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Winning a Kentucky Derby is the dream of every man or woman that's ever put a saddle on a Thoroughbred race horse. To have success in the American classic restricted to 3-year-olds, a trainer must find that one horse with the talent and determination to step to the forefront of a yearly foal crop that can number anywhere up to 35,000. Winning a Kentucky Derby gives a trainer entry into an exclusive club. It takes expert horsemanship to select the right horse, guide them along the Triple Crown trail without incident and to have them peak on that first Saturday in May when history is there for the making. An even more exclusive club consists of trainers that have won multiple Kentucky Derbys. A total of 16 trainers have won at least two of the 137 Kentucky Derbys ever run. However, an even more exclusive group than that are those trainers with more than two wins. Here's the list of the most successful trainers in Kentucky Derby history: 1. Ben Jones 6 (1938, 1941, 1944, 1948, 1949, 1952) 2. D. Wayne Lukas 4 (1988, 1995, 1996, 1999) 3. H.J. Thompson 4 (1921, 1926, 1932, 1933) 4. Bob Baffert 3 (1997, 1998, 2002) 5. Jim Fitzsimmons 3 (1930, 1935, 1939) Ben Jones is the gold standard by how all other trainers are judged when it comes to the Kentucky Derby. Shortly after winning the 1938 Derby with Lawrin, Jones was hired to be the private trainer for the famed Kentucky breeding and racing operation Calumet Farm. With a seemingly never-ending string of talented racehorses coming from the farm, Jones would go on to win the Derby five more times and the Triple Crown twice with Whirlaway in 1941 and Citation in 1948. Lukas and Baffert continue to train horses and remain in search of their next winners. Lukas turned the Thoroughbred racing world on its head when he migrated from Quarter Horse racing in the early 1980's. He boasted an operation that had hundreds of horses from racing’s biggest owners and breeders located at tracks all around the country. Lukas won his first Kentucky Derby with a filly, Winning Colors, in 1988, and nearly won the Triple Crown 11 years later with Charismatic. He's not nearly the force he once was, but if you find a Lukas horse in the Kentucky Derby starting gate it’s probably wise to take note. Baffert remains as strong as ever as he typically has several contenders in the lead-up to the Kentucky Derby each year. He nearly won the Triple Crown two years in a row as Real Quiet in 1997 and Silver Charm in 1998 were beaten less than a length in the Belmont Stakes after sweeping the Kentucky Derby and Preakness. In recent Kentucky Derby history, several new trainers have entered the club of Kentucky Derby winners. Still, the fact remains trainers with the proven ability to win a Kentucky Derby warrant a big look when making their run for the roses.
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