10 Top Winning Kentucky Derby Jockeys of All Time

May 3rd, 2024

Only the best jockeys are chosen to ride the premier three-year-old Thoroughbreds who earn a spot in the annual Kentucky Derby (G1).

Here we recount the riders who have celebrated triumph inside the Winner's Circle most, as we list the 10 winningest Kentucky Derby jockeys of all time.

Third-most Kentucky Derby wins: 3

a. John Velazquez

Winning Derby horses: Animal Kingdom (2011), Always Dreaming (2017), Authentic (2020)

John Velazquez was supposed to ride Uncle Mo in the 2011 Derby, but after the top contender scratched and Animal Kingdom's rider got injured, Velazquez picked up the mount for the 30-1 longshot and clinched his first Derby win with the chestnut colt.

The all-time leader in career earnings by a jockey, Velazquez became the third oldest rider (age 48) to win the Derby with Authentic in 2020. He also crossed the line first for a fourth time in 2021 with the Bob Baffert-trained Medina Spirit, but the dark bay colt was later disqualified for testing positive for a banned substance.

b. Victor Espinoza

Winning Derby horses: War Emblem (2002), California Chrome (2014), American Pharoah (2015)

Victor Espinoza won the Preakness S. (G1) with all three of his Derby winners, but had to wait until age 41 to finally achieve the Triple Crown.

A year after finishing fourth in the Belmont S. (G1) aboard California Chrome, Espinoza rode to a 5 1/2-length victory in the Belmont with American Pharoah, who broke a 37-year Triple Crown drought in 2015.

c. Calvin Borel

Winning Derby horses: Street Sense (2007), Mine That Bird (2009), Super Saver (2010)

In 2007, Calvin Borel kicked off an unprecedented run, winning three of the next four Kentucky Derby races.

His 2009 victory aboard 50-1 longshot Mine That Bird marked one of the biggest upsets in the most exciting two minutes in sports. That year, he also won the Kentucky Oaks with Rachel Alexandra and later that month guided her to a historic Preakness win over second-place finisher Mine That Bird, ridden that day by Mike Smith.

With his Preakness victory, Borel became the first rider to win the first two jewels of the Triple Crown on different mounts.

d. Kent Desormeaux

Winning Derby horses: Real Quiet (1998), Fusaichi Pegasus (2000), Big Brown (2008)

Only Bill Shoemaker and Smith have more rides in the Derby than Kent Desormeaux's 22. The Hall of Fame jockey first won with Real Quiet, who went on to claim the 1998 Preakness but lost by a nose in the Belmont to Victory Gallop. 

Desormeaux prevailed in the Preakness three times, the Belmont once, and owns the U.S. record for most races won (598) in a single year, in 1989.

e. Gary Stevens

Winning Derby horses: Winning Colors (1988), Thunder Gulch (1995), Silver Charm (1998)

Tied for the second-most Derby mounts (22), Gary Stevens won the race three times, aboard Bob Baffert-trained Silver Charm in 1998, and two D. Wayne Lukas trainees, Thunder Gulch and Winning Colors.

The famed rider just missed out on a Triple Crown with Derby and Preakness champion Silver Charm, who lost by 1 3/4 lengths to Touch of Gold in the Belmont.

Stevens' first Derby win was particularly notable, as Winning Colors became the third and most recent filly to win the Kentucky Derby.

f. Angel Cordero Jr.

Winning Derby horses: Cannonade (1974), Bold Forbes (1976), Spend a Buck (1985)

The first Puerto Rican jockey to win all three of the American Classic Races, Angel Cordero Jr. is another three-time Derby winner. He celebrated his first Derby win at the age of 31 and his last at 42. Only four jockeys have been older at the time of their final Derby victories.

Cordero Jr. also triumphed in the Preakness twice (1980 and 1984) and finished first in the Belmont with Derby winner Bold Forbes.

g. Earle Sande

Winning Derby horses: Zev (1923), Flying Ebony (1925), Gallant Fox (1930)

With eight career rides in the Derby, from 1918-1932, Earle Sande failed to finish in the money just twice.

He won aboard Zev, Flying Ebony, and Triple Crown winner Gallant Fox, while he finished second to the first Triple Crown winner Sir Barton in 1919 and was second aboard Osmand in 1927.

h. Isaac Murphy

Winning Derby horses: Buchanan (1884), Riley (1890), Kingman (1891)

One of six jockeys to win the Derby back to back, Isaac Murphy accomplished all three of his victories at 1 1/2 miles, the original distance of the race, before it was shortened to 1 1/4 miles in 1896.

Murphy is also one of seven jockeys to win the Kentucky Oaks and Derby in the same year. He achieved the feat by winning aboard Buchanan on May 16, 1884 and three days later won with Modesty in the race for three-year-old fillies.

Second-most Kentucky Derby wins: 4

Bill Shoemaker

Winning Derby horses: Swaps (1955), Tomy Lee (1959), Lucky Debonair (1965), Ferdinand (1986)

Bill Shoemaker's first Kentucky Derby win in 1955 robbed jockey Eddie Arcaro of what could have been a record sixth victory in the Run for the Roses. Instead, Shoemaker guided Swaps to a 1 1/2-length win at 1 1/4 miles, beating Arcaro's mount Nashua, and went on to claim the garland of roses three more times.

Shoemaker may have ended with five Derby victories but for misjudging the finish line and standing up in his stirrups too early aboard Gallant Man in 1957, leading to a second-place finish behind Iron Liege.

Shoemaker has the second-most Derby mounts (26) and became the oldest jockey to win the Derby, at age 54, with Ferdinand in 1986.

Most Kentucky Derby wins: 5

a. Bill Hartack

Winning Derby horses: Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), Majestic Prince (1969)

During a career that spanned two decades, Bill Hartack rode in only 12 Kentucky Derbys but tied the record for most victories (five) in just his ninth appearance.

While he never won the Triple Crown, he did guide Majestic Prince and Northern Dancer to Preakness wins, but finished second with the former in the Belmont and placed third with Northern Dancer in the final leg of the Triple Crown.

b. Eddie Arcaro

Winning Derby horses: Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948), Hill Gail (1952)

With a total of 21 career Kentucky Derby mounts, Hall of Fame jockey Eddie Arcaro finished first five times in the Run for the Roses, beginning in 1938 with Lawrin and ending with Hill Gail in 1952.

With the exception of Hoop Jr., trained by Ivan H. Parke, Arcaro paired up with six-time Derby-winning trainer Ben Jones for all his other Derby victories.

Arcaro also finished second in the Derby three times and placed third twice, while he has the most Preakness victories by a jockey (six) and is tied for the most in Belmont history (six).

Arcaro is also the only jockey to win the Triple Crown twice, securing it aboard Whirlaway and Citation in 1941 and 1948, respectively.

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