Hall of Fame racing trainer Jonathan Sheppard died Aug. 27 at his home in Hollywood, Florida. He was 82. In remembrance of him, we are republishing this story, which first ran in July 2013. Read an obituary of the legendary trainer here, courtesy of the Temple Gwathmey Steeplechase Foundation.

After a hard crank of the steering wheel to the right, the truck reverses, pivots, and we’re suddenly facing the opposite side of what is referred to as the “Hundred Acre Field” on the grounds of Ashwell Training Stables, an hour or so west of Philadelphia. The undulating landscape is covered by the brilliant green meadow grass of early summer, interrupted only by the occasional tree. A small stream divides the field, the far side being reserved for fast works and the area on our side used for conditioning.

“Do you see them?” Jonathan Sheppard asks me. “Do you see the horses anywhere? Ah, yes! There they are! It’s quite different, isn’t it? From the racetrack?”

Talk about an understatement. Silently, we watch a set of three Thoroughbreds gallop single file across the far ridge, turn and race down the hill toward us where we sit idling in the middle of the field. Leaning out the open window, his eyes trained on the horses, he absentmindedly asks me in his Anthony Hopkins-esque accent, “What is this article about again?”

I remind him it’s for a Living Legends feature in the Chronicle’s Steeplechasing Issue. With this, the dapper and elegant Sheppard swivels back to face me and snorts, “A legend? I’m not dead?!”

“Well,” I respond, “it’s a lot easier to interview someone if they’re still alive.”

Sheppard pauses a beat, his blue eyes holding mine, measuring my response, and then he throws back his head laughing. “Well, that is a good point,” he concedes.

He turns his attention back to the horses, and as they approach, the exertion of galloping up and down the hills can be heard on their breath. They will make two to three large figure-8s in this field, each shift in their direction forcing a change in ours, the truck again rotating in reverse. We wait and watch until they finish their works and their riders confer with Sheppard.

He sticks his head out of the truck window again and queries each rider in turn, “How did they go today?” following up with specific questions about each of the mounts, knowing where they’d left off the day before, who had rested, and what needed to be accomplished today. This type of interaction with his staff (of which there are 80) and his horses (150) continues throughout the entire day, intersecting our conversation and illuminating the essential truth about Jonathan Sheppard: The horse always, always, always comes first.

This passion, obsession—whatever one chooses to call it—defines Sheppard’s life. It is his life, and yet, for all the success this multi-Eclipse Award winning, Hall of Fame trainer has known, he’s also experienced episodes of extraordinary heartbreak, rife with emotional hurdles much more challenging than those dotting the steeplechase track.

A Childhood Ambition

As Sheppard admits, such single-minded dedication to his lifestyle and career comes with its price.

“It may have cost me two marriages. My father, a pretty old-fashioned, traditional English gentleman, used to be somewhat critical of the fact that I am not a better husband, and eventually he said, ‘I think I’ve figured out why: You’re really married to your job more than anything else. That’s your first priority,’ ” Sheppard says, then pauses. “And that’s not really something to be too proud of, but it’s hard to have one without the other. If you want to do really well at something, you have to give up something in another area a little bit.”

Sheppard is one of two trainers to win Eclipse Awards for both flat racing and steeplechasing. His devotion to the sport and his equine athletes has resulted in numerous Eclipse Awards as an owner, countless others as a trainer and entry into the Racing Hall of Fame.

Growing up in England as one of four children and the son of a racing official, Sheppard, now 73, was passionate about racing and as a young boy idolized jockeys. While other children were dreaming about becoming football players or firemen, Sheppard was plotting a course to become a jockey or trainer. At the age of 6, he found encouragement to pursue his passion from a most unusual source: the Queen of England.

“We had a governess, and she was trying to encourage me to write and showed me an article in the newspaper about Princess Elizabeth, who is now the Queen of England,” he says. “She had a couple of race horses of her own and had had a winner. So, with a bit of prompting, I wrote to Princess Elizabeth at Buckingham Palace, congratulating her and telling her of my interest in racing. I got a letter back from her, written by her Lady-in-Waiting, saying, ‘Her Majesty has instructed me to thank you for your nice letter, and she’s most interested to know it’s your ambition to be a jockey when you grow up!’ ”

Sheppard adds, laughing, “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!”

After attending Eton College and trying a brief and soul-draining job in the stock market, he circled back to his childhood ambition of a racing career. He left England and his family for America at the age of 19, bouncing around and staying with distant relatives. Sheppard worked as an exercise rider and a jockey at various farms until his path crossed with his soon-to-be mentor, Burley Cocks. After three years of a sort of apprenticeship with Cocks, Sheppard was musing over his next step with a friend who was visiting from England.

