Top 5 Most Successful Kentucky Derby Trainers of All Time

The Kentucky Derby is the pinnacle of American horse racing. When a thoroughbred is awarded a blanket of roses, the trainer enters a heaven of their own.

Most trainers spend all of their careers running towards this goal, but there is a handful that seems to take the challenge in their stride.

This course can make a person’s career, and you can see that in our list of the 5 most successful Kentucky Derby trainers. One win can affect betting odds for years to come.

  1. 6 Winners – Bob Baffert

Baffert’s 6 winners were Silver Charm in 1997, Real Quiet in 1998, Warm Emblem in 2002, American Pharoah in 2015, Justify in 2018, and Authentic in 2020.

When Baffest’s Warm Emblem crossed the finish line in 2002, he joined the greats among this list. That was his third-ever win, and as many horse race fans know, it’s hard enough to get one win let alone two or even three.

Little did this growing star know, he had just begun his road to success, and soon he would be leagues above everyone else.

Of course, Baffert didn’t feel like the champion we know him to be. The 13-year drought of no Kentucky Derby wins would have cemented the idea that 3 was his maximum. But when American Pharoah came around, it sprang a new lease of life into the trainer.

2. 6 Winners – Ben Jones

Jones’ 6 winners were Larwin in 1938, Whirlaway in 1941, Pensive in 1944, Citation in 1948, Ponder in 1949, and Hill Gail in 1952.

Ben Jones was the ultimate legend of horse training. Not only was he the only person (for a long time) to achieve 6 wins in the Kentucky Derby, he also managed to do it almost every year.

We had to really consider which trainer would come first and which second, and we almost swapped the two around. The question that made our head spin was, “what’s more impressive, the constant domination of Jones or the high-class competition that Baffert had to compete against?”.

Every year the breeders, riders, and trainers get better and better – that’s why Baffert took the top ranking.

Jones, unfortunately, passed away just 9 years after Hill Grail won the Derby. In that race, the horse was seconds away from breaking the 2-minute barrier. The horse was pushing so hard that he completed the race injured.

3. 4 Winners – Darrell Wayne Lukas

Lukas’ 4 winners were Winning Colors in 1988, Thunder Gulch in 1955, Grindstone in 1996, and Charismatic in 1999.

Lukas won his first Kentucky Derby at an age close to retirement. We all celebrated his well deserved victory, but no one expected this man to continue much longer. Flash forward to now, and Darrell is still training amongst the youngsters.

Lukas has become a major influencer in the community. Even though he hasn’t won a Kentucky Derby since 1999, his 2013 horse Oxbow has proven to all the neigh sayers that he still knows what he’s doing.

4. 4 Winners – Herbert J Thompson

Thompson’s 4 winners were Behave Yourself in 1921, Bubbling Over in 1926, Burgoo King in 1932, and Brokers Tip in 1933.

Thompson was another trainer whose horses started to gain massive traction near the end of this life. As you can see from the date, each win was only years apart from the other.

Unfortunately, Thompson passed away in November 1937, just 4 years after his last Kentucky Derby win. He was on a roll, and if he managed to hold on a little longer, it might have been his winning streak that pushed past the future numbers of Lukas.

5. 3 Winners – Jim Fitzsimmons

Fitzsimmons’ 3 winners were Gallant Fox in 1930, Omaha in 1935, and Johnstown in 1939.

Although Fitzsimmons only took the roses 3 times, he has a total of over 2,200 wins throughout every racing tournament. He was one of the few people to win the Triple Crown twice!

Although Fitzsimmons was obsessed with winning, the Kentucky Derby always slipped out of his hands. It took multiple years and multiple horses for Jim to finally land a win.

Fitzsimmons took great pride from his amazing wins and settled for his lot. But when he was reaching the tender age of 90, Jim had a resurgence.

Jim Fitzsimmons passed away just a couple of years later, at the age of 91, unsuccessful in his quest for a 4th Kentucky Derby win.


The Kentucky Derby is famously described as the fastest two minutes in sport, and the same can be said for the fleeting wins.

Usually, if an athlete is good at their sport, they will win time and time again. But the competition in the Kentucky Derby is so fierce that greatness alone isn’t sure to pull you through.

These 5 excellent trainers are proof that you can win more than once – and if you do, you will be remembered for a lifetime.

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