Ranking the Best Jockeys in Kentucky Derby History

Fact Checked by Nate Hamilton
Jockeys racing in the Kentucky Derby

The first Saturday in May is almost upon us and a field of 20 will leave from the gates after 6 p.m. ET in the greatest two-plus minutes in sports. 
You must have good pedigree, talent and a little bit of luck to capture the most famous race annually in thoroughbred racing history. You also better have a good jockey as well to navigate through the other 19 horses to the finish line and history.

With Kentucky sports betting working its way to the state, the Derby will have company in the wagering game next year. 

Who Are The Top Kentucky Derby Jockeys Ever?

Utilizing Wikipedia.com, BetKentucky.com gathered the jockeys that have won the most Kentucky Derbys in their career from the start of the race in 1875 to last year in 2022. 
Four jockeys are still active on the list, and all four are vying to get to the top three all-time. 
Here is what we found out:

RankJockey # of Wins Years Won
T-1Bill Hartack51957, 1960, 1962, 1964, 1969
T-1Eddie Arcaro51938, 1941, 1945, 1948, 1952
3 Bill Shoemaker4 1955, 1959, 1965, 1986
T-4 Earl Sande 31923, 1925, 1930
T-4 Angel Cordero Jr. 31974, 1976, 1985
T-4 Isaac Murphy 31984, 1990, 1991
T-4 Gary Stevens 31988, 1995, 1997
T-4 Kent Desormeaux 31998, 2000, 2008
T-4 Calvin Borel 32007, 2009, 2010
T-4 Victor Espinoza32002, 2014, 2015
T-4John R. Velazquez32011, 2017, 2020

Read up on all the top Kentucky sportsbook apps before sports betting is officially live in Kentucky.

Tied For Greatness

Eight jockeys are tied with three victories all-time, one behind legendary Bill Shoemaker, who sits along in third place with four (1955, 1959, 1965, 1969).

The four active jockeys tied at three victories are:

  • Calvin Borel (2007, 2009, 2010)
  • Kent Desormeaux (1998, 2000, 2008)
  • Victor Espinoza (2002, 2014, 2015)
  • John R. Velazquez (2011, 2017, 2020)

Borel is still active and is currently riding at Oaklawn Park.

Desormeaux is also active as he returned to riding a few months ago after dealing with personal issues.  

Who Can We Expect To See This Year?

As of today, Desormeaux or Espinoza do not have a mount for the 149th running of the Kentucky Derby, but there are still a few horses that don't have confirmed mounts yet, so that could change. Espinoza did ride Skinner in his last race, but he would need scratches to get into the field of 20.   

Velazquez, known to many as “Johnny V,” is the most recent jockey to enter the jockey leaderboard. While it is not 100% confirmed, Velazquez is expected to retain the mount aboard Reincarnate, trained by Tim Yakteen and owned by SF Racing, Starlight Racing and Madaket Stables. 
In his last race, he finished third in the Arkansas Derby at 4-1 odds, posting a Beyer Figure of 86. 
The Kentucky Derby & Kentucky Oaks (Friday, May 5) Post-Position Draws will take place May 1 at the Aristides Lounge at Churchill Downs (2-3 p.m. ET). 
As for the remaining Triple Crown races, The Preakness Stakes will be on May 20th and The Belmont Stakes will be on June 10th.

Start handicapping! 

Maybe next year's Kentucky Derby we will have all the best Kentucky sportsbook promos for you to use!



Lou Monaco is a contributing writer for BetKentucky.com. Lou had been East Coast Scene columnist for Gaming Today in Las Vegas since June 2019, covering the East Coast sportsbook scene with emphasis on NJ and PA. He also currently is a part-time writer for the high school sports department for NJ Advanced Media (NJ.com) in Iselin, NJ. Lou has over 30 years sports experience with previous stints at ESPN SportsTicker, Daily Racing Form and Oddschecker.

Cited by leading media organizations, such as: