date=22 May 2020a |title=Spanish archaeologists recover bones in search for remains of Red Hugh O'Donnell |url=https://www.irishtimes.com/news/ireland/irish-news/spanish-archaeologists-recover-bones-in-search-for-remains-of-red-hugh-o-donnell-1.4259973 |access-date=12 February 2025 |newspaper=[[The Irish Times]]}}</ref>}}

=== Cause of death ===
[[File:George Carew, Earl of Totnes from NPG.jpg|left|thumb|[[George Carew, 1st Earl of Totnes|George Carew]] believed that the merchant James Blake poisoned O'Donnell, but it is more likely he died from a tapeworm infection.]]
A now-debunked popular legend claims that O'Donnell was poisoned by [[James "Spanish" Blake|James Blake]],{{sfnm|1a1=Morgan|1y=2002|1p=16|2a1=McGreevy|2y=2020b}} a Galway merchant hired as a spy for the government.{{sfn|Jones|1950|p=|pp=1–3}} Blake approached Lord President Carew with an offer to travel to Spain to assassinate O'Donnell.{{sfn|Morgan|2002|p=16}} In a ciphered letter dated 28 May 1602, Carew informed Mountjoy that "''James Blake''...took a solemn oath to do service...and is gone into ''Spain'' with a determination (bound with many oaths) to ''kill O'Donnell''".<ref>{{harvnb|Brewer|Bullen|1870|p=421}}. Words in italics were encrypted in the original.</ref> O'Donnell was aware that Blake was a security threat.{{sfnm|2a1=Morgan|2y=2002|3a1=McGettigan|3y=2005|3p=114|2p=16|1p=35|1a1=Jones|1y=1951}} Despite Blake's oath to Carew, on 19 August [<nowiki/>[[Old Style and New Style dates|N.S.]] 29 August] at Valladolid he outlined a detailed plan to the Duke of Lerma for a Spanish expedition aimed at retaking Galway from English control.{{sfnm|1a1=Jones|1y=1950|1pp=6–7, 17|2a1=Walsh|2y=1996|2p=34}} Given Blake's apparent pro-Spanish sentiments, historians Frederick M. Jones and [[Micheline Kerney Walsh]] have questioned whether he was truly an English spy, and speculate that Blake was a Spanish agent who proposed the mission as a means of securing safe passage to Spain.{{sfnm|1a1=Jones|1y=1950|1pp=17–18|2a1=Walsh|2y=1996|2pp=32–33}}

Another ciphered letter was sent from Carew to Mountjoy on 9 October: "O'Donnell is dead... he is ''poisoned'' by ''James Blake'', of whom your lordship hath been formerly acquainted... He never told the ''President'' in what ''manner'' he would ''kill'' him, but did assure him it ''should'' be effected".<ref>{{harvnb|Brewer|Bullen|1870|pp=350–351}}. Words in italics were encrypted in the original.</ref> After O'Donnell's death, Blake was arrested in Valladolid{{sfn|Walsh|1996|p=34}} on suspicion of being an English spy.{{sfn|Jones|1951|p=35}} Despite two months of interrogation he was never suspected of poisoning O'Donnell.{{sfn|Walsh|1996|p=34}} None of O'Donnell's companions, nor his physicians, suspected foul play;{{sfnm|1a1=Jones|1y=1951|1p=34|2a1=Walsh|2y=1996|2p=32|3p=115|3y=2005|3a1=McGettigan}} at the time, they credited his anguish over the diplomatic situation with causing his death.{{sfnm|1a1=Jones|1y=1951|1p=33|2a1=McGettigan|2y=2005|2p=115}} There is no evidence that Blake was successful in his promised assassination;{{sfnm|1a1=Jones|1p=38|1y=1951|2a1=Walsh|2p=33|2y=1996|3a1=Morgan|3p=16|3y=2002|4a1=Ekin|4p=317|4y=2015}} when Carew heard of O'Donnell's death, he would have naturally assumed that Blake was responsible.{{sfn|Morgan|2002|p=16}}

Historians dismiss the theory that O'Donnell was poisoned. It is more likely he died of illness.<ref>{{Harvnb|Jones|1951|pp=30–38}}; {{harvnb|Purcell|1966|pp=256–257}}; {{Harvnb|Morgan|2002|p=16}}; {{harvnb|Silke|2004|ps=, 12th paragraph}}; {{Harvnb|McGettigan|2005|p=116}}; {{Harvnb|Connolly|2007|p=424}}; {{Harvnb|Morgan|2009|ps=, 13th paragraph}}; {{Harvnb|Ekin|2015|p=317}}; {{harvnb|McGreevy|2020b}}.</ref> Prior to his death he vomited a worm ten measures long, "a thing unheard of by the doctors and regarded by them as extraordinary".<ref>{{harvnb|Jones|1951|p=33}}: cites Ludovico Mansoni who clarifies that the worm, initially reported to be 14 measures long, was later measured and found to be 10 measures long; {{harvnb|McGettigan|2005|p=115}}.</ref> It was also reported that "a kind of snake or serpent was found within him".{{Sfnm|1a1=McGettigan|1y=2005|1p=116|2a1=Ekin|2y=2015|2p=317}} This could indicate a [[tapeworm]] infection<ref>{{harvnb|McGettigan|2005|p=116}}. "It is more than likely that Red Hugh was killed by a particularly large and virulent tapeworm..."; {{harvnb|McGreevy|2020b}}. "...it is more likely he died of an infection caused by a tapeworm."; {{harvnb|Jones|Carroll|2020}}. "...died of a suspected tapeworm infection..."</ref> or a cancerous tumour.{{sfn|Ekin|2015|p=317}}

=== End of the Nine Years' War ===
[[File:Rory O'Donnell, Earl of Tyrconnell.png|thumb|The English government recognised [[Rory O'Donnell, 1st Earl of Tyrconnell|Rory O'Donnell]] (Hugh Roe O'Donnell's younger brother) as the successive ruler of Tyrconnell.]]
With O'Donnell's death, Spanish plans to send further assistance to the confederacy were abandoned. At this time the Spanish court was dominated by the Duke of Lerma who sought peace with England.{{sfn|Ekin|2015|p=317}} The Spanish Council of State ignored O'Donnell's request to withhold notice of his death,{{sfn|Morgan|2002|p=16}} believing that the confederates "should be undeceived, so that they may be able to make the best terms [with the English] they can, bad as the consequences may be".{{sfn|Ekin|2015|p=317}}

Mountjoy sent Rory news of O'Donnell's death and stated that "the war was at an end by his death". Rory convened a council of his advisors. The faction advocating for peace prevailed, though some of Hugh Roe O'Donnell's supporters still refused to believe he was dead. In December, Rory surrendered to Mountjoy at [[Athlone]].{{Sfn|McGettigan|2005|p=117}} Tyrone went into hiding for several months, but eventually surrendered by signing the [[Treaty of Mellifont]] on 30 March 1603, which ended the Nine Years' War.{{Sfn|O'Neill|2017|pp=191–192}} Furthermore, the [[Treaty of London (1604)|Treaty of London]] in 1604 ended the Anglo-Spanish War.{{Sfn|McGettigan|2005|p=117}} The historian John McCavitt has stated that "had [O'Donnell] lived... It could have changed the course of Irish history forever."<ref name="HI"/>

== Legacy ==

=== Succession ===
Following their surrender, Tyrone and Rory were confirmed in their titles and core estates by King [[James VI and I|James I]].{{sfn|Walsh|1996|p=37}} Rory was created hereditary [[Earl of Tyrconnell]] and granted most of Tyrconnell's lands, which greatly incensed Niall Garve.<ref>{{harvnb|Clavin|2009|ps=, 9th paragraph.}}</ref> Per the terms of his surrender, Rory was required to give up his Gaelic titles and thus was not traditionally inaugurated as the O'Donnell clan chief.{{sfn|Ó Canann|2007|pp=104–105}}<ref name="RO" /> Niall Garve had himself inaugurated as clan chief in Kilmacrennan.<ref name="j">{{harvnb|Clavin|2009|ps=, 8th paragraph.}}</ref>

Hugh Roe O'Donnell was the last undisputed chief of the O'Donnell clan.<ref name="fdo">{{Cite web |title=The O'Donnells of Tyrconnell – A Hidden Legacy (Maunsel Irish Research Series) |url=https://www.academicapress.com/node/330 |url-status=live |archive-url=https://web.archive.org/web/20240621162454/https://www.academicapress.com/node/330 |archive-date=21 June 2024 |access-date=2025-03-16 |website=Academica Press |quote=Hugh Dubh and his family were the last undisputed dynasts to rule effectively.}}</ref> Rory died of illness in 1608,<ref name="RO" /> and the following year Niall Garve, along with his son Naghtan, was imprisoned in the [[Tower of London]] for life for his role in [[O'Doherty's rebellion]].<ref>{{harvnb|Clavin|2009|ps=, 10–11th paragraph.}}</ref> Rory had only one son, [[Hugh O'Donnell, 2nd Earl of Tyrconnell|Hugh Albert, Baron of Donegal]], who died without issue,<ref>{{cite book |last=Burke |first=Bernard |url=https://archive.org/details/agenealogicalhi00burkgoog |title=A Genealogical History of the Dormant: Abeyant, Forfeited, and Extinct Peerages of the British Empire |publisher=Harrison |location=London |publication-date=1866 |pages=410}}</ref> making the subsequent line of succession unclear.<ref>{{Cite book|page=274 |last=Ellis |first=Peter Berresford |author-link=Peter Berresford Ellis |url=https://archive.org/details/erinsbloodroyal00elli |title=Erin's Blood Royal: The Gaelic Noble Dynasties of Ireland |publisher=Palgrave |year=2002 |isbn=978-0-312-23049-4}}</ref>{{sfn|O'Donnell|2006|p=39}} Today, branches of the O'Donnell clan which can trace their pedigree to the ruling O'Donnell clan live in Newport, Larkfield and [[Castlebar]], as well as in Spain and [[Austria]].{{sfn|O'Donnell|2006|pp=31–44}}<ref>{{Cite journal |last=O'Donnell |first=Francis Martin |date=2021 |title=The O'Donnell Clan Revival |url=https://www.academia.edu/61340457 |journal=Journal of the Genealogical Society of Ireland |volume=22 |pages=29–39}}</ref>

