Top Kentucky Derby Trainers

The Kentucky Derby at Churchill Downs is the big prize all owners of 3-year-old thoroughbreds lust after. For a trainer to win this race is the highlight of his career, and only a select few have won this race more than once. Here are those elite trainers who have won the Kentucky Derby twice or more. While most are long gone and part of history, a few are still training and could have a horse in this year's Kentucky Derby.

1
Ben A. Jones

Kentucky Derby horse racing
Kentucky Derby History. Cindy Pierson Dulay

Ben Jones is the only trainer so far to have six Kentucky Derby winners: Lawrin (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), Hill Gail (1952). He trained from 1909 through 1953 and all of his Derby winners except the first came during the period he trained for the powerful Calumet Farm stable. While he was the trainer of record for this last three Derby winners, he was semi-retired since 1946 and trained with his son, Jimmy Jones.

Wikipedia bio

2
Bob Baffert

horse racing Bob Baffert
Trainer Bob Baffert on his pony Smokey. Cindy Pierson Dulay

Bob Baffert has also trained four Kentucky Derby winners so far in 25 starters, as well as a Triple Crown winner: Silver Charm (1997), Real Quiet (1998), War Emblem (2002), and American Pharoah (2015).  Baffert has won 12 Triple Crown races and has trained 11 champions to win a total of 15 Eclipse Awards. All 4 of his Kentucky Derby winners went on to win the Preakness but the first three failed to complete the Triple Crown, losing in the Belmont Stakes, while American Pharoah went all the way to win the Triple Crown. Baffert is a also a member of the Horse Racing Hall of Fame.

American Pharoah wins the 2015 Kentucky Derby
War Emblem wins the 2002 Derby
Real Quiet wins the 1998 Derby
Silver Charm wins the 1997 Derby
Baffert's Derby starters

3
D. Wayne Lukas

D. Wayne Lukas horse racing
Trainer D. Wayne Lukas. Cindy Pierson Dulay

D. Wayne Lukas has had four Kentucky Derby winners so far: Winning Colors (1988), Thunder Gulch (1995), Grindstone (1996), Charismatic (1999). Lukas has been training since 1974 and has conditioned more champions than any other trainer in history. Most dominant in the 1980's and 90's, he has been more low profile recently. In fact, 2001 was the first time in 20 years that he didn't have a horse entered in the Derby. So far he as had 47 horses to run in the Derby, the last being Mr. Z in 2015. His legacy lives on in his assistants who have gone out successfully on their own, such as Todd Pletcher, Kiaran McLaughlin, and Dallas Stewart.  Lukas is also a member of the Horse Racing Hall of Fame.

Charismatic wins the 1999 Derby
Wikipedia bio
 

4
Henry J. Thompson

horse racing kentucky derby
The Kentucky Derby Trophy. Cindy Pierson Dulay

Henry Thompson had four Kentucky Derby winners: Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932), Brokers Tip (1933). Twice he even had the first and second place finishers in the race. He began training for E.J. (Lucky) Baldwin on the West Coast, and after seven years moved east to train for Col. E.R. Bradley and stayed with his stable for the rest of his career. All his Derby winners were for Bradley's stable. Probably his most famous Derby winner was Broker's Tip who beat Head Play in the infamous "Fighting Finish" Derby of 1933.

5
James Fitzsimmons

horse racing kentucky derby
"Sunny Jim" Fitzsimmons in 1959. Fitzbook.com

James "Sunny Jim" Fitzsimmons had three Kentucky Derby winners: Gallant Fox (1930), Omaha (1935), Johnstown (1939). His career lasted 70 years and included two Triple Crown winners, two of the world's leading money-winners, and 11 Derby starters. His two Derby winners came during the time he trained for William Woodward's Belair Stable, and later he trained for the Phipps family until the end of his career. His most famous Derby loser was probably Nashua, who lost as the favorite to Swaps in 1955 but went on to be Horse of the Year.

Wikipedia bio

6
Max Hirsch

assault kentucky derby
Assault commemoration pewter plate. Cindy Pierson Dulay

Max Hirsch had three Kentucky Derby winners: Bold Venture (1936), Assault (1946), Middleground (1950). His career lasted 70 years and he was the trainer for King Ranch from the 1930's until his death in 1969. His best known horse was Assault, the Triple Crown winner of 1946, but he also trained Sarazen, Horse of the Year in 1924-25.

Wikipedia bio

7
Nick Zito

horse racing Nick Zito
Trainer Nick Zito. Cindy Pierson Dulay

Nick Zito has trained two Kentucky Derby winners so far: Strike the Gold (1991), Go for Gin (1994). He began training in 1972 and has had 20 Derby starters through 2008. He has also won 1 Preakness and 2 Belmonts, giving him 5 wins, 8 seconds, and 7 thirds from his 60 Triple Crown starters so far. His two Belmont wins are remembered for breaking up the last two Triple Crown bids, with Birdstone defeating Smarty Jones in 2004, and Da' Tara defeating Big Brown in 2008. He was inducted into the Hall of Fame in 2005.

Wikipedia bio
 

8
Carl Nafzger

horse racing Carl Nafzger
Trainer Carl Nafzger with 2007 Kentucky Derby winner Street Sense. Cindy Pierson Dulay

Carl Nafzger has trained two Kentucky Derby winners so far: Unbridled (1990), Street Sense (2007). Known for not sending horses to the Derby unless they really have a chance, his two wins come from only three starters. He started out in rodeo and is also a member of the Texas Cowboy Hall of Fame and the Professional Bull Riders’ Ring of Honor. After he retired from rodeo he started training and had his first winner in 1971. So far he is the only trainer to win both the Breeders' Cup Juvenile and the Kentucky Derby with the same horse, Street Sense.

Street Sense wins the 2007 Derby
Wikipedia bio
 

9
Trainers who have won the Kentucky Derby twice

horse racing twin spires
The Twin Spires at Churchill Downs. Cindy Pierson Dulay

Since none of them are still training, I will just list the rest of the double Derby winners with a link to their bios.  All of them are members of the Hall of Fame.

Lazaro Barrera - Bold Forbes (1976), Affirmed (1978)
Henry Forrest - Kauai King (1966), Forward Pass (1968)
LeRoy Jolley - Foolish Pleasure (1975), Genuine Risk (1980)
H.A. "Jimmy" Jones - Iron Liege (1957), Tim Tam (1958)
Lucien Laurin - Riva Ridge (1972), Secretariat (1973)
Horatio Luro - Decidedly (1962), Northern Dancer (1964)
Woody Stephens - Cannonade (1974), Swale (1984)
Charlie Whittingham - Ferdinand (1986), Sunday Silence (1989)