Jonathan Sheppard Seeks New Worlds to Conquer

Robbie Walsh, Robby Walsh, Robert Walsh

Jonathan Sheppard Seeks New Worlds to Conquer

Nearing age 80, Jonathan Sheppard has amassed just about every accolade possible in thoroughbred racing. In a career that began in the U.S. nearly 60 years ago, the soft-spoken and self-effacing Sheppard was inducted into the Hall of Fame in 1990. Since that time, he has conditioned to produce champions on both the flat and over jumps and is the all-time leader in wins and earnings among steeplechase trainers. Only a couple of weeks ago, he recorded his unprecedented 25th training title on the National Steeplechase Association circuit.

The Hall of Fame conditioner shipped six jumpers to Ireland for a winter campaign, aiming Eclipse-award champion Winston C to the biggest prize – the Cheltenham Festival.

Jonathan Sheppard
Jonathan Sheppard

But contrary to the old saying, you can teach a venerable veteran new tricks. Sheppard, a native of Ashwell, Hertfordshire, England (hence, the name of his Pennsylvania farm — Ashwell), has been based in the U.S. since 1961, yet this is his first European foray with a string of horses over an entire season. With Sheppard riding out the pandemic in his Florida home, assistant Keri Brion is preparing the runners along with Gerard Galligan, the newly crowned champion NSA jockey who rode six Sheppard winners in his last nine mounts to clinch the award. Brion left for Ireland shortly after the final meeting of the season in Charleston on Nov. 15, and is based at James Doyle’s stables in Wexford. The horses shipped out on Nov. 24.

On the trip with dual Grade 1 star and 2019 Eclipse Award winner Winston C are (up-and-comers) French Light (owned by Irv Naylor), Clondaw Camp, Baltimore Bucko, and Fancy Pance (Buttonwood Farm), and Francois. Winston C and Francois are both owned by Hudson River Farm.

Winston C, a six-year-old Irish-bred son of Rip Van Winkle, had a slight injury this spring and was given extra time off with the uncertainty of racing at Saratoga this summer due to Covid-19. The plan was to return to Belmont in September for the 2020 Lonesome Glory, but when that race was cancelled, owner Ed Swyer had the idea to send him overseas because of the bounty of opportunities available for a winter campaign.

Brian Crowley and Jonathan Sheppard share congratulations after Smithwick
Brian Crowley and Jonathan Sheppard share congratulations after Smithwick

He (Winston) was bought as a horse that could run in the champion hurdle at Cheltenham, so we thought why not send him back over and take a chance?”

Brion said recently, adding that his first goal is a race at Punchestown on Dec. 31; the Cheltenham Festival is in mid-March.

Winston C finished seventh in a training race on the flat at the Pennsylvania Hunt Cup on Nov. 1, an event intended to allow the champ to stretch his legs in competition and gain some fitness. Former leading NSA jockey Jack Doyle, now back home in Europe, will pilot Winston C at Punchestown because of an injury to regular rider Tom Garner, who will regain the mount for the champ’s following starts.

Robbie Walsh with Jonathan Sheppard
Robbie Walsh with Jonathan Sheppard

On Tuesday, Brion said,

We don’t have the exact races picked out for French Light and Baltimore Bucko, but they should run around Christmas as well. Our ratings do not carry over to Ireland so all of the horses will have to run in open races in order to get a rating here. Gerard (Galligan) will be coming over in a few weeks and he will be riding Bucko and French Light.”

Plans are less certain for Francois, Clondaw Camp and Fancy Pance, who are expected to start sometime after the new year.

In looking over Sheppard’s long and illustrious career, NSA President Al Griffin remarked,

Jonathan Sheppard is the most notable figure in American steeplechasing history. We are thrilled by his 2020 success as he climbed back atop the trainer’s ranks, and we are proud and honored to have him represent us in Europe this winter.  We wish him and his team the best of luck.”

Jonathan Sheppard by the numbers

  • One of only two trainers — the other being fellow Hall of Famer Sidney Watters Jr. — to win championships with flat and jump horses.
  • Won at least one race at Saratoga for 47 consecutive years, from 1969 to 2015.
  • Captured the Breeders’ Cup Grand National four times, Colonial Cup 11 times, and the New York Turf Writers Cup 12 times.
  • As of the end of the 2020 NSA season, Sheppard runners had posted 20,992 starts, with 3,424 wins, 3,098 seconds, and 2,974 thirds. His total purse earnings: $88,632,633.
  • 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).
  • Among his top flat horses were Forever Together, Informed Decision, and With Anticipation. He also trained Storm Cat, one of the most influential sires of all time.

For more information about the National Steeplechase Association, please visit

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