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Top 10 Most Successful Trainers in Kentucky Derby History

Profile Picture: Ashley Anderson

May 4th, 2022

Steve Asmussen has collected more wins than any other trainer in North America, and yet a first-place finish in the Kentucky Derby (G1) alludes him.

While the two-time Eclipse Award winner could finally reach the winner's circle in 2022, he will face heavy competition from a handful of talented trainers, a few of which have already tasted victory in the first leg of the Triple Crown.

As we inch closer to the 148th Run for the Roses, let's look back on some of the best to prep three-year-old Thoroughbreds for the 1 1/4-mile trek at Churchill Downs Racetrack.

Based on overall number of victories, as well as second- and third-place finishes, here are the 10 most successful trainers in Kentucky Derby history.

Fourth-most Kentucky Derby wins: 2

a. Horace A. "Jimmy" Jones

Winning Derby horses: Iron Liege (1957), Tim Tam (1958)

The son of prominent trainer Ben Jones, Jimmy became head trainer of Calumet Farm in 1948 and found instant success with Triple Crown winner Citation. Although his father is the trainer of record for Citation's Kentucky Derby win, Jimmy guided his preparations and is credited for Citation's victories in Preakness S. (G1) and Belmont S. (G1) victories.

Jimmy won his first official Kentucky Derby in 1957 with Iron Liege and his second the following year with Tim Tam.

Along with James "Jimmy" Rowe Sr. and James Rowe Jr., Jimmy and his father Ben are the only other father-son trainer duo to each win the fastest two minutes in sports.

b. LeRoy Jolley

Winning Derby horses: Foolish Pleasure (1975), Genuine Risk (1980)

A year before his first Kentucky Derby start, LeRoy Jolley gained notoriety for training Ridan to an undefeated two-year-old season, with victories in the Arlington Futurity and Washington Park Futurity. In Ridan's three-year-old season, he won the Hibiscus S. in record time, along with the Blue Grass S. and Florida Derby, but finished third in the Kentucky Derby after running wide throughout the race.

In 1975, Jolley got his first Derby win with Foolish Pleasure and earned a second in 1980 with Genuine Risk.

In 13 career Derby starts, Jolley saddled two second-place finishers (Honest Pleasure in 1976 and General Assembly in 1979), and one third-place finisher. Jolley also won a number of major stakes races, including the Breeders' Cup Turf (1986) and Breeders' Cup Juvenile Fillies (1990), as well as the Arlington Million (1987).

c. Woody Stephens

Winning Derby horses: Cannonade (1974), Swale (1984)

Woody Stephens finished in the money in nearly 60% of his 14 Kentucky Derby starts. His first winner was Cannonade, ridden by decorated jockey Angel Cordero Jr., and his second came with Swale in 1984.

Over the course of his career, Stephens trained 11 Eclipse Award winners and won more than 100 Grade 1 stakes races. He also triumphed in the Kentucky Oaks (G1) a record five times, and won an unprecedented five consecutive Belmont races from 1982 to 1986.

d. Todd Pletcher

Winning Derby horses: Super Saver (2010), Always Dreaming (2017)

With a record 59 career Kentucky Derby starts, Todd Pletcher has collected the garland of roses twice, with Super Saver and Always Dreaming, while he has a pair of second-place finishes (Invisible Ink in 2001 and Bluegrass Cat in 2006) and finished third four times.

He has twice saddled five horses in a single Derby (2007, 2013), and trained four horses in the same Derby five times, including most recently in 2021. 

The seven-time Eclipse Trainer of the Year has also won the Belmont and Kentucky Oaks four times each, as well as the Breeders' Cup Classic (G1) in 2019.

Third-most Kentucky Derby wins: 3

a. Max Hirsch

Winning Derby horses: Bold Venture (1936), Assault (1946), Middleground (1950)

Max Hirsch won the third leg of the Triple Crown four times in his career, but was unable to run 1936 Kentucky Derby and Preakness winner Bold Venture in the Belmont because of an injury to the horse.

