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Top Kentucky Derby Winners

Winning the Kentucky Derby is the highlight of a jockey's carrer.  Only a few have won this famous race more than once.
 

Eddie Arcaro - 5 time Kentucky Derby Winner

Eddie Arcaro - 5 time winner of the Kentucky Derby   Eddie Arcaro, nicknamed "The Master", rode in the Kentucky Derby 21 times, his last in 1961, and won with five of them. His Derby winners were: Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Arcaro considered Citation the best of all (1948), Hill Gail (1952). Arcaro is a member of the Racing Hall of Fame and his career spanned 30 years, from 1931 to 1961. Eddie Arcaro Hall of Fame Bio
     
     

Bill Hartack - 5 time Kentucky Derby Winner

Bill Hartack - 5 time Kentucky Derby Winner   Bill Hartack got his five Kentucky Derby wins, two in record time, from only 12 tries. His Derby winners were: Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), Majestic Prince (1969). Hartack is a member of the Racing Hall of Fame and rode from 1953 to 1974. Bill Hartack Hall of Fame Bio
     
     

Willie Shoemaker - 4 time Kentucky Derby Winner

Willie Shoemaker - 4 time Kentucky Derby Winner   William Shoemaker rode in the Kentucky Derby 26 times - more times than any other jockey, from 1952 to 1988 he won four times. His Derby winners were: Swaps (1955), *Tomy Lee (1959), Lucky Debonair (1965), Ferdinand (1986). He may be remembered more for his loss in the Derby aboard Gallant Man in 1957, when he misjudged the finish and stood up in the irons too early allowing Bill Hartack and Iron Liege to pass and win the race. With 18-1 longshot Ferdinand, Shoemaker became the oldest jockey to win the Kentucky Derby (at age 54) in 1986. His riding career was 41 years, from 1949 to 1990.  William Shoemaker Hall of Fame Bio
     
     

Isaac Murphy - 3 time Kentucky Derby Winner

Isaac Murphy - 3 time Kentucky Derby Winner  

Isaac Murphy rode in the Kentucky Derby 11 times - from 1877 to 1893, and he was the first jockey to win three times. Many consider Isaac Murphy the greatest American jockey of all time. He was the first jockey to be elected to the Hall of Fame in 1955. His Derby winners were: Buchanan (1884), Riley (1890), Kingman (1891). Murphy is a member of the Racing Hall of Fame and rode from 1876 to 1895. He died of pneumonia at age 34 and is buried at the Kentucky Horse Park in Lexington next to Man O'War. Isaac Murphy Hall of Fame Bio

     
     

Earl Sande - 3 time Kentucky Derby Winner

Earl Sande - 3 time Kentucky Derby Winner   Earl Sande rode in the Kentucky Derby eight times from 1918 to 1932 and won three times. Sande rode the best horses of his day. His Derby winners were: Zev (1923), Flying Ebony (1925), Gallant Fox (1930). Sande is a member of the Racing Hall of Fame and rode from 1918 to 1953. Earl Sande Hall of Fame Bio
 
 

Angel Cordero, Jr. - 3 time Kentucky Derby Winner

Angele Cordero, Jr. - 3 time Kentucky Derby Winner   Angel Cordero Jr. rode in the Kentucky Derby 17 times from 1968 to 1991 and won three times. His Derby winners were: Cannonade (1974), Bold Forbes (1976), Spend a Buck (1985). Cordero is a member of the Racing Hall of Fame and rode from 1960 to 1992. Angel Cordero, Jr. Hall of Fame Bio
     
     

Gary Stevens - 3 time Kentucky Derby Winner

Gary Stevens - 3 time Kentucky Derby Winner   Gary Stevens rode in the Kentucky Derby eight times from 1985 to 2005 and won three times. His Derby winners were: Winning Colors (1988), Thunder Gulch (1995), Silver Charm (1997). Stevens is a member of the Racing Hall of Fame and rode from 1979 to 2005. He is also known for playing the role of jockey George Woolf in the movie "Seabiscuit" in 2003. Gary Stevens Hall of Fame Bio
     
     

Kent Desormeaux - 3 time Kentucky Derby Winner

Kent Desormeaux - 3 time Kentucky Derby Winner   Kent Desormeaux has ridden in the Kentucky Derby 15 times from 1988 to 2008. His Derby winners were: Real Quite (1998), Fusaichi Pegasus (2000), and Big Brown (2008).  In 1989, he rode 598 winners, a record that still stands. Kent Desormeaux Hall of Fame Bio
     
     

Calvin Borel - 3 time Kentucky Derby Winner

Calvin Borel - 3 time Kentucky Derby Winner   Calvin Borel's win in 2010 made him the first jockey to ever win the Derby 3 times in a 4-year span. Calvin Borel's second Kentucky Derby victory of his career in 2009 was on Mine That Bird, an upset win at odds of 50-1; the second biggest upset in Derby history behind Donerail; and was the biggest winning margin of 6-3/4 lengths in Derby history since 1946. The day before that winning run, he rode Rachel Alexandra to a triumph in the Kentucky Oaks and decided to stay with her in the Preakness, where she defeated males, including Mine That Bird, in 2009. In doing so, Borel became the first jockey to win the first two jewels of the Triple Crown on different mounts. 

Victor Espinoza - 3 time Kentucky Derby Winner

Victor Espinoza Victor Espinoza won the Triple Crown in 2015 riding American Pharoah. His three Kentucky Derby wins are: 2002 on War Emblem, 2014 on California Chrome, and in 2015 on American Pharoah. In those same years and with the same horses, three times he won the Preakness Stakes. He was the first jockey in history to enter the Belmont Stakes with a third opportunity to win the Triple Crown, finally winning the elusive honor in 2015 on American Pharoah—becoming the oldest jockey and first Hispanic jockey to win the Triple Crown.
     
 
 

 

Click here for a complete listing of

Kentucky Derby Winners from 1875 to present 

 

 


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