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From Eddie Arcaro to John Velazquez, here are the winningest jockeys in Derby history

Brooks Holton, Louisville Courier Journal
·2 min read

Javier Castellano is one of the most successful jockeys of all time, with more than $398 million in career earnings.

It took him 16 tries to win the Kentucky Derby. Finally doing so, he said, was a dream come true.

"It's not (an) easy job; we all go up and down," the Maracaibo, Venezuela, native told reporters at Churchill Downs after riding Mage to victory in Derby 149 last year. "I never give up; I always try to do the right thing, work hard and try to find the right horse to win the race."

Ahead of the 150th Run for the Roses on May 4, The Courier Journal has put together a list of the winningest jockeys in the race's storied history.

It's rare company; only 11 have reached the winner's circle three or more times.

Two men, Eddie Arcaro and Bill Hartack, lead the group with five victories apiece.

John Velazquez would be vying for a seat at the table this go-around, but Medina Spirit's disqualification in 2021 cost him a fourth Derby win.

Here's a look at the all-time greats:

Eddie Arcaro

Jockey Eddie Arcaro holds up five fingers for each of the five winners he had ridden in the Kentucky Derby, after bringing Hill Gail home to victory in the 1952 race.
Jockey Eddie Arcaro holds up five fingers for each of the five winners he had ridden in the Kentucky Derby, after bringing Hill Gail home to victory in the 1952 race.

Derby mounts: 21

First-place finishes: 1938 (Lawrin), 1941 (Whirlaway), 1945 (Hoop Jr.), 1948 (Citation) and 1952 (Hill Gail)

Second-place finishes: Three

Third-place finishes: Two

Bill Hartack

Jockey Bill Hartack brought Majestic Prince to victory in the 1969 Kentucky Derby.
Jockey Bill Hartack brought Majestic Prince to victory in the 1969 Kentucky Derby.

Derby mounts: 12

First-place finishes: 1957 (Iron Liege), 1960 (Venetian Way), 1962 (Decidedly), 1964 (Northern Dancer) and 1969 (Majestic Prince)

Second-place finishes: One

Third-place finishes: N/A

Bill Shoemaker

Derby mounts: 26

First-place finishes: 1955 (Swaps), 1959 (Tomy Lee), 1965 (Lucky Debonair) and 1986 (Ferdinand)

Second-place finishes: Three

Third-place finishes: Four

Isaac Murphy

Isaac Murphy, winning jockey of three Kentucky Derby races: 1884, 1890 and 1891.
Isaac Murphy, winning jockey of three Kentucky Derby races: 1884, 1890 and 1891.

Derby mounts: 11

First-place finishes: 1884 (Buchanan), 1890 (Riley) and 1891 (Kingman)

Second-place finishes: One

Third-place finishes: Two

Earle Sande

In 1930, Gallant Fox became the second Triple Crown winner. Earl Sande, who rode Gallant Fox in the Derby, was the jockey on Billy Kelly, who finished second to Sir Barton, the first Triple Crown winner, in the 1919 Derby.
In 1930, Gallant Fox became the second Triple Crown winner. Earl Sande, who rode Gallant Fox in the Derby, was the jockey on Billy Kelly, who finished second to Sir Barton, the first Triple Crown winner, in the 1919 Derby.

Derby mounts: Eight

First-place finishes: 1923 (Zev), 1925 (Flying Ebony) and 1930 (Gallant Fox)

Second-place finishes: Two

Third-place finishes: N/A

Angel Cordero Jr.

Jockey Angel Cordero Jr. reacts at the finish line after guiding Bold Forbes to victory in the 1976 Kentucky Derby.
Jockey Angel Cordero Jr. reacts at the finish line after guiding Bold Forbes to victory in the 1976 Kentucky Derby.

Derby mounts: 17

First-place finishes: 1974 (Cannonade), 1976 (Bold Forbes) and 1985 (Spend a Buck)

Second-place finishes: One

Third-place finishes: N/A

Gary Stevens

Jockey Gary Stevens congratulates 1988 Kentucky Derby winner Winning Colors after the filly was presented with the blanket of roses.
Jockey Gary Stevens congratulates 1988 Kentucky Derby winner Winning Colors after the filly was presented with the blanket of roses.

Derby mounts: 22

First-place finishes: 1988 (Winning Colors), 1995 (Thunder Gulch) and 1998 (Silver Charm)

Second-place finishes: Three

Third-place finishes: One

Kent Desormeaux

Derby mounts: 22

First-place finishes: 1998 (Real Quiet), 2000 (Fusaichi Pegasus) and 2008 (Big Brown)

Second-place finishes: One

Third-place finishes: Four

Calvin Borel

Jockey Calvin Borel celebrates after winning the 2009 Kentucky Derby aboard long shot Mine That Bird.
Jockey Calvin Borel celebrates after winning the 2009 Kentucky Derby aboard long shot Mine That Bird.

Derby mounts: 12

First-place finishes: 2007 (Street Sense), 2009 (Mine That Bird) and 2010 (Super Saver)

Second-place finishes: N/A

Third-place finishes: One

Victor Espinoza

Jockey Victor Espinoza celebrates atop American Pharaoh after winning the 141st Kentucky Derby in 2015.
Jockey Victor Espinoza celebrates atop American Pharaoh after winning the 141st Kentucky Derby in 2015.

Derby mounts: 10

First-place finishes: 2002 (War Emblem), 2014 (California Chrome) and 2015 (American Pharoah)

Second-place finishes: N/A

Third-place finishes: One

John Velazquez

Authentic and jockey John Velazquez are draped with the blanket of roses after winning the 146th Kentucky Derby in 2020.
Authentic and jockey John Velazquez are draped with the blanket of roses after winning the 146th Kentucky Derby in 2020.

Derby mounts: 25

First-place finishes: 2011 (Animal Kingdom), 2017 (Always Dreaming) and 2020 (Authentic)

Second-place finishes: Two

Third-place finishes: N/A

Reach Louisville men's basketball reporter Brooks Holton at bholton@gannett.com and follow him on X at @brooksHolton.

This article originally appeared on Louisville Courier Journal: Kentucky Derby jockeys with most wins at Churchill Downs