The death was announced by the National Steeplechase Association. Mr. Sheppard had complications from Lyme disease.
Mr. Sheppard’s influence on the sport was all-encompassing — shattering records for first-place finishes and earnings and whose training techniques virtually rewrote the book for steeplechase, races up to 4.5 miles in which horse and rider face obstacles such as fences, hedges, ditches and water jumps.
The British-born Mr. Sheppard was involved in 1,242 steeplechase wins between 1966 and his retirement after the pandemic-shortened 2020 racing season. His horses earned nearly $25 million in prize money in steeplechase, according to the racing tracker Equibase. He also trained horses that pulled in more than $62 million more in purses in flat-track thoroughbred racing, where his greatest success came with Storm Cat in 1985. The 2-year-old male, ridden by Chris McCarron, won the Young America Stakes at the Meadowlands and was nosed out by Tasso at the Breeders’ Cup Juvenile at the Aqueduct racecourse.
But steeplechase was where Mr. Sheppard made his enduring mark, winning at least one race each season at the venerable Saratoga Race Course during a 47-year span from 1969 to 2015. “The Babe Ruth of steeplechasing,” said the National Steeplechase Association’s director of racing, Bill Gallo.
Mr. Sheppard’s mystique may have been strongest far from the winner’s circles. He crafted his own training regimes — part inherited knowledge passed down by generations of British trainers and part personal intuition. He allowed his horses to roam for hours at his Ashwell Stable in West Grove, Pa., and then often took them for training runs over what he called the “Hundred Acre Field” rather than a groomed track.
He felt the uneven terrain and exposure to the elements helped strengthen horses and, for steeplechase, adapt them to the unpredictable conditions during a race.
“Most horses have a key that brings out the best in them, the same as people, I guess,” he told the Tennessean in 1988. “Finding that key, that’s the enjoyable side of it.”
In 1970, Mr. Sheppard was handed the task of trying to rehabilitate the 9-year-old Mabrouk, owned and ridden by George Strawbridge Jr., a scion of the Campbell Soup Co. family fortune. Mabrouk had an injured leg tendon and Strawbridge wanted the horse ready for the 1971 Iroquois Memorial Steeplechase in Nashville.
Mr. Sheppard came up with a novel approach: leaving Mabrouk free to walk the winter meadows through ice and snow while the tendon healed. Mabrouk won the 1971 Iroquois in a record time and repeated the victory the following year.
Mr. Sheppard turned to Guinness beer to help one of his best flat-course horses, Forever Together, a thoroughbred mare that had trouble sweating and risked overheating during hot weather workouts and races. He gave her Guinness because he believed “it helps to promote perspiration,” said an account in equestrian site Bloodhorse, adding that “an added bonus is that she likes the taste and therefore cleans up her feed.”
Mr. Sheppard’s greatest steeplechase horse, Flatterer, began as an unpromising prospect on the flat track. The gelding lost 14 of 18 races in the early 1980s. Mr. Sheppard then followed a hunch because of the horse’s stamina and power. He tried Flatterer jumping over some fences. It was a match. Flatterer dominated steeplechase and hurdle races and is considered one of the sport’s finest horses, including four straight Eclipse Awards as champion steeplechaser, before being retired from racing in 1987.
Janet Elliot, Mr. Sheppard’s former protégée and a Hall of Fame trainer, said Mr. Sheppard had a “second sense” for a horse’s potential. “He lets the horses dictate how he would train them,” she said in 2019.
The successes were balanced by tragedies. Irish jockey Michael O’Brien, riding a horse trained by Mr. Sheppard, Athenian Idol, was paralyzed in 1974 from the waist down after the horse collapsed and died following a jump. O’Brien, who had been racing at the front of the back alongside his brother Leo O’Brien, received severe spinal injuries.
During the 1985 Iroquois race, one of Mr. Sheppard’s horses, Double Reefed, ridden by Strawbridge, fell after a jump and shattered its shoulder bone. The horse was euthanized at the scene with an injection.
“It takes a couple of days to get hold of yourself after something like that,” Mr. Sheppard recalled. “If that doesn’t get to you, then the high points don’t either.”
Jonathan Eustace Sheppard was born on Dec. 2, 1940, in Ashwell, England, in the Hertfordshire countryside between London and Cambridge. His mother was a homemaker, and his father was a senior official at the Jockey Club, one of the overseers of British horse racing tradition.
As a boy, the family governess showed him an article about the horses owned by the future Queen Elizabeth II. Mr. Sheppard wrote to the then Princess Elizabeth about his interest in becoming a jockey. He received an encouraging reply from the royal staff.
“It’s not very often some 6-year-old boy writes to a princess and even more unusual to get a letter back saying how interested she is,” he recalled in a 2013 profile by the equestrian journal the Chronicle of the Horse.
His father’s job, however, meant that no relatives could be involved in training or other roles in competitive horse racing in Britain. Mr. Sheppard attended Eton College and then tried his hand in finance. “I was more interested in reading the Racing Form than the Financial Times,” he told the Tennessean.
In 1961, he traveled to the United States to ride for Hall of Fame steeplechase trainer W. Burling Cocks. Mr. Sheppard returned to Britain in 1963, only to come back across the Atlantic two years later to seek work as a trainer.
His first victories came in 1966 with Haffaday at My Lady’s Manor in Maryland. Haffaday went on win a series of races including the 1968 Maryland Hunt Cup.
Mr. Sheppard was inducted into the Racing Hall of Fame in 1990. He received steeplechasing’s highest honor, the F. Ambrose Clark Award, in 2013.
Survivors include his wife of 33 years, retired jockey Cathy Montgomery Sheppard, and three children from two previous marriages. A son from his second marriage, Jonathan Parker Sheppard, died in 2006 from injuries sustained from an assault in Durango, Colo. Complete information on survivors was not immediately available.
Even after stepping down from full-time training, Mr. Sheppard wasn’t done. He shifted some of his horses to a stable in Ireland, where he was planning for future races.
“As long as I have mares spinning them out,” he once said, “I will have horses to train.”