<P> 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 . </P>
<P> 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 . </P>
who is the oldest jockey to win the kentucky derby
who is the oldest jockey to win the kentucky derby
Shoemaker
Shoemaker