Jonathan Sheppard: Master of the Turf

Jonathan Sheppard gives instruction prior to a race at Colonial Downs. (Photo by Eclipse Sportswire)
Famous Jonathan Sheppard story: One winter morning, longtime owner George Strawbridge, Jr. is watching a group of his young horses canter around the training track.
“I was really taken by a striking bay named Crowd Pleaser,” confessed Strawbridge. “Well, Jonathan strolls up and says, ‘he's nice but he's better suited for heading into battle centuries ago. The one you need to pay attention to is that gray, he'll be one of your best horses.’ ”
With Anticipation — that gray — won the 2002 Breeders' Cup Turf, and twice captured the Sword Dancer and Man o' War Stakes. A fan favorite, the handsome gray posted 15 wins, nine seconds and eight thirds in 38 career starts, retiring at age nine with career earnings more than $2.6-million. 
Point is, the man has an inner sense about racehorses. He knows how to read them and how to keep them fit and happy. And for Sheppard, it is always, always about the horse.
This passion — or obsession as many would say—defines Sheppard's life. His achievements are legendary. Sheppard is one of just two trainers to win Eclipse Awards for both flat and steeplechase racing. In 2009, he did it in the same year with Informed Decision and steeplechaser Mixed Up. He has won more than 3,144 races, scored six Breeder's Cup victories and has trained 11 Eclipse Awards champions, including the legendary champion steeplechaser Flatterer (1983, 1984, 1985, and 1986). He has been the leading steeplechase trainer by earnings 27 times. He has won a race at every Saratoga meet since 1967.
The British-born Sheppard was inducted into the National Museum of Racing and Hall of Fame 24 years ago. And at 73, he's still going strong. 
On Preakness day 2014, Strawbridge's 6-year-old homebred Utley rallied in the stretch to sweep by the top three runners on the outside to capture the $400,000 Dixie Stakes. For most of the year, Utley trained traveling loops of a figure-8 path and charging up and down the hillsides at Sheppard farm. He has performed this trick with older horses for decades.
The trainer's operation is centered at Ashwell Stables about an hour southwest of Philadelphia. Just down the road from his training grounds, you’ll find a Quaker settlement that dates back to the earliest days of the Colonies. The territory was part of the original land grant to William Penn and is still farmed and maintained by his descendants.
Southern Chester County, Pa. is an enchanted land celebrated for its luxuriant pastures framed by post-and-rail fences weathered to a pleasant grayish brown. For generations the limestone-rich soil has fostered speed and stamina in the superior horses the land breeds and trains.
A HORSE IN TRAINING AT ASHWELL

Photo courtesy of Ashwell Stables
Sheppard's training style revolves around being kind, patient and trusting in what the horse is trying to say. Graham Motion worked at Ashwell Stables from 1985 to 1990. One of the country's elite trainers, Motion trained 2011 Kentucky Derby winner and 2012 Dubai World Cup Champion Animal Kingdom.
“I don't think Jonathan's operation is comparable to anything anywhere in America,” said Motion, who is based at Fair Hill Training Center, about 20 miles from Sheppard's farm. “For me, it was the equivalent of going to college. I've tried to model my career after his philosophy. Jonathan is always about the horse and about getting the horse to settle and relax. I don't believe there are many trainers left who are real horsemen like Jonathan.”
English roots
Ashwell Stables is named for Sheppard’s hometown in the East Midlands of England. One of four children, his father, Daniel, worked as a Jockey Club Handicapper, where he assigned Thoroughbreds specific weights for races. He often traveled with his father to race meets.
When Daniel went off to World War II, Jonathan and his mother lived with his grandparents. As a young lad, he spent countless hours with foals on an adjacent farm, playing and talking with them. By age nine, he was correcting the faults of certain ponies, teaching the stubborn ones what the good ponies had taught him. He joined the local pony clubbers and frequently fox-hunted.  
“I fancied myself as being just as successful as English jockey Lester Piggott,” said Sheppard, his blue eyes dancing. “He started his riding career at 14 and I was only a few years younger.”
Jonathan dreamed of becoming a trainer, but an English racing law prevented that since his father was a racing official. So, he rode as an amateur in point-to-point races. After attending Eton College, Sheppard set off for London, taking a position with Sheppards & Co. Ltd., a stock brokerage founded by distant relatives in 1827.
“I was able to use a family connection to get the job, but I soon saw myself as being doomed to a working life in a office,” admitted Sheppard with a shrug. “I worked with a cousin of mine who always used to tell me ‘we don’t know what else we can do in life. You’ve got a passion for racing, go chase it.’ ”
He did. In 1961, at age 19, Sheppard traveled to America and wound up at the Griswold family farm in Maryland, where he exercised their timber racing and point-to-point horses. He won 25 or so amateur races and along the way met Hall of Fame steeplechase trainer W. Burling Cocks of Unionville, Pa. Sheppard lived with the family for three years, rode in amateur races and apprenticed as Cocks’ assistant trainer. In 1965, he embarked on a training career of his own, starting off with a few saddles and bridles and a bucket of good will. He notched his first career winner in a steeplechase race with Haffaday.
“Burley used to tell me he could get inside the horse’s mind,” Sheppard recalled. “Rather than force the horse, he would work around a problem, always looking for the horses’ best qualities and tendencies. In his mind, every horse that came to him had the potential to be a champion. His credo was that you have to see the best in a horse to get the best out of a horse.”  
On the Farm 
Far from the majestic stables of Kentucky, Sheppard runs his operation out of a late 19th century dairy barn converted for racehorses. Ashwell comprises 65 acres and he rents two adjacent farms bringing the total acreage to 300. Inside the main barn, a cluster of thick leather and brass halters hang from an overhead hook. A chestnut filly gets a foot trimming with very little fuss. Feed bags are stacked neatly in a corner. Horses poke their heads out of adjoining stalls, while a pair of crescent-horned goats wander at will keeping both animals and humans company.
A HORSE GALLOPS AT ASHWELL 

