Born in 1940, Leo O’Brien’s racing career began at the tender age of 13. He was apprenticed to the steeplechase stable of trainer Tom Taaffe, in Newcastle county Dublin. In 1964, he was signed on by Raymond Guest and became his stable steeplechase jockey in the United States. At the time, Raymond Guest was the U.S. ambassador to Ireland and he maintained a very powerful flat and steeplechase stable on both sides of the Atlantic. Among Guest’s great horses of the time were Tom Rolfe, Larkspur, Sir Ivor, and L’Escargot.
Leo was a successful steeplechase jockey for 12 years. During that time he also galloped some notoriously difficult horses for many hall of fame trainers. Trainers that included Frank Whiteley, Sidney Watters, Elliott Burch, Laz Barrera, Leroy Jolley, and Frank Martin to name but a few. Injury curtailed his riding career in 1976 and he subsequently embarked on a joint training career with his brother, Michael who had been tragically paralyzed from a fall in a steeplechase race in 1974. Returning to Ireland in 1977, they became champion steeplechase trainers in 1980. A separate training career in the United States had always been Leo’s dream, and in 1981 with one steeplechase horse, Sports Reporter, he returned.
In 1986, Leo achieved his first grade I victory with an Irish-bred filly named Valley Victory. She won the Coaching Club American Oaks in impressive fashion. Fourstardave was the horse that further displayed Leo’s intuitive and natural horsemanship. Fourstardave was a multiple graded stakes winner on both the dirt and turf, but it was his sequence of victories at Saratoga for eight successive years that made him legendary. With Fourstars Allstar, Leo devised a plan that resulted in an historic victory. In 1991, Fourstars Allstar became the first and only American based racehorse to capture a European classic when he won the Irish 2000 Guineas. He later trained Irish Linnet to five successive wins in Saratoga’s Yaddo Stakes. In 1996, Leo orchestrated a campaign with 3-year-old filly Yanks Music that resulted in four grade I victories in a row. They were the Mother Goose, the Alabama, the Ruffian, and the Beldame. In the final two, she defeated that great racemare, Serena’s Song.
Leo rode two Eclipse champions. In 1971, he rode Shadow Brook, and in 1974 he rode Gran Kan. Both horses were trained by Sidney Watters, who was recently elected to the Hall of Fame. In 1996, Leo trained an Eclipse champion Yanks Music. Leo has proven his affinity with both male and female racehorses and with both turf horses and dirt horses. The knowledge continues and the ambition continues, but the most important ingredient are the horses.
Keith O’Brien - The Son
On August 23, 1968 Leo O’Brien won the Saratoga Steeplechase on a horse called Apollon. A few hours earlier, his son Keith Leo was born. Keith is the product of a purely racing background, and it’s only natural that he chose to follow in the footsteps of his father.
A graduate of the College of the Holy Cross in 1990, Keith matriculated with a Bachelor’s degree in political science. Following the completion of his education, Keith embarked on a steeplechase riding career. He successfully rode in both the United States and Ireland, as well as winning races in England and France. While riding steeplechase races, Keith rode for such prominent trainers as Janet Elliot, Tom Voss, and his uncle Michael. He returned to New York to become assistant trainer to his father in 1994.
In 2002, Keith began his own training career. His first winner was the first horse he saddled, Summing Stars. She also happened to be a daughter of Fourstars Allstar. A natural horseman, Keith combines intellect with quality horse sense.
Leo O’Brien - The Patriarch
