A totally unnecessary, but long overdue, remembrance of Jonathan Sheppard

A few days before the last Carolina Cup, John Cushman stopped in to pick up his race tickets. When he did, I caught up with him and we had a nice chat about the museum. He asked what plans we had to further memorialize Jonathan Sheppard. We had our exhibit about him, and we had a program ad at the Cup after he passed, but as we spoke it became clear that we had failed to give Jonathan Sheppard his due. Now, I will do my best to rectify that mistake.

Unlike seemingly everyone else in the horse world, I never had the privilege to meet Jonathan (I learned some time ago that if you just say Jonathan everyone in the horse world intuitively understands who you are talking about). The last time he came to the National Steeplechase Museum I was just a part-time intern and was not in on the day he visited. During his visit he spoke with Toby Edwards and Hope Cooper, took them to his houses here in Camden, and gave permission for the museum to take everything out of them and make a new exhibit. I was one of the people that brought the collection to the museum and catalogued it (it totals over 500 items), but, in that whole process, I never did meet the man.

As I sat down to write this, I struggled to come up with something to say. What can I say about Jonathan that the people who actually knew him haven’t already said far better? I could tell you that Jonathan won 1,150 jump races during his career that spanned almost fifty-five years, but the extent of his full race record will likely never be known, as prior to 1972 the NSA listed only the winning trainer of a race, leaving off all others. I could say that he won $24,902,442 off those jump races, more than any other trainer in history. I could tell you that he won the Trainer’s Championship by money won twenty-nine times, with twenty-six Championships by races won. I could tell you about his streak of eighteen consecutive Trainer’s Championships by money won, snapped only by his own disciple, Janet Elliot. I have never even attempted to figure out how many stakes winners he trained, but suffice it to say “a lot” would probably qualify as a correct answer. I could tell you he won an inconceivable fifteen Colonial Cups, nearly a third of every running of that race. I could tell you he won the New York Turf Writer’s Cup so many times that the race now bears his name. I could tell you he won a race at Saratoga every year for forty-seven straight years. I could tell you that he trained fifteen Eclipse Award winners, thirteen steeplechase and two on the flat. I could tell you that he trained two horses who are now enshrined alongside him in the Hall of Fame: Cafe Prince and Flatterer. I could tell you that he was the recipient of steeplechasing’s highest honor, the F. Ambrose Clark Award in 2013.

However, the chances are if you’re reading this you likely already knew all of that. Because you knew Jonathan the man better than I did.

One thing that few people talked much about was Jonathan’s breeding operations. Jonathan, alongside longtime friend and business partner Bill Pape, was one of the few people who actually set out to breed chasers. The most successful horse to come out of this arrangement is unquestionably a dark bay gelding, foaled in 1979, named Flatterer. Second on the list would be Divine Fortune, 2013’s Champion Steeplechaser, and winner of six stakes races over his career. Lap of the Gods is the only Sheppard bred that I know of still running, though he has not appeared on an NSA entry form in 2025. I’m sure someone with better knowledge of the horses currently in training will prove me wrong though.

Another old friend and business partner of Jonathan’s is George Strawbridge. Jonathan approached Strawbridge in the early 1960s and helped him get into the jumping game. Disaster struck almost immediately. After the first race of a horse Strawbridge had purchased for $15,000, Jonathan called him and told him: “The whole thing is my fault. I put the bandages on too tightly and the foot boots were wrong. His legs are now terrible, he’ll never race again, and your entire investment is now worthless.”

Sixty years later, Strawbridge sits second on the NSA’s all-time earnings list with over $9,000,000. I think the appraisal of the investment as worthless may have been premature.

While Jonathan was always quick to compliment his jockeys, and he certainly had some good ones in his barn, and the quality of horses his owners provided him, he was modest about his own abilities. When discussing his horses’ success he would say “Hopefully my training helps, too.” An observer once noted that he was the only trainer schooling his horses in a torrential rain and asked him if that told him anything. Sheppard remarked “sure, it tells me that maybe I’m wrong and everybody else is right.” Another time, when talking about training he offered the pearl: “You put a part of yourself into every horse you train. I suppose it’s 50% guesswork and the successful trainers get it right most of the time.”

What does all this say about Jonathan? The statistics are plain to see. But Jonathan is more than just statistics. Jonathan left behind a legacy greater than most sportsmen can ever dream of. It is greater than the profuse praise and lists of career records recorded in the numerous annals of American Steeplechasing. It is the legacy of countless hours of training, of innumerable early mornings, and late nights. It is a legacy measured not in number of races won, awards received, or championships earned. It is the legacy instead measured in number of lives touched and impacted. It is a legacy of redefining the word “Greatness” in a sport older than the nation in which it is run. It is a legacy that lives on in the hearts and minds of all members of the family of the sport of Steeplechase. It is a legacy of raising a bar so high it may never be topped.

When Marion duPont Scott died in 1983, she was said to have been the heart and soul of American steeplechasing. Far be it for me, to try to take one of that grand lady’s titles. However, I think it is fair to say that Jonathan, a son of England, was very the spirit of American steeplechasing. He embodied all that is good and noble in the sport: optimism, perseverance, dedication, and a quiet humility.

He will be missed, but Jonathan Sheppard will never be forgotten.

“The only goal I’ve had really is to do the best I can with what I’ve got, not specifically to be leading trainer every year or set records. Take it day by day, do the best you can and at the end of the year, you look and say, ‘That’s good, leading trainer.’” – Jonathan Sheppard