Photo courtesy of Ashwell Stables
With a staff of 70, Sheppard and his top assistants oversee 137 horses on the farm as well as leasing stables at Delaware Park, Presque Isle Downs, Saratoga Race Course, Keeneland Race Course and Gulfstream Park. But for 45 years everything has revolved around Ashwell's training grounds. For the past 15 years, Jim Bergen has been Sheppard's main training assistant on the farm where their stakes horses typically return after each race.
“I think the thing I've learned from Jonathan is these horses are herd animals,” said Bergen, who grew up outside of Saratoga. “They're meant to be outside as much as they possibly can be, and it has a huge impact upon their mental capabilities.
“Horses are creatures of habit and they can get sour at the racetrack. Tracks are designed for efficiency and convenience for people, being at a farm allows the horses freedom. It keeps the animals happy and if all goes well we're able to maintain their racing form.”
For more than four decades, Sheppard's horses have galloped on open fields and jumped over natural obstacles on trails weaving through the woods and creeks, even on the shoulder of a paved road. The heart of his craft are the morning workouts staged in locales known as the One-Hundred-Acre Field, Apple Orchard, the lower barn field, the five-furlong Fibar wood chip track, Bob's Old Straw Ring, and the Forgiven Strip. Serious workouts take place in the One-Hundred-Acre Field. Typically, six horses at a time train two-to-three loops over a figure-eight shaped path.
It's a world away from the loud speakers, and hustle and bustle of U.S. racetracks. There are no clocker stands or furlong markers in the open fields, so timing workouts is a bit tricky. Stopwatch in hand under towering pine trees, Sheppard times roughly a five-furlong workout that is measured from a pole stuck in a fence line to a stand of broad-armed trees.
Up on the 926 Gallop — a rolling, grass course — a string of Thoroughbreds charge past a border fence of post and rail, the thud of their hooves punctuated by blasts of their heavy breathing. The horses start at a canter up a demanding hill and come back down with the brakes on, but still moving at a solid clip. They pick up the pace heading back up the steepest slope of the hill and down to the base that is bordered by stands of trees. Two-and-a-half times around equates to seven furlongs. 
“These are tough horses, both physically and mentally,” Bergen noted. “The workouts foster strength and stamina, toughening up the horses' bones, muscles and tendons. That's very important to young horses who aren't full grown until age five.”
Here's a splendid memory. Back in the winter of 2010, I visited Ashwell. The morning after a light snowfall two dazzling grays were led out to an adjacent field joining a cluster of other fillies.  The grays — Forever Together and Informed Decision — dug and picked at hidden shoots of grass, then suddenly wheeled around and galloped off, white plumes steaming from their nostrils in the frosty air.
FOREVER TOGETHER AND INFORMED DECISION TURNED OUT IN THE SNOW

