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The Kentucky Derby at Churchill Downs has been the crowning jewel of the Triple Crown horse racing series. The Grade 1 stakes race is also one of the most heavily bet sporting events in the United States and around the world. As time goes on, the Kentucky Derby resumes its quest to be the “greatest two minutes in sports.”
Among the three-year-old thoroughbreds of the year to enter the Kentucky Derby, trainers and jockeys take part in this major graded stakes race that is known as “The Run for the Roses” on the first Saturday in May.
In 1919, Sir Barton was awarded the first Triple Crown with his win of the Kentucky Derby, Preakness Stakes and Belmont Stakes. Secretariat won the 1973 Kentucky Derby on his way to an illustrious Triple Crown. He is recognized as the all-time greatest racehorse in the country.
The greatest trainer and the greatest jockey with racehorses are a toss-up in a very tight competition. However, here are the trainers and jockeys with the most Kentucky Derby wins.
Trainers With the Most Kentucky Derby Wins
Trainer Todd Pletcher has two Kentucky Derby wins with Super Saver in 2010 and Always Dreaming in 2017. He also had two second place finishes in 2001 (Invisible Ink) and 2006 (Blue Grass Cat).
Trainer B. James Fitzsimmons won the Kentucky Derby three times in the 1930’s. Gallant Fox (1930) and Omaha (1933) won the Triple Crown in those years.
Max Hirsh also won the Kentucky Derby three times from 1936 to 1950. He trained Bold Venture in 1936, Assault in 1946 and Middleground in 1950. Assault went on to win the Triple Crown.
Next in line to win the Kentucky Derby four times are trainers Herbert Thompson and D. Wayne Lukas. Thompson trained Behave Yourself (1921), Bubbling Over (1926), Burgoo King (1932) and Broken Tip (1933). In 1988, Lukas trained Winning Colors in his Kentucky Derby victory. He also trained Thunder Gulch (1995), Grindstone (1996) and Charismatic (1999).
The trainer with the most Kentucky Derby wins is Bob Baffert with six crowned jewels. He started in 1997 with Silver Charm. As an active trainer, Baffert has six Kentucky Derby titles after Authentic won this Grade 1 stakes race in 2020.
Jockeys With the Most Kentucky Derby Wins
There are seven jockeys who have three victories in the Kentucky Derby including Angel Cordero Jr. (1974, 1976 and 1985), Gary Stevens (1988, 1995 and 1997) and Victor Espinosa (2003, 2014 and 2015).
Jockey Bill Shoemaker has won four Kentucky Derby’s starting with Swaps in 1955. He also took first place in the Kentucky Derby with Tommy Lee (1959), Lucky Debonair (1965) and Ferdinand (1986).
The two jockeys with the most victories in the Kentucky Derby with five titles are Eddie Arcaro and Bill Hartack.
Arcaro completed the feat in 14 years with Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948) and Hill Gail (1952). Whirlaway and Citation were Triple Crown winners.
Hartack took 13 years to accumulate five Kentucky Derby wins starting with Iron Liege in 1957. He also won the Kentucky Derby with Venetian Way (1960), Decidedly (1962), Northern Dancer (1964) and Majestic Prince (1969).
