The Outside Rail

It was 2008. Jonathan Sheppard was in yet another chapter of his storied career and The Blood-Horse magazine wanted a feature story. Steeplechase Times still existed, and I still wrote freelance articles for other racing publications.

Of course, Sheppard was no easier to corral for an interview then than he ever was but I signed on probably at the request of the magazine’s managing editor Dan Liebman. I remember a phone interview or two, but not much depth and even less access. It was early spring. Sheppard was splitting time between Florida, South Carolina, Keeneland, maybe brief stops in Pennsylvania all the while changing rental cars like another person might change socks.

At the Middleburg Spring Races in April, I still had yet to secure a long conversation with the man. I was there, covering things for Steeplechase Times. Sheppard was there, having ridden from Camden, S.C., in the horse van. At the end of the day, he planned to get back on the van – well, maybe not that van – and head to Pennsylvania. Until somebody did the math.

“Joe, do you have a car here?” Sheppard asked at some point.

“I do.”

“Well, maybe I could ride home with you and we could have that interview,” he replied, surely doing mental math on the difference between riding in a car and a horse van. “I can drive your car if you want, and you can take notes.”

It sounded like a plan, though riding three hours home in the car with the Hall of Fame trainer I may or may not have still called Mr. Sheppard seemed like a bit much. At least I knew enough not to worry about his impression of my Subaru. I’d seen a steady stream of Caprice Classics and other hard-driven Sheppard vehicles come through the gates at steeplechase meets. Maybe he could drive and I could take notes. Maybe this plan could work.

Then I got a warning. A Sheppard staffer – and man I wish I remember who it was – stopped me at the races.

“You giving Jonathan a ride home to Pennsylvania?” she asked.

“Uh, yeah, I need to talk to him anyway for a story.”

“Whatever you do, don’t let him drive your car,” she said, looking at me like a judge passing sentence. “I mean it.”

There went half the plan. I drove, Sheppard sat and talked. I tried to record some of it but mostly got background noise. We did stop for gas and snacks – he paid – and we made it to Ashwell Stable in the obligatory three hours and change. I have no idea why we didn’t just stop for dinner and talk there.

After I dropped him off and backed out of the driveway, I remember pulling over somewhere and just scribbling down as much as I could. My journalism professors Chuck Stone and Bill Fleischman used to tell us about listening, really listening, and trying to pull a few nuggets out of an interview even if you couldn’t record the whole conversation. “Remember them,” they’d say. “Use them.”

I still remember Sheppard’s descriptions of operating the lift (elevator) at his family’s investment firm in London with a co-worker named Sarge, training some point-to-pointers in England before work and how he felt about getting a $100,000 budget from George Strawbridge to buy some yearlings at Saratoga in 1971. The rest is a blur.

I wrote the story, sent it to The Blood-Horse and kind of forgot about it until Sheppard announced his retirement from training last week. Published in the May 17, 2008 edition, my story came 42 years into his training career and after he’d trained five steeplechase champions and two Hall of Famers. Reading it now, the end hits. Sheppard never did get a top 3-year-old to the Kentucky Derby but he somehow added a dozen years, three more steeplechase champions and his only two flat champions to one of Thoroughbred racing’s greatest careers.

And now it’s finished. It started the year after I was born and rolled right up to the year I turned 55. I watched Tall Award, Arctic Joe, Café Prince, Michael’s Mad, Leaping Frog, French Hollow, Double Reefed, Martie’s Anger, Flatterer, Jimmy Lorenzo, Highland Bud, Yaw, Double Bill, Mistico, Ninepins, With Anticipation, Forever Together, Informed Decision, Arcadius, Mixed Up, Sovereign Duty, Divine Fortune, Winston C and so many others.

Honestly, I rooted against his horses for a big part of my life, while working in my father’s barn. We took down Leaping Frog with Owhata Chief a couple times and ousted the great Flatterer with Gogong once. Gradually, it turned to respect, awe, head-shaking wonder, whatever. Sheppard’s horses won. You weren’t going to do anything about it. His focus on his horses turned into success on the racetrack – be it with 2-year-old phenom and future stallion legend Storm Cat or teenaged steeplechaser Ninepins – and did so for more than 50 years.

