Trainer Jonathan Sheppard, Who Won Races at Saratoga for 47 Consecutive Straight Years, Retires

Sheppard, who has the most wins of any steeplechase trainer in horse racing history, most recently competed at Saratoga in 2020.

Jonathan Sheppard trained at least one winner at Saratoga Race Course from 1969 through 2015. (Brien Bouyea)

The Joe DiMaggio of horse racing is calling it quits, at least in America, after 56 years. Hall of Fame trainer Jonathan Sheppard, best known for having won at least one race for 47 straight years at Saratoga Race Course through 2015, announced today that he will be retiring from the American racing circuit.

Sheppard will continue to train a small stable in Ireland.

Sheppard, who turned 80 last month, is the National Steeplechase Association’s all-time leading trainer, having collected 1,242 career wins and purse earnings just shy of $25 million. He has been the winningest trainer 26 times and has led the sport by purses in 29 years, both records.

Sheppard has also won 15 Eclipse awards, behind only D. Wayne Lukas and Bob Baffert, and his 11 individual winners have included two Hall of Fame members, Cafe Prince and Flatterer, a four-time champion, who was bred by Sheppard and William Pape, a longtime client and partner.

“People undoubtedly will ask why I am retiring now,” Sheppard said in a statement. “There’s no one single reason, and the reasons combined to say that now was the time to step back from American racing. I always wanted to go out on top, and the past year’s championships checked that box.”

Sheppard was inducted into the National Museum of Racing’s Hall of Fame in 1990.

—additional reporting by Don Clippinger

Will Levith

Will Levith is Editorial Director at Saratoga Living and Capital Region Living magazine. He's a native Saratogian and graduate of Saratoga Springs High School. His work has been published by Esquire, Playboy, Condé Nast Traveler, Men's Health, RealClearLife and many others. He lives in Troy with his wife, Laura, and dog, Esopus.


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