The Winningest Trainers in Kentucky Derby History

Posted by Evan Chronis on Thu, Sep 5, 2019 @ 13:30 PM

Behind every great Kentucky Derby® winning horse is a trainer who put in countless hours of work that will never be seen by the general public. 

As a Derby winning horse and jockey revel in victory as the garland of roses is draped upon them, the victorious trainer stands in the background and celebrates the victory outside of the spotlight. 

That's not to say that trainers aren't ones for the fame and glory — 5-time Derby winner Bob Baffert is arguably the biggest name in the sport — but often they are put on the back burner as a winning horse ascends into fame. 

But there's a catch.

A horse can only win the Kentucky Derby once, but a trainer can claim victory in the two-minute dash multiple times throughout their careers. 

But which trainer prepared a horse for a conquest at Churchill Downs® the most?

We've broken down the winningest trainers in Kentucky Derby history. 

Kentucky Derby Trainers


Ben Jones

6 1938, 1941, 1944, 1948, 1949, 1952

Lawrin ('38), Whirlaway ('41), Pensive ('44), Citation ('48), Ponder ('49), Hill Gail ('52)

Bob Baffert

5 1997, 1998, 2002, 2015, 2018

Silver Charm ('97), Real Quiet ('98), War Emblem ('02), American Pharoah ('15), Justify ('18)

D. Wayne Lukas

4 1988, 1995, 1996, 1999

Winning Colors ('88), Thunder Gulch ('95), Grindstone ('96), Charismatic ('99)

Herbert J. Thompson

4 1921, 1926, 1932, 1933

Behave Yourself ('21), Bubbling Over ('26), Burgoo King ('32), Brokers Tip ('33)

Jim Fitzsimmons

3 1930, 1935, 1939

Gallant Fox ('30), Omaha ('35), Johnstown ('39)

Max Hirsch

3 1936, 1946, 1950

Bold Venture ('36), Assault ('46), Middleground ('50)

Nick Zito

2 1991, 1994

Strike the Gold ('91), Go for Gin ('94)

Lazaro Barrera

2 1976, 1978

Bold Forbes ('76), Affirmed ('78)

Henry Forrest

2 1966, 1968

Kauai King ('66), Forward Pass ('68)

LeRoy Jolley

2 1975, 1980

Foolish Pleasure ('75), Genuine Risk ('80)

Jimmy Jones

2 1957, 1958

Iron Liege ('57), Tim Tam ('58)

Lucien Laurin

2 1972, 1973

Riva Ridge ('72), Secretariat ('73)

Horatio Luro

2 1962, 1964

Decidedly ('62), Northern Dancer ('64)

Woody Stephens

2 1974, 1984

Cannonade ('74), Swale ('84)

Charlie Whittingham

2 1986, 1989

Ferdinand ('86), Sunday Silence ('89)


Join Derby Experiences at the 2020 Kentucky Derby

Will Bob Baffert lead another horse to history at the 146th Kentucky Derby, or will a new trainer take the stage to produce a champion? Watch it unfold live at Churchill Downs with an Official Ticket Package from Derby Experiences. 

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About the Bloggers

Kristen Doolan

Kristen Doolan was born and raised a Florida State Seminole. Making her way from Florida to North Carolina, Kristen achieved her B.S. in Business Administration, Marketing at The University of North Carolina Wilmington. She is an avid traveler, college football addict, beach bum and loves spending time with her family and friends. 


Jazzy Morgan

Jazzy Morgan is originally from London, England and a die-hard Manchester United Fan. She grew up in Connecticut and made the move down south in 2011 where she attended Winthrop University and received her B.S. in Family & Consumer Sciences and a minor in Marketing. Jazzy enjoys traveling, working out, reading her monthly Vogue & Cosmo and keeping up with fashion trends.


Evan Chronis

Evan Chronis was born in Omaha, Nebraska but has made his home in south Charlotte for almost two decades. A Tar Heel born and bred, Evan received his B.A in Media and Journalism from UNC-Chapel Hill. He is an avid Boston sports fan thanks to his family’s New England roots, and a fanboy of Wes Anderson films.