Big Brown won the 2008 Kentucky Derby after starting from the far outside post. He was assigned post position 20, which was the widest starting position in that year’s field.
Ridden by Kent Desormeaux and trained by Richard Dutrow Jr., Big Brown overcame the difficult draw to win by four and three-quarter lengths. The victory made him the first horse since Clyde Van Dusen in 1929 to win the Derby from post 20.
Big Brown later won the Preakness Stakes but was pulled up in the Belmont Stakes after losing his chance to complete the American Triple Crown. His Derby is sometimes confused with Mine That Bird’s 2009 victory, another famous upset, but Big Brown was the 2008 champion.