Kentucky Derby History: Jockeys With Most Wins

With the 150th edition of The Run For The Roses in 2024, the jockeys with the most wins in Kentucky Derby history have done so on contenders and longshots in Derby odds, alike. In this piece, we'll look at the three winningest riders in the first jewel of horse racing's Triple Crown.

History could be made this time as John Velazquez rides big favorite Fierceness in 2024. Johnny V is one victory away from tying for second-most wins by a jockey in Kentucky Derby history.

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Not sure how to place bets? We can show you how to bet on the Kentucky Derby online.

Kentucky Derby odds: all-time winningest jockeys

T1. Eddie Arcaro (5)

Arcaro was the first jockey to ride five Kentucky Derby winners and two American Triple Crown titles. In 31 years as a Thoroughbred's horseman, he produced 549 victories in stakes events, a grand total of 4,779 races, and over $30,000,000 in purses. On Feb. 20, 1958, he entrenched himself as the third jockey — behind Sir Gordon Richards and Johnny Longden — to achieve 4,000 career wins at Santa Anita Race Track in California.

T1. Bill Hartack (5)

Hartack nabbed his first Derby trophy with Iron Liege in 1957. More than a decade later, he delivered the same result with Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969). Hartack rode in America until 1974, tallying 4,272 victories via 21,535 mounts. That equated to winning almost 20 percent of his races. He followed that up with a stint in Hong Kong from 1978-80.

3. Bill Shoemaker (4)

Shoemaker is the oldest rider (54) and one of the youngest (23) riders to win the Kentucky Derby. His final victory came with Ferdinand in 1986, guiding the winning horse through a tiny opening along the rail. After retiring from horse racing in 1990, Shoemaker notched his record-setting 8,833 races, including 11 American Triple Crown races.

Will John Velazquez tie for second?

Medina Spirit's disqualification in 2021 cost him a fourth Derby win, so Velazquez will not be vying for a spot atop the jockey leaderboard.

He's in an eight-way tie for third place, having notched three career victories at Churchill Downs. Authentic helped Velazquez claim his last win in the 2020 Kentucky Derby, holding off pre-race favorite Tiz The Law.

No. 17 Fierceness, whom Velazquez will ride in the 150th renewal of The Most Exciting Two Minutes in Sports, projects to be the favorite on the 2024 Kentucky Derby morning-line odds board.

Nevertheless, Fierceness isn't in great historical company after being upended in the Holy Bull on Feb. 3. Kentucky Derby favorites, who lost in their three-year-old campaign, are just 1-for-17 among first-place finishes. The other nine winning favorites went 26-for-26 in their pre-Derby starts.

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