Jonathan Sheppard
Trainer Bios

Jonathan Sheppard

Born: December 2, 1940 in Ashwell, England

Record at Keeneland

Total Wins: 63

Stakes Wins: 18

Career Firsts

First Grade 1 Win: 1982 Flower Bowl at Belmont Park with Trevita (IRE)

First Stakes Win: (jumps) 1967 Radnor Hunt Cup in Pennsylvania with Haffaday. (flat) 1976 Oil Capital at Hawthorne with Hurricane Ed.

First Graded Stakes Win: 1977 Riggs (G3) at Pimlico with Ripon

First Career Win: 1966 at the Rosetree Hunt Meet in Pennsylvania with Haffaday

Starters in the Toyota Blue Grass





Ever So Lucky


At Keeneland

Won first Keeneland race during the 1985 Fall Meet.

First Keeneland stakes win was the 1996 Transylvania with More Royal.

Won five stakes, all graded, in 2009, including the Vinery Madison (G1) with champion Informed Decision.

Saddled three winners of Keeneland’s former Grade 1 steeplechase, the Royal Chase for the Sport of Kings Hurdle: It’s a Giggle (2002), Mixed Up (2007) and Sovereign Duty (2008).

Other Keeneland Grade 1 stakes winner is champion Forever Together, winner of the 2008 First Lady (G1).


Inducted into the Racing Hall of Fame in 1990. 

All-time leading money-winning steeplechase trainer who has been highly successful on the flat.

Breeders’ Cup wins (5): 2008 Filly and Mare Turf with Forever Together; 2009 Filly and Mare Sprint with Informed Decision; Breeders’ Cup Steeplechase in 1988 with Jimmy Lorenzo (GB) and in 1989 and 1992 with Highland Bud.

Trained two Eclipse Award winners: 2008 turf female Forever Together and 2009 female sprinter Informed Decision.

North American career earnings near $86 million with 3,338 wins through June 24, 2018.

2017 earnings were $1,283,738 with 37 wins, inclluding the Lonesome Glory (G1) at Belmont with All the Way Jose.

2016 earnings were $1,453,124 with 39 wins.

2015 earnings were $1,930,070 with 53 wins.

Won a race at Saratoga on the flat or over jumps for 47 consecutive years, from 1969-2015.

2014 earnings were $3,318,985 with 78 wins, including the Dixie (G2) victory with Utley.

Trained steeplechase champions Athenian Idol (1973), Café Prince (1977-1978), Martie’s Anger (1979), Flatterer (1983-1986), Jimmy Lorenzo (GB) (1988), Highland Bud (1989), Mixed Up (2009) and Divine Fortune (2013).

Won the 3,000th race of his career on Sept. 17, 2012, when Fugitive Angel won the seventh race at Philadelphia Park.


Jonathan’s father was a racing official in Britain for 40 years. A rule of the British Jockey Club prohibited his immediate family members from training racehorses in the country. Jonathan attended Eton College and worked at a stock brokerage firm in London.

He took a year off to go to the U.S. In 1961 and met W. Burling “Burley” Cocks, a renowned steeplechase trainer who was inducted into the Racing Hall of Fame in 1985. Sheppard did return to England, but after about sixth months, he decided to return to the U.S. to explore training opportunities.