Hobbies Card Games & Gambling A List for the Top Winning Kentucky Derby Jockeys Kentucky Derby jockeys with the most wins Share PINTEREST Email Print Peter Willert / EyeEm / Getty Images Card Games & Gambling Sports Gambling Gambling Strategies & Tips Casinos Poker Blackjack By Cindy Pierson Dulay Cindy Pierson Dulay is a horse-racing expert, journalist and award-winning photographer. She is the owner and editor of Horse-Races.Net. our editorial process Cindy Pierson Dulay Updated January 29, 2019 Winning the Kentucky Derby is the big prize all owners and trainers lust after. Jockeys vie to ride the best horses and to guide the winner home. Winning the Derby is indisputably the highlight of a jockey's career, and a select few have won this race more than once. Here's a list of elite jockeys who have won the Kentucky Derby three times or more. 01 of 10 Eddie Arcaro Bettmann Archive / Getty Images Eddie Arcaro rode in the Kentucky Derby 21 times, the last time in 1961. He won with five of them. His Derby winners were Lawrin in 1938, Whirlaway in 1941, Hoop Jr. in 1945, Citation in 1948 and Hill Gail in 1952. Arcaro was a member of the Racing Hall of Fame. His career spanned 30 years from 1931 to 1961. He retired with a total of 24,092 mounts and 4,779 wins and died in 1997 at the age of 81. 02 of 10 Bill Hartack Robert Riger / Getty Images Bill Hartack got his five Kentucky Derby winners out of only 12 rides. His Derby winners were Iron Liege in 1957, Venetian Way in 1960, Decidedly in 1962, Northern Dancer in 1964 and Majestic Prince in 1969. Hartack was a member of the Racing Hall of Fame and rode from 1953 through 1974. He retired with a total of 21,535 mounts and 4,272 wins, dying in 2007 in Texas. 03 of 10 Bill Shoemaker Corbis via Getty Images / Getty Images Bill Shoemaker rode in the Kentucky Derby more times than any other jockey: 26 races from 1952 to 1988. He won four times. His Derby winners were Swaps in 1955, Tomy Lee in 1959, Lucky Debonair in 1965 and Ferdinand in 1986. But he might be most remembered for his loss in the Derby aboard Gallant Man in 1957. He misjudged the finish and stood up in the irons too soon, allowing Bill Hartack and Iron Liege to pass them and win. His riding career spanned 41 years from 1949 to 1990. He retired with a total of 40,350 mounts and 8,833 wins. Shoemaker was tragically paralyzed in a car accident a year after he retired. He died in 2003 at the age of 72. 04 of 10 Isaac Murphy Wikimedia Commons/Creative Commons 3.0 Isaac Murphy rode in the Kentucky Derby 11 times from 1877 to 1893. One of many African American jockeys to ride in that era, he won three times. His Derby winners were Buchanan in 1884, Riley in 1890 and Kingman in 1891. Murphy is a member of the Racing Hall of Fame. He rode from 1876 through 1895 and retired with a total of 1,538 mounts and 530 wins, an impressive 33-percent rate. He died of pneumonia at age 34 and is buried at the Kentucky Horse Park in Lexington next to Man o' War. 05 of 10 Earl Sande Bettmann Archive / Getty Images After beginning his career as a bronco buster, Earl Sande rode in the Kentucky Derby eight times between 1918 and 1932 and won three times. His Derby winners were Zev in 1923, Flying Ebony in 1925 and Gallant Fox in 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. 06 of 10 Angel Cordero Jr. Matthew Stockman / Getty Images Angel Cordero Jr. rode in the Kentucky Derby 17 times from 1968 to 1991 and he won three times. His Derby winners were Cannonade in 1974, Bold Forbes in 1976 and Spend a Buck in 1985. Cordero was the first Puerto Rican inducted into the Racing Hall of Fame and he also won the Eclipse Award for Outstanding Jockey in 1982, 1983 and 1985. He rode from 1960 to 1992 and retired with a total of 38,646 mounts and 7,057 wins. 07 of 10 Gary Stevens Sean M. Haffey / Getty Images Gary Stevens rode in the Kentucky Derby eight times from 1985 through 2005 and he won three times. His Derby winners were Winning Colors in 1988, Thunder Gulch in 1995 and Silver Charm in 1997. Stevens is a member of the Racing Hall of Fame and rode from 1979 through 2005 when he retired with a total of 27,594 mounts and 4,888 wins. But Stevens wasn't done yet. In a move that Stevens admitted was "middle-age crazy," he returned to racing in 2013 after years as a horse racing analyst for major networks including NBC. He was the regular rider of Beholder in 2016, an Eclipse Award finalist. Then he announced in December that he would undergo hip replacement surgery, adding emphatically that he "had not retired." 08 of 10 Kent Desormeaux Kent Desormeaux runs number 8. Sean M. Haffey / Getty Images Kent Desormeaux has ridden in the Kentucky Derby 17 times from 1988 to 2011. He won his third Derby in 2008 aboard Big Brown. His two other winners were Real Quite in 1998 and Fusaichi Pegasus in 2000. Desormeaux was elected to the Racing Hall of Fame in 2006. He battled alcohol addiction and entered rehab in 2016 after guiding Exaggerator, trained by his brother Keith, to a win in the Belmont Stakes. Exaggerator has since retired, but Desormeaux is still racing. 09 of 10 Calvin Borel Rob Carr / Getty Images Calvin Borel has been a regular on the Kentucky and Midwest circuits for over 25 years. He's ridden in the Kentucky Derby only nine times, but he is the only jockey to ever win three Derbies in a four-year span and he finished third in the year he didn't win. His first Kentucky Derby win came in 2007 aboard Street Sense. He next won with Mine That Bird in 2009, a huge upset by a long shot. He came back to win again in 2010 with Super Saver. He retired from racing in March 2016 because he said he had "fractured every bone in his body at one time or another." But, like Gary Stevens, Borel found that he wasn't particularly comfortable with retirement and he was back in the saddle in August. His nickname is "Bo-rail" because he has a way of guiding his mounts to the rail to save ground almost against impossible odds. Borel is also known for his ebullient celebrations after winning. 10 of 10 Victor Espinoza Eclipse Sportswire / Getty Images Victor Espinoza is the newest member of the three-plus Derby winning club. He has been a regular rider in California for over two decades. He picked up the mount aboard War Emblem in 2002 when the colt was purchased by Prince Ahmed Salman and transferred to trainer Bob Baffert. They won the Derby and Preakness together but didn't take the Triple Crown due to a poor start in the Belmont. Espinoza had to wait until 2014 and California Chrome before winning the Derby again. They then won the Preakness but checked in fourth in the Belmont for trainer Art Sherman. As the regular rider of American Pharoah, again for Baffert, Espinoza went into the 2015 Belmont with the Triple Crown again on the line. This time the jockey-and-horse team did not disappoint, breaking the 37-year drought since the last Triple Crown. Will Some Keep on Winning? Tune in on the first weekend in May to find out if any of these jockeys who are still active will add to their win totals.