=== Historiography ===

==== ''Beatha Aodh Ruadh Ó Domhnaill'' ====
Hugh Roe O'Donnell was highly praised by seventeenth-century Irish chroniclers,<ref>{{Cite journal |last=Ó Ciardha |first=Éamonn |date=2007 |title=Cáit ar ghabhadar Gaoidhil? (Where Will the Irish Go?) |url= |journal=History Ireland |volume=15 |issue=4 |pages=5–6 |issn=0791-8224 |jstor=27725645}}</ref> such as [[Philip O'Sullivan Beare]]{{Sfn|O'Sullivan Beare|1903|pp=68–70}} and the Four Masters,{{Sfn|Annals of the Four Masters|2008|pp=2297–2299}} as well as in [[Irish bardic poetry]].{{Sfn|Breatnach|1986|p=199}} Most notably, the [[Classical Gaelic]] biography ''Beatha Aodh Ruadh Ó Domhnaill'' (''{{langx|ga|The Life of Red Hugh O'Donnell}}''), written between 1616 and 1627 by [[Lughaidh Ó Cléirigh]], is a highly important source about O'Donnell's life and times.<ref name="beathaadapted"/><ref name="oclery"/> It begins with O'Donnell's birth and ends with his death and funeral in Spain.{{sfn|Walsh|1939|p=|pp=232, 235–236}}<ref name="lo">{{cite DNB|wstitle=O'Clery, Lughaidh|volume=41|last=Moore|first=Norman|author-link=Sir Norman Moore, 1st Baronet|pages=366-367|year=|short=}}</ref>

[[File:Plaque, Drones River - geograph.org.uk - 1422094.jpg|thumb|Monument to the Four Masters, located by the Drowes River near [[Kinlough]], where the ''[[Annals of the Four Masters|Annals]]'' were compiled.<ref>{{Cite book |url=https://archive.org/details/annalsofkingdomo01ocle |title=Annals of the Kingdom of Ireland, by the Four Masters, from the Earliest Period to the Year 1616 |publisher=Hodges, Smith, and Co. |year=1856 |editor-last=O'Donovan |editor-first=John |editor-link=John O'Donovan (scholar) |edition=2 |volume=1 |location=Dublin |pages=xxviii–xxix}}</ref>]]

''Beatha'' is essentially a eulogy of Hugh Roe O'Donnell, placing him as the central figure of the Nine Years' War and minimising Tyrone's involvement.{{sfn|Morgan|2002|p=1}} Ó Cléirigh was motivated to write the biography when Spanish interest in Ireland was renewed during the [[Anglo-Spanish War (1625–1630)|Anglo-Spanish War (1625-1630)]]. Ó Cléirigh places O'Donnell at the forefront of the confederacy with the hope that another O'Donnell clansman would retake Ireland.<ref name="HP">{{Harvnb|Morgan|2009|ps=, 14th paragraph}}.</ref> Ó Cléirigh lionises O'Donnell; he claims that Hugh McHugh Dubh submitted willingly to Hugh Roe, when it reality it took O'Donnell beheading followers to obtain a submission.{{Sfnm|1a1=Walsh|1y=1939|1pp=238–239|2a1=Morgan|2y=1993|2pp=133–134}} ''Beatha'' is written in a deliberately archaic style which further venerates O'Donnell.<ref name="oclery"/><ref>{{Citation |last=Ryan |first=Salvador |title=Popular Religion in Gaelic Ireland: 1445 - 1645 |date=November 2002 |volume=1 |pages=17–19, 90 |url=https://mural.maynoothuniversity.ie/id/eprint/5072/1/Salvador_Ryan_Vol-1_20140620153419.pdf |access-date=16 March 2025 |archive-url=https://web.archive.org/web/20250124093036/https://mural.maynoothuniversity.ie/id/eprint/5072/1/Salvador_Ryan_Vol-1_20140620153419.pdf |archive-date=24 January 2025}}</ref> It was typical for Irish scribes to take liberties to gratify their patrons. They frequently omitted details which would be disagreeable to their patrons or scandalous to the Church.<ref>{{Cite book |last=Todd |first=James Henthorn |author-link=James Henthorn Todd |url=https://archive.org/details/cogadhgaedhelreg00todd |title=Cogadh Gaedhel re Gallaibh – The War of the Gaedhil with the Danes and Other Norsemen |date=1867 |publisher=Longmans, Green, Reader, and Dyer |pages=xvi–xvii}}</ref><ref>{{Cite journal |last=Gillespie |first=Raymond |date=2014 |title=Scribes and manuscripts in Gaelic Ireland, 1400-1700 |url=https://www.jstor.org/stable/24778308 |journal=Studia Hibernica |issue=40 |pages=9–34 |doi=10.3828/studia.40.9 |issn=0081-6477 |jstor=24778308 |quote=Scribes might also improve on their texts...}}</ref>

As a result, ''Beatha'' has distorted historical interpretation.{{sfnm|1a1=Walsh|1y=1939|1p=235|2a1=Connolly|2y=2007|2p=424}} According to Paul Walsh, "O'Neill, if not eliminated, is certainly reduced in stature... if one were to read only the Life, [one could say] that O'Donnell and O'Neill were of equal importance".{{sfn|Walsh|1939|p=235}} ''Beatha'' "is an immense panegyric of a young chief who had just expired in a foreign land, and it cannot be expected to be quite impartial, especially when dealing with Red Hugh's enemies." Ó Cléirigh's portrayal of Niall Garve would have been particularly biased.{{sfn|Walsh|1922|p=363}}

It is possible that Ó Cléirigh attended O'Donnell's inauguration{{sfn|Ó Canann|2007|p=105}} and participated in O'Donnell's expeditions, and he may have kept notes.{{sfn|Walsh|1939|p=247}} His description of O'Donnell's last days and funeral is based on the recollections of the two friars both named Maurice Ultach. Sections of the ''[[Annals of the Four Masters]]'' which pertained to O'Donnell's life were adapted from ''Beatha''.<ref name="beathaadapted">{{Cite web |date=2024-04-30 |title=Beatha Aodha Ruaidh Uí Dhomhnaill / Life of Red Hugh O'Donnell |url=https://www.ria.ie/collections/manuscripts/irish-language-manuscripts/beatha-aodha-ruaidh-ui-dhomhnaill-life-of-red-hugh-odonnell/ |access-date=2025-03-01|archive-url=https://web.archive.org/web/20241112221905/https://www.ria.ie/collections/manuscripts/irish-language-manuscripts/beatha-aodha-ruaidh-ui-dhomhnaill-life-of-red-hugh-odonnell/|archive-date=12 November 2024|website=Royal Irish Academy |language=en}}</ref><ref name="oclery">{{cite journal|journal=[[Dictionary of Irish Biography]]|last=McGettigan|date=2009|first=Darren|title=Ó Cléirigh (O'Clery), Lughaidh|doi=10.3318/dib.006306.v1|url=https://www.dib.ie/biography/o-cleirigh-oclery-lughaidh-a6306|archive-url=https://web.archive.org/web/20240615035304/https://www.dib.ie/biography/o-cleirigh-oclery-lughaidh-a6306|archive-date=15 June 2024|url-access=subscription}}</ref>

==== Gaelic Revival ====
The dramatic content of O'Donnell's short life, which includes his escape from prison and his early overseas death, has "enabled much mythologising of his life and character".{{sfn|Mitchell|2024|p=76}} He is considered an archetypal hero whose personal struggles against [[Tudor England]] served as an allegory to represent Ireland's incarceration, escape from [[British rule in Ireland|British rule]] and spirit of resistance.<ref>{{Harvnb|Morgan|2020|ps=. "Red Hugh's life was, like an archetypal hero's, short and dramatic... His struggles against the English naturally came to represent an indomitable spirit of resistance."}}; {{Harvnb|Mitchell|2024|p=76}}. "[O'Donnell's] personal struggle served as an allegory to explain Ireland's incarceration and escape from imprisoning and oppressive rule."</ref> Seventeenth-century annalists and eighteenth-century Catholic authors in Ireland typically admired O'Donnell over Tyrone.{{sfn|Canny|2022|p=30}} During the nineteenth-century [[Gaelic revival]], O'Donnell was embraced as a Celtic national hero, to the exclusion of Tyrone, whose "Machiavellian" nature and partially-English cultural identity were viewed as incompatible with [[Irish nationalism]].{{sfn|Power|2010|p=382}}[[File:Dramatic actors in costume, Kilkenny.png|thumb|The Neophytes, a Belfast acting troupe, dressed for a 1902 performance of the [[masque]] ''Hugh Roe O'Donnell'' in Kilkenny. O'Donnell's life has been mythologised and depicted in various mediums.{{sfn|Mitchell|2024|pp=71–89}}]]

==== Modern reappraisal ====
[[James MacGeoghegan]] rehabilitated Tyrone's reputation in the eighteenth century.{{Sfn|Canny|2022|p=50}} Twentieth-century historians, such as [[John Mitchel]], [[Seán Ó Faoláin]]{{sfnm|1a1=McGinty|1y=2013a|1pp=14–15|2a1=Canny|2y=2022|2p=30}} and Hiram Morgan,{{sfnm|1a1=Power|1y=2010|1pp=382|2a1=McGinty|2y=2013a|2p=15}} restored Tyrone to the status he was formerly afforded by contemporary English commentators, and gave him more prominence as the Irish confederacy's leader.{{sfn|Power|2010|p=382}} In most modern depictions of the Nine Years' War, O'Donnell is portrayed as the junior partner and thus his reputation has been overshadowed by Tyrone's.<ref>{{harvnb|Kelly|2004|p=160}}; {{harvnb|Power|2010|p=382}}; {{harvnb|McGinty|2013a|pp=14–15}}; {{harvnb|Canny|2022|pp=30–31}}.</ref>

The Aodh Ruadh Ó Domhnaill Guild was formed in 1977 to seek O'Donnell's cause for [[canonization]] as a [[saint]] of the Catholic Church.{{Sfn|Starke|1984|p=37}}<ref>{{Cite journal |date=1998 |editor-last=O'Donnell |editor-first=Vincent |title=Red Hugh's Beatification |url=https://archive.org/details/o-domhnaill-abu-issues/26%20-%20Spring%201998/ |journal=Ó Domhnaill Abú |volume= |issue=26 |pages=2 |issn=0790-7389}}</ref> The historian James Kelly states that, in opposition to the image of O'Donnell as a Catholic martyr, "it can be argued [that] O'Donnell was first and foremost a traditional Gaelic chieftain intent on affirming the regional authority of his clan and the dynastic aspirations of his immediate family... it was the threat posed by the expanding presence of the English Crown that constituted the major threat to Red Hugh's ambitions".{{Sfn|Kelly|2004|p=161}} Morgan considers O'Donnell to be "too Catholic and too violent for today's Ireland",{{sfn|Morgan|2020}} and also calls O'Donnell "a [[Counter-Reformation|counter-reformation]] Irish dynast living in the world of [[The Prince|Machiavelli's ''Prince'']] rather than the [[Táin Bó Cúailnge|cattle-raid of Cooley]]".<ref name="HP" />

=== Commemoration ===
[[Ballyshannon Castle]], Hugh Roe O'Donnell's key residence, was demolished in 1720.<ref name="CD">{{Cite web |last= |date=11 June 2020 |title=Clans differ on Red Hugh's final burial site |url=https://donegalnews.com/clans-differ-on-red-hughs-final-burial-site/ |url-status=live |archive-url=https://web.archive.org/web/20241227172743/https://donegalnews.com/clans-differ-on-red-hughs-final-burial-site/ |archive-date=27 December 2024 |access-date=2024-11-18 |website=Donegal News |language=en-US}}</ref> [[Donegal Castle]] was granted to Sir Basil Brooke in 1616. It was eventually restored in the 1990s<ref>{{Cite web |title=Donegal Castle |url=https://heritageireland.ie/places-to-visit/donegal-castle/ |archive-url=https://web.archive.org/web/20240415052647/https://heritageireland.ie/places-to-visit/donegal-castle/ |archive-date=15 April 2024 |access-date=18 November 2024 |website=Heritage Ireland |language=en}}</ref> and it is now open to the public as a tourist attraction.<ref>{{Cite web |title=Donegal Castle's Celtic History |url=http://www.ourdonegal.com/donegalcastle.html |archive-url=https://web.archive.org/web/20241206040558/http://www.ourdonegal.com/donegalcastle.html |archive-date=6 December 2024 |access-date=2025-03-05 |website=OurDonegal}}</ref> O'Donnell's birthday has been celebrated in County Donegal.<ref name="HB">{{Cite news |last=Heaney |first=Kate |date=8 November 2023 |title=Hundreds turn out to celebrate Red Hugh's birthday |url=https://donegalnews.com/hundreds-turn-out-to-celebrate-red-hughs-birthday/ |archive-url=https://web.archive.org/web/20231212052325/https://donegalnews.com/hundreds-turn-out-to-celebrate-red-hughs-birthday/ |archive-date=12 December 2023 |work=Donegal News}}</ref><ref name="FR">{{Cite news |last=Murray |first=Eavan |date=19 October 2023 |title=Spanish city holds a funeral for Red Hugh O'Donnell four centuries after Irish hero's death |url=https://m.independent.ie/irish-news/spanish-city-holds-a-funeral-for-red-hugh-odonnell-four-centuries-after-irish-heros-death/a1477418044.html |url-status=live |archive-url=https://web.archive.org/web/20241008123847/https://m.independent.ie/irish-news/spanish-city-holds-a-funeral-for-red-hugh-odonnell-four-centuries-after-irish-heros-death/a1477418044.html |archive-date=8 October 2024 |access-date=2 November 2024 |work=Irish Independent}}</ref><ref name=":4">{{Cite web |last=Meehan |first=Dionne |date=2024-09-07 |title=Honouring Red Hugh in Spain |url=https://donegalnews.com/honouring-red-hugh-in-spain/ |access-date=2024-11-10 |website=Donegal News |language=en-US}}</ref>

A large cross in honour of Art MacShane O'Neill stands near the site of his death and burial in the [[Wicklow Mountains]].<ref name="irishexaminer.com" />{{sfn|McCormack|Clavin|2009|ps=, 2nd paragraph.}} Since 1954<ref name="FMcN">{{Cite news |last=McNally |first=Frank |date=14 January 2017 |title=Hardship for Art's Sake - An Irishman's Diary about the Art O'Neill Challenge |url=https://www.irishtimes.com/opinion/hardship-for-art-s-sake-an-irishman-s-diary-about-the-art-o-neill-challenge-1.2936402 |access-date=28 December 2024 |newspaper=[[The Irish Times]] |language=en}}</ref> (and as an official event since 2006),<ref>{{Cite web |title=About |url=https://www.artoneill.ie/about |archive-url=https://web.archive.org/web/20250103163004/https://www.artoneill.ie/about |archive-date=3 January 2025 |access-date=2025-01-13 |website=The Art O'Neill |language=en}}</ref> O'Donnell and Art MacShane's escape is commemorated each January in the [[Art O'Neill Challenge]], an [[ultramarathon]] endurance event in which participants retrace the same 55km journey from Dublin to Glenmalure on foot.{{Sfn|Cowley|2015|p=|pp=6–7}}<ref name="irishexaminer.com" />

A sculpture by [[Maurice Harron]], titled ''The Gaelic Chieftain'', was unveiled in 1999 near Boyle. Overlooking the [[N4 road (Ireland)|N4]], the sculpture depicts O'Donnell on horseback and commemorates his victory at the battle of Curlew Pass.<ref>{{Cite AV media |url=https://www.youtube.com/watch?v=UhOXbDw5rCs |title=The Gaelic Chieftain {{!}} Interview with sculptor Maurice Harron {{!}} Ep4 |date=11 February 2022 |type=Television production |series=A Sculpted Journey of Ireland}}</ref>

O'Donnell's will became lost for a period, but in 1983 it was discovered by Donegal priest John J. Silke in the archives of Simancas.{{sfn|Silke|1988|p=51}} In 1991, a commemorative plaque was erected at the Castle of Simancas.<ref>{{Cite web |title=About Hi! – The Hispano-Irish Association & Red Hugh O'Donnell |url=https://www.hispano-irish.com/ga/who-we-are/ |archive-url=https://web.archive.org/web/20241213062906/https://www.hispano-irish.com/ga/who-we-are/ |archive-date=13 December 2024 |access-date=2025-03-05 |website=Hispano Irish |language=}}</ref> As of 2023, plans are afoot to erect statues of O'Donnell in both Lifford and Simancas.<ref name="HB" /> It has also been proposed that the two towns be [[Twinned cities|twinned]].<ref name=":4" /> The proposed twinning was passed by the Donegal County Council in March 2024, and as of April is yet to be validated by Simancas.<ref>{{Cite web |date=2024-04-16 |title=Red Hugh O'Donnell Association hail Lifford-Simancas twinning as important step in recognition of chieftain |url=https://www.derryjournal.com/heritage-and-retro/heritage/red-hugh-odonnell-association-hail-lifford-simancas-twinning-as-important-step-in-recognition-of-chieftain-4593502 |access-date=2025-03-06 |website=Derry Journal |language=en}}</ref><ref>{{Cite web |date=2024-03-09 |title=Red Hugh O'Donnell link could see Lifford twined with Spanish village |url=https://highlandradio.com/2024/03/09/red-hugh-odonnell-link-to-see-lifford-to-twined-with-spanish-village/ |access-date=2025-03-06 |website=Highland Radio|language=en-GB}}</ref>

Following an unsuccessful dig for O'Donnell's remains, Valladolid has [[Historical reenactment|reenacted]] O'Donnell's [[funeral procession]] in 2022, 2023<ref name="FR" /> and 2024, on the instigation of chairman of the Hispano-Irish Society, Carlos Burgos.<ref name="honours">{{Cite news |last=McGreevy |first=Ronan |date=14 September 2024 |title=Spanish city honours Irish chieftain Red Hugh O'Donnell with a mock funeral fit for a king |url=https://www.irishtimes.com/history/2024/09/14/spanish-city-honours-irish-chieftain-red-hugh-odonnell-with-a-mock-funeral-fit-for-a-king/ |url-status=live |archive-url=https://web.archive.org/web/20240914113022/https://www.irishtimes.com/history/2024/09/14/spanish-city-honours-irish-chieftain-red-hugh-odonnell-with-a-mock-funeral-fit-for-a-king/ |archive-date=14 September 2024 |access-date=20 September 2024 |newspaper=The Irish Times |language=en}}</ref> The reenactors wear period costumes and carry an empty casket draped with an [[Irish tricolour]].<ref name="FR" /><ref name="honours" /> It is based on historical records of the real procession.<ref name="HS" />

=== Search for remains ===
{{Quote box
| quote = ''But he never said''<br />
''And -- it seemed odd -- he''<br />
''Never had heard''<br />
''The aspirated name''<br />
''Of the centuries-dead''<br />
''Bright-haired young man''<br />
''Whose grave I sought''<br />
(...)

''They brought''<br />
''His blackening body''<br />
''Here''<br />
''To rest''<br />
''Princes came''<br />
''Walking''<br />
''Behind it''<br />
''And all Valladolid knew''<br />
''And out to Simancas all knew''<br />
''Where they buried Red Hugh.''
| source = Excerpt from [[Thomas MacGreevy]]'s 20th-century poem ''Aodh Ruadh Ó Domhnaill'', which describes a search for O'Donnell's grave<ref name="mac">{{cite book |last=MacGreevy |first=Thomas |author-link=Thomas MacGreevy |url=http://faculty.georgetown.edu/jod/texts/redhugh.html |title=Collected Poems of Thomas MacGreevy: An Annotated Edition by Susan Schreibman |date=1991 |publisher=Anna Livia Press |editor-last=Schreibman |editor-first=Susan |location=Dublin |chapter=Aodh Ruadh Ó Domhnaill |access-date=21 January 2017|archive-url=https://web.archive.org/web/20201110075818/https://faculty.georgetown.edu/jod/texts/redhugh.html|archive-date=10 November 2020}}</ref>
| width = 25%
| quoted =
}}The Convent of St. Francis was later secularised and O'Donnell's body was disinterred; its current location is unknown.<ref>{{harvnb|Silke|2004|ps=, 12th paragraph}}.</ref> The Chapel of Wonders was sold and destroyed in 1836 during a wave of monastic expropriations, and its exact location was lost.{{sfnm|2a1=Jones|2a2=Carroll|2y=2020|1a1=O'Neill|1y=2020|1p=7}} In 2019, Donegal man and retired soldier Brendan Rohan visited Valladolid and persuaded city authorities to conduct a dig for O'Donnell's grave.<ref>{{Cite news |last=Heaney |first=Kate |date=21 May 2020 |title=Dig starts to find remains of Red Hugh O'Donnell |url=https://donegalnews.com/2020/05/dig-starts-to-find-remains-of-red-hugh-odonnell/ |archive-url=https://web.archive.org/web/20200610073821/https://donegalnews.com/2020/05/dig-starts-to-find-remains-of-red-hugh-odonnell/ |archive-date=10 June 2020 |work=Donegal News}}</ref><ref name="flanagan2020">{{Cite news |last=Flanagan |first=Eimear |date=31 May 2020 |title=Red Hugh: Spanish dig for the bones of 'Fighting Prince of Donegal' |url=https://www.bbc.co.uk/news/world-europe-52832801 |access-date=2 November 2024 |work=BBC News |language=en-GB}}</ref> The following year, a week-long excavation of Valladolid's Constitution Street revealed the walls of what was believed to be the Chapel of Wonders underneath a four-storey building.{{sfn|Jones|Carroll|2020}}<ref name="flanagan2020"/> On 22 May 2020, archaeologists began a dig inside the chapel's remains.{{Sfn|O'Neill|2020|p=6}}