At some point during my writing career, he told me to stop calling him Mr. Sheppard. At another, he gave me his mobile number and I no longer had to call the office and leave a message with his overworked secretary Lisa. At some other, I moved up to riding in his car – to the watch horses train at Saratoga, Fair Hill and Ashwell (I had to ride in the back seat once because his briefcase was on the front seat and wouldn’t close).

And that one time I drove him home.


Reprinted from The Blood-Horse magazine. May 17, 2008. Thanks to Debbie Tuska and Claire Crosby for digging this out of the archives.

Jump Start. Trainer Jonathan Sheppard keeps winning all kinds of races. By Joe Clancy.

Go to Saratoga. Buy some yearlings. And kick-start a racing career.

Sounds easy enough, right? Now 67, Jonathan Sheppard points to the summer of 1971 as a keystone to his training career that reached Thoroughbred racing’s Hall of Fame in 1990 and shows no signs of slowing down despite being in its fifth decade.

“I was training a few horses for George Strawbridge then, mostly steeplechasers and some he rode himself,” said Sheppard. “He said we ought to buy some yearlings at Saratoga and gave me a $100,000 budget. We bought four.”

The quartet (with their purchase prices and sires) turned out to be:

• Cafe Prince ($17,000, by Creme dela Creme), who won two Eclipse Awards as champion steeplechaser for Strawbridge’s Augustin Stable and was elected to racing’s Hall of Fame.

• Northern Fling ($35,000, Northern Dancer), who won graded stakes on the flat for Augustin/Sheppard and went on to sire $2-million earner Yankee Affair.

• Fast Approach ($39,000, First Landing), who became one of Strawbridge’s foundation broodmares by producing Grade 1 winner First Approach (by Northern Fling), Grade 2 winner Last Approach, Grade 3 winner Summer Fling, and six other winners.

• Social Conscience ($10,500, Flag Raiser), who didn’t live up to the others, but won steeplechase races and became a foxhunter at Augustin.

All great achievements owe their true growth to a catalyst, and Sheppard’s training career rocketed from there – although it officially began in 1966.

From Saratoga 1971, Strawbridge built a classy breeding program that funneled quality horses (jump and flat) to Sheppard. Other clients soon followed and Sheppard dominated American steeplechasing for most of the next 25 years.

The success translated to flat racing as well, with stars such as Storm Cat, With Anticipation, Crowd Pleaser, Rochester, Ratings, Trevita, Mo Bay, and others crossing through the barn. Along the way, Sheppard built a breeding program of his own (often in partnership with another longtime client, Bill Pape), and now trains roughly 100 horses at the farm near Unionville, Pa., a training center near Camden, S.C., Delaware Park racetrack, Gulfstream Park, Keeneland, Saratoga, or wherever the stable is running. Through April, Sheppard’s horses had won more than 2,600 races and nearly $56 million in purses – both top 30 all-time in Thoroughbred racing.

Not bad for a guy who started out driving a “lift” in a London brokerage house.

Sheppard grew up in England the son of Dan Sheppard, the country’s chief handicapper for Thoroughbred racing. While providing a great introduction to the sport, Sheppard’s father’s job also limited the son’s future. By rule, he could not be a public trainer as long as his father held the position. He was instead dispatched to the family business, Sheppards and Co., to learn to be a stockbroker under the tutelage of various uncles and cousins.

Sheppard first worked on the company elevator, a massive box of polished oak that expressed customers from the office building’s lobby directly to the Sheppards and Co. floor. His co-worker, a war veteran named Sarge, wore a uniform and drove the elevator. Sheppard mainly watched, later moving to the mailroom, the dividend department, and so on. He hated it, and gravitated toward racing despite the limited career prospects.

He could train for himself or immediate family members and ride as an amateur, so he trained two point-to-point horses before dashing off to catch the 8:06 train to London.

Once he got the idea there might be other venues in which to pursue training horses, Sheppard bolted like a loose horse, taking a year’s leave from the brokerage firm and gaining a spot on a cargo ship from Rotterdam to New York. The ride lasted 10 days, twice as long as normal thanks to engine trouble. Sheppard kicked off his American adventure in 1961 at the home of some cousins in Connecticut, and took a job with the Griswold family in Maryland exercising foxhunters. The post paid $20 a week and came with a room and a car. He met Mikey Smithwick, Sidney Watters (both future Hall of Fame trainers), and others in the horse community and eventually went north to Unionville, Pa., and a job with another future Hall of Fame trainer, Burley Cocks. The job paid nothing, but came with a room, meals, gas for his car, and a chance to ride races. He stayed about a year, working in the barn and riding a few races in 1962 (he went 2-for-49 that year).

