The Kentucky Derby is the big prize all owners of 3-year-old thoroughbreds lust after. For a jockey to win this race is the highlight of his career, and only a select few have won this race more than once. Here are those elite jockeys who have won the Kentucky Derby three times or more.
1. Eddie Arcaro
Eddie Arcaro 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), Citation (1948), Hill Gail (1952). Arcaro is a member of the Racing Hall of Fame and his career spanned 30 years, from 1931 to 1961. He retired with a total of 24,092 mounts and 4,779 wins.
2. Bill Hartack
Bill Hartack got his five Kentucky Derby winner 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. He retired with a total of 21,535 mounts and 4,272 wins.
Bill Shoemaker rode in the Kentucky Derby more times than any other jockey, 26 in all from 1952 to 1988 and 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. This allowed Bill Hartack and Iron Liege to pass them and win. His riding career was a lengthy 41 years, from 1949 to 1990. He retired with a total of 40,350 mounts and 8,833 wins.
4. Isaac Murphy
Isaac Murphy rode in the Kentucky Derby 11 times from 1877 to 1893 and won three times, one of many black jockeys to ride in that era. 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 retired with a total of 1,538 mounts and 530 wins, an impressive 33% win rate. He died of pneumonia at age 34 and is buried at the Kentucky Horse Park in Lexington next to Man O'War.
5. Earl Sande
Earl Sande rode in the Kentucky Derby eight times from 1918 to 1932 and won three times. 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. He retired with a total of 3,673 mounts and 968 wins.
Review of Triple Crown Winner, Earl Sande's biography
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. He retired with a total of 38,646 mounts and 7,057 wins.
7. Gary Stevens
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 retired with a total of 27,594 mounts and 4,888 wins. He is also known for playing the role of jockey George Woolf in the movie "Seabiscuit" in 2003.
Kent Desormeaux has ridden in the Kentucky Derby 17 times from 1988 to 2011 and won his third Derby in 2008. His Derby winners were: Real Quite (1998), Fusaichi Pegasus (2000), and Big Brown (2008). Desormeaux was elected to the Racing Hall of Fame in 2006 and is still riding. Through May 9, 2008, he had 4,971 wins and $205,886,219 in earnings. The latest figure I could find for total mounts was 23,898 as of December 31, 2006.
9. Calvin Borel
Calvin Borel is another of the great Louisiana Cajun riders and has been a regular on the Kentucky and mid-west circuit for over 25 years. Only recently has he come to light as a top Kentucky Derby jockey, with only 9 rides in it so far, but he is the only jockey to ever win 3 Derbies in a 4 year span and he finished 3rd in the year he didn't win. Best know for his ebullient celebrations after winning, his first Kentucky Derby win came in 2007 with Street Sense. He next won with huge longshot Mine That Bird in 2009 then came back to win again in 2010 with Super Saver. He still doesn't get as many big rides outside Kentucky, but watch out for him at Churchill Downs, especially if he gets on the rail!