A number of modern descendants of O'Donnell's kin were "lined up for DNA tests" to confirm O'Donnell's identity if his remains were found.{{sfn|McGreevy|2020b}} There was call for [[repatriation]] of O'Donnell's remains if discovered,<ref name="CD" /><ref>{{Cite news |last=McGreevy |first=Ronan |date=1 June 2020c |title=Carrier of O'Donnell flame waits as search for Red Hugh continues |url=https://www.irishtimes.com/news/ireland/irish-news/carrier-of-o-donnell-flame-waits-as-search-for-red-hugh-continues-1.4266976 |access-date=2025-02-11 |newspaper=The Irish Times |language=en}}</ref> even though O'Donnell himself asked to be buried in the Convent of St. Francis in his will.{{sfn|O'Neill|2020|p=7}} It was hoped his skeleton would be easy to identify due to his two missing big toes.<ref name="NA" /><ref name="FR" /> However many of the skeletons discovered were in a state of decay and did not have any existing feet.<ref>{{Cite news |date=2 June 2020 |title=Hunt for Red O'Donnell: Does Spain Chapel House Irish Rebel Remains? |url=https://www.courthousenews.com/hunt-for-red-odonnell-does-spain-chapel-house-irish-rebel-remains/ |archive-url=https://web.archive.org/web/20201213124115/https://www.courthousenews.com/hunt-for-red-odonnell-does-spain-chapel-house-irish-rebel-remains/ |archive-date=13 December 2020 |work=Courthouse News Service}}</ref> Eventually twenty skeletons were discovered during the dig,<ref name="SC" /><ref name="FR" /><ref name="NA" /> though DNA testing showed they were from an earlier period.<ref name="NA" /><ref name="HS" /> The site has been used for burials for hundreds of years, making O'Donnell's discovery near-impossible.{{sfn|Jones|Carroll|2020}}

In March 2021, archaeologists believed the Chapel of Wonders extended further beneath the dig site, and went into negotiations to resume the excavation.<ref name="SC">{{Cite news |last=McNamara |first=Siobhan |date=22 March 2021 |title=Update on search for Red Hugh O'Donnell's remains in former Spanish capital, Valladolid |url=https://www.leitrimobserver.ie/news/home/619070/update-on-search-for-red-hugh-o-donnell-s-remains-in-former-spanish-capital-valladolid.html |archive-url=https://web.archive.org/web/20240816125349/https://www.leitrimobserver.ie/news/home/619070/update-on-search-for-red-hugh-o-donnell-s-remains-in-former-spanish-capital-valladolid.html |archive-date=16 August 2024 |access-date=2 November 2024 |work=Leitrim Observer}}</ref><ref>{{Cite web |last=McLoughlin |first=Laura |date=2021-03-19 |title=Search for Red Hugh's remains to resume |url=https://donegalnews.com/search-for-red-hughs-remains-to-resume/ |archive-url=https://web.archive.org/web/20241227164736/https://donegalnews.com/search-for-red-hughs-remains-to-resume/ |archive-date=27 December 2024 |access-date=2024-11-18 |website=Donegal News |language=en-US}}</ref> The search ended in October 2021.<ref>{{Cite journal |last=O'Donnell |first=Francis Martin |date=November 2021 |title=Red Hugh O'Donnell |url=https://issuu.com/gensocireland/docs/ireland_s_genealogical_gazette_november_2021_ |journal=Ireland's Genealogical Gazette |volume=16 |issue=11 |pages=2 |issn=1649-7937}}</ref> By September 2022, McCavitt had come across an inscription on an early 17th-century tombstone about O'Donnell. According to McCavitt, if O'Donnell's burial place still exists, it would have been marked by such a gravestone.<ref name="HI" />

As of 2024, O'Donnell's grave has not been discovered, though the media attention garnered by the dig has promoted [[Ireland–Spain relations|Hispano-Irish relations]].{{sfn|McGreevy|2020b}}<ref name="honours"/><ref name="HS">{{Cite web |last=Flanagan |first=Eimear |date=18 October 2023 |title=Red Hugh: Spanish funeral for the Fighting Prince of Donegal |url=https://www.bbc.co.uk/news/articles/c4n65jy8gr1o |url-status=live |archive-url=https://web.archive.org/web/20231019183353/https://www.bbc.com/news/articles/c4n65jy8gr1o |archive-date=19 October 2023 |access-date=2 November 2024 |website=BBC News |language=en-GB}}</ref> The dig was spearheaded by the local Hispanic-Irish Association.<ref name="NA" /> As of October 2023, the investigation is not closed.<ref name="HS" /> If discovered intact, O'Donnell's remains may provide insight into his health, nutrition and diet.<ref name="GR">{{Cite news |last=Ohlmeyer |first=Jane |author-link=Jane Ohlmeyer |date=1 June 2020 |title=Who was Red Hugh O'Donnell? The 'fiery' symbol of Gaelic resistance |url=https://www.irishtimes.com/culture/heritage/who-was-red-hugh-o-donnell-the-fiery-symbol-of-gaelic-resistance-1.4266919 |archive-url=https://web.archive.org/web/20201204222940/https://www.irishtimes.com/culture/heritage/who-was-red-hugh-o-donnell-the-fiery-symbol-of-gaelic-resistance-1.4266919 |archive-date=4 December 2020 |access-date=19 February 2025 |newspaper=The Irish Times |language=en}}</ref> Tests may also determine his specific cause of death.{{sfn|Morgan|2020|p=}}

== Character ==

=== Personality ===
{{Blockquote|text=[O'Donnell's] voice was musical. In action he was quick and decisive. He loved justice and was stern with evildoers. He was resolute, faithful to his word and steadfast in time of trial. Maintaining a rigorous military discipline, he led by example in battle. To all he was courteous and affable. He was not married. He was gracious, without pretension.|author=Fr. Donagh O'Mooney{{efn|O'Mooney was a Franciscan friar who knew O'Donnell personally, though in this description he was drawing from the work of [[Polydore Vergil]].{{sfn|Silke|2004}}}}|source=}}

Described as "fiery and flamboyant",<ref name="tudor">{{Cite book |url=https://books.google.com/books?id=nHasAgAAQBAJ&pg=PA517 |title=Tudor England: An Encyclopedia |publisher=Garland Publishing |year=2001 |isbn=978-1-136-74530-0 |editor-last=Kinney |editor-first=Arthur F. |pages=517 |editor-last2=Swain |editor-first2=David W.}}</ref> Hugh Roe O'Donnell was a highly charismatic individual.<ref>{{Harvnb|Morgan|1993|p=217}}. "...the charisma of O'Donnell..."; {{harvnb|Jones|Carroll|2020|ps=. "'He was a formidable operator – powerful and probably quite charismatic.'"}}</ref> 17th-century sources opined on his great powers of command, and stated that the look of amiability on his face captivated onlookers.{{Sfn|O'Clery|O'Clery|p=|Murphy|1895|pp=326–327|ps=. fn. 3.}} He also had an aggressive and bellicose personality and could not always control his impulses.<ref>{{Harvnb|Morgan|1993|p=217}}; {{Harvnb|Connolly|2007|p=424}}; {{Harvnb|McGinty|2013b}}, pp. 6, 12.</ref> As Edward Alfred D'Alton put it, "the ordinary Irish chief... boasted much, and talked much, and did little, and... heedlessly rushed into war without estimating his difficulties or his resources".<ref name="DAlton">{{Cite book |last=D'Alton |first=Edward Alfred |url=https://archive.org/details/historyofireland03dalt/page/130/mode/2up?q=impulse |title=History of Ireland: from the earliest times to the present day |publisher=The Gresham Publishing Company |volume=Half-volume III |location=London |publication-date=1913 |pages=129–130}}</ref>

In his youth, a bardic poet claimed that O'Donnell was arrogant and in need of maturity.{{Sfn|McGettigan|2005|p=38}} Thomas Lee warned the government that because of O'Donnell's youth, he could become radicalised by his imprisonment.{{Sfnm|1a1=McGettigan|1y=2005|1pp=42–44|2a1=McGinty|2y=2013b|2p=6}} Indeed, O'Donnell's four years in prison instilled within him a profound anti-English stance{{Sfnm|1a1=McGinty|1y=2013a|1p=23|2a1=McGinty|2y=2013b|2pp=5–6|3a1=Morgan|3y=2002|3p=10|4a1=McGettigan|4p=120|4y=2005}} which shaped his aggressive military approach.{{sfnm|1a1=Kelly|1y=2004|1p=161|2a1=McGinty|2y=2013b|2p=6}} The bardic poet Maolmuire mac Con Uladh Mic an Bhaird addressed a composition to O'Donnell in 1590, urging O'Donnell to "show fortitude in his adversity", but also indicating that the period in prison would lead O'Donnell to cultivate the discipline and solemnity "appropriate to kingship".{{Sfn|Breatnach|1986|p=199}} Particularly because he had not committed any offence, O'Donnell saw his imprisonment as unjust and villainising. His distrust of English people affected the 1596 peace talks,{{Sfn|McGinty|2013a|p=23}} and is why he was more committed to an alliance with Spain than Tyrone was.{{sfn|Morgan|2002|p=15}} O'Donnell's insolence was remarked on by English officials, who described him as the "firebrand of all the rebels".{{Sfn|McGinty|2013b|p=6}} McGettigan notes that O'Donnell was "only anti-English on a political level", as he willingly purchased English goods and firearms for his own purposes.{{Sfn|McGettigan|2005|p=121}} [[Jane Ohlmeyer]] describes O'Donnell as "a wily negotiator, an effective and pragmatic power broker, and a brave soldier".<ref name="GR" />

=== Personal relationships ===
Morwenna Donnelly notes that it is unusual that O'Donnell had no further marriages after his divorce from Rose. Excluding his rejected proposal to Joan FitzGerald, he appeared uninterested in securing an heir. Despite his desirable status as a prominent and powerful lord, O'Donnell had no known mistresses or illegitimate children.{{Sfn|Donnelly|1986|p=|pp=49–50}} This is in stark contrast to Tyrone, who had four wives, many concubines and various children.{{Sfn|Casway|2016|pp=69, 73}} Donnelly suggests that O'Donnell remained single because he coveted Donnell Gorm's wife, Honora MacSweeney na dTuath (daughter of O'Donnell's foster-father).{{Sfn|Donnelly|1986|pp=50–51}} Another explanation for O'Donnell's celibacy comes from the Franciscan Donagh O'Mooney, who stated that O'Donnell sought to join the Franciscan clergy if he survived the war. O'Mooney also stated that O'Donnell was "not married", possibly in keeping with [[Clerical celibacy in the Catholic Church|clerical celibacy]].{{Sfn|Donnelly|1986|pp=|p=51}}{{Sfn|Silke|2004|pp=}} As the war progressed, O'Donnell came under the influence of Franciscan Archbishop Conroy.{{Sfn|McGettigan|2005|p=123}}

