Editing Middleground (section)

==Racing career==
Middleground was ridden throughout his career by 16-year-old [[jockey|apprentice jockey]] [[William Boland|Bill Boland]], and he was trained by [[Max Hirsch]], both future [[National Museum of Racing and Hall of Fame|U.S. Hall of Fame]] inductees.

As a two-year-old in 1949, Middleground won the [[Hopeful Stakes]] and came third in the [[Arlington Futurity]].

The following year, Middleground started the year with second-place finishes both the [[Withers Stakes]] and [[Wood Memorial]].

He then won the [[Kentucky Derby]], only the second horse to win it with an apprentice jockey after his sire Bold Venture who won with jockey Ira Hanford. Five time Kentucky Derby winning jockey [[Eddie Arcaro]] had the chance to ride Middleground, but he chose to ride [[Hill Prince]] instead, who finished second.

After the Kentucky Derby, Middleground finished second to Hill Prince after a rough trip in the [[Preakness Stakes]], and won the [[Belmont Stakes]].

As a three-year-old he also won the [[Leonard Richards Stakes]].

In the 1950 [[Jerome Handicap]], Middleground broke a bone in his foot and was retired.