Famous Kentucky Derby Jockeys

Eddie Arcaro was the first jockey to have five Kentucky Derby wins, with two of those horses eventual Triple Crown winners. His Derby wins were with Lawrin in 1938, Whirlaway in 1941, Hoop Jr. in 1945, Citation in 1948 and Hill Gail in 1952. In all, Arcaro rode in the Kentucky Derby 21 times from 1935 to 1961. His career spanned 31 years, in which he won 549 stakes events and rode in a total of 4,779 races for a 19.80 winning percentage. Arcaro won more than $30 million in purses and broke several records of the era for most money earned. Arcaro was inducted into the Hall of Fame in 1958, with a total of 24,092 mounts throughout his career.

Bill Hartack was a Pennsylvania-born jockey that began as an exercise rider before competing in races. Hartack made his Kentucky Derby debut in 1956, where he rode Fabius for a second place finish. It was the following year that Hartack won his first Kentucky Derby aboard Iron Liege with a finishing time of 2:02 1/5. Hartack went on to win the Derby four more times, tying him with Eddie Arcaro for five Kentucky Derby wins. His winners include Majestic Prince in 1969, Northern Dancer in 1964, Decidedly in 1962, and Venetian Way in 1960. Hartack was inducted into the Hall of Fame in 1959, with 21,535 mounts, 4,272 wins, and a 19.80 winning percentage.

With 26 appearances in the Kentucky Derby from 1952 to 1988, Bill Shoemaker set a record for most Derby appearances. He won four times, with his winners being Swaps in 1955, Tomy Lee in 1959, Lucky Debonair in 1965, and Ferdinand in 1986. Ferdinand was an 18-1 longshot to win the Run for the Roses. Shoemaker may have had a fifth win, but he misjudged the finish in the 1957 Derby and ultimately lost to Bill Hartack after standing up too soon. The jockey had a career that spanned from 1949 to 1990, with 40,350 mounts and 8,833 wins. A 1958 Hall of Fame inductee, Shoemaker had a winning percentage of 21.90%.

A Lexington, KY native, Isaac Burns Murphy started out as an apprentice to a horse owner at the age of 14. He became one of the many successful African-American jockeys of the time period, riding in the Kentucky Derby a total of 11 times from 1877 to 1893. Murphy was the first jockey to ever win the Run for the Roses three times, winning with Buchanan (1884), Riley (1890), and Kingman (1891). Riding from 1876 through 1895, Murphy had a total of 1,538 mounts and 530 wins throughout his jockey career. In 1955, Murphy was inducted into the National Museum of Racing's Hall of Fame. In 1995, the National Turf Writers Association presented the first Isaac Murphy Award, an honor given to the jockey with the highest winning percentage for the year in the U.S.

Victor Espinoza was born May 23rd, 1972, in Hidalgo, Mexico, before moving to the United States in 1990. Espinoza’s first big break was not necessarily the Kentucky Derby, but another stakes races hosted at Churchill Downs – the 2000 Breeders’ Cup Distaff. It was in 2001 that Espinoza rode in his first Derby, where he finished third place on the Bob Baffert-trained Congaree. The following year, Espinoza was aboard War Emblem when he won first place in the Kentucky Derby. Espinoza went on to win the Kentucky Derby two more times, once with California Chrome in 2014 and then with American Pharoah in 2015. Espinoza is one of the only jockeys to have three Triple Crown opportunities, with American Pharoah finally getting the win. Espinoza was inducted into the Hall of Fame in 2017, with 21,694 mounts, 3,320 wins, and $193,380,176 in earnings in counting.

Earl Sande was born in South Dakota but began his riding career in New Orleans. Borel rode in the Kentucky Derby eight times between 1918 and 1932, with three wins and a Triple Crown title with Gallant Fox in 1930. His other Derby wins were with Zev in 1923 and Flying Ebony in 1925. One of Sande’s mounts outside of the Run of the Roses was Man o' War, which the jockey considered his best. Sande was considered the leading jockey in the nation in 1921, 1923, and 1927, and was welcomed into the Hall of Fame in 1955. Sande had a total of 968 wins, 3,673 mounts, and a 26.40 winning percentage before retiring to become a trainer.

Calvin Borel’s riding career spanned over 25 years, with the Louisiana native beginning his professional career in 1983. Borel rode in the Kentucky Derby nine times with three wins from 2007 to 2010. He was the first jockey to amass three Derby wins within a four-year time period. Borel’s 2009 victory with Mine That Bird was one of the most memorable moments of the Run for the Roses, as the horse was a 50-1 longshot on the tote board. The jockey also secured first place finishes in the race with Street Sense in 2007 and Super Saver in 2010. Borel had a total of 33,984 over his career and had 5,031 wins for a 15.00 winning percentage.

Kent Desormeaux was born in Louisana but resided in Maryland and Southern California throughout his career. Desormeaux rode in the Kentucky Derby seventeen times, with his first appearance in 1988. He had his first Kentucky Derby win in 1998 while riding Real Quiet, with the jockey-horse duo coming extremely close to winning the Triple Crown. Desormeaux then won the Kentucky Derby with Fusaichi Pegasus in 2000 and Big Brown in 2008. The National Museum of Racing’s Hall of Fame initiated Desormeaux in 2004. He has 31,251 starts and 5,954 wins in counting as of 2018.

Born on March 6, 1963, Gary Stevens began his professional career in his home state of Idaho. Stevens made his Kentucky Derby debut in 1985, but his first winning mount was on filly Winning Colors in 1988. It was in 1995 that Stevens won both the first and third jewels of the Triple Crown with Thunder Gulch. Stevens won the Derby with Silver Charm in 1997 and was only 1 3/4th lengths from winning the Triple Crown. In all, Stevens rode in the Kentucky Derby eight times from 1985 through 2005. Stevens became a Hall of Famer in 1997, with over 29,205 starts and 5,150 wins to date.

Angel Cordero, Jr. was born in Santurce, Puerto Rico in 1942. Though known as the “King of Saratoga”, Cordero also had multiple successes in the Run for the Roses. He first won with Cannonade in 1974 and then Bold Forbes in 1976. It was nine years later that Cordero won with Spend A Buck by a margin of 5 ¼ lengths. Cordero appeared in the Kentucky Derby a total of seventeen times from 1968 to 1991. He was the first Puerto Rican to receive Hall of Fame honors, with 38,646 mounts and 7,057 wins. After his retirement in 1992, Cordero became a jockey agent.