=== Partnership with Tyrone ===
[[File:Reputed Portrait of Hugh O'Neill.webp|left|thumb|Mountjoy called the two confederate leaders "the two vipers of the kingdom".{{sfnm|1a1=McGurk|1y=2001|1p=17|2a1=O'Neill|2y=2017|2p=154}}]]
Historians have debated on whether O'Donnell or his father-in-law held a more influential position within the confederacy in its early years.{{efn|name=debate}} Many of Tyrone's contemporaries who knew Tyrone, such as John Perrot, considered O'Donnell to be the junior partner in the confederacy.{{Sfn|McGinty|2013a|pp=14–15}} In 1596, O'Donnell described Tyrone as his senior.{{Sfn|Morgan|2002|p=4}} In 1596, a list of the confederates drawn up by Alonso Cobos' secretary was altered to place Tyrone's name above O'Donnell's.{{sfn|Morgan|1993|p=208}} By 1599, O'Donnell saw his partnership with Tyrone as one of two equals, as evident from their treaty of equality.{{Sfn|McGettigan|2005|p=66}}

O'Donnell and Tyrone had contrasting temperaments, which often caused disputes over military tactics.{{Sfn|McGinty|2013b|pp=3, 6, 9}} In contrast to Tyrone, who was known for bribing or elaborately bluffing his way out of trouble,{{sfn|Morgan|1993|pp=146–148, 149–150, 173, 216}} O'Donnell was uncompromising and preferred military solutions over negotiations.{{Sfnm|1a1=McGinty|1y=2013a|1p=21|2a1=McGinty|2y=2013b|2p=13}} Tyrone attempted to restrain O'Donnell from openly attacking English forces in the early stages of the war.{{Sfn|McGinty|2013b|p=8}} O'Donnell's absence from the Battle of Beleek (per Tyrone's request) suggests that Tyrone had a level of control over his son-in-law.{{Sfn|McGinty|2013b|p=8}} English Privy Councillor [[Geoffrey Fenton]] stated that Tyrone could "command and rule" O'Donnell at will.<ref>{{Harvnb|Morgan|1993|p=173}}. fn. 46.</ref> That being said, Canny and Silke suggest that Tyrone's failure to manage O'Donnell led to the former's decision to reluctantly go into open rebellion.{{sfnm|1a1=McGinty|1y=2013a|1p=40|2a1=O'Neill|2y=2017|2p=25}}

By 1596, the pair had developed a sophisticated double-act{{sfn|Morgan|2007a|pp=823–824}} as O'Donnell played the "bad cop" to Tyrone's "good cop" during their negotiations with the government. They used the absence of one of them to delay and stall further negotiations.{{Sfn|Morgan|2002|pp=5–6}} Spanish emissaries noted that the pair "acted like one man and were respected by the rest".{{Sfn|Morgan|1993|p=210}} Throughout the war the two leaders got on remarkably well,{{sfnm|1a1=McGettigan|1y=2005|1p=123|2a1=McCavitt|2y=2007|2p=562}} and O'Donnell probably learned the virtue of patience from his father-in-law.<ref>{{Harvnb|Morgan|2020}}. "...in alliance with the more patient Hugh O'Neill had to learn to bide his time." {{Harvnb|McGettigan|2005|pp=122–123}}. "Red Hugh showed himself to be very willing to learn from Hugh O'Neill, especially in military matters..."</ref> Their partnership was under heavy strain by the war's end,<ref name="OA" /> and it is possible that their differences in temperament led to the disastrous failure at Kinsale.{{sfn|McGinty|2013b|p=11}} O'Donnell warned against Tyrone violating their agreements after his death: "in case the Earl O'Neill (though I know and believe he will not do so) should wish to violate the agreement and settlements arranged and made between him and me and our heirs, I hereby beg his Majesty to uphold my brother [Rory] in his rights and to retain him in his service".{{Sfn|O'Clery|O'Clery|p=cliii|Murphy|1895}}

The age difference between the two men may have been a source of conflict; Tyrone was O'Donnell's senior by 22 years.{{Sfn|McGinty|2013a|pp=20–21}} Unlike Tyrone, who was raised in the Pale and had received generous assistance from the government during his early years in Ulster, O'Donnell had a traditional Gaelic upbringing and associated the government with his time in captivity.{{Sfnm|1a1=McGinty|1y=2013a|1pp=20–21|2a1=McGinty|2y=2013b|2p=13}}

=== Generalship ===
[[File:The Image of Irelande - plate09.jpg|thumb|[[John Derricke]]'s ''[[The Image of Irelande, with a Discoverie of Woodkarne|The Image of Irelande]]'' (1581) depicts a battle between Irish forces and the Crown's army.]]
Tyrone and O'Donnell's military approaches were representative of their personalities.{{Sfn|McGinty|2013b|p=6}} Tyrone typically won out in arguments over military strategy, though not always.{{Sfn|McGinty|2013b|p=9}} Donnelly and Lucius Emerson argued that O'Donnell's success early in the war indicate a leader wise beyond his years.<ref>{{harvnb|O'Donnell|1993|p=3}}.</ref> Donnelly stated that "any statement of Red Hugh which seeks to imply that a dynamic temperament was not under control of a keen and realistic mind, is a superficial one. Within eighteen months, young and totally inexperienced, he had radically changed the situation in West Ulster; what he effected could only have been accomplished by a highly disciplined man with balanced judgment".<ref>{{harvnb|O'Donnell|1993|p=3}}. Cites {{Cite journal |last=Donnelly |first=Morwenna |date=1957 |title=Red Hugh at Dundalk |journal=Donegal Annual |pages=107–112}}</ref> O'Donnell's notes on the [[Battle of Moyry Pass]] show that he could develop complex battle plans, as he stated that it was better to attack Mountjoy's forces when they were deep in Irish territory, away from reinforcements, and in poor weather.{{sfn|McGinty|2013b|pp=11–12}}

McGettigan praises O'Donnell's leadership abilities and vision,{{Sfn|McGettigan|2005|p=|pp=78, 127}} but McCavitt notes that his failure to foresee Niall Garve's betrayal displays clear flaws in his foresight.{{sfn|McCavitt|2007|p=562}} The pitfalls of O'Donnell's aggressive approach are evident—he lost over 100 confederate soldiers in an ill-fated 1598 assault on the Blackwater Fort,{{sfn|McGinty|2013b|p=11}} and his poor foresight may have led to the defeat at Kinsale.{{sfn|McGettigan|2005|p=109}} Morgan states that credit for the victory at Curlew Pass should go to O'Rourke and McDermot rather than O'Donnell. He describes O'Donnell as a "gung-ho leader" whose military successes were limited.{{sfn|Morgan|2020}}

=== Physical appearance ===
There are no surviving portraits or visual representations of Hugh Roe O'Donnell made in his lifetime.<ref name="GR" /> Donagh O'Mooney described him as "above middle height, strong, handsome, well-built and of pleasing appearance".{{Sfn|Silke|2004|p=}} He presumably had [[red hair]],<ref name="hair">{{harvnb|O'Clery|O'Clery|Murphy|1895|p=xxxi|ps=. fn. 5.}} "Roe, i.e., Ruadh, from the colour of his complexion or hair."; {{Harvnb|Morgan|2020|ps=. "The shock of red hair, we all presume he had..."}}</ref> as adjectives such as ''ruadh'' (Irish for ''red'') were commonly employed in Irish names to refer to hair colour. This epithet would have differentiated him from kinsmen also named "Hugh O'Donnell".<ref>{{Cite book |last=Mac Mathúna |first=Liam |url=https://publishup.uni-potsdam.de/opus4-ubp/files/3908/CelticEnglishesIV_btr03.pdf |title=What's in an Irish Name? A Study of the Personal Naming Systems of Irish and Irish English |location=St Patrick's College, Dublin |pages=64–87 |archive-url=https://web.archive.org/web/20200728042919/https://publishup.uni-potsdam.de/opus4-ubp/frontdoor/deliver/index/docId/3908/file/CelticEnglishesIV_btr03.pdf |archive-date=28 July 2020}}</ref> After losing his big toes to frostbite, Hugh Roe O'Donnell would have hobbled around or travelled on horseback for the rest of his life.{{Sfn|Morgan|2002|p=10}} If discovered intact, O'Donnell's skeleton would reveal his stature and height, and technology might allow researchers to recreate his facial features.<ref name="GR" />

Although O'Donnell was fiercely patriotic, he had no aversion to foreign dress. He was described in 1601 as wearing English clothing and even going to mass in a "fine English gown".{{sfnm|1a1=Morgan|1y=2002|1p=11|2a1=McGettigan|2y=2005|2p=121}} Historian [[Francis Martin O'Donnell]] suggests that Hugh Roe O'Donnell dressed in Spanish clothing, as his grandfather Manus was known for preferring continental fashion over traditional Gaelic clothing.<ref name="2020c"/>

== Ancestry ==
{{ahnentafel|ref={{efn|Hugh McManus's parents were [[Manus O'Donnell]] and Siobhán O'Neill.<ref name="c">{{harvnb|O'Byrne|2009b|ps=, 1st paragraph.}}</ref> Fiona MacDonald's parents were [[James MacDonald, 6th of Dunnyveg]], and [[Agnes Campbell]].<ref name="ob1"/> Manus O'Donnell's father was [[Hugh Duff O'Donnell|Hugh Dubh O'Donnell]].{{sfn|Morgan|1993|pp=114–115}} Siobhán O'Neill's father was [[Conn O'Neill, 1st Earl of Tyrone|Conn Bacagh O'Neill, 1st Earl of Tyrone]].<ref name="c"/> James MacDonald's parents were [[Alexander Carragh MacDonnell, 5th of Dunnyveg]], and Catherine MacDonald.{{sfn|O'Clery|O'Clery|Murphy|1895|p=xxx}} Agnes Campbell's parents were [[Colin Campbell, 3rd Earl of Argyll]] and Jean Gordon.<ref>{{Cite journal |archive-url=https://web.archive.org/web/20220429205811/https://www.dib.ie/biography/campbell-lady-agnes-a6945 |archive-date=29 April 2022 |last=Barry |first=Judy |date=October 2009c |title=Campbell, Lady Agnes |url=https://www.dib.ie/biography/campbell-lady-agnes-a6945 |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.006945.v1|access-date=2 June 2024|url-access=subscription }}</ref>}}|1. Hugh Roe O'Donnell|2. [[Sir Hugh O'Donnell|Hugh MacManus O'Donnell, Lord of Tyrconnell]]|3. [[Iníon Dubh|Fiona MacDonald]]|4. [[Manus O'Donnell|Manus O'Donnell, Lord of Tyrconnell]]|5. Siobhán O'Neill|6. [[James MacDonald, 6th of Dunnyveg]]|7. [[Agnes Campbell]]|8. [[Hugh Duff O'Donnell|Hugh Dubh O'Donnell, Lord of Tyrconnell]]|10=10. [[Conn O'Neill, 1st Earl of Tyrone|Conn Bacagh O'Neill, 1st Earl of Tyrone]]|12=12. [[Alexander Carragh MacDonnell, 5th of Dunnyveg]]|13=13. Catherine MacDonald|14=14. [[Colin Campbell, 3rd Earl of Argyll]]|15=15. Jean Gordon|collapsed=no|align=center|boxstyle_1=background-color: #fcc;|boxstyle_2=background-color: #fb9;|boxstyle_3=background-color: #ffc;|boxstyle_4=background-color: #bfc;}}