A decade later, Hirsch won all three Triple Crown races in the same year with Assault, the son of Bold Venture, and got his third Derby trophy with another Bold Venture son, Middleground, in 1950.

Out of 14 Derby starts, Hirsch also placed third two times, with On Watch in 1920 and Dit in 1940. His daughter, Mary Hirsch, was the first female trainer to saddle a Derby runner, with No Sir in 1937.

b. James “Sunny Jim” Fitzsimmons

Winning Derby horses: Gallant Fox (1930), Omaha (1935), Johnstown (1939)

"Sunny Jim" Fitzsimmons became the second trainer to win the Triple Crown and the first to do it twice, with Gallant Fox in 1930 and the colt's son Omaha in 1935.

Additionally, Fitzsimmons trained a total of six Belmont and four Preakness winners, including 1957 American Horse of the Year Bold Ruler, the sire of Secretariat and great-grandsire of Seattle Slew.

Second-most Kentucky Derby wins: 4

a. D. Wayne Lukas

Winning Derby horses: Winning Colors (1988), Thunder Gulch (1995), Grindstone (1996), Charismatic (1999)

With the second most starts in Kentucky Derby history, D. Wayne Lukas has trained four winners, one second-place finisher, and five third-place horses.

His first trip to the winner's circle was in 1988 with Winning Colors, the third and most recent filly to win the first leg of the Triple Crown.

In 1995, Lukas became the first trainer to win the Triple Crown Classic races with two different horses in one season, with Thunder Gulch (Derby and Belmont) and Timber Country (Preakness). He went on to win two of the next four Kentucky Derby races, and trained a record-tying five horses in the 1996 Kentucky Derby, including victor Grindstone.

Lukas has won a record 20 Breeders' Cup races, four Kentucky Oaks races, and is the only trainer in Derby history to also start a horse in Quarter Horse racing's All American Futurity (1970).

b. Herbert J. “Derby Dick” Thompson

Winning Derby horses: Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932), Brokers Tip (1933)

Herbert J. Thompson earned the nickname "Derby Dick" after he led four horses to the winner's circle from the span of 1921 to 1933.

The Hall of Fame trainer has saddled the fourth most Kentucky Derby starters (26) in history and finished in the money with eight. In 1933, he became the first trainer to win the Derby back to back, and also won the Kentucky Oaks that year with Barn Swallow.

Most Kentucky Derby wins: 6

a. Bob Baffert

Winning Derby horses: Silver Charm (1997), Real Quiet (1998), War Emblem (2002), American Pharoah (2015), Justify (2018), Authentic (2020)

Bob Baffert's first Kentucky Derby start resulted in a second-place finish by Cavonnier, who lost by a nose to Grindstone in the 1996 Derby. The following year, Baffert celebrated his first winner's circle appearance with Silver Charm and fell just short of the Triple Crown, with a second-place finish in the Belmont.

Baffert got his first of two Triple Crown titles in 2015 with American Pharoah, who became the first horse to achieve the feat since Affirmed in 1978.

In 2018 with Justify, Baffert joined Fitzsimmons as the only other trainer to win the Triple Crown twice.

b. Ben “Plain Ben” Jones

Winning Derby horses: Lawrin (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), Hill Gail (1952)

Hall of Fame trainer Ben Jones won his first Derby with Woolford Farm's Lawrin, before he accepted a job as trainer of Calumet Farm for the 1940 racing season. A year later, Jones saddled Whirlaway in the 1941 Kentucky Derby and went on to claim the Triple Crown with the chestnut colt. 

Jones won four more Derby trophies with Calumet Farm and guided another Triple Crown winner, Citation, to a Derby win — although, his son, Jimmy, saddled the bay in Preakness and Belmont victories.

Jones, who owned an 11-6-2-1 record in the Kentucky Derby, is one of six trainers with back-to-back Derby victories, and is one of two to pull off the Oaks/Derby double in the same year. Jones accomplished the latter twice, in 1949 with Wistful and Ponder, and in 1952 with Real Delight and Hill Gail.

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