Editor's Note: Hall of Fame trainer Jonathan Sheppard died Sunday, Aug. 27, 2023.

There are few certainties in life or in the sport of horse racing. But just as you could count on the changing of the seasons, you could count on Jonathan Sheppard sending out winners by the dozen, year after year, in tests of both pure speed and dexterity over jumps. He retired from training in the U.S. before the 2021 season, maintained a small stable in Ireland for a short while, and passed away at 82 on Aug. 27, 2023.

Sheppard was patient, skilled, and a craftsman who ascended to the top of his trade. How else can you explain the fact that he won at least one race at the competitive Saratoga race meet every year from 1969 through 2015, an almost unfathomable streak of 47 years?

Sheppard and George Strawbridge Jr. in 1975. (Courtesy of BloodHorse)

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 career numbers are nothing short of staggering. His horses earned more than a million dollars in purse money every year from 1982 to 2019. He trained the winners of 3,426 races according to Equibase statistics, including more than a thousand steeplechase events. He 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 led all steeplechase trainers in North America by earnings on 28 occasions and by wins 25 times. And – oh yes – there was his streak of success at Saratoga, where he was the leading trainer in 1984 and 1985.

How did he do it? Sheppard’s career was built on patience and perseverance. He was always willing to take his time to work through the quirks and needs of individual horses and uncover their full potential, even if it required thinking well outside the box.

Training steeplechase runners. (Courtesy of BloodHorse)

One of Sheppard’s best flat runners, Forever Together, had to work through myriad issues before she found her championship form. Karen Johnson, writing for BloodHorse.com, noted how Forever Together would occasionally refuse to train and had trouble running to her potential on dirt because she didn’t care for kickback. Patience and a switch to turf remedied these issues, but a bigger one still remained – she was unable to sweat very well, an obvious problem for a racehorse. Sheppard’s solution? He “started feeding her Guinness beer because he said it helps to promote perspiration – an added bonus is that she likes the taste and therefore cleans up her feed.”

Sheppard’s willingness to experiment certainly reaped great dividends with Flatterer, arguably the greatest horse he ever trained. Some might have given up on the Pennsylvania-bred gelding after he lost 14 of his first 18 starts, including nine claiming races at tracks across the East Coast. But then Sheppard gave Flatterer a try over fences and the son of Mo Bay turned into an absolute beast, utilizing his terrific stamina and athleticism to dominate some of the most prestigious steeplechase and hurdle races in North America. By the time he retired in 1987, he had won four straight Colonial Cups and four straight Eclipse Awards as champion steeplechaser.

Truthfully, Sheppard’s training techniques were uncommon in North America, bearing a much closer resemblance to approaches found in Europe. His base of operations was not a racetrack like Santa Anita Park or Belmont Park – it was his own Ashwell Stables in Pennsylvania, a facility uniquely its own. You can forget timing workouts with the bland precision found at racetracks; Sheppard’s horses tackled high-speed breezes in the “100-acre field,” where distances were less than exact and times had to be considered in context with the specifics of the course.

Sheppard’s style of training was considered more old-fashioned than most, and in the best possible way. His horses spent more time outside than they would at a racetrack. They were able to train left-handed and right-handed while negotiating hills and undulating ground. This, coupled with Sheppard’s patience, allowed him to bring high-class but delicate horses back from long layoffs. Just consider his work with the veteran Cloudy’s Knight, who returned from a tendon injury to win three graded stakes races in 2009, when he was 9 years old.

Sheppard's numbers began to dwindle in his late 70s, but the occasional big winner still came his way – he sent out All the Way Jose to win the Grade 1 Lonesome Glory Handicap in 2017 – right up until his retirement, because just like his horses, you could never count out Jonathan Sheppard.

Note: This story was originally published in 2019 and has been updated.

Fun Facts

• Sheppard was inducted into the National Museum of Racing’s Hall of Fame in 1990.
• Sheppard is one of just two trainers to have conditioned champions on both the flat and over fences since the Eclipse Awards were inaugurated in 1971.
• Sheppard trained the Grade 1 winner and 1985 Breeders’ Cup Juvenile runner-up Storm Cat, who went on to become one of the most successful and influential stallions in U.S. racing history.
• Some of Sheppard’s former assistants have gone on to achieve great success on their own, including the Hall of Fame steeplechase trainer Janet Elliot and the Kentucky Derby-winning trainer Graham Motion.