== In popular culture ==
=== Poetry ===
* In his 1861 poem ''Eirinn a' Gul'' ("Ireland Weeping"), [[Scottish Gaelic]] poet [[William Livingston (poet)|William Livingston]] laments the loss of the heroism displayed by O'Donnell, Tyrone and Maguire.<ref>{{Cite book |url=https://archive.org/details/in.ernet.dli.2015.75098 |title=The Golden Treasury of Scottish Poetry |publisher=The Macmillan Company |year=1941 |editor-last=MacDiarmid |editor-first=Hugh |editor-link=Hugh MacDiarmid |pages=63–65}}</ref>
* [[James Clarence Mangan]]'s poem ''Ceann Salla'' dramatises O'Donnell's last words on his deathbed.<ref>{{Cite book |last1=Clarence Mangan |first1=James |author-link=James Clarence Mangan |url=https://archive.org/details/poemsjames00mangrich |title=Poems by James Clarence Mangan |last2=Mitchel |first2=John |author-link2=John Mitchel |location=New York |publication-date=1859 |pages=445–446}}</ref>
* [[Thomas MacGreevy]]'s 20th-century poem ''Aodh Ruadh Ó Domhnaill'' describes a search for O'Donnell's grave.<ref>{{Cite journal |last=O'Grady |first=Thomas |date=2020 |title=The Flesh Made Word and the Word Made Place: Thomas McGreevy's 'Aodh Ruadh O Domhnaill' |url=https://www.jstor.org/stable/10.35939/studiesirishrev.109.434.0191 |journal=Studies: An Irish Quarterly Review |volume=109 |issue=434 |pages=191–201 |issn=0039-3495 |jstor=10.35939/studiesirishrev.109.434.0191}}</ref>

=== Music ===
* ''[[Róisín Dubh (song)|Róisín Dubh]]'', which is one of Ireland's most popular political songs,<ref name="q"/><ref>{{cite book |url=https://archive.org/details/duanaire160019000000unse_t3d2 |title=Duanaire, 1600–1900: Poems of the Dispossessed |date=1981 |publisher=Dolmen Press |isbn=0-85105-364-5 |editor=Kinsella |editor-first=Thomas |page=309 |editor-last2=Ó Tuama |editor-first2=Seán}}</ref> is addressed in O'Donnell's voice to his wife [[Rose O'Neill (Irish noblewoman)|Rose]].<ref name="mangan" /> The song is reputed to have originated in the rebel encampments during the Nine Years War,<ref>{{Cite wikisource|title=Róisín Dubh|first=Pádraig|last=Pearse|author-link=Patrick Pearse|year=}} "Róisín Dubh, ''meaning "Dark Little Rose"'', written in the 16th to 19th century, is one of Ireland's most famous political songs. It is based on an older love-lyric in which the title referred to the poet's beloved rather than, as here, being a pseudonym for Ireland. The intimate tone of the original carries over into the political song. The song, the Roisin Dubh, is reputed to have originated in the camps of Red Hugh O'Donnell."</ref> and has also been attributed to a Tyrconnellian poet under O'Donnell's reign.<ref name="mangan">{{Cite book |last1=Mangan |first1=James Clarence |url=http://archive.org/details/jamesclarenceman00mangiala |title=James Clarence Mangan, His Selected Poems, with a Study|last2=Guiney |first2=Louise Imogen |date=1897 |publisher=Lamson, Wolfte, and Company |others=Digitized by the [[Internet Archive]] in 2007|pages=115 |postscript=. fn. 1.}}</ref><ref>{{Cite book |last=Mangan |first=James Clarence |author-link=James Clarence Mangan |url=http://archive.org/details/poetspoetryofmun00mang |title=The poets and poetry of Munster: a selection of Irish songs by the poets of the last century |publisher=Edward Bull |others=Boston College Libraries |editor-last=O'Daly |editor-first=John |edition=3 |location=Dublin |publication-date=1851 |pages=210–217}}</ref> Conversely, music scholar Donal O'Sullivan claims there is no evidence it was composed that early.<ref>{{Cite web |date=2024-01-15 |title=Annotation:Róisín Dubh (1) |url=https://tunearch.org/wiki/Annotation:R%C3%B3is%C3%ADn_Dubh_(1) |archive-url=https://web.archive.org/web/20240805200456/https://tunearch.org/wiki/Annotation:R%C3%B3is%C3%ADn_Dubh_(1) |archive-date=5 August 2024 |access-date=2025-02-04 |website=The Traditional Tune Archive |language=en}}</ref> The most popular version of ''Róisín Dubh'' was adapted by James Clarence Mangan from a fragmentation of an existing romantic poem to Rose.<ref name="q">{{Cite journal |last=Dalton |first=G. F. |date=1974 |title=The Tradition of Blood Sacrifice to the Goddess Éire |url=https://www.jstor.org/stable/30088757 |journal=Studies: An Irish Quarterly Review |volume=63 |issue=252 |pages=343–354 |jstor=30088757 |issn=0039-3495}}</ref> Although superficially a love song, it has been described as a patriotic song that covertly hides its nationalism via allegory.<ref name="mangan"/><ref>{{Cite journal |last=Deffenbacher |first=Kristina |date=2014 |title=Revisioning of Cultural Memory and Identity through Dialogic Mythmaking in Roddy Doyle's The Last Roundup Trilogy |url=https://www.jstor.org/stable/24332398 |journal=Nordic Irish Studies |volume=13 |issue=1 |pages=149–168 |issn=1602-124X |jstor=24332398}}</ref>
* In 1843, the [[Young Ireland]]er Michael Joseph MacCann wrote the song ''[[O'Donnell Abu|O'Donnell Abú]]'' in tribute to O'Donnell, drawing on the tradition of [[romantic nationalism]] which was popular during the era.<ref>{{Cite book |last=Ronayne |first=Liam |title=Donegal Highlands: Paintings and Stories from Northwest Donegal |publisher=Dundurn |year=1998 |pages=73|isbn=978-1-900935-07-4 |url=https://books.google.com/books?id=A98pFmN_FO4C}}</ref><ref>{{Cite journal |last1=Sturgeon |first1=Sinéad |last2=Clarke |first2=Frances |date=October 2009 |title=McCann, Michael Joseph |url=https://www.dib.ie/biography/mccann-michael-joseph-a5118 |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.005118.v1 |access-date=17 April 2025}}</ref>
* Hugh Roe O'Donnell is the subject of the Irish ballad ''If These Stones Could Speak'', as featured on the [[Phil Coulter]] album ''Highland Cathedral''.<ref>{{Cite journal |date=2000 |title=Phil Coulter's song to Donegal Castle |url=https://www.academia.edu/2453767 |journal=Ó Domhnaill Abú |issue=29 |pages=3–4 |issn=0790-7389}}</ref>
* For [[Seville Expo '92]], composer [[Bill Whelan]] composed ''The Seville Suite'' to commemorate the 390th anniversary of O'Donnell's arrival in Galicia. The suite was commissioned by the [[Taoiseach]]'s office and was performed by a 50-piece orchestra at the [[Teatro de la Maestranza]] on 4 October 1992.<ref>{{Cite web |title=The Seville Suite |url=https://billwhelan.com/work/the-seville-suite/ |archive-url=https://web.archive.org/web/20241227162938/https://billwhelan.com/work/the-seville-suite/ |archive-date=27 December 2024 |access-date=2024-11-23 |website=Bill Whelan |language=en-GB}}</ref>
[[File:FightingPrinceofDonegal Still.png|thumb|[[Peter McEnery]] portrayed O'Donnell in [[The Fighting Prince of Donegal|''The Fighting Prince of Donegal'']] (1966).]]
=== Novels ===
Novels based on O'Donnell's life (particularly centred on his escape from Dublin Castle) include:
* ''O'Donel of Destiny'' (1939) by Mary Kiely<ref>{{Cite book |last=Kiely |first=Mary |url=https://archive.org/details/odonelofdestiny0000mary |title=O'Donel of Destiny |publisher=[[Oxford University Press]] |year=1939 |location=New York}}</ref>
* ''Red Hugh, Prince of Donegal'' (1957) by Robert T Reilly<ref>{{Cite book |last=Reilly |first=Robert T |url=https://archive.org/details/redhughprinceofd0000reil_p5w5 |title=Red Hugh, Prince of Donegal |publisher=Farrar, Straus & Giroux |year=1957 |location=United States}}</ref>
* ''Red Hugh: The Kidnap of Hugh O'Donnell'' (1999) by Deborah Lisson<ref>{{Cite book |last=Lisson |first=Deborah |url=https://archive.org/details/redhugh00debo |title=Red Hugh: The Kidnap of Hugh O'Donnell |publisher=The O'Brien Press |year=1999 |isbn=0-86278-604-5 |location=Dublin}}</ref>

=== Film ===
* Hugh O'Donnell was portrayed by English actor [[Peter McEnery]] in the 1966 [[The Walt Disney Company|Disney]] adventure film ''[[The Fighting Prince of Donegal]]'', which was based on Robert T Reilly's 1957 book ''Red Hugh, Prince of Donegal''.<ref>{{Cite book|last=Klossner|first=Michael|url=https://archive.org/details/europeof150018150000klos |title=The Europe of 1500–1815 on Film and Television: A Worldwide Filmography of Over 2550 Works, 1895 through 2000 |publisher=McFarland & Company |year=2002 |isbn=0-7864-1223-2|page=139}}</ref><ref>{{Cite web |title=Fighting Prince of Donegal, The (film) |url=https://d23.com/a-to-z/fighting-prince-of-donegal-the-film/ |archive-url=https://web.archive.org/web/20240517012232/https://d23.com/a-to-z/fighting-prince-of-donegal-the-film/ |archive-date=17 May 2024 |access-date=17 May 2024 |website=D23 |language=en-US}}</ref>

