Sheppard has also had success with thoroughbreds. He has saddled numerous graded stakes winners, and he was the leading trainer at Saratoga in 1984 and 1985.
"Back then, the meet was shorter, and you had fewer races," said Sheppard. "In fact, I don't think I had more than 10 winners in any meet here, both steeplechase and flat (racers)."
Sheppard grew up in a family that was involved in horse racing. His father was a racing official in Great Britain, and at a young age, Sheppard expressed an interest in being a jockey.
"I wanted to be a flat course jockey, but I was too big for that," said Sheppard. "So, I turned to riding steeplechase horses."
Sheppard moved to the United States in the early 1960s and rode for legendary steeplechase trainer Burley Cocks for two years. Then, Sheppard started training his own steeplechase horses. His first horse, Haffaday, posted several wins in its career including a victory in the 1966 Maryland Hunt Club " one of the biggest traditional steeplechase races in the United States.
"Not only was (Haffaday) my first horse and my first winner, he was my first big winner," said Sheppard. "He helped put me on the map."
It was the only time Sheppard won the Maryland Hunt Club, but it spawned a career that is still going strong today. He currently ranks third among steeplechase trainers in victories and second in money earned this season.
Sheppard said the secret to turning a horse into a champion steeplechaser is getting to know its personality before trying to teach it technique.
"You have to know your horse before you can train it so you know what you have to do," said Sheppard. "If it's the type of horse that requires positive reinforcement, you have to pat it on the behind and say it's doing a good job."