Gallant Man
Two of Shoemaker's most noted rides were in the Kentucky Derby. He lost the 1957 Kentucky Derby aboard Gallant Man, when he stood up in the stirrups too soon, having misjudged the finish line, where Gallant Man finished second to Iron Liege, ridden by Bill Hartack. At the 1986 Kentucky Derby, Shoemaker became the oldest jockey ever to win the race (at age 54) aboard the 18-1 outsider Ferdinand. The following year, he rode Ferdinand to a victory over Alysheba in the Breeders' Cup Classic; Ferdinand later captured Horse of the Year honors.