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Arguably the most famous horse race in the world, the Grand National was founded in the first half of the nineteenth century, while the Hennessy Cognac Gold Cup did not come into existence until the second half of the twentieth century. The latter race still exists, as the Coral Gold Cup, run over three-and-a-quarter miles at Newbury in late November or early December, as it has been since 1960, but was actually established at Cheltenham in 1957. Hennessy ceased to be the title sponsor in 2016, so, strictly speaking, the Hennessy Gold Cup and the Grand National co-existed for sixty years.

In that period, just one horse won both races. That horse was the ill-fated Many Clouds, who tragically collapsed and died after winning the Cotswold Chase at Cheltenham in January 2017; an autopsy revealed that a severe pulmonary haemorrhage was the cause of his death.

Many Clouds carried the familiar yellow, green and white colours of the late Trevor Hemmings and was trained at Rhonehurst Stables in Upper Lambourn, Berkshire by Oliver Sherwood. Described by the latter as a ‘natural chaser’, the Cloudings gelding stayed on strongly to win the Hennessy Gold Cup on November 29, 2014 and followed up in the Cotswold Chase at Cheltenham on January 24, 2015. He disappointed in the Cheltenham Gold Cup in March, finishing a distant sixth behind Coneygree, but returned to winning form at Aintree the following month, winning the Grand National under 11st 9lb in the second fastest time ever.

For readers unfamiliar with the exploits of Rooster Booster – and, in fairness, he did run his last race two decades ago – he was a popular grey gelding who won 10 of his 46 races under National Hunt Rules, but is best remembered for winning the Champion Hurdle at the Cheltenham Festival on March 11, 2003. Indeed, that was his second successive Festival success, having won the Vincent O’Brien County Handicap Hurdle the previous year, but ultimately proved to be the only Grade 1 victory of his career.

Foaled on April 1, 1994, Rooster Booster was initially trained by his original owner, Richard Mitchell, having been bred by his wife, Elsie, at their East Hill Stables in Piddletrenthide, Dorset. The Riverwise gelding made an inauspicious start to his racing career, when, as an unconsidered 50/1 chance, he finished seventh of 18 in a National Hunt Flat Race at Wincanton on February 25, 1999. Having hung badly left inside the final half a mile, he was unable to recover, eventually finishing 31 lengths behind the winner, Mestre Sala.

Rooster Booster opened his account in a maiden hurdle at Taunton on January 6, 2000, but was subsequently acquired by leading owner Terry Warner, in whose yellow and black colours he would eventually win the Champion Hurdle. However, following his transfer to Somerset trainer Philip Hobbs in April 2000, Rooster Booster remained winless for 14 races and would not enter the winners’ enclosure again until the 2002 Cheltenham Festival. The trest, as they say is history and he made a low-key end to his career when fourteenth of 19 in the Greatwood Handicap Hurdle at Cheltenham on November 13, 2005.

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.