Photo by Shawn Faust
Back then they were George Strawbridge's champion girls. Forever Together captured the 2008 Eclipse Award in the turf female division. Informed Decision took home an Eclipse in 2009 as champion female sprinter. Both had ongoing issues when Strawbridge purchased them as 2-year olds. Once in Sheppard's hands, the fillies were coddled and controlled. Rather than force them, the trainer and his crew worked around their problems and eventually figured things out. The payoff was a pair of top racehorses that excelled at 6 and 12 furlongs. 
But here's the thing: Thoroughbred trainers just don't turn out two champion-level animals together. The risk is far too great. But for Sheppard, it is yet another of the natural approaches that sets him apart from other top American trainers.
“Turning those two great fillies out in a field together, turning out a lot of racehorses in a field together, no one does that,” said Motion. “But, Jonathan has gotten tremendous results. I have pictures of Flatterer galloping in the field together with Storm Cat, who was there then. You just wouldn't see that.”
Sheppard developed his regimen starting in the late 1960s when he and an assistant handled a dozen horses. To cool them out, the horses were ridden round and round in the barn, and put out in a nearby paddock.
“Then I thought, why not turn them out first before we rode them so they would be loosened up,” related Sheppard. “It's almost like interval training. They fly around the field a bit and it tends to relax them. I believe you can train a horse better if the horse is relaxed.”
His Thoroughbreds spend as much time as possible outdoors, even if that means his staff needs to hook a snow blade to the tractor and plow a path to the paddocks.
“We try to be creative,” Sheppard said. “In the snow, they get good, strong gallops. That helps build a strong foundation so when they ship south to our facility in Aiken [South Carolina] and to Gulfstream, they’re ready to roll as we prepare them for their racing schedules.”
Longtime partners
If you try and pin him down, Sheppard will tell you that Flatterer, Forever Together and Storm Cat are his favorite horses. But it's not their stellar racing records that he cherishes.
“It's my respect for them as an athlete,” Sheppard observed. “You have to be really talented, and you have to try really hard. They did it, all the time. And, they had very different temperaments.”
In 1985, a 2-year old named Storm Cat had his last major drills in the One-Hundred-Acre Field before finishing second by a nose in the 1983 Breeder's Cup Juvenile. Injured the next year, he began his legendary stud career at William T. Young's Overbrook Farm in Kentucky. Back then, Young wanted Sheppard to become his primary trainer on the East Coast, but he would have to be based at Belmont Park.
“I would have had to give up all this [at Ashwell],” said Sheppard, shaking his head. “I declined.”
That was welcome news for George Strawbridge. A former amateur steeplechase jockey in Chester County, Strawbridge has been deeply involved in Thoroughbred racing for most of his life. A member of The Jockey Club since 1976, he is the all-time leading money-winning steeplechase owner in the United States. His green and white Augustin Stable silks are familiar on both sides of the Atlantic with a parade of top-notch flat runners.
MR. AND MRS. STRAWBRIDGE, JOCKEY LEPAROUX AND SHEPPARD AFTER AN INFORMED DECISION WIN

