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Remembering Top Steeplechase Trainer Jonathan Sheppard: 1940–2023

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Photos by Jim Graham

Jonathan Sheppard, one of the most accomplished and honored trainers in the American steeplechasing world, passed away on Aug. 27 at age 82. A former West Grove, Pennsylvania, resident, Sheppard was a native of Ashwell in Hertfordshire, England. There, he began his working life as a stockbroker in the family business. His father was a racing official, and British rules wouldn’t allow him to find work as a trainer.

Sheppard came to the United States in the early 1960s, riding for Hall of Fame steeplechase trainer W. Burling Cocks. In 1966, he won his first race in a steeplechase event at My Lady’s Manor, Maryland. One of his great racing partnerships was with George Strawbridge Jr., an accomplished amateur steeplechase jockey who wanted to spread his wings as an owner in the Augustin Stable silks. Beginning in 1974, Sheppard helped Strawbridge and his Augustin operation become steeplechasing’s leading owner a record 23 times.

Unequaled in the steeplechase community, Sheppard’s list of accolades is staggering. Amongst other things, he was one of the winningest trainers in United States jump-racing history, with 1,242 victories. Between 1972 and his retirement in 2020, he led with the most U.S. steeplechase wins per year a record 26 times. He was also one of only two trainers to earn championships with flat and jump horses.

According to the National Museum of Racing and Hall of Fame, Sheppard had a 16.1% probability of winning a start. In a career that spanned 60 years, he had 3,426 wins, and his charges had earnings of $88,679,925. He retired as the National Steeplechase Association’s all-time leading trainer by wins (1,242) and earnings ($24,902,442). As a mentor to up-and-coming trainers, Sheppard’s steady hand aided in the development of Graham Motion (winner of the Kentucky Derby and Dubai World Cup with Animal Kingdom), Leslie Young (last year’s champion steeplechase trainer with 37 wins) and Keri Brion (leading jumps trainer for 2022 by earnings, with more than $1.1 million in purses).

Sheppard at the 2015 Pennsylvania Hunt Cup with jockey Keri Brion.

Jonathan Sheppard at the 2015 Pennsylvania Hunt Cup with jockey Keri Brion.

In a career that spanned 60 years, Sheppard had 3,426 wins, and his charges had earnings of $88,679,925. He retired as the National Steeplechase Association’s all-time leading trainer by wins (1,242) and earnings ($24,902,442).

Here some of Sheppard’s other stunning stats, courtesy of the museum:

  • North America’s leading steeplechase trainer in earnings: 1973-1994, 1996, 1999, 2007, 2010–13, 2020.
  • North America’s leading steeplechase trainer in wins: 1970, 1972, 1974–79, 1981–85, 1987–90, 1992–95, 1999, 2006, 2010, 2013, 2020.
  • At least one race win at Saratoga, New York: 1969–2015.
  • Breeders’ Cup Grand National wins: 4.
  • Colonial Cup wins: 11.
  • New York Turf Writers Cup wins: 12.
  • Trained 15 Eclipse Award champions: Athenian Idol (1973), Cafe Prince (1977–78), Martie’s Anger (1979), Flatterer (1983–86), Jimmy Lorenzo (1988), Highland Bud (1989), Forever Together (2008), Informed Decision (2009), Mixed Up (2009), Divine Fortune (2013) and Winston C (2019).

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