=== Theatre ===
* On 15 August 1902 in [[Kilkenny]], Captain [[Otway Cuffe]] staged a single performance of a [[masque]] (titled ''Hugh Roe O'Donnell'') recounting O'Donnell's kidnapping, escape and inauguration. The masque was authored by [[Standish James O'Grady]], produced by [[Francis Joseph Bigger]], and performed by the Neophytes, a north Belfast theatre troupe. It was well-received and formed part of the [[Gaelic revival]] movement.{{sfn|Mitchell|2024|p=71}}
* O'Donnell is a major character in [[Brian Friel]]'s 1989 play ''[[Making History (play)|Making History]]'', which focuses on Tyrone reckoning with his own legacy.<ref>{{Cite journal |last=Campbell |first=Patrick J. |date=1989 |title=Brian Friel's 'Making History' |url=https://www.jstor.org/stable/29742391 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=13 |issue=2 |pages=291–293 |issn=0488-0196 |jstor=29742391}}</ref>{{sfn|Morgan|2007b|pp=62–63}} According to historian [[Jane Ohlmeyer]], "Friel portrayed the youthful Red Hugh as fiery, headstrong, quick-witted, passionate, committed to Catholicism, and to the preservation of the values, language, and culture of the Gaelic world into which he had been born and reared."<ref name="GR" /> In its original production by [[Field Day Theatre Company|Field Day]], O'Donnell was played by Peter Gowen.<ref>{{Cite web |title=Production of Making History |url=https://theatricalia.com/play/71h/making-history/production/sne |archive-url=https://web.archive.org/web/20210921211957/https://theatricalia.com/play/71h/making-history/production/sne |archive-date=21 September 2021 |access-date=2025-02-04 |website=Theatricalia}}</ref><ref>{{Cite web |title=Making History |url=https://irishplayography.com/play?playid=30598 |archive-url=https://web.archive.org/web/20240527220657/https://irishplayography.com/play?playid=30598 |archive-date=27 May 2024 |access-date=2025-02-04 |website=Playography Ireland |publisher=Irish Theatre Institute |language=en-GB}}</ref>

=== Other ===
* Several [[Gaelic sports]] clubs in County Donegal are named after Red Hugh O'Donnell, such as [[Aodh Ruadh CLG]] in [[Ballyshannon]]<ref name="history">{{cite news |last=Daly |first=Tom |title=One Hundred Years |url=http://aodhruadh.org/history/one_hundred_years.php |archive-url=https://web.archive.org/web/20241213185521/http://aodhruadh.org/history/one_hundred_years.php |archive-date=13 December 2024 |work=Aodh Ruadh CLG}}</ref><ref>{{cite news |date=15 December 2011 |title=History at Aodh Ruadh |url=http://www.donegaldemocrat.ie/news/local/history_at_aodh_ruadh_1_3341051 |archiveurl=https://web.archive.org/web/20150827143028/http://www.donegaldemocrat.ie/news/donegal-news/history-at-aodh-ruadh-1-3341051 |archivedate=27 August 2015 |accessdate=15 December 2011 |work=[[Donegal Democrat]]}}</ref> and Red Hughs [[Gaelic Athletic Association|GAA]] Club in [[Killygordon]].<ref>{{Cite web |title=Red Hughs Killygordan |url=https://donegalgaa.ie/clubs/red-hughs-killygordan/ |archive-url=https://web.archive.org/web/20250116155325/https://donegalgaa.ie/clubs/red-hughs-killygordan/ |archive-date=16 January 2025 |access-date=2025-02-04 |website=Donegal GAA |language=en}}</ref>

== Notes ==
{{Notelist}}

==References==
=== Citations ===
{{reflist|30em}}

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* {{Cite journal |last=Jones |first=Frederick M. |date=1951 |title=James Blake of Galway and the death of Red Hugh O'Donnell |url=https://books.google.com/books?id=U0Y5j5XrD5sC&q=i+have+been+informed+that |journal=[[Irish Ecclesiastical Record|The Irish Ecclesiastical Record]] |issue=75 |pages=30–38}}
* {{Cite news |last1=Jones |first1=Sam |last2=Carroll |first2=Rory |date=27 May 2020 |title=Spanish dig closes in on burial site of Irish lord Red Hugh O'Donnell |url=https://www.theguardian.com/world/2020/may/27/spanish-dig-closes-in-on-burial-site-of-irish-lord-red-hugh-odonnell |access-date=2 November 2024 |work=The Guardian |language=en-GB |issn=0261-3077}}
* {{Cite journal |last=Kelly |first=James |date=2004 |title=Review of Red Hugh O'Donnell and the Nine Years War |url=https://www.jstor.org/stable/20495169 |journal=Studia Hibernica |issue=33 |pages=160–162 |issn=0081-6477 |jstor=20495169}}
* {{Cite journal |last=Manning |first=Conleth |date=2017 |title='But You Are First to Build a Tower' — the Bermingham Tower, Dublin Castle |url=https://www.jstor.org/stable/26788441 |journal=Ulster Journal of Archaeology |volume=74 |pages=145–154 |jstor=26788441 |issn=0082-7355}}
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* {{Cite journal |last1=McCormack |first1=Anthony M. |last2=Clavin |first2=Terry |date=October 2009 |title=O'Neill, Art |url=https://www.dib.ie/biography/oneill-art-a6915 |url-status=live |journal=[[Dictionary of Irish Biography]] |doi=10.3318/dib.006915.v1 |archive-url=https://web.archive.org/web/20240513110038/https://www.dib.ie/biography/oneill-art-a6915 |archive-date=13 May 2024|url-access=subscription}}
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* {{Cite news |last=McGreevy |first=Ronan |date=24 May 2020b |title=Archaeologists are 'quite sure' they have found Red Hugh O'Donnell's burial place |url=https://www.irishtimes.com/news/ireland/irish-news/archaeologists-are-quite-sure-they-have-found-red-hugh-o-donnell-s-burial-place-1.4261382 |access-date=1 July 2024 |newspaper=The Irish Times |language=en}}
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* {{Cite journal |last=Morgan |first=Hiram |author-link= |date=2002 |editor-last=Ó Riain |editor-first=Pádraig |title=The Real Red Hugh |url=https://www.academia.edu/29979093 |journal=Irish Texts Society |location=London |issue=12 |others=Published through academia.edu |pages=1–17}}
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* {{Cite web |last=Morgan |first=Hiram |date=2 June 2020 |title=Red Hugh hunt shines light on gung-ho hero |url=https://www.independent.ie/opinion/comment/red-hugh-hunt-shines-light-on-gung-ho-hero/39252532.html |archive-url=https://archive.today/20231020100407/https://www.independent.ie/opinion/comment/red-hugh-hunt-shines-light-on-gung-ho-hero/39252532.html |archive-date=20 October 2023 |access-date=2025-02-13 |website=Irish Independent |language=en}}
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* {{cite web |last=O'Donnell |first=Francis Martin |date=4 Jun 2020a |title=We should avoid being 'holier than Pope' about Red Hugh |url=https://www.independent.ie/opinion/letters/we-should-avoid-being-holier-than-pope-about-red-hugh/39258949.html |access-date=2025-02-18 |website=Irish Independent |language=en}}
* {{Cite book |last1=O'Donovan |first1=John |url=https://archive.org/details/ordnancesurveyle00john/mode/2up |title=Ordnance survey letters: Letters containing information relative to the antiquities of the County of Donegal collected during the progress of the Ordnance Survey in 1835 |last2=Herity |first2=Michael |date=2000 |publisher=Four Masters Press |isbn=978-1-903538-00-5 |location=Dublin}}
* {{Cite journal |last=O'Neill |first=James |date=April 2015 |title=Death in the lakelands: Tyrone's proxy war, 1593–4 |url=https://www.academia.edu/13884177 |journal=[[History Ireland]] |volume=23 |issue=2 |pages=14–17 |jstor=43235412}}
* {{Cite journal |last=O'Neill |first=James |date=2016 |title=Maguire's revolt but Tyrone's war: proxy war in Fermanagh 1593–4 |url=https://www.jstor.org/stable/48568218 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=26 |issue=1 |pages=42–68 |issn=0488-0196 |jstor=48568218}}
* {{Cite book |last=O'Neill |first=James |title=The Nine Years War, 1593-1603: O'Neill, Mountjoy and the Military Revolution |date=2017 |publisher=Four Courts Press |isbn=978-1-84682-754-9 |location=Dublin |url=https://archive.org/details/nineyearswar15930000onei}}
* {{Cite journal |last=O'Neill |first=James |date=2020 |title=Red Hugh O'Donnell, Tirconnell's missing lord—: but for how long? |url=https://www.jstor.org/stable/26934602 |journal=[[History Ireland]] |volume=28 |issue=4 |pages=6–7 |jstor=26934602 |issn=0791-8224}}
* {{Cite journal |last=Power |first=Gerald |date=2010 |title=Darren McGettigan, Red Hugh O'Donnell and the Nine Years War |url=https://www.brepolsonline.net/doi/10.1484/J.PERIT.1.102404 |journal=[[Peritia]] |language=en |volume=21 |pages=382–384 |doi=10.1484/J.PERIT.1.102404 |issn=0332-1592|url-access=subscription}}
* {{Cite journal |last=Purcell |first=Mary |date=1966 |title=Red Hugh O'Donnell |url=https://www.jstor.org/stable/27659140 |journal=The Furrow |volume=17 |issue=4 |pages=255–257 |jstor=27659140 |issn=0016-3120}}
* {{Cite journal |last=Silke |first=John J. |date=1988 |title=The Last Will of Red Hugh O'Donnell |url=https://www.jstor.org/stable/20496218 |journal=Studia Hibernica |issue=24 |pages=51–60 |doi=10.3828/sh.1988.24.3 |issn=0081-6477 |jstor=20496218|url-access=subscription }}
* {{Cite ODNB |title=O'Donnell, Hugh [Aodh Ó'Dónaill; known as Red Hugh, Hugh Roe, Aodh Rua], lord of Tyrconnell (1572–1602), chieftain and rebel |url=https://www.oxforddnb.com/display/10.1093/ref:odnb/9780198614128.001.0001/odnb-9780198614128-e-20554 |date=2004 |language=en |doi=10.1093/ref:odnb/20554 |last=Silke |first=John J.|archive-date=4 March 2025|archive-url=https://web.archive.org/web/20250304094936/https://www.oxforddnb.com/display/10.1093/ref:odnb/9780198614128.001.0001/odnb-9780198614128-e-20554}}
* {{Cite book |last=Starke |first=Shirley |url=https://archive.org/details/completeeBook/page/3/mode/2up |title=Red Hugh: The Story of Hugh Roe O'Donnell |date=1984 |publisher=The Aodh Ruadh Ó Domhnaill Guild |location=[[Valley City, North Dakota]]}}
* {{Cite journal|author-link=Paul Walsh (priest)|last=Walsh |first=Paul |date=1922 |title=Hugh Roe O'Donnell's Sisters |url=https://archive.org/details/s5p1irishecclesi19dubluoft |journal=[[The Irish Ecclesiastical Record]] |location=Dublin |volume=XIX |pages=358–364}}
* {{Cite journal |last=Walsh |first=Paul |date=1929 |title=The Book of O'Donnell's Daughter |url=https://archive.org/details/irishecclesiasti33dubl/page/564/mode/2up |journal=[[The Irish Ecclesiastical Record]] |volume=XXXIII |pages=561–575 |location=Dublin}}
* {{Cite book |url=https://archive.org/details/g-004983 |title=The Will and Family of Hugh O'Neill, Earl of Tyrone [with an Appendix of Genealogies] |publisher=Sign of the Three Candles |year=1930 |editor-last=Walsh |editor-first=Paul |location=Dublin}}
* {{Cite journal |last=Walsh |first=Paul |date=1939 |title=Historical Criticism of the Life of Hugh Roe O'Donnell |url=https://www.jstor.org/stable/30005953 |journal=Irish Historical Studies |volume=1 |issue=3 |pages=229–250 |doi=10.1017/S0021121400030819 |issn=0021-1214 |jstor=30005953|url-access=subscription }}
* {{Cite journal |last=Walsh |first=Micheline Kerney |date=1990 |title=Archbishop Magauran and His Return to Ireland, October 1592 |url=https://www.jstor.org/stable/29742439 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=14 |issue=1 |pages=68–79 |doi=10.2307/29742439 |issn=0488-0196 |jstor=29742439|url-access=subscription }}
* {{Cite book |last=Walsh |first=Micheline Kerney |author-link= |url=https://archive.org/details/exileofirelandhu0000wals |title=An exile of Ireland, Hugh O'Neill, Prince of Ulster |date=1996 |publisher=Four Courts Press |isbn=978-1-85182-234-8 |location=Dublin}}
* {{Cite book |last=Webb |first=Alfred |author-link=Alfred Webb |url=https://archive.org/details/compendiumofiris00webb |title=A Compendium of Irish Biography |date=1878 |publisher=M. H. Gill & Son |postscript=. "Maguire, Hugh". pp. 324–325. "O'Donnell, Hugh Roe". pp. 391–393.}}{{refend}}

