From Bill Hartack to Bill Shoemaker, these 5 jockeys have defined Kentucky Derby standard
The owners foot the bills. Trainers prepare horses to race. But, ultimately, it's the jockeys who must guide a thoroughbred to victory once it leaves the starting gate. In the 150 years of the Kentucky Derby, the prestigious race has had its share of iconic jockeys. Of the many who have vied to reach the Winner's Circle at Churchill Downs, only 11 jockeys have done so three (or more) times.
Here’s a list of five jockeys, in alphabetical order, who have defined the Kentucky Derby heading into the 150th running of the race May 4.
Eddie Arcaro
Eddie Arcaro became the first jockey to win the race five times, a record he still shares. His five Derby winners were Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948) and Hill Gail (1952). Whirlaway and Citation went on to complete the Triple Crown in the years they won the Derby. Arcaro, who won nearly 4,800 races in his career, holds the record for Triple Crown wins by a jockey, with 17 (a record six victories in the Preakness Stakes and a record-matching six wins in the Belmont Stakes to go along with his record-tying five Derby triumphs).
Calvin Borel
Calvin Borel has three wins in the Derby, and he made them count: He became the first — and to date, still the only — jockey in history to capture the Run for the Roses three times in a four-year span. Borel did so with Street Sense (2007), Mine That Bird (2009) and Super Saver (2010). His only other Triple Crown victory came in 2009, aboard the filly Rachel Alexandra, in the Preakness.
Bill Hartack
Bill Hartack shares the Derby mark for wins alongside Arcaro, with five apiece. But while Arcaro competed in the race 21 times, Hartack had just 12 mounts. His five victories — 1957 (Iron Liege), 1960 (Venetian Way), 1962 (Decidedly), 1964 (Northern Dancer) and 1969 (Majestic Prince) — unfolded over a 12-year stretch, which also included a second-place finish. Hartack also won the Preakness three times (1956, 1964, 1969) and the Belmont (1960) once in his Hall of Fame career.
Isaac Murphy
In the earliest days of the Derby, no jockey was more successful than Isaac Murphy. Born in Fayette County to an enslaved person, Murphy had 11 mounts in the Run for the Roses. He set the standard, becoming the first jockey to win the Derby in consecutive years (1890 and 1891, with Riley and Kingman, respectively). And he also was the first jockey with three Derby victories; his first win came in 1884 aboard Buchanan. It wasn't until Arcaro's victory in 1948, with legendary Citation, that a jockey surpassed Murphy's Derby win total. He also finished second once to go along with two third-place finishes in the Derby. "Isaac Murphy is still considered by many in the industry to be the greatest jockey ever," Chris Goodlett, the Kentucky Derby Museum's senior director of curatorial and educational affairs, told The Courier Journal earlier this year.
Bill Shoemaker
Bill Shoemaker had four Derby wins — and nearly had far more. In 26 starts in the Run for the Roses, he had a remarkable 11 top-three finishes; he took second three times and third on four other occasions. His Derby wins came in 1955 (Swaps), 1959 (Tomy Lee), 1965 (Lucky Debonair) and 1986 (Ferdinand). Upon the Hall of Famer's retirement in 1990, Shoemaker had accumulated a record-setting 8,833 victories, with 11 in Triple Crown races. In addition to his four Derby wins, he captured the Belmont five times and the Preakness twice.
Honorable mention
Angel Cordero Jr.: In a Hall of Fame career featuring more than 7,000 wins, Cordero placed first in the Derby three times (and had one runner-up showing). He completed the personal Triple Crown sweep with a pair of Preakness victories and one triumph in the Belmont (1976 with Bold Forbes).
Kent Desormeaux: Possessing a long track record of success in the Derby, Desormeaux has three wins, a runner-up and four third-place finishes in 22 career starts. A Hall of Famer, Desormeaux also claims three Preakness victories and a Belmont win (in 2009 with Summer Bird).
Victor Espinoza: He has three wins in the Derby: 2002 (War Emblem), 2014 (California Chrome) and 2015 (American Pharoah). The most recent doubles as the most notable: Espinoza helped American Pharoah capture the Triple Crown, ending a drought that had lasted since Affirmed's sweep of the races in 1978.
Oliver Lewis: As the winner of the first Derby, aboard Aristides, Lewis, a Black jockey, always will have a place in the history of the Run for the Roses — and horse racing as a whole.
Earl Sande: While Sande competed in the Derby just eight times, he claims three victories (1923, 1925 and 1930) and two runner-up finishes. His most well-known mount: Gallant Fox, who in 1930 became the second winner of the Triple Crown. Upon Sande's retirement in 1953, he had won more than 26% of his races (968 of 3,673). He had nine wins in Triple Crown races; along with his three Derby triumphs, Sande had five victories in the Belmont and one in the Preakness.
Gary Stevens: A three-time Derby winner (1988 with Winning Colors, 1995 with Thunder Gulch and 1998 with Silver Charm), Stevens retired in 2018 as one of the winningest jockeys of all time. Among his nearly 5,200 victories are nine Triple Crown wins, three each across the Derby, Preakness and Belmont.
John Velazquez: The most recent addition to the Derby's three-win club among jockeys, Velazquez was on board for victories in 2011 (Animal Kingdom), 2017 (Always Dreaming) and 2020 (Authentic). He also has two Belmont wins (2007 and 2012) and one Preakness victory (2023 with National Treasure). In terms of earnings, Velazquez is the winningest jockey of all time, totaling more than $478 million.
Reach Kentucky men’s basketball and football reporter Ryan Black at rblack@gannett.com and follow him on X at @RyanABlack.
This article originally appeared on Louisville Courier Journal: Top 5 Kentucky Derby jockeys who have won the most at Churchill Downs
