Remembering Leo O’Brien: ‘The consummate horseman’

Keith O’Brien worked alongside his father Leo O’Brien in the barn as his assistant for 25 years and he knows that the late renowned thoroughbred trainer and former steeplechase jockey genuinely loved his horses, horse racing, and racing in New York.
 
“It was always very special to him,” said the son.
 
The New York Racing Association, Inc. (NYRA), in company with the National Steeplechase Association (NSA), will celebrate O’Brien, who passed away in January at age 85 following a lengthy illness, during the July 4th Racing Festival at Saratoga Race Course with a top-level steeplechase race named in his honor - the inaugural running of the Grade 1, $150,000 Leo O’Brien at 2 3/8 miles for older horses on Sunday, July 5.
 
“Leo was a wonderful person who was beloved in New York. Aside from his remarkable skill as a trainer, anyone who knew Leo O’Brien would tell you that he was a wonderful human being. He was very likeable and very lovable. He was a very kind man, and he was utterly charming,” said Bill Gallo, the director of racing for the National Steeplechase Association.
 
O’Brien is best known as the trainer of the immensely popular New York-bred full brothers Fourstardave and Fourstars Allstar, who achieved legendary status on the racetrack during their lengthy, multiple graded stakes-winning careers.
 
Fourstardave won at least one race at Saratoga Race Course each year from 1987 to 1994, plus he captured at least one stakes race here between 1987 to 1992, earning him the nickname, ‘The Sultan of Saratoga.’ He made 100 starts, earning $1,636,737, and is interred at Clare Court on the Saratoga backstretch. Each Saratoga season, NYRA runs the Grade 1 Fourstardave in his honor.
 
Fourstars Allstar won seven graded stakes in America and in 1991 O’Brien, who was born in County Dublin, Ireland, took him across the Atlantic to The Curragh. Fourstars Allstar captured the Group 1 Irish Two Thousand Guineas and became the first American-trained horse to win a European Classic. In 59 starts he bankrolled $1,596,760.
 
“As a flat trainer, Leo has the history of Fourstardave and Fourstars Allstar. That was the real connection. There are multiple reasons why this race is being held to honor him at Saratoga,” Gallo explained.
 
O’Brien rode steeplechase horses in his native land until he moved to the United States in 1964 and began riding over the jumps stateside. He achieved fame, winning 141 races for top trainers until injuries from a spill at Monmouth Park in 1967 forced him to the sidelines.
 
“Leo O’Brien, his brother Michael O’Brien, Tom Skiffington, and a few of the other guys were my steeplechase jockey heroes,” said Joe Clancy, the owner and editor of ST Publishing and a noted expert in both thoroughbred and steeplechase racing. “He rode for a lot of the big-name guys like Sidney Watters [Jr.] and the Clark family.”
 
Watters is a member of the National Museum of Racing and Hall of Fame and a six-time national champion steeplechase trainer. He was the conditioner of Shadow Brook, who was the 1971 national champion with O’Brien as his regular rider. O’Brien also partnered with Gran Kan, the 1974 champion.
 
“When he was a jockey, and even after, he would have been an exercise rider for Sidney Watters. He probably rode some horses for [Hall of Famer] Jonathan Sheppard, too. When steeplechase racing had a bigger footprint in New York with racing at all three tracks, he would have been riding regularly in New York,” said Clancy.
 
O’Brien’s superior horsemanship was evident as well with the thoroughbreds early on.
 
“A lot of things people don’t know about dad is that when he was a jump jockey, he developed a reputation for being an exquisite horseman for sorting out problem horses. He galloped some horses who turned out to be really good. Honest Pleasure is an example,” said Keith O’Brien, who is now the National Steeplechase Association’s assistant racing director.
 
Honest Pleasure, the Champion 2-Year-Old Colt of 1975 trained by Hall of Famer LeRoy Jolley, was victorious in seven Grade 1 races, including the 1975 Champagne at Belmont Park and the 1976 Travers at Saratoga.
 
“That horse became a runaway and LeRoy Jolley came to dad one day and said, ‘Leo, can you get on this horse for me? None of my riders can hold him. He’s running off every morning.’ My dad got on him, and settled him, and he ended up winning the Travers that year. Then Frank Martin [Sr.] had a horse named Northerly, who refused to leave the barn. He could not get the horse to the track. My dad was getting on horses for [Hall of Famer] Elliott Burch at the time and Frank sent his assistant to Elliott’s barn with the message that Frank needed him. My dad got on Northerly and sure enough, he got him to train. That horse won several stakes and became a stakes record holder,” recalled Keith O’Brien.
 
Due to the spectacular success of Fourstardave and Fourstars Allstar it might be easy to classify Leo O’Brien as a trainer of male turf horses. That would be a mistake as he had a special knack with female runners, too, on both the dirt and the grass.
 
He trained Valley Victory, who won the Grade 1 Coaching Club American Oaks and was the runner-up in the Grade 1 Alabama during the 1986 Saratoga meet. He also conditioned the New York-bred, multiple graded stakes-winner Irish Linnet, who earned $1,220,180 in her career and took the Yaddo in five successive years from 1991-95; and the supremely talented Yanks Music, who was a four-time Grade 1-winner that captured 7-of-9 career starts topped by wins over future Hall of Famer Serena’s Song in the Grade 1 Ruffian Handicap and Grade 1 Beldame in 1996. Yanks Music sustained an ankle injury training up to that year’s Breeders’ Cup Classic and was retired in January 1997.
 
“Leo was the consummate horseman,” said Clancy. “It’s rare to be able to cross over and be so successful in both the steeplechase and thoroughbred racing worlds. You don’t see that very often, shifting gears like that. He made it work no matter what type of horse he was involved with. His horsemanship came through. I’m sure people saw that when he was a jockey and we all saw it when he got a chance to train flat horses. That’s horsemanship. It’s the definition of horsemanship when someone can be talented enough to ride horses that well and then to train horses that well.”
 
Said Gallo, “He absolutely was the consummate horseman.”
 
During his four decades as a thoroughbred trainer, he won 568 races with 6,477 starters who earned $27,078,739 in purses, according to Equibase, until he turned the stable over to his son. “What makes me proudest is that he did it with a limited number of horses. I don’t think he ever had more than 29 in the barn at Saratoga,” said Keith O’Brien.
 
Leo O’Brien was highly regarded as an exemplary family man. He and his late wife Joan were also parents to 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. In addition to his children, he is survived by his grandchildren Lerina, Michael, Darby, Liam, Jacinta, Muireann and Jonjo.
 
“He was a great dad. Leona and I were very lucky to have him. He was very kind and very supportive. He gave us unconditional love. No matter what you did or didn’t do he was always there for you, and you were always a star in his eyes,” said Keith O’Brien. “I thank God every day for him.”
 
Presenting the trophy for the Fourstardave was always a highlight of O’Brien’s Saratoga summers, and now his family will be in the winner’s circle to do the same with the race named in his honor.
 
“I’ll be there, my sister will be there, and hopefully all our kids will be there. He was a horseman through and through and Saratoga was a very special place for him. We as a family appreciate this so much. It’s beyond wonderful. This means the world to us,” said Keith O’Brien.