Which trainers have the most Kentucky Derby wins?

Most trainers will tell you the Kentucky Derby is the one race they dream of winning. While it is an accomplishment to pull the feat off once, some have been lucky enough to win multiple times. Still today, others are trying to join the list below.

Ben A. Jones (6): No other trainer has seen the success of Jones in the Kentucky Derby and no one has tied his record. The closest trainers have gotten is two wins less. Jones’ Kentucky Derby winners were Lawrin, (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), and Hill Gail (1952). Except for Lawrin, each horse was owned by Calumet Farm, with Whirlaway and Citation both being Triple Crown winners. Jones is one of two trainers to have won the Triple Crown twice.

Herbert J. Thompson (4): Switching from harness racing to Thoroughbred racing served Thompson well. He picked up horses for Colonel E.R. Bradley and won the Kentucky Derby with four horses, each owned by the Colonel. The four winners were Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932), and Brokers Tip (1933). Brokers Tip is one of two maidens to win the Run for the Roses.

D. Wayne Lukas (4): Lukas is one of the best known names in racing. His first Kentucky Derby win came with the filly Winning Colors (1988), followed by Thunder Gulch (1995), Grindstone (1996), and Charismatic (1999). Thunder Gulch won the Kentucky Derby and Belmont while Charismatic won the Kentucky Derby and Preakness.

Bob Baffert (4): The fourth time was the charm for Baffert. He missed the Triple Crown with three different horses, but finally got the glory in 2015 with American Pharoah. Silver Charm (1997), Real Quiet (1998), and War Emblem (2002) all won the Kentucky Derby and Preakness, but missed the third jewel. Mor Spirit provides Baffert the chance to earn his fifth win in the 2016 edition.

Jim Fitzsimmons (3): “Sunny Jim” Fitzsimmons is the only other trainer besides Ben A. Jones to win two Triple Crowns. His three Kentucky Derby wins came with Gallant Fox (1930), Omaha (1935), and Johnstown (1939), the first two being the horses that won the Triple Crown. Belair Stud was the owner of all three horses.

Max Hirsch (3): Hirsch’s first Kentucky Derby winner was Bold Venture (1936), who ended up siring two more Kentucky Derby winners for Hirsch. Bold Venture’s sons Assault (1946) and Middleground (1950) followed in their father’s footsteps, and Assault even won the Triple Crown.

By Christine Oser