Sad news from the racing community. Retired trainer and former steeplechase jockey Leo O’Brien has died aged 85. Leo was the father of Keith O’Brien, the NSA’s new assistant racing secretary. Here’s a tribute from the New York Racing Association:
NYRA mourns the passing of Leo O’Brien
OZONE PARK, NY – The New York Racing Association, Inc. (NYRA) mourns the loss of the legendary Leo O’Brien – trainer of New York-bred millionaires Fourstardave, Fourstars Allstar and Irish Linnet – who passed away on Thursday morning at the age of 85 after a long battle with Lewy Body Dementia.
O’Brien and his late wife, Joan, raised two children together, including their son Keith, a longtime equestrian, who worked with his father from 1997 until the elder O’Brien’s retirement in 2022; and their daughter, Leona, who grew up in the sport, worked in the NYRA press box from 1992 to 1995 and is married to Hall of Fame jockey John Velazquez.
Irish-born O’Brien, born in Newcastle in County Dublin, rose to prominence in the United States as a steeplechase jockey from 1964 to 1976. When his riding career was cut short due to injury, he returned to Ireland to begin training Steeplechase horses with his brother Michael, also a former Steeplechase jockey who became a trainer after a riding accident and earned championship titles in 1980.
“He came here from Ireland in 1964 to race jumps and fell in love with racing in New York. He fell in love with New York and over time he made it his home,” said Keith O’Brien. “He was a quiet man; a dignified man and he always gave his best. He gave everything he had to the game, and he got a lot in return. He loved horse racing, and he loved racing in New York. It was always very special to him.”
Leo O’Brien returned to the US in 1981 with a lone horse, Sports Reporter, who captured the International Gold Cup Steeplechase Handicap at Ligonier in September and finished sixth in the Temple Gwathmey Steeplechase Handicap, at Belmont Park, a month later.
“Sports Reporter was an obstacle horse in Ireland and not only did he win over jumps, but he also broke his maiden over the flat at Belmont Park one day,” O’Brien said. “I remember Allen Jerkens being furious and saying, ‘The horse had won eight races on the jumps, how can he be a girl!’”
O’Brien would make a name for himself on the flats with the illustrious multiple stakes winner Fourstardave, who won at least one race at Saratoga Race Course every year from 1987 to 1994, earning him the nickname “The Sultan of Saratoga.”
Richard Migliore was the regular driver for Fourstardave’s final two racing seasons and was on board for his final score at Saratoga on July 24, 1994.
“My last win at Fourstardave was my favorite. It was the last hurray, the last go-around, and there was so much pressure that day to keep the streak alive and come out on top at Saratoga,” Migliore said. “The horse was by far 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 there eight years in a row, let alone win eight years in a row.”
Migliore credited O’Brien with not only giving him – and many other riders – an edge, but also setting an example about the importance of family.
“Leo was very good with everyone. If you were willing to work in the morning and get on horses, he would give you a chance,” Migliore said. ‘He had a very old-fashioned look, but he rewarded hard work.
“Family was everything to him and for me the measure of a man is his family,” Migliore added. “Leo and his wife Joan, who died before him, were inseparable and their children are everything I hope for in my children. They raised very good people.”
After his death, Fourstardave was buried in Clare Court on the Saratoga backstretch and every summer NYRA runs the Grade 1 Fourstardave in his honor.
“Dad was very proud of his New York-born millionaires,” O’Brien said. “Fourstardave was very special because he came along at a time when he really needed him and he only had a small number of horses.
“Fourstardave was kind of an obscure breeding stock, from Compliance and from an unraced mother,” O’Brien added. “What he became was a source of tremendous pride for Dad. Just the fact that he came back year after year to win at Saratoga, he loved the horse and being able to do that for him. Presenting the Fourstardave Trophy was always a highlight of Dad’s summer. It was a huge thing for him.”
While Fourstardave enjoys legend status at Saratoga, his full brother Fourstars Allstar would make history for O’Brien, becoming the first American-trained horse to win a European classic by winning the Group 1 Irish 2000 Guineas in 1991 with future Hall of Famer Mike Smith at the helm.
Keith O’Brien recalled that traveling abroad was no small task, made even more special by the fact that Fourstars Allstar won a race at Belmont Park just a week before showing his stuff at The Curragh.
“Dad told me about this idea when Fourstars Allstar was 2 years old and had come second to a very good horse [River Traffic] at Laurel,” O’Brien recalls. “He told me he was taking the horse to Ireland for the 2000 Guineas. I said, ‘What are you talking about daddy, are you crazy?’ But he said to me: ‘I think this horse is special, maybe he can do it.’ I laughed, as many people did, but he had a plan and he trained him all winter for it.
“Fourstars Allstar ran a week before he was due to go to Ireland and won a really good race on the turf at Belmont and Dad said, ‘Now I know he’s ready,’” O’Brien continued. ‘Seven days later he won the 2000 Irish Guineas.’
Fourstars Allstar earned more than $1.5 million in a career of 14 wins, including scores on the New York circuit in the Grade 2 Bernard Baruch Handicap [1992, 1995]Grade 3 Saratoga Breeders’ Cup Handicap [1993]and Grade 3 Fort Marcy Handicap [1995].
O’Brien and his son-in-law John Velazquez worked with some of the venerable trainer’s best horses, including multiple stakes winner Irish Linnet, who won 19 of 62 starts for a purse of more than $1.2 million; and the supremely talented four-time Grade 1 winner Yanks Music, who captured 7 of 9 career starts, highlighted by victories over future Hall of Famer Serena’s Song in the Grade 1 Ruffian Handicap and Grade 1 Beldame in 1996. Yanks Music suffered an ankle injury in training up to that year’s Breeders’ Cup Classic and retired in January 1997.
“Yanks Music was a spectacular horse,” O’Brien said. “She came from nowhere. Her upbringing didn’t indicate she was going to be such a filly, and you wouldn’t have looked twice if she was a little on the small side, but boy did she have a motor. She could run.”
O’Brien said his father had a special gift that allowed him to connect with the equine athletes he trained, a trait that carried him through a long career in the sport he loved.
“He was always very patient and loved to listen to the horses. He let them tell him when they were ready and what they were ready to do,” O’Brien said. “He wasn’t afraid to run them. If they were healthy and happy, he would run them. He loved going to the races and he loved racing horses.”
According to Equibase statistics, O’Brien posted a record of 6,477-568-677-691 for wallet earnings of over $27 million during his storied career.
In addition to his children Keith and Leona, he is survived by his grandchildren Lerina, Michael, Darby, Liam, Jacinta, Muireann and Jonjo.
Details about the funeral are still pending. In lieu of flowers, the family requests donations in his name to the Permanently Disabled Jockeys Fund and/or the New York Racetrack Chaplaincy.
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