Photo by Eclipse Sportswire
Strawbridge met Sheppard in 1968 at a dinner party in Aiken, S.C., which set into motion a legendary friendship and business partnership. Strawbridge and Sheppard teamed up with a pair of timber horses that year. Gaddo followed. An Irish-bred runner, Gaddo won 21 races in his career. It was the beginning of a steeplechase dynasty.
“George has given me free rein with my program,” Sheppard said. “If they look like they’re not quite right physically or mentally for the rigors of racing, I don’t push them at age two or three. I guess I could be guilty of being too patient.”
“Don’t I know,” laughed Strawbridge. “Jonathan is a very kind man and very conscientious. He has produced so many good horses for me. He cares deeply about all of his horses. He absolutely loves them. He loves them whether they're champions or maiden claimers. He just flat-out loves the animal.”
Strawbridge tells the story of how early on his 2008 champion turf filly Forever Together would get so keyed up, so anxious, she couldn't sweat. On top of that, she was a finicky eater. Sheppard climbed inside the filly's mind. Tried to get her to relax in workouts, and when he switched her to turf and added Guinness to her diet, Forever Together really came into her own.
“The horse just loved the taste of Guinness,” Strawbridge insisted. “Sheppard started mixing the Guinness with her food and she began sweating and started to eat the proper level of feed for a top-level competitor. It worked like magic and she was marvelous from then on out.”
But, Sheppard's single-minded dedication to his career and nomadic lifestyle has come with a price. It probably cost him two marriages. In the end, he admits he was married more to his job more than anything else. In a tragic event one of his two sons, Parker, 25, died from a fractured skull when he was attacked by a man in Durango, Colo. in 2006. Sheppard has been married former jockey Cathy Montgomery for 26 years. She lives year-round in Florida, where Sheppard joins her when he's wintered at Gulfstream Park.
Chester County's William Pape has been a steeplechase client for 47 years. Together with Sheppard he owned the great Flatterer, who died this past spring at age 35. The first horse to capture steeplechasing’s Triple Crown, Flatterer came back from a four-month winter layoff to finish second of 18 in the 1987 Champion Hurdle Stakes at Cheltenham in England. He also triumphed in the National Hunt Cup at Radnor under an American record 176-pound weight.
Last year, Divine Fortune was Pape’s fifth individual Eclipse winner either as sole owner or co-owner. Preceding Divine Fortune were Athenian Idol (1973), Martie’s Anger (1979), Hall of Fame member Flatterer (1983-1986), and Mixed Up (2009). All of his champions have been developed by Sheppard, who has trained 11 individuals to a total of 14 Eclipse Awards.
“It’s been an equal partnership for all these years,” reflected Pape. “Jonathan is extraordinarily intelligent, very observant, enormously patient, totally dedicated and he really loves what he’s doing. We had a horse named Asking For Luck, even won a stakes race for us, but he wound up being claimed from us. Well, Jonathan was determined to get him back, not to race, but to retire him. He brought the horse back to my farm. Not many horsemen would have that kind of compassion."
TRAINING AT ASHWELL

Photo courtesy of Ashwell Stables
Bergen talks about the 1980s, when an ornery Storm Cat was brought to Ashwell, and over time, Sheppard and his team turned the colt around.
“He needed to be a horse again, to go play, roughhouse with other horses,” he observed. “This guy had been through the wringer. Then one day being a horse was fun again. Jonathan is constantly thinking about the mental aspect. It’s what puts good horses over the top.”
Sheppard owns mares, breeds them, takes horses from outside clients and treats those colts and fillies as if they were his own. Bergen laments that in today's Thoroughbred world the horses are such a high-dollar investment that that they are insulated at the racetrack to protect their owner's investment.
“The thing I respect about Jonathan is he's a breeder and owner as well as trainer, so he has a vested interest,” Bergen explained. “In addition, he owns the farm and rents two others, so he's invested in both the horses and the land.”
Among Sheppard's top runners at the farm are Utley, Beyond Strike and Cat's Claw, a 4-year-old mare who has won twice recently on the turf at Belmont Park at 1 1/4 miles and 1 1/2 miles. Like clockwork, after each race Cat's Claw returns to Ashwell.
At the farm, Bergen and his crew try to keep the horses as close to nature as they can.
“Horses get to roam around, roll around, pick some grass,” he said. “They behave like horses. Most of the land is in conservancy [protected] which allows us to go to seven or eight different locations to exercise the horses. All that variety keeps them fresh and happy.
“It's easier to be at the racetrack but your hands are tied as far as training regimens. There are a lot more headaches working them here at the farm, but over my 15 years what I've seen consistently is our imaginative training has paid big dividends with so many top-flight horses that have come through here.”
Bergen notes that horses are just like people, they have personalities and quirks. 
“They will do what you want them to do, unless they've had bad training,” Bergen observed. “They're like a blank blackboard. You can put up good marks, or bad marks. They need a lot of positive reinforcement and to develop trust. And, Jonathan is truly the master.”
Major Accomplishments

Won first race in 1966 
Has trained 14 Eclipse winners, including flat champions Forever Together (2008 Champion Turf Female) and Informed Decision (2009 Champion Female Sprinter)
NSA Leading Trainer by Earnings 27 times
Earned 1,000th win over fences in 2010. Won 3,000th race overall in 2012
Trained Hall of Fame jumpers Flatterer and Café Prince
Inducted into National Museum of Racing’s Hall Of Fame in 1990