In the realm of life’s uncertainties and the unpredictable world of equestrian sport, there existed a constant. Much like the dependable shift of seasons, Jonathan Sheppard consistently produced triumphant horses, year after year, showcasing their abilities in both swift sprints and challenging obstacle courses. He concluded his training career in the U.S. prior to the 2021 season, briefly managed a small stable in Ireland, and peacefully passed away at the age of 82 on August 27, 2023.
Sheppard possessed a patient demeanor, refined skills, and an artisan’s touch that propelled him to the pinnacle of his profession. How else can one elucidate his remarkable feat of securing at least one victory at the highly competitive Saratoga race meet annually from 1969 to 2015, an extraordinary streak spanning 47 years?
Born in Ashwell, Hertfordshire, England in 1940, Sheppard initially appeared destined for a career as a stockbroker within his family’s enterprise, and to his credit, he did dedicate some time to this endeavor. However, early in his adulthood, Sheppard recognized his deep-seated desire to work with horses and went to considerable lengths to realize his aspiration, commencing when he departed from his job in 1961. “[I] aspired to train horses rather than be confined to an office all day,” Sheppard conveyed in the August 10, 1990, issue of the Owensboro, Ky. Messenger-Inquirer.
The realization of that aspiration would prove more challenging than anticipated for Sheppard. Pursuing training in England seemed unattainable, given his father’s role as a racing official, which would have imposed restrictions on Sheppard’s ability to participate as a trainer under British racing regulations. Undeterred, Sheppard relocated to the United States, where he engaged in racing and served as an assistant to steeplechase trainer Burley Cocks before venturing out on his own in 1965. Aptly, Sheppard achieved his inaugural victory the subsequent year with Haffaday, a resilient jumper whom Sheppard would eventually guide to triumphs in the 1967 Pennsylvania Hunt Cup, the 1968 New Jersey Hunt Cup, and the 1968 Maryland Hunt Cup.
Over five decades later, Sheppard’s career statistics are nothing short of awe-inspiring. From 1982 to 2019, his horses consistently earned over a million dollars in prize money annually. According to Equibase data, he trained the victors of 3,426 races, including more than a thousand steeplechase events. He mentored champion flat runners and steeplechasers, notably the Hall of Fame inductees Flatterer and Café Prince, as well as the Breeders’ Cup champions Forever Together and Informed Decision, the latter three all owned by his longtime client George Strawbridge Jr. On 28 occasions, he led all steeplechase trainers in North America by earnings, and 25 times by wins. And, of course, there was his triumphant streak at Saratoga, where he held the title of leading trainer in 1984 and 1985.
What was the secret to his success? Sheppard’s career was founded on patience and unwavering determination. He displayed a consistent willingness to invest time in addressing the unique traits and requirements of each horse, unlocking their full potential, even if it necessitated unconventional approaches.
One of Sheppard’s premier flat runners, Forever Together, encountered numerous obstacles before attaining her championship caliber. Karen Johnson, contributing to BloodHorse.com, recounted how Forever Together occasionally resisted training and struggled to perform at her best on dirt due to her aversion to kickback. With patience and a transition to turf, these challenges were resolved, but a more significant issue persisted – her limited ability to sweat, a considerable concern for a racehorse. Sheppard’s solution? He “initiated feeding her Guinness beer, believing it would aid in promoting perspiration – an added benefit being her fondness for the taste, leading her to consume her feed entirely.”
Sheppard’s inclination to experiment undoubtedly yielded substantial rewards with Flatterer, arguably the most exceptional horse he ever trained. Some might have dismissed the Pennsylvania-bred gelding after he suffered defeat in 14 of his initial 18 starts, including nine claiming races at various tracks along the East Coast. However, Sheppard introduced Flatterer to steeplechasing, and the son of Mo Bay transformed into an absolute force, harnessing his remarkable stamina and athleticism to dominate some of the most prestigious steeplechase and hurdle races in North America. By the time of his retirement in 1987, he had secured four consecutive Colonial Cups and four consecutive Eclipse Awards as champion steeplechaser.
In reality, Sheppard’s training methodologies were atypical in North America, more closely resembling those employed in Europe. His operational base was not a racetrack like Santa Anita Park or Belmont Park – rather, it was his own Ashwell Stables in Pennsylvania, a unique facility. Forget about meticulously timed workouts commonly found at racetracks; Sheppard’s horses engaged in high-speed training sessions in the “100-acre field,” where distances were not precisely measured, and times had to be assessed in relation to the specific characteristics of the course.
Sheppard’s training approach was widely regarded as more traditional, in the most positive sense. His horses spent more time outdoors compared to their counterparts at racetracks. They had the opportunity to train both left-handed and right-handed while navigating hills and uneven terrain. This, combined with Sheppard’s patience, enabled him to rehabilitate high-caliber yet fragile horses following extended periods of inactivity. Consider his work with the seasoned Cloudy’s Knight, who made a comeback from a tendon injury to claim three graded stakes races in 2009, at the age of 9.
Sheppard’s statistics began to decline in his late 70s, but he still achieved the occasional significant victory – he sent out All the Way Jose to secure the Grade 1 Lonesome Glory Handicap in 2017 – until his retirement, because, like his horses, Jonathan Sheppard could never be underestimated.
Note: This story was originally published in 2019 and has been updated.
Fun Facts
- Sheppard was inducted into the Racing 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.