“I told him I was anxious to get into training, but I didn’t really have any potential prospective horses or owners,” Sheppard says.

They were at the track in Saratoga, where the friend noted the steeplechase course differed greatly from those in England. As Sheppard recalls, “He pointed out the hurdles in Saratoga were on the inside of the turf course, a very tight little track only about 7 furlongs around with hard ground and smaller jumps, the opposite of what you find in England.”

They noted that the prize steeplechase horses in England are larger, sturdier mounts and that the smaller, quicker horses don’t have much value over there. That’s when a light bulb went on: They might be able to cheaply pick up a few of these European castoffs and race them in America.

In no time, Sheppard and his friend had a business—the latter fronting a bit of money to buy the horses, and the former training them and selling them for a profit.

The Luck Of Opportunity

Sheppard and his first wife, Penny, traveled to Europe and with the help of a bloodstock agent, selected six horses to bring back to the States. Of those, two were later purchased by George Strawbridge, Jr., as part of the wealthy financier’s first foray into race horse ownership. One horse didn’t amount to much, but the other was a big success, winning 21 races and setting into motion a legendary friendship and business partnership spanning some 47 years.

To this day, Strawbridge remains Sheppard’s biggest owner, one of his dearest friends and godfather to his daughter, Diana Sheppard.

“Other than his honesty, he is a very kind man and very conscientious,” says Strawbridge. “He does everything himself! He schedules the horses! He does the bills like Charles Dickens did—by hand! He does! Honest to God! He is the only person I have ever gotten handwritten bills from—and they are very legible.”

“I’ve been extremely fortunate,” says Sheppard, “because however good you are, you can’t do it without the horses, and you can’t really get the horses if you don’t get the owners, so I’ve always maintained that yes, there is luck in it: The luck is getting the opportunity. Once you have the opportunity, then I don’t think it is luck. It’s up to how good or bad you might be. But I was presented with opportunities, more than I probably deserved, and more than most people have been. I couldn’t have done it without that.”

A Career’s Cost

But beyond the wins and achievements, there’s another story of what’s happened to Sheppard—in the spaces between the early morning workouts and afternoon racing, the things that he sacrificed, the casualties of his workaholic tendencies.

“I think he’s a very complicated man who has had a complicated personal life, and I’m sure a lot of that revolved around his drive to succeed,” says Sheppard’s friend and protégée Graham Motion, trainer of Animal Kingdom, the 2011 Kentucky Derby and 2012 Dubai World Cup winner. “It’s not easy to balance—training is a 24-hour-a-day, seven-day-a-week job, and I think to be as committed as he has been for his entire life takes an extraordinary amount of your time and your energy, and you don’t really escape from it, quite frankly. It is difficult, especially on the scale that Jonathan does it, and it’s extraordinary that he has done it so well for so long.”

We’re still in the truck, now bouncing down the dirt road that connects the Hundred Acre Field to his house. We pass the horses making their way back to the barn, walking along the grassy shoulder on a loose rein, sweaty and as calm as children’s ponies, and three more heading out. He points out other structures on the property, a magnificent fieldstone main house, cottages, barns, an indoor ring, gesturing and explaining that at one time, it was all one farm belonging to his first wife’s grandparents.

Sheppard and Penny divorced after 14 years of marriage and two children.

His mood shifts abruptly, and he suddenly seems vulnerable and apologetic as he shoulders part of the blame for relationships gone awry.

“I think she thought her life was too boring, just following along in my shadow, my footsteps, because by that time I was doing quite well, and she was just kind of known as ‘Jonathan Sheppard’s wife’ and wanted to do her own thing or something. I don’t know what it was exactly,” he trails off, pensive. “[The divorce] was not easy, you know. And not my idea.”

Sheppard remained on good terms with his mother-in-law, even moving into her house, also on the property. He chuckles now at the memory, saying, “So I moved out from my wife and in with my mother-in-law!”

But the melancholy creeps back in his voice as he continues.

“It was extremely hard,” he admits. “And when we first got divorced I said, ‘I am never going to have a relationship with another woman again,’ but eventually, after a longish period of time, maybe a year or something, it suddenly dawned on me, ‘You know what? I’m still quite young. I’ve been given my freedom back, I can do what I want, and maybe it wasn’t such a bad thing.’ ”

Diana was about 10, and her brother, Daniel, was about 12 at the time of the split. The family remained close, if not by vows then by proximity, with Sheppard and his ex-wife sharing parental responsibilities, the bulk of which fell to Penny.

