LEO O’Brien, trainer of 1991 Irish 2000 Guineas winner Fourstars Allstar, has died in the USA, aged 85.

Brother of the late Michael O’Brien, a leading National Hunt trainer of the 1980s and ‘90s, Leo made history in 1991 when becoming the first US-based trainer to win a race in Ireland - and it came in a classic. He remains the only American-based trainer to win a European classic.

Six years ago O’Brien explained the background to the achievement in an interview with The Irish Field. “It was always a dream of mine to maybe one day return to the Curragh, where I rode and won my first race on a horse called Similar,” he says. “The whole idea was to bring a US-based horse with an American jockey. That was the sport and challenge of it.

“I began to think about the Irish 2000 Guineas at the end of October, after ‘Allstar’ was a very good second in the Grade 3 Laurel Futurity, which had been run on the turf that year.

“He was a beautiful mover on the grass, a true daisy-cutter, very much a firm ground type with great natural speed. He was easy to settle and really, in terms of tactics, could be ridden from anywhere. We trained him all winter with the Guineas in mind and I was very confident.”

Fourstars Allstar had run 10 times as a two-year-old, winning four races. He was runner-up in an allowance race at Aqueduct on his reappearance and then won his prep run at Belmont a week before the Guineas by a length and a quarter.

It was a good Guineas that year. The even-money favourite was the French-trained Lycius, runner-up in the 2000 Guineas at Newmarket two weeks earlier.

Fourstars Allstar was ridden at the Curragh by Mike Smith. “He broke from the inside gate like a rocket and was a length in front at the first call,” O’Brien remembered. “Mike put his hands on his neck and just let him settle in front. Christy Roche, on Star Of Gdansk, was sitting right behind him.

“Roche was cute because he knew the rail opened up (there was a cutaway) around the three-furlong marker and when it did he punched his horse up the inside. This is where Mike was so brilliant, though. He never panicked because he knew when he reached up to grab a hold of Allstar that he would produce a great kick.”

Fourstars Allstar won by a head from Star Of Gdansk, with six lengths back to Lycius. The winner landed a Grade 2 race at Saratoga later that summer and finished a close third in the Breeders’ Cup Mile the same season.

O’Brien is also best remembered for his training of Fourstardave, a New York-bred who won 21 times from 100 starts in the late 1980s and early 90s. Saratoga still stages a Grade 1 race named in memory of the horse and Leo O’Brien presented the trophy each year up to recently.

Born in Dublin and one of 11 children, Leo O’Brien got his first job in racing with Tom Taaffe. He rode work for Tom Taaffe Snr and claimed to have ridden future Gold Cup winner Mill House in his first piece of work. O’Brien rode over jumps in the 1960s and 1970s, finishing his riding career in America. He returned home for a short period to work with his brother Michael before returning to the US and setting up his own stables, backed by owner Richard Bomze, who owned the ‘Fourstar’ horses.

O’Brien trained a total of 568 winners before he retired in 2002, handing the licence over to his son, Keith. His daughter Leona married jockey John Velazquez.