Over Flat or Fences, Jonathan Sheppard Wins Them All

Born in Ashwell, Hertfordshire, England in 1940, Sheppard initially seemed destined for life as a stockbroker in his family’s business, and to his credit he did give the task a try for a time. But early in his adult life, Sheppard knew he wanted to work with horses and went to great lengths to make his dream come true, beginning when he left his job in 1961.

“[I] wanted to train horses and not sit in an office all day,” Sheppard explained in the Aug. 10, 1990, edition of the Owensboro, Ky. Messenger-Inquirer.

Fulfilling that dream would be easier said than done for Sheppard. Training in England seemed out of the question since he was the son of a racing official, and the rules of British racing would thus have restricted Sheppard’s ability to participate as a trainer. No matter though – Sheppard simply pulled up stakes and moved to the United States, where he rode races and worked as an assistant to steeplechase trainer Burley Cocks before going out on his own in 1965. Fittingly, Sheppard scored his first victory the following year with Haffaday, a tough-as-nails jumper whom Sheppard would eventually train to victories in the 1967 Pennsylvania Hunt Cup, the 1968 New Jersey Hunt Cup, and the 1968 Maryland Hunt Cup.

More than five decades later, Sheppard’s results are nothing short of staggering. His horses have earned over a million dollars in purse money every year since 1982. He’s trained the winners of more than 3,300 races, including more than a thousand steeplechase events. He’s trained champion flat runners and steeplechasers, including the Hall of Fame inductees Flatterer and Café Prince and the Breeders’ Cup champions Forever Together and Informed Decision, the latter three all owned by his longtime client George Strawbridge, Jr. He’s led all steeplechase trainers in North America by earnings on 28 occasions and by …

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