Now adults, Diana and Daniel still live within miles of their parents.

“They all did quite well, under the fact; you know how broken marriages are,” says Sheppard’s friend and business partner of 46 years, Bill Pape. “It’s not easy, but he worked hard to see that they did well.”

More Trials

We now hop out of the truck, leaving it parked in Sheppard’s dirt driveway surrounded by birdhouses, evidence of his love of animals beyond horses. He leads me into his house and motions for me to sit down at the cluttered kitchen table. Orderly stacks of magazines, bloodstock catalogs, files and books surround us. Perched on these are dozens of framed family snapshots of Sheppard as a young man and his children when they were little, and on the walls hang photos and news clippings.

“Where were we?” he asks. “Oh right….” Unexpectedly, our conversation picks up the personal thread where we left off.

Despite Sheppard’s pronouncement of never getting involved with another woman, he soon married his second wife, Mary. After spending a good part of their relationship living apart, even after the birth of their son Parker, the two eventually decided to give cohabitation a try. Mary brought not only their son but also her horse, pony and Sicilian donkey, but the arrangement didn’t last. Pregnant again, Mary moved with Parker to Kentucky shortly after to help care for her ailing mother.

The couple’s second son, David, was born soon after, but the marriage only lasted about 18 months; like any relationship, it was filled with highs and lows, but, as Sheppard recalls, “We had a lot of fun together.”

Sheppard visited Parker and David when he could and kept up with Mary until, at age 47 in 2005, she died from a heart problem.

“She’d had two or three spells where she just sort of collapsed, and they weren’t sure if it was exhaustion from her registered nurse schedule or something more serious, so she agreed to have a proper check-up following the Christmas holidays, after the boys went back to college,” Sheppard recalls. “They had both been home for Christmas break from their school in Durango, Colo. She was found dead in her bed on Jan. 5, 2005.”

He taps a pen absentmindedly on the table, flipping it end over end. Flip, tap. Flip, tap.

“So now I’ve got these two college-age boys living in Colorado, and I’m here, and no mother. And then… Um…”

He pauses and then exhales.

“The oldest boy was killed. Parker was killed.”

Tragedy After Tragedy

It was Halloween 2006, and Parker, who was then 24, and David, 22, were attending college in Durango, living in a house together outside of town. They went out to celebrate the holiday, reserving a taxi as they knew they would be drinking. After some time, David called it a night and caught a ride home with a friend.

Parker had been chatting with a girl, and they headed to another bar, at which point they met a group of firefighters who asked Parker if he could drop them back at their hotel, as they didn’t have a car. Parker agreed, but about halfway to the hotel the firemen wanted to stop and eat.

Parker reluctantly obliged but, as Sheppard recounts, “They were really being a nuisance, and Parker was getting pissed off at them. They got into an argument, and this one big bruiser, a 6’5″, 220-pound fireman, cold-cocked my son, and he fell over backwards and fractured his skull on the sidewalk. He never regained consciousness.”

We sit in silence for a moment, and when Sheppard speaks again, this time his soft, lilting voice is loud and shaking with anger.

“You know what they did? These people? These people who knew better, because they teach firefighters paramedic skills? They were hoping it was just that he had too much to drink and would suddenly come out of it,” he says. “Instead of calling 911, they took him back to their motel room! And laid him on the bed for about two hours! So it’s possible, if he had immediate attention to it, it would have made a huge difference.”

Parker was eventually medevaced to Denver, where he remained on life support for two weeks until it was determined there was nothing else to be done. Shaking his head, lost in the horrific memory, Shepard whispers, “It was a nasty experience and so tragic.”

As hard as it was on Sheppard and his other children, it was most devastating to David.

“To lose his mother and brother like that, so close together, in less than two years—it’s been very difficult on him,” says Sheppard. “But he’s doing much better and has started his life over in Taos, N.M.”

Sheppard pushes his chair back, steps over to the shelves and starts passing me framed family snapshots, one after another, continuing to reminisce. There’s one of Parker as an adorable dark-haired little boy, one of Daniel, another of Diana, David and Parker as young adults on a college visit, and several of his current wife of 25 years, former jockey Cathy Montgomery Sheppard. There’s another of a younger Jonathan with his siblings and mother.

Pointing at the laughing group in the picture, he says, “These are my two brothers and sister with my mother when I was visiting England. My brother, Gurney, was always goofing around, and my mother was always telling him to be sensible.

“Anyway,” he continues almost matter-of-factly, “he died, as did my sister.”

Sheppard stares at the photo for another moment and places it back atop the stack of books. Their deaths occurred about five years ago, he says, around the same time as Parker’s. His brother was one of 150 people to die from Mad Cow disease, and his sister from breast cancer. Their mother’s death followed not long after.

The mood is now somber, but with a small shake of his head, Sheppard suddenly seems to return to the present.

“So anyway, this is pretty morbid,” he says. “We’re supposed to be talking about my horses.”

A Lifetime Of Achievements

With that, he turns and opens the door of the kitchen.

“I should mention, even though I’m married, I live on my own,” he says.

Cathy lives year-round at their house in Florida where she has her garden and animals, and Sheppard joins her after the summer meets end.

“Because of this, I just kind of dump stuff in here,” he says. “It’s not tidy, of course.”

The door opens a portal to another world. We step into a large living room, circa 1730, with a low-beamed ceiling and a big fireplace.

It isn’t that it’s not tidy; it’s merely no match, despite its size, for the bountiful treasures it holds. There’s no surface—walls, floor-to-ceiling shelves, tables, even the floor—not covered with trophies, silver cups, platters, Eclipse Awards. On the floor, stacked side-by-side, some 300 framed stakes win photos lean against couches and tables; there’s simply not wall space enough to display them. It’s an overwhelming visual representation of a lifetime of achievements.

Still reeling a bit from the personal tragedy this reputedly very private man has just shared and wanting to lighten his mood, I ask him to tell about his favorite horse. I’m met with silence so I give him an out and tell him he can pick three.

His blue eyes dance, and without missing a beat he smiles and answers, “Storm Cat, Flatterer and Forever Together. And not because they were so successful, but because of my respect for them as athletes. You know, you have to be good, and you have to try really hard. And they did. And they all had very different temperaments.”

Always The Horse First

Sheppard’s astonishing triumphs as a trainer are only eclipsed by his complete devotion to his horses. Just last month, he rounded up a few people from his staff and visited Flatterer to celebrate the horse’s birthday. At age 34, Flatterer is the oldest surviving Hall of Fame Thoroughbred.

After a quick glance at his watch, Sheppard announces it’s time to return to the field and watch another set of horses train before he needs to leave for the afternoon races at Delaware. We hop back in the truck and make a quick detour to the barns, going first into the mare and foal barn. He leads me to one of the stalls, opens the door and gestures for me to enter. A beautiful bay mare with a kind eye stands quietly, taking me in, and curled up on the straw near her hindquarters is one of the tiniest foals I’ve ever seen.

“Go ahead, go in, he’s very friendly. He’s only about half the size he should be because she was pregnant with twins, and mares aren’t supposed to have twins; there isn’t room for them,” he says. “The other one was born dead, and this one is real small. I probably shouldn’t have kept him; he’s not going to be able to race. Everyone kind of feels sorry for him and has made a bit of a fuss, so he’s particularly attuned to people petting him. His nickname is Tadpole, but I don’t think it’s a very nice name. The first three to four days he couldn’t even get up to nurse; they had to lift him and also feed him with a bottle.”

Tadpole is now two weeks old and the size of a small fawn, so little I could easily pick him up. He lies in the straw, letting me stroke his face, his ears, his muzzle, eventually unfolding his spindly legs and haltingly standing up to nurse.

Tadpole’s story doesn’t surprise Strawbridge. “Sheppard believes if you’re living, you have a fighting chance to be good,” he says. “That’s it. He is a great, great supporter of the underdog, and I can just see him loving this weakling foal—he’ll love it forever. Oh my goodness gracious, but that is typical of him! You saw something absolutely that is true. And unusual.”

Laughing, he continues, “Last year I sold 15 horses, and most of them were out of Jonathan’s barn. Of the 15 he bought four of them back; I swear to God. He can’t let go!”

Strawbridge can’t stop laughing now, charmed by his friend’s devotion. “Absolutely, he loves them,” he adds. “He loves them whether they’re champions or maiden claimers. He just loves the animal.”

Pape concurs, “I think he’s enormously patient. He sees the best in the horse, and he really takes care of his horses. He doesn’t—in any way—overextend them and is totally devoted to them. And the evidence of that is by his behavior and his daily work ethics.”

A key distinction in the Sheppard training method, beyond galloping and working his horses in the open field and jumping them over natural obstacles on a trail weaving through the woods, is the unwavering routine of morning turnout prior to working the animal.

Motion considers the five years he spent working under Sheppard “the equivalent of going to college for me, and I’d say—very much—that my career has been modeled after his philosophy. Jonathan is always all about the horse and about getting the horse to settle and relax. I don’t think there are many trainers left who are real horsemen like Jonathan. He turns his horses out religiously, and I’ve tried to duplicate that as much as I can.”

Fellow Sheppard protégée and Hall of Fame trainer Janet Elliot agrees: “I have a huge amount of respect for him. He is a tremendous man and a tremendous horseman.”

Sheppard, ever humble and a bit reluctant, eventually concedes his friends and colleagues may have a point.

“Well, I suppose I kind of thrive on horses that are a little bit more of a challenge,” he says, “maybe getting something out of a horse that someone else couldn’t.”

Perhaps, under the love and guidance of Sheppard, this little weakling foal will one day surprise us all.

Passing It On

What does Sheppard hope his legacy will be?

“It sounds trite, but that maybe I made a difference in some way?” he says. “There are a lot of people involved in racing now that came through the stable here at different times or have gone on to train or be involved in some aspect of the horse business and, hopefully, use a little bit of the same philosophy. Not that it’s a huge mantra that’s written down or anything, but just the fact that you know, to get the best out of a horse, you have to see the best in the horse. How to put the horse first, how to take care of the horses, how to be responsible for them when they’re getting towards the end of their career or their career is over; we try to find good homes for them.”

He stops for a moment, thinking, and says, “I think we try to keep the horse in as close to nature as you can, which a lot of people don’t, necessarily, and I think if people can see it’s possible to be successful being kind to the horses, being patient, not being too greedy, not using more medication than is essential just for normal ailments and things, not cheating. I try to be pretty transparent.

“I think to be a successful trainer it’s several different things: It’s not someone who gets the horses fitter than somebody else,” he continues. “You have to be good at communicating with your owners; you have to be good at dealing with your help and staff.”

And, of course, you have to be good to the horse. Sheppard pauses again to ruminate.

“Consistency. I think consistency is the mark of success, and if you can do something well for a long time—not that you are necessarily the best at any given moment or any one year—but over a long period of time, if you have consistently done well at a top level, that would be something I would be proud of and would hope to continue to do.”

“You Gotta Like Him”

Sheppard’s kindness and generosity extend to those who help care for his beloved equine athletes. Bob Bailey has been working for Sheppard for 42 years, starting one year after Sheppard set up shop. As Bailey describes it, they were introduced by a mutual friend one day at the track when Bailey was looking for work following an injury that prevented him from further riding.

“Jonathan invited me to come up and take a look around, and if I liked it, I could have the job, and if not, no hard feelings,” he says. “That was a Sunday. I started work the next morning, and I’ve been here ever since.”

Bailey is now at the age where he’s slowing down a bit, and I find out—quite by accident—that he lives in a house on the property purchased for him by Sheppard. Bailey still pitches in around the farm, doing whatever needs to be done.

“Jonathan is such a good horseman. I mean, you gotta like him. He knows what he’s doing,” Bailey says, “and he treats me as good as gold.”

I ask Sheppard what he would be doing if he wasn’t a trainer, and we circle back to his old friend Bob.

“Twenty or so years ago, a little store in town started carrying lottery tickets, and Bob was one of the first to purchase one, and as such, was asked what he would do with the money if he won,” he says. “His answer? ‘The same thing I’m doing now—playing the ponies and chasing women.’ ”

The hour has come for Sheppard to head to the track and play the ponies; he has two runners in the afternoon races at Delaware. The truck slows to a crawl one last time, keeping pace with the final exercise rider on the back of a gorgeous bay returning from the Hundred Acre Field.

“How was he today? How did Parker’s Project go?”

I give him a quizzical look.

“Yes, he’s named for my son,” he says. “At the time of his death he was co-authoring a math textbook. He was brilliant at math. That was the project he was working on when he died, so I named this horse Parker’s Project, and he’s quite a good horse. He won a stakes race in Saratoga two years ago, steeplechase.”

Clearing hurdles, jumping life’s obstacles one at a time, Sheppard steadily moves through life and racing with elegance, perseverance, grace and humility, always believing the best is there to find—in horses and in life—if one just looks hard enough and is patient.

This article originally appeared in the July 29, 2013, issue of The Chronicle of the Horse. You can subscribe and get online access to a digital version and then enjoy a year of The Chronicle of the Horse and our lifestyle publication, Untacked. If you’re just following COTH online, you’re missing so much great unique content. Each print issue of the Chronicle is full of in-depth competition news, fascinating features, probing looks at issues within the sports of hunter/jumper, eventing and dressage, and stunning photography.