Five of the greatest gambles landed at the Cheltenham Festival including Blowing Wind & Destriero

Mister Donovan (1982 Sun Alliance Novices’ Hurdle)

Mister Donovan has an important place in the history of the Cheltenham Festival as he was the very first winner there in the colours of J. P. McManus. But as well as starting the ball rolling for the man who is now the Festival’s most successful owner, with a lifetime total that now stands at 67, Mister Donovan’s victory also established his owner’s reputation as one of jump racing’s shrewdest gamblers.

Trained by Edward O’Grady, Mister Donovan had won a couple of bumpers in Ireland but his profile was such a low one that Chasers & Hurdlers claimed that ‘as recently as the turn of the year, anyone outside Ireland who knew of Mister Donovan’s existence could consider himself a rarity.’

He ran four times over hurdles without success, seemingly unfancied each time. In the last of those races, at Naas, he made late headway to finish third at odds of 25/1. That form hardly looked good enough to win even an average renewal of what is nowadays the Ballymore Novices’ Hurdle.

But having led three out after showing prominently throughout and then staying on well, Mister Donovan landed a gamble at Cheltenham by a length and a half from Spider’s Well. Mister Donovan was backed down from 6/1 to 9/2, though his owner remarked afterwards that he’d been hoping to get 12/1 or 14/1 before ‘word got out.’

Destriero (1991 Supreme Novices’ Hurdle)

The 1991 Festival got off to a bad enough start for the bookmakers when Destriero landed a £1.5 million gamble in the opener, but things would have been a whole lot worse for them if The Illiad had followed suit in the Champion Hurdle later on the card. The pair were owned by Irish businessman Noel Furlong who would reputