Alongside his exploits with the ‘Sultan of Saratoga’, Irish expat famously saddled Fourstars Allstar to become first-ever US-trained horse to win a European Classic in Irish 2,000 Guineas in 1991 at the Curragh
The New York Racing Association (NYRA) mourns the loss of Leo O’Brien – trainer of New York-bred millionaires Fourstardave, Fourstars Allstar and Irish Linnet – who died on Thursday morning [Jan 8] following a lengthy battle with Lewy Body Dementia. He was 85.
O’Brien and his late wife Joan raised two children together, namely their son Keith – a longtime horseman, 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 1992-95 and is married to Hall of Fame jockey John Velazquez.
Irish-born O’Brien, a native of Newcastle in County Dublin, rose to prominence in the US as a steeplechase jockey from 1964-76.
When his riding career was cut short due to injury, he returned to Ireland to begin training jumps horses with his brother Michael, also a former jump jockey who became a trainer following a riding accident.
Leo’s son Keith told the story of his father’s arrival in the US, saying: “He came here from Ireland in 1964 to ride over jumps and fell in love with New York racing – he fell in love with New York and, in time, he made it his home.
“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 back out of it. 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 solitary horse, Sports Reporter, who captured the International Gold Cup Steeplechase that September at Ligonier and a month later finished sixth in the Temple Gwathmey Steeplechase at Belmont Park.
"Sports Reporter was a hurdle 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 was furious, saying, ‘the horse had won eight races over the jumps, how can he be a maiden!’”
The Sultan of Saratoga
O’Brien would make his name on the Flat with the illustrious multiple Graded stakes winner Fourstardave, who won at least one race at Saratoga each year from 1987 to 1994, earning him the nickname, the ‘Sultan of Saratoga’.
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,” he 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?”
Migliore credited O’Brien for giving him – and many other riders – not only a leg-up, but for setting an example on the importance of family.
Old school
“Leo was very good with everybody,” said the former jockey. “If you were willing to work in the morning and get on horses, he was going to give you an opportunity. He had a real old-school way about him, but he rewarded hard work.
“Family was everything to him and, to me, the measure of a man is his family,” Migliore added. “Leo and his wife Joan, who passed before he did, were inseparable and their children are everything I would hope for in my children. They raised really good people.”
Upon his passing, Fourstardave was laid to rest at Clare Court on the Saratoga backstretch and each summer NYRA runs the G1 Fourstardave in his honor.
“Dad was immensely proud of his New York-bred millionaires,” O'Brien said. “Fourstardave was extremely special because he came along at a time when he really needed him and he only had a small amount of horses.
“Fourstardave was kind of obscure breeding, by Compliance and out of an unraced dam,” O'Brien added.
“What he became was a source of immense pride to Dad. Just the fact that he came back year-after-year to win in Saratoga, he loved the horse and that he was able to do that for him. Presenting the Fourstardave trophy was always a high point of dad's summer. It was a huge thing for him.”
Classic history
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 Irish 2,000 Guineas in 1991 with future Hall of Famer Mike Smith at the helm.
Keith O’Brien recalled that an overseas trip was no small task, made that much more special by the fact that Fourstars Allstar won a race at Belmont Park just one week before strutting his stuff at the Curragh.
“Dad was telling me about this idea when Fourstars Allstar was a two-year-old and had finished second to a very good horse [River Traffic] at Laurel,” recalled O’Brien.
“He told me he was going to take the horse over to Ireland for the 2,000 Guineas. I said, ‘What are you talking about dad, are you crazy?’
“But he said to me, ‘I think this horse is special, he might be able to do it.’ I laughed, like a lot of people did, but he had a plan, and he trained him over the winter for it.
“Fourstars Allstar ran a week before he was to go to Ireland and won a really good allowance race on the turf at Belmont and dad said, ‘Now, I know he's ready,’” O’Brien continued. “Seven days later, he won the Irish 2,000 Guineas.”
Fourstars Allstar banked in excess of $1.5m in a 14-win career that included scores on the New York circuit in the G2 Bernard Baruch Handicap (1992, 1995), G3 Saratoga Breeders’ Cup Handicap (1993), and G3 Fort Marcy Handicap (1995).
O’Brien and his son-in-law John 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 $1.2m; and the supremely talented four-time G1-winner Yanks Music.
The latter captured 7-of-9 career starts topped by wins over future Hall of Famer Serena’s Song in a pair of G1s, the Ruffian and the Beldame, in 1996. Yanks Music sustained an ankle injury training up to that year’s Breeders’ Cup Classic and was retired in January 1997.
“Yanks Music was a spectacular horse,” O’Brien said. “She came from nowhere – her breeding didn't suggest she was going to be that kind of filly, and you wouldn't have looked twice at her being a little on the small side, but boy did she have an engine. She could run.”
O’Brien said his father had a special gift that allowed him to connect to the equine athletes that he trained, a trait that carried him through a lengthy career in the sport he loved so well.
“He was always very patient and liked to listen to the horses,” he said. “He let them tell him when they were ready and what they were ready to do.
“He wasn't afraid to run them. If they were sound and happy, he would run them. He loved going to the races and he loved running horses.”
According to Equibase statistics, O’Brien posted a record of 6,477-568-677-691 for purse earnings in excess of $27m over his long career.
In addition to his children Keith and Leona, he is survived by his grandchildren Lerina, Michael, Darby, Liam, Jacinta, Muireann and Jonjo.
• Funeral details are pending. In lieu of flowers, the family requests donations in his name to the Pemanently Disabled Jockeys Fund and/or the New York Racetrack Chaplaincy
• Visit the NYRA Aqueduct website
Seven Days in Racing: Racing mourns Ian Balding and Diane Crump
This one goes up to 11: Meet Sharp Warning, the winningmost horse in North America in 2025
NYRA best of 2025: Sovereignty through the binoculars of Frank Mirahmadi
A life after racing: NY-bred millionaire Naughty New Yorker thrives as aftercare ambassador
View the latest TRC Global Rankings for horses / jockeys / trainers / sires