Jonathan Sheppard retired Monday, and now racing knows how baseball felt the day Joe Dimaggio retired from the Yankees. The center fielder was an all-timer, author of a 56-game hitting streak, a three-time MVP, a nine-time World Series winner and an all-star in each of his 13 seasons when he retired in 1951.

Sheppard probably couldn’t hit a curveball or the cutoff man, but he could train a horse and called time on a career of unmatched achievement in Thoroughbred racing. The 80-year-old trained his first winner in 1966, and ran the total to 3,426 (a record 1,150 over jumps) through 2020. He won 26 National Steeplechase Association training championships, trained the winners of 15 Eclipse Awards (13 champion steeplechasers, two champion flat runners), sent two horses to racing’s Hall of Fame, was inducted himself in 1990, trained legendary stallion Storm Cat and sent horses of all description to success on the steeplechase circuit and beyond.

The English native goes out on top, after winning the NSA championship with a 20-win season in 2020. The victory gave him at least one title in six decades from the 1970s to the 2020s. He spent much of the Covid-shortened season in Florida, relying on assistant Keri Brion to organize the stable, which closed the season with a four-win day in November at Charleston.

Sheppard’s horses earned more than $88.7 million in purses, and fortified a deep roster of success consisting of some of the game’s true greats including:

  • Flatterer. Bred by Sheppard and then business partner Bill Pape, the son of Mo Bay and the Nade mare Horizontal won four steeplechase championships (1983-86) represented the United States admirably in two overseas starts (seconds in the English and French champion hurdles), set a weight-carrying record when he won a stakes under 178 pounds in 1986 and was inducted to racing’s Hall of Fame in 1994.
  • Café Prince. Racing for longtime Sheppard client Augustin Stable, the Saratoga yearling purchase won steeplechase titles in 1977 and 1978, and made the Hall of Fame in 1985. The California-bred won 18 races (including one 2-mile flat race with Sheppard himself on board ) and earned $228,238 back when it was difficult to do. Café Prince won the Colonial Cup and the Lovely Night (a big Saratoga stakes at one time) twice each.
  • Seven other steeplechase champions: Winston C (2019), Divine Fortune (2013), Mixed Up (2009), Highland Bud (1989), Jimmy Lorenzo (1988), Martie’s Anger (1979) and Athenian Idol (1973). Sheppard trained other jump stars such as Mistico, Ninepins, All The Way Jose, Double Bill, Romantic, It’s A Giggle, Summer Colony, Yaw, Double Reefed and Polar Parallel.

Sheppard won a Maryland Hunt Cup with Haffaday in 1968, won the Colonial Cup and the New York Turf Writers Cup 15 times each, the A.P. Smithwick Memorial 13 times, the American Grand National eight times.

In Steeplechase Times, The Saratoga Special, Mid-Atlantic Thoroughbred and beyond, we covered Sheppard’s career for more than 25 years – from Arcadius to Zoom Zoom Zoe and everything in between.

Find some highlights from the pages of The Special below.

The Best Of Jonathan Sheppard.

 And check back for more from Steeplechase Times and beyond.