Which was the last grey horse to win the Cheltenham Gold Cup?

The last grey horse – in fact, the only grey horse – to win the Cheltenham Gold Cup was Desert Orchid in 1989. The iconic grey had been beaten of five previous appearances at the Cheltenham Festival, twice in the Champion Hurdle, once in the Arkle Challenge Trophy and twice in the Queen Mother Champion Chase. Nevertheless, on treacherous, barely raceable ground and going left-handed – he was, according to jockey Simon Sherwood, ‘a two stone lesser horse going that way’ – Desert Orchid was sent off 5/2 favourite for his first attempt in the ‘Blue Riband’ event of steeplechasing.

‘Dessie’, as he was affectionately known to his legions of supporters, raced prominently for most of the way and was left in the lead when Ten Plus fell at the third last. However, the confirmed mudlark Yahoo, clearly relishing the atrocious underfoot conditions, arrived on the scene, travelling well, on the home turn and looked all over the winner. Galvanised by Simon Sherwood, Desert Orchid rallied gamely between the final two fences and was almost upsides again jumping the last. On the climb to the winning post, he first drifted right towards the stands’ side and then left towards his rival but, in the last hundred yards or so, Desert Orchid forged ahead to win by 1½ lengths, with Sherwood punching the air in celebration.

Who is Paul Nicholls?

Formerly stable jockey to David Barons, for whom he won the Hennessy Gold Cup, now the Ladbrokes Trophy, on Broadheath in 1986 and Playschool in 1987, Paul Nicholls retired from the saddle in 1989 with 133 winners to his name. He subsequently spent two years as assistant trainer to Barons before starting out on his own, at Manor Farm in Ditcheat, Somerset, with just a handful of horses, in 1991. He gradually increased his winning tally, season by season, but first came to public attention in 1998/99, when he saddled 110 winners and won £1.19 million in prize money.

Indeed, at the Cheltenham Festival in 1999, Nicholls became the leading trainer for the first time, courtesy of victories for Flagship Uberalles in the Arkle Challenge Trophy, Call Equiname in the Queen Mother Champion Chase and See More Business in the Cheltenham Gold Cup. In an era dominated by Martin Pipe, Nicholls regularly played ‘second fiddle’ to the Master of Pond House in the National Hunt Trainers’ Championship; it was not until 2005/06 season, at the end of which Pipe retired, due to ill health, that he claimed the trainers’ title for the first time.

However, Nicholls has gone on to win the National Hunt Trainers’ Championship eleven times in total, most recently in 2018/19, and has handled some of the out-and-out superstars of National Hunt racing. He has saddled 46 winners at the Cheltenham Festival, where he is, jointly, the leading trainer in the history of the Queen Mother Champion Chase. He has also won the Cheltenham Gold Cup four times, the Stayers’ Hurdle four times – with the same horse, Big Buck’s, in 2009, 2010, 2011 and 2012 – and the Champion Hurdle once.

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.

Who is Nicky Henderson?

Nicholas ‘Nicky’ Henderson is the son of the late Major John ‘Johnny’ Henderson, a founder of the Racecourse Holdings Trust and, as such, credited with helping safeguard the future of Cheltenham Racecourse in the Sixties. The name of Nicky Henderson, too, is synonymous with Cheltenham, predominantly the Cheltenham Festival, where he has saddled 68 winners, making him the second most successful trainer in history, behind only perennial Irish Champion Trainer Willie Mullins.

Indeed, Henderson is the leading trainer in the history of both the Champion Hurdle, which he has won eight times and, jointly, alongside Tom Dreaper and Paul Nicholls, the Queen Mother Champion Chase, which he has won six times. He has also won the Cheltenham Gold Cup and the Stayers’ Hurdle twice apiece.

Henderson has also won the National Hunt Trainers’ Championship six times including, most recently, in 2019/20. The National Hunt season was brought to a premature end on March 25, as the result of the coronavirus pandemic but, at its close, Henderson had saddled 118 winners, including 15 at Graded level and, more importantly, amassed £2.53 million in total prize money; his seasonal total was £192,550 higher than his nearest rival, reigning Champion Trainer Paul Nicholls.

Henderson, who turns 70 in December, 2020, began his training career as assistant to eight-time Champion Trainer Fred Winter in 1974, before taking out a training licence in his own right four years later. He is currently based at Seven Barrows in Upper Lambourn, Berkshire, the yard to which he moved in 1992.

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