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Is Jonathan Sheppard Horse Racing’s Joe DiMaggio?

For steeplechase and on the turf, this horse trainer's been hard to beat.

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

Like many Saratogians, I like to gamble a bit at Saratoga Race Course. For decades, horseplayers have been rewarded with solid ROIs when they wager on Thoroughbreds trained by Jonathan Sheppard. Whether it’s over the jumps in a steeplechase race or on the turf, Sheppard has always been a solid play at the Spa’s betting windows. How good has Sheppard been? Well, he owns a seemingly unbreakable Saratoga record. Judge for yourself.

If Chad Brown, the reigning Eclipse Award winner and Saratoga Race Course’s leading trainer in 2018, were to be able to best Sheppard’s record, he’d have to still be conditioning racehorses at a high level in the year 2055. In fact, between now and that summer 36 years away, Brown would need to win at least one race every year at Saratoga. Sheppard’s record? He trained at least one winner at Saratoga Race Course every year from 1969 through 2015, a 47-year run of consistent excellence.

Although not as heralded in the annals of sports history as, say, the New York Yankees’ Joe DiMaggio’s 56-game hitting streak or Baltimore Oriole Cal Ripken Jr.’s 2632 consecutive games played, Sheppard’s run should certainly be in that prestigious company. The streak came to an end in 2016, but Sheppard still remains one of the top steeplechase trainers in the country (he ranked second in the National Steeplechase Association’s 2019 standings in both wins and earnings through May) and is looking forward to returning to the Saratoga Winner’s Circle this summer. “Saratoga is always an experience I enjoy,” says Sheppard, a 78-year-old native of Ashwell, Hertfordshire, England. “Everyone wants to win at Saratoga, and I’m no different. I’ve got a few good ones in the barn that should be competitive there this summer, and hopefully, we’ll get our picture taken a time or two.”

Sheppard, who was inducted into the racing Hall of Fame in 1990, has won more than 1000 jump races and more than 3300 overall races in a career that began in 1965. He has purse earnings of more than $86 million and no plans of retiring anytime soon. “I still enjoy it,” he says. “As long as I’m capable and the challenge still excites me, I’m going to stay on the ride. The game’s been really good to me.”

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