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Legendary Trainer Who Made Big Impact on Saratoga Passes Away at 85

Photo of Leo O’Brien by Coglianese Photo, provided by the New York Racing Association (NYRA).

SARATOGA SPRINGS — The New York Racing Association (NYRA) recently mourned the loss of legendary trainer Leo O’Brien, who passed away on Jan. 8 at the age of 85 following a lengthy battle with Lewy Body Dementia.

O’Brien trained New York-bred millionaires Fourstardave, Fourstars Allstar, and Irish Linnet. Fourstardave was nicknamed “The Sultan of Saratoga” because he won at least one race at the Saratoga Race Course every year from 1987 to 1994. The Fourstardave sports bar at the track was named in the horse’s honor, as was the Grade 1 Fourstardave race run each summer at the Spa.

O’Brien and his late wife, Joan, raised two children together. Their daughter Leona worked in the NYRA press box from 1992-95 and is married to Hall of Fame jockey John Velazquez, who is the all-time leading rider at Saratoga. 

The Irish-born O’Brien rose to prominence in the United States as a steeplechase jockey from 1964-76. When his riding career was cut short due to injury, he returned to Ireland to begin training steeplechase horses. He came back to the U.S. in 1981 with a solitary horse, Sports Reporter, who captured the International Gold Cup Steeplechase Handicap that September at Ligonier and, one month later, finished sixth in the Temple Gwathmey Steeplechase Handicap at Belmont Park. O’Brien would later make his name on the flat with the illustrious multiple graded stakes-winner Fourstardave.

Richard Migliore was the regular rider for Fourstardave’s last two seasons of racing and was aboard for his final score at Saratoga on July 24, 1994.

“My last win on Fourstardave was my favorite,” Migliore said. “It was the last hurrah, the last go-around, and there was so much pressure that day to keep the streak alive and go out a winner at Saratoga. The horse ended up being much the best that day, and I just had to keep him out of trouble. He was a special horse – how many horses will even race up there eight years in a row, let alone win eight years in a row?”

Upon his passing, Fourstardave was laid to rest at Clare Court on the Saratoga backstretch.

While Fourstardave enjoys legend status in Saratoga, his full-brother Fourstars Allstar would make history for O’Brien, becoming the first American-trained horse to win a European Classic by taking the Group 1 Irish 2000 Guineas in 1991 with future Hall of Famer Mike Smith at the helm.

O’Brien and his son-in-law Velazquez teamed up with a number of the venerable trainer’s top horses, including the multiple graded stakes-winner Irish Linnet, who won 19-of-62 starts for purse earnings in excess of $1.2 million.

According to Equibase statistics, O’Brien posted a record of 6,477-568-677-691 for purse earnings in excess of $27 million over his storied career.

In addition to his children Keith and Leona, he is survived by his grandchildren Lerina, Michael, Darby, Liam, Jacinta, Muireannm, and Jonjo.

In lieu of flowers, the family requests donations in O’Brien’s name to the Permanently Disabled Jockeys Fund and/or the New York Racetrack Chaplaincy.