== Further reading ==
{{Refbegin|30em|indent=yes}}
===Primary sources===
* {{cite AFM}}
* ''Calendar of the State Papers relating to Ireland''. Full scans at [[Internet Archive]]: [[iarchive:calendarofstatep3158grea/page/n9/mode/2up|1586 – 1588, July]]; [[iarchive:calendarofstatep04greauoft/page/n7/mode/2up|1588, August – 1592, September]]; [[iarchive:calendarofstatep5159grea/page/n9/mode/2up|1592, October – 1596, June]]; [[iarchive:calendarireland06greauoft/page/n5/mode/2up|1596, July – 1597, December]]; [[iarchive:1895calendarofstatep07greauoft/page/n5/mode/2up|1598, January – 1599, March]]; [[iarchive:calendarireland08greauoft/page/n5/mode/2up|1599, April – 1600, February]]; [[iarchive:1903calendarofstatep09greauoft/page/n5/mode/2up|1600, March – October]]; [[iarchive:1905calendarofstatep10greauoft/page/n5/mode/2up|1 November, 1600 – 31 July, 1601]]; [[iarchive:1912calendarofstatep11greauoft/page/n3/mode/2up|1601-3]]
* {{Citation |title=Dispatches and Letters between Ireland and Spain |url=https://cartlann.org/dicilimt/2021/01/Dispatches-Letters-between-Ireland-and-Spain-4.pdf |archive-url=https://web.archive.org/web/20240616142710/https://cartlann.org/dicilimt/2021/01/Dispatches-Letters-between-Ireland-and-Spain-4.pdf |archive-date=16 June 2024 |publisher=An Chartlann}}
* {{Cite book |last=Meehan |first=Charles Patrick |author-link=Charles Patrick Meehan |url=http://archive.org/details/fatefortunesofhu00meehrich |title=The fate and fortunes of Hugh O'Neill, earl of Tyrone, and Rory O'Donel, earl of Tyrconnel; their flight from Ireland, their vicissitudes abroad, and their death in exile |date=1868 |location=Dublin |publisher=J. Duffy}}
* {{Cite book |last= |first= |url=https://books.google.com/books?id=dAf6Eo_F4isC |title=Docwra's Derry: A Narration of Events in North-west Ulster 1600-1604 |date=2003 |publisher=Ulster Historical Foundation |isbn=978-1-903688-22-9 |editor-last=O'Donovan |editor-first=John |language=en |orig-year=1849 |editor-last2=Kelly |editor-first2=William}}
* {{Cite book |url=https://archive.org/details/annalsofkingdomo06ocleuoft/annalsofkingdomo06ocleuoft/page/2384/mode/2up |title=Annals of the Kingdom of Ireland by the Four Masters from the Earliest Period to the Year 1616 |publisher=Hodges, Smith and Co. |others=Digitized by the [[Internet Archive]] in 2007 with funding from Microsoft Corporation |year=1854 |editor-last=O'Donovan |editor-first=John |edition=2nd |volume=VI |location=Dublin}}
* {{cite book|url=https://celt.ucc.ie/published/T100080.html|editor-last=Walsh|editor-first=Paul|editor-link=Paul Walsh (priest)|title=Beatha Aodha Ruaidh Uí Dhomhnaill|others=Electronic edition compiled by Benjamin Hazard|translator-last=Walsh|translator-first=Paul|publisher=CELT: Corpus of Electronic Texts}}

===Secondary sources===
* {{Cite book |publisher=Longman, Green, Longman and Roberts |location=Paternoster Row, London |date=1861 |title=Vicissitudes of Families |pages=125–148 |last=Burke |first=Bernard |others=Ulster King of Arms}}
* {{Cite book |last=Falls |first=Cyril |url=https://books.google.com/books?id=lu4mmpO-MnUC |title=Elizabeth's Irish Wars |date=1997 |publisher=Syracuse University Press |isbn=978-0-8156-0435-8 |language=en}}
* {{Cite book |title=A View of the Legal Institutions, Honorary Hereditary Offices, and Feudal Baronies established in Ireland |last=Lynch |first=William |publisher=Longman, Rees, Orme, Brown, and Green |location=Paternoster Row, London |year=2016 |orig-year=Originally published 1830 |isbn=978-1-357-67945-3 |page=190}}
* {{Cite journal |last=Mac Cuinneagáin |first=Conall |date=1994 |title=Aodh Ruadh Ó Domhnaill - what caused his death? |journal=Donegal Annual |volume=46 |pages=18–22}}
* {{cite EB1911|wstitle=O'Donnell|display=|volume=20|pages=6–8|first=Ronald John|last=McNeill|author-link=Ronald McNeill, 1st Baron Cushendun|date=1911}}
* {{Cite journal |last=Morgan |first=Hiram |date=October 2005 |title=Gaelic lordship and Tudor conquest: Tír Eoghain, 1541–1603 |url=https://www.historyireland.com/gaelic-lordship-and-tudor-conquest-tir-eoghain-1541-1603/ |url-status=dead |journal=[[History Ireland]] |volume=13 |issue=5 |jstor=27725334 |pages=38–43}}
* {{Cite news |last=Murray |first=Eavan |date=13 September 2022b |title='I know where it's not...': Historian hints at new clue in hunt for the missing remains of Red Hugh O'Donnell |url=https://www.belfasttelegraph.co.uk/news/republic-of-ireland/i-know-where-its-not-historian-hints-at-new-clue-in-hunt-for-the-missing-remains-of-red-hugh-odonnell/41983289.html |access-date=2025-05-12 |language=en-GB |issn=0307-1235}}
* {{Cite journal |last=O Domhnaill |first=Adhamhnan |title=Simancas Castle Address |journal=Journal of the County Donegal Historical Society |pages=94–96}}
* {{Cite journal |last=O'Donnell |first=Eunan |date=2000 |orig-date=1941 |title=Niall Garbh O'Donnell – A man more sinned against than sinning |journal=Journal of the County Donegal Historical Society}}
* {{Cite journal |last=O'Donnell |first=Vincent |date=2001b |title=Was Red Hugh married? |journal=Ó Domhnaill Abú |issue=30 |pages=4–7}}
* {{Cite book |last=Silke |first=John J. |url=https://archive.org/details/kinsalespanishin0000silk_z6b5 |title=Kinsale; the Spanish intervention in Ireland at the end of the Elizabethan wars |date=1970 |location=New York |publisher=Fordham University Press |others=Digitized by the [[Internet Archive]] in 2022 with funding from Kahle/Austin Foundation |isbn=978-0-8232-0865-4}}
*{{cite web|url=https://historia-hispanica.rah.es/biografias/32913-red-hugh-odonnell|archive-url=https://web.archive.org/web/20241204092508/https://dbe.rah.es/biografias/61978/red-hugh-odonnell |archive-date=4 December 2024|title="Red" Hugh O'Donnell|language=es|website=dbe.rah.es}}
{{refend}}


==See also==
* [[O'Donnell dynasty]]
* [[Irish kings]]
* [[Tyrconnell]]
* [[County Donegal]]
* [[Kings of Tir Connaill]]
* [[Early Modern Ireland 1536-1691]]
* [[Nine Years' War (Ireland)]]

== External links ==
* [http://www.ucc.ie/celt/published/G100080 The Life of Aodh Ruadh Ó Domhnaill, transcribed from the Book of Lughaidh Ó Clérigh]
* [http://valkyriepub.tripod.com/guild.htm The Hugh O'Donnell Guild]
* [https://web.archive.org/web/20190724172727/http://www.araltas.com/features/odonnell/ The O'Donnell Coat of Arms and Family History]

{{s-start}}
{{s-hou|[[O'Donnell dynasty|O'Donnell clan]]}}
{{s-reg}}
{{succession box
| before = [[Sir Hugh O'Donnell|Hugh MacManus O'Donnell]]
| title = [[Kings of Tír Chonaill|Lord of Tyrconnell]]
| after = [[Rory O'Donnell, 1st Earl of Tyrconnell|Rory O'Donnell]]
| years = 1592–1602|
}}
{{s-end}}

{{Authority control}}

{{DEFAULTSORT:O'Donnell, Hugh Roe}}
[[Category:1572 births]]
[[Category:1602 deaths]]
[[Category:16th-century Irish people]]
[[Category:17th-century Irish people]]
[[Category:16th-century Roman Catholics]]
[[Category:17th-century Roman Catholics]]
[[Category:Irish chiefs of the name]]
[[Category:Irish escapees]]
[[Category:Irish people of Scottish descent]]
[[Category:Irish rebels]]
[[Category:Irish Roman Catholics]]
[[Category:Irish Servants of God]]
[[Category:Kings of Tír Chonaill]]
[[Category:O'Donnell dynasty|Hugh]]
[[Category:People of Elizabethan Ireland]]
[[Category:People of the Nine Years' War (Ireland)]]
[[Category:16th-century Irish nobility]]