Kentucky Derby Jockeys—The Ride of a Lifetime

Winning the Kentucky Derby is the pinnacle of every jockey's racing career. To find the right horse and then provide it with the perfect ride on the first Saturday in May can certainly be viewed as a fitting culmination of a lifetime of work.

In the 137 runnings of the Kentucky Derby, first run in 1837, only nine jockeys have won it at least three times. That list, as astute racing fans probably know, is topped by the great Bill Hartack. The Hall of Fame rider won an unprecedented five Kentucky Derby's, all between 1957-1969. During that time, Hartack's most famous ride was in 1964 aboard Northern Dancer, who would set a new Kentucky Derby speed record (later broken by Secretariat) and would go on to be named that year's champion 3-year-old colt.

Hartack's other Derby victories were aboard Iron Liege (1957), Venetian Way (1960), Decidedly (1962) and Majestic Prince (1969).

Eddie Arcaro with five and Bill Shoemaker with four are the only other jockeys with more than two Kentucky Derby wins.

Arcaro, who won his first Kentucky Derby aboard Lawrin in 1938, holds a pair of Triple Crown riding records that are likely to never be broken. The Hall of Fame rider is the only jockey to sweep the Triple Crown on two separate occasions—with Whirlaway in 1941 and Citation in 1948—and has the most overall wins in Triple Crown races with 17.

Shoemaker's four Kentucky Derby wins were spread over 41 years, beginning with Swaps in 1955 and ending with Ferdinand in 1986, which came at the age of 54 to make him the oldest jockey to ever win the Kentucky Derby. “The Shoe” also won the Derby in 1959 with Tomy Lee and 1965 with Lucky Debonair.

Interestingly, Shoemaker also provided one of the most infamous rides in Derby history. In 1957 aboard Gallant Man, Shoemaker inexplicably misjudged the finish line while on the lead in deep stretch and the error allowed Bill Hartack and Iron Liege to sneak by for the victory.

Among the six jockeys with three Kentucky Derby wins to their credit, two are still active—Calvin Borel and Kent Desormeaux.

Borel recently accomplished an unprecedented feat when winning three Kentucky Derbys in a four-year period. Known as “Bo-Rail” because of his fearless rides along the inside, Borel won his first Derby with with Street Sense in 2007 and added wins in 2009 and 2010 with Mine that Bird and Super Saver, respectively.

Desormeaux won his first Kentucky Derby aboard Real Quiet in 1998 and added the 2000 Derby with Fusaichi Pegasus. He won his third Kentucky Derby aboard Big Brown in 2008.

There are only 20 jockeys who can ride in the Kentucky Derby each year. The reality is that most professional jockeys will never ride in the world’s most recognized horse race. Here’s your chance to not only jockey in the Kentucky Derby, but do it on some of the most recognized thoroughbreds throughout history. There is an exciting race horse game out there that allows you to not only breed, train and race your horse against other players, but actually jockey your horse through competitive tou
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