Bob Baffert & 5 Most Successful Kentucky Derby Trainers

Do you know the man behind the horse? No, not the jockey—Today we're counting down the top 5 trainers behind some of the Kentucky Derby's biggest winners.


The Kentucky Derby is described as the ‘fastest two minutes in sport’, but what many racing betting fans don’t realize is that behind the horse and the jockey is another figure who has major influence in the race—so who are the most successful Kentucky Derby trainers?

Trainers are to horse racing, what NFL and NBA coaches are to football and basketball. They are vastly knowledgeable figures who train thoroughbred horses to perfection and decide which ones should run in sprints like the Kentucky Derby, and which should feature in steeplechases or longer distances.

It’s a trainer’s job to know their horse inside out. They’ll know exactly how fast the horse can run, what condition its in and even its relationship with the jockey. That’s why winning a horse race is considered a team effort between beast, rider and trainer.

As of 2020 there are two trainers at the top of the all-time list of successful Kentucky Derby winners. They are Ben A. Jones, who was active over 70 years ago, and Bob Baffert, the veteran trainer who is still going strong today.

Here, we look at the five most successful trainers at the Kentucky Derby, and what were the secrets to their success…

1. Bob Baffert: 6 Winners

  • (Silver Charm, 1997; Real Quiet, 1998; Warm Emblem, 2002; American Pharoah, 2015; Justify, 2018; Authentic, 2020)

When Bob Baffert won his third Kentucky Derby with Warm Emblem in 2002, the Arizona-born trainer must have thought he was at the peak of his powers. And indeed it seemed like he was. Baffert had successfully trained horses from various owners to victory and he’d also enjoyed success in the Preakness Stakes and Belmont Stakes–The two other American Classics.

But then came a period of drought when he fail to discover another Kentucky Derby winner until American Pharoah in 2015. What happened during that drought? Nothing out of the ordinary, only that Baffert just couldn’t produce a winner. Second-place finishes in 2009 and 2012 left the trainer frustrated but not devastated.


But American Pharoah shot the trainer to surperstardom. The horse went on to win the Triple Crown, claiming victory in the Preakness Stakes and Belmont Stakes that year. Three years later and Justify achieved the exact same feat to cement Baffert as one of the greatest racehorse trainers of all time. When Authentic won the Kentucky Derby in 2020 Baffert drew level with Ben A. Jones for most wins at the Churchill Downs race – can he go one clear this year?

2. Ben A. Jones: 6 Winners

  • (Larwin, 1938; Whirlaway, 1941; Pensive, 1944; Citation, 1948; Ponder, 1949; Hill Gail, 1952)

Born in Missouri in 1882, Ben A. Jones was a member of the old school of thoroughbred racehorse trainers. He began life in the industry training horses to ride in the West and Mexico, and eventually got a job in Kansas at a stables. It was at Woolford Farm that he began to earn real recognition as an elite horse trainer, when Larwin won the 1938 Kentucky Derby.

After that Jones moved to Kentucky, where he trained five more winners for Calumet Farm. From these winners, Whirlaway in 1941 and Citation seven years later helped cement Jones’ name in racing folklore for their Triple Crown triumphs.

Jones’ last Kentucky Derby win was with Hill Gail in 1952. The horse almost broke the two-minute barrier and was in fact injured during the race – so much so that he never reached similar heights again in his career. Jones died in 1961 having entered into the Racing Hall of Fame three years previous.

3. D. Wayne Lukas: 4 Winners

  • (Winning Colors, 1988; Thunder Gulch, 1995; Grindstone, 1996; Charismatic, 1999)

When D. Wayne Lukas won his first Kentucky Derby with Winning Colors in 1988, few would have believed the Wisconsin-born trainer would still be active all these years later. But Lukas still has influence in horse racing midway through his 80s. Lukas claimed four Kentucky Derby winners between 1988 and 1999, while his 2013 success with Oxbow in the Preakness Stakes was a reminder that this trainer still knows his stuff.

Lukas holds the record for the most Kentucky Derby starts of any trainer in history (48) and is regarded as one of the best flat racing trainers on the planet. He has won over 4,800 flat races during his career–and there’s every chance he’ll win plenty more, and continue to build his reputation as one of the most successful Kentucky Derby trainers.

4. Herbert J. Thompson: 4 Winners

  • (Behave Yourself, 1921; Bubbling Over, 1926; Burgoo King, 1932; Brokers Tip, 1933)

Herbert J. Thompson was born in Detroit in 1881 and claimed his first major racing victory at the age of 38 when Busy Signal cruised to victory in the Golden Rod Stakes at Churchill Downs.

Two years later Thompson was back at the racecourse watching Behave Yourself beat Black Servant by a head to win the Kentucky Derby. The winning purse that day was $38,450 and it marketed the started of an incredible year for Thompson, who oversaw winners in the Ben Ali Handicap, Blue Grass Stakes and Falls City Handicap.

Thompson would have to wait five years for his next taste of Kentucky Derby glory, while his last victory in the famous race came in 1933, when Brokers Tip claimed a +1600 outsider triumph. Thompson died just four years later and was retroactively inducted into the US Racing Hall off Fame in 1969.

5. Jim Fitzsimmons: 3 Winners

  • (Gallant Fox, 1930; Omaha, 1935; Johnstown, 1939)

A New Yorker by birth, Jim Fitzsimmons claimed over 2,200 wins during his racing career and famously won the Triple Crown on two occasions. His first Kentucky Derby win with Gallant Fox in 1930 resulted in victories at Preakness and Belmont as well. Five years later and he repeated the feat with Omaha – another horse from the Belair Stud.

Jim Fitzsimmons holds reins of bold ruler 81st preakness stakes winner

Jockey Eddie Arcaro and Trainer ‘Sunny’ Jim Fitzsimmons with winner Bold Ruler at the 81st Preakness Stakes (the second event in the Triple Crown event).

A third Kentucky Derby win in 1939 with Johnstown (another Belair Stud horse) would mark a final victory in this iconic race. Fitzsimmons would enjoy Classic victories in the the 1950s during a career revival later in life but the Kentucky Derby eluded him until he died at the age of 91 in 1966.

Meanwhile, another owner – Max Hirsch – was also winning Kentucky Derbies during the time of Fitzsimmons’ peak. Hirsch also claimed three triumphs at Churchill Downs, in 1936, 1946 and 1950. Of those winners, Assault (1946) went on to claim the Triple Crown.

It’s never too early to get your bets in—Get the latest odds from our guide to betting on the Kentucky Derby.

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