Sheppard returned to England and the brokerage job, moving up in the world to an office, some dealings with clients, a potentially lucrative bonus package, and more misery. In short order, he came back to America (this time by plane) and never left. Sheppard worked for Cocks for a few years – crossing paths with Billy Turner (who trained Seattle Slew), among others—and moved to a job as trainer Joe Nash’s assistant until hanging out a shingle of his own in 1966.

His first official winner came that spring with timber horse Haffaday, for owner Redmond Stewart and Stewart’s son-in-law, jockey Paddy Neilson. That theme – amateur jockeys and family horses – continued for a while and led to relationships with future owners Strawbridge, Dixon Stroud, and others. Those riders all pursued professional careers and left the horses to Sheppard, who needed raw material for his fledgling racing stable. He called on David Crossley-Cook, one of his stock market connections, to help import six English flat horses to convert to American steeplechasers. Strawbridge bought one, Gaddo, who won 17 races.

Summing up the philosophy behind the next 40 years of training in a few sentences would be akin to counting grains of sand at the beach, but Sheppard tried.

“Every horse is a project, and you feel you have to put something of yourself into it,” he said. “The horses run the race, but you feel like you’re putting your skills on the line when they run. It’s a very competitive business and you want to do well.”

That individualism merged with competitiveness to create a juggernaut on the steeplechase circuit. All told, he’s won 23 National Steeplechase Association championships by races won and 24 by money won. His charges have won 10 steeplechase Eclipse Awards, with Cafe Prince and Flatterer going on to the Hall of Fame. Still playing at the top of the jump game, he led all trainers in earnings in 2007 ($919,944) and won an NSA Grade 1 stakes at Keeneland in April with Sovereign Duty.

But most people in racing know that, or can guess it. The steeplechase success comes as a label. Sheppard’s “that steeplechase guy” and has been forever.

However, some time ago, Sheppard bridged the gap between steeplechasing and flat racing with Thoroughbreds of quality.

“I don’t think it’s a secret that his forte is turf horses, and getting horses to relax,” said trainer Graham Motion, a Sheppard employee for five years in the 1980s. “Whether they are steeplechase horses or not, you have to get them to settle, get them to relax. But he gets horses fit. When he runs a horse, it’s ready to run.”

Motion worked for Sheppard at the time of Storm Cat, who missed winning the Breeders’ Cup Juvenile (Gr. 1) by a nose in 1985. Nobody in the barn realized the horse’s future impact on the breed, but everyone knew how much ability Storm Cat had. Motion remembers watching the Juvenile from Sheppard’s living room like it was yesterday. In a stark illustration of Sheppard’s training, Storm Cat shared a barn with Flatterer, arguably the greatest American steeplechaser in history. The four-time champion and the future leading sire sometimes even galloped together. Like Storm Cat, Flatterer just missed on the world’s biggest stage – finishing second in the 1986 French Grande Course de Haies d’Auteuil Hurdle and 1987 English Waterford Crystal Champion Hurdle Challenge Trophy.

“I have a photo of Storm Cat galloping behind Flatterer in the field at the farm,” Motion said. “To have those two horses in the barn at the same time says something. They were so different, but they were both trained to perfection.”

Sheppard is simply a horse trainer, and he has the schedule to prove it.

“His travel schedule involves a lot of change fees – a lot,” said longtime secretary Lisa Clay. “He should own U.S. Air by now. I usually do most of his travel, and it’s pretty hectic. He has me book everything and then he changes everything. He flies three times a week, somewhere. He tries to be everywhere, but it’s all done to follow his horses around.”

In late March, Sheppard flew from his winter base in Florida to saddle six horses at the Carolina Cup steeplechase meet in Camden, S.C., and was back at Gulfstream Park to run Cliffrose in the Orchid Handicap (Gr. 3 turf) the next day. April was more hectic, with trips to Kentucky, Florida, South Carolina, Pennsylvania, and steeplechase meets in Georgia and Virginia stirred together. He traveled by commercial airline, private jet, and car (owned, rented, and borrowed).

