Which are, or were, the greatest racehorses of all time?

In the absence of an objective measure of the abilities of racehorses from different generations, any discussion of the ‘greatest’ racehorses of all time is inevitably highly subjective. According to Longines World’s Best Racehorse Rankings World, formerly Thoroughbred Racehorse Rankings, which began in 1977, Frankel, who retired, unbeaten, in October, 2012, is the highest-rated horse in the history of official classifications. Even so, Frankel only achieved that position after a controversial ‘recalibration’ of the ratings, which saw Dancing Brave, winner of the Prix de l’Arc de Triomphe in 1986, downgraded by 3lb.

Timeform agrees that Frankel is the highest-rated horse, on the Flat, at least, since its first ‘Racehorses’ annual, published in 1948, 2lb superior to Sea Bird, winner of the Derby and Prix de l’Arc de Triomphe in 1965 and fully 7lb superior to Dancing Brave. Timeform also has Arkle, winner of the Cheltenham Gold Cup in 1964, 1965 and 1966 at the head of its all-time list of steeplechasers; his rating of 212 is 20lb superior to any steeplechaser, bar stable companion Flyingbolt, in over five decades. According to Timeform, Brigadier Gerard, who tasted defeat just once in his eighteen-race career in the early Seventies, is rated 3lb inferior to Frankel, but must be considered one of the greatest racehorses of all time. So, too, must Eclipse, who won all eighteen starts between April, 1764 and February, 1789 without being asked a serious question.

Who is the most successful owner in the history of the Cheltenham Gold Cup?

In the history of the Cheltenham Gold Cup, which was inaugurated, as a steeplechase, in 1924, several owners have won what is, nowadays, the most prestigious race in the British National Hunt calendar three or more times. The three-time winners are, in chronological order, Frank Vickerman, owner of Cottage Rake, victorious in 1948, 1949 and 1949, and Jim Lewis, owner of Best Mate, successful in 2003, 2004 and 2005. Anne Grosvenor, Duchess of Westminster, owner of Arkle – who completed a notable hat-trick in 1964, 1965 and 1966 – went one better, courtesy of Ten Up in 1975 and is, in fact, the only four-time winner in the history of the Cheltenham Gold Cup.

However, beyond a shadow of a doubt, the most successful owner in the history of the Cheltenham Gold Cup was the Honourable Dorothy Paget, who was as eccentric as she was rich, but nevertheless amassed seven wins in the mid-twentieth century. The indomitable Miss Paget was, of course, the owner of Golden Miller, the most famous steeplechaser on the inter-war years, who completed an unprecedented five-timer in the Cheltenham Gold Cup in 1932, 1933, 1934, 1935 and 1936. She also owned Roman Hackle and Mont Tremblant, winners in 1940 and 1952, respectively.

Which Cheltenham Gold Cup winner started and ended his career by falling at Kempton?

Without wishing to give away too much too soon, the Cheltenham Gold Cup winning horse in question made his racing debut in a novices’ hurdle at Kempton, on January 21, 1983. Having made the running, he crashed, exhausted at the final flight and took so long to get to his feet that it appeared, for a time, as if he might not do so. Thankfully, he did.

He went on to win 34 of his 70 starts over hurdles and fences and over £650,000 in prize money, but on his final start, in the King George VI Chase at Kempton on Boxing Day, 1991, again fell, when beaten, at the third-last fence. On that occasion, though, he was quickly back on his feet and received a heartwarming round of applause as he galloped, riderless, past the packed grandstands. Two seasons previously, he had enjoyed what was probably his finest hour, overcoming bottomless ground and racing left-handed – he was two stone better going left-handed, according to his regular jockey – to win the ‘Blue Riband’ event of steeplechasing, the Cheltenham Gold Cup.

You may well have guessed by now that the horse in question is Desert Orchid who, despite an inauspicious start and end to his career, not only won the Cheltenham Gold Cup, but also the King George VI Chase, four times, the Irish Grand National and the Whitbread Gold Cup, to name but a few of his major successes. He was awarded a Timeform Annual Rating of 187, inferior only to such luminaries of National Hunt racing as Arkle, Flyingbolt, Sprinter Sacre, Kauto Star and Mill House.

Who was Flyingbolt?

Trained by the late Thomas William ‘Tom’ Dreaper at Greenogue, Kilsallaghan, County Dublin, Flyingbolt was a contemporary and stable companion of Arkle and, according to Timeform, had the distinction of being the second-highest rated steeplechaser since the mid-Sixties. Indeed, Arkle and Flyingbolt, with Timeform Annual Ratings of 212 and 210, respectively, stand head and shoulders above any other steeplechaser in the past five decades or so; Sprinter Sacre, winner of the Queen Mother Champion Chase at the Cheltenham Festival twice, in 2013 and 2016, comes in a remote third in the all-time list, with a rating of 192p.

Speaking of the Cheltenham Festival, Flyingbolt was successful at the March showpiece three years running in 1964, 1965 and 1966 in the Supreme Novices’ Hurdle, Arkle Challenge Trophy and Queen Mother Champion Chase, respectively. According to racing historian John Randall, in the latter race, Flyingbolt ‘triumphed with breathtaking ease by 15 lengths’. Such ease, in fact, that 24 hours later he reappeared in the Champion Hurdle, finishing a close, and arguably unlucky, third behind Salmon Spray.

Less than a month later, in the Irish Grand National at Fairyhouse, Flyingbolt put up arguably his best performance ever. Shouldering the welter burden of 12st 7lb, he beat the useful mare Height O’Fashion, who was receiving 2st 12lb, by two lengths, with the reigning champion Splash, who was receiving 3st 0lb, further behind in third place. Reflecting on that stage of his career, jockey Pat Taaffe said of Flyingbolt, ‘It seemed only a matter a time until he took over from Arkle.’ Sadly, he never did; shortly afterwards he contracted a recurring disease, known as equine brucellosis, and never showed the same level of form again.

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