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On November 2, 2024, Aidan O’Brien saddled Henri Matisse to victory in the Breeders’ Cup Juvenile Turf at Del Mar Racetrack in Southern California and, in so doing, drew level with American veteran Darrell Wayne Lukas as the most prolific trainer in the history of the Breeders’ Cup. Of course, O’Brien did not become private trainer to John Magnier and his Coolmore associates at Ballydoyle Stables in County Tipperary until 1996, but has essentially been trying, and failing, to win the Breeders’ Classic since 2000.

The Breeders’ Cup Classic, run over a mile and a quarter on dirt and worth $7 million in prize money, is nowadays the most valuable and arguably the most prestigious race contested on American soil. The fact that O’Brien, one of the most decorated trainers of all time, has failed to win the race with some of the best three-year-olds of their respective generations serves mainly to highlight the challenges faced by European-trained horses, in terms of adapting to the American racing style and the dirt surface.

Ironically, the closest O’Brien has ever come to winning the Breeders’ Cup Classic was on his first attempt, with Giant’s Causeway, at Churchill Downs in 2000. Making his debut on dirt, the so-called ‘Iron Horse’ was hard ridden by jockey Mick Kinane inside the final quarter of a mile, but despite holding every chance could not quicken in the closing stages and was beaten a neck by Tiznow. He has since been joined on the losers’ list by the likes of Galileo, Hawk Wing,George Washington and, most recently, City Of Troy, who was slowly away at Del Mar and never looked like recovering the lost ground.

In reality, Ras Prince Monolulu, whose real name was Peter Mckay, was born on St. Croix in the United States Virgin Islands, in the Caribbean Sea, on October 26, 1881. Nonetheless, he claimed to be a chief of the Falashas, a tribe of black Jews in Abyssinia, as Ethiopia was historically known, and styled himself as such, in brightly colourful robes, a plumed, ostrich-feather headdress.

Monolulu first arrived in London in 1902 and first attended the Derby at Epsom the following year, but first attracted wider acclaim when offering the 1920 Derby winner Spion Kop, trained by Peter ‘P.P.’ Gilpin, as a free tip at rewarding odds of 100/6. A flamboyant character with quickfire patter, including his memorable catchphrase, “I gotta horse, I gotta horse to beat the favourite…”, he went on to become a fixture not only of Derby Day, but of major racing fixtures throughout the country almost until his death, in London on February 14, 1965, aged 84. In another, probably apocryphal, account, he is said to have choked on a strawberry cream, from a box of Black Magic chocolates, given to him by journalist Jeffrey Bernard.

Monolulu reportedly won £8,000, or just over £300,000 by modern standards, on Spion Kop alone, but his exploits as a maverick tipster aside, became one of the best-known black people in Britain. He made regular media appearances, both in newsreel footage and, briefly, in several films, including ‘Derby Day’, starring Anna Neagle and Michael Wilding, during the fifties.

The late Sir Henry Cecil, who was knighted for services to horse racing in June 2011 and died two years later, aged 70, was one of the most successful trainers in British history. In his heyday, he was champion trainer on ten occasions between 1976 and 1993 and, in a career spanning six decades, saddled a total of 25 British Classic winners. Cecil won the Oaks nine times and the 1,000 Guineas eight times, highlighting his prowess as a trainer of fillies, but also won the Derby and the St. Leger four times apiece and the 2,000 Guineas three times. In the latter years of his career, he was best known for his handling of Frankel, who retired unbeaten in 14 races in October 2012 and was susbequently announced as the highest-rated horse in the history of World Thoughbred Rankings.

Born near Aberdeen, Scotland on January 11, 1943, Cecil gained work experience at studs in Newmarket, France and America before completing his education at the Royal Agricutural College (now the Royal Agricultural University) in Cirencester, Gloucestershire. In November 1964, he became assistant trainer to his stepfather, Sir Cecil Boyd-Rochfort, at Freemason Lodge Stables on the Bury Road in Newmarket. By that stage, Boyd-Rochfort was coming towards the end of his career, but had already become champion trainer five times, in 1937, 1938, 1954, 1955 and 1958. He retired in 1968 and the following year Cecil took out a training licence in his own right, saddling his first winner, Celestial Cloud, at Ripon in May, 1969.

In short, Aidan O’Brien has never won the British jump trainers’ title, but it would be fair to say that is the only accolade missing from his enviable training CV. Born and raised in County Wexford, O’Brien, 55, took over the licence at the family yard in Piltown, County Kilkenny from his wife, Anne-Marie (née Crowley), in 1993 and went on to win the Irish jump trainers’ title five years running between 1993/94 and 1997/98. On the opposite side of the Irish Sea, he became best known for his handling of Istabraq, owned by J.P. McManus, who won the Champion Hurdle at the Cheltenham Festival three years running, in 1998, 1999 and 2000.

In 1996, O’Brien was approached by John Magnier, founder of Coolmore Stud, with a view to replacing his unrelated namesake Vincent O’Brien as his private trainer as Ballydoyle Racing Stable in County Tipperary. At the helm of what is widely considered to to be the finest training establishment in the world, O’Brien won the Irish flat trainers’ title for the first time in 1997 and, while he ceded the crown to Dermot Weld in 1998, regained it the following year and has remained the perennial champion ever since.

In Britain, O’Brien became champion trainer for the first time in 2001, making him the first Irishman since Vincent O’Brien, 30 years earlier, to do so. He has since won the British flat trainers’ championship five more times, in 2002, 2007, 2008, 2016 and 2017, placing him joint-sixth, alongside Fred Darling, on the all-time list.