The frenetic lifestyle leads to few meals at home, huge telephone bills, and a reputation as a workaholic, but Sheppard considers it a duty. His wife, Cathy, spends most of the year at their home in Florida (though they speak by phone daily about horses, his schedule, life in general). His three children (a son, Parker, died at 24 in 2006) from previous marriages are adults. He signed up for this. Horses are his life. He’s the trainer, even if he can’t see them all train every day. And he’s not going to stop now.

“I don’t feel 67 is that old, but I have been doing it a long time,” he said. “There are plenty of people out there doing it. Barclay Tagg (another former jump jockey) is at the peak of his career, and he’s a year or two older than I am. There are times it gets to be a little bit too much. When the horses aren’t running well and you’ve got lots of problems or things going on and you’re stressed, you wonder if it’s worth it, but that’s all part of it too.”

Sheppard relies on a cast of employees spaced wherever his horses are, but has no chief assistant trainer. Jim Bergen (racehorses on the farm), John Hughes (broodmares and yearlings), Amy Lippincott (young horses), Joan Abse (Delaware Park), Barry Wiseman (Kentucky and Saratoga), and Jonathan Smart (Camden) help drive the stable. In all, some 60 people work for Sheppard. Despite its chaotic nature, the operation breeds loyalty and steadfast care.

“He’s a complicated guy; most smart people are,” said Bergen, who started with Sheppard in 1999. “But there’s a camaraderie here that I haven’t seen at other stables. I have no idea why. There’s a camaraderie here among the people who work for him and have worked for him before. He doesn’t always come off that way, but the people who work here matter to him.”

Bergen, who also worked for Hall of Famers Scotty Schulhofer and Jim Conway, marvels at Sheppard’s training methods.

“Compared to other racing stables, the methods are different,” Bergen said. “He leaves his options open as to how he’s going to train them, what he’s going to do with them – even at the track, he does things differently than other trainers and it pays off. It’s not the same thing every day, and the horses appreciate that.”

For Motion, the Sheppard job changed his life. He knew a little about horses, and even less about racehorses, when he started.

“Everything,” Motion deadpanned when asked what he learned while with Sheppard. “I hadn’t done it before, so I learned it all. It was a foundation for what I’m doing now; it taught me the business and the ability to understand horses and how they tick. Anyone can train horses and some people have a knack for it. He has a feel for it that’s beyond that, a feel for what it takes to get any given horse to any given race.”

Sheppard’s employees have long spoken of being part of the team, of enjoying the spoke-in-the-wheel atmosphere. For his part, Sheppard sees the staff in a similar light.

“I like being around my help because they keep me motivated,” Sheppard said. “I kind of feel I’m doing it for the team a little bit. They put a lot into it and I don’t want to let them down.”

Like many, Sheppard trains at least half by intuition or feel. He can’t describe his training profile, other than to admit he does have an affinity for older horses and horses that want to run longer distances. He doesn’t use a computer, and laughs when people talk about having his horses on “Stable Mail.” Sheppard is awed by horsemanship conversations with the likes of Allen Jerkens – they’ve debated the merits of Lasix, studied conformation, and generally talked shop for years. Neither man, despite their combined 6,400 victories, knows the answers.

“It doesn’t take a rocket scientist, but that’s why I’m training horses and not working on Wall Street,” Sheppard said. “You try to use good horsemanship and good common sense, then let the horses do the rest. If they turn out to be sprinters, fine; if they turn out to be stayers, fine; if they turn out to be jumpers, fine.”

Sheppard has never started a horse in a Triple Crown race, but thought about the Kentucky Derby (Gr. 1) with Crowd Pleaser and With Anticipation early in their careers. Both turned out to be better later in life as turf horses – by design or not, no one knows. Recent performers Forever Together (a Grade 2 winner last year) and Informed Decision (a stakes-bound Keeneland winner) proved successful on dirt and at shorter distances.

“I remember thinking the closest I’ll ever get to winning the Kentucky Derby was when With Anticipation finished second (in the Woodford Reserve Turf Classic, Gr. 1T, in 2002) one race before,” Sheppard said. “(A top 3-year-old on the national scene) is about the only thing missing from my training resume, so it would be nice to someday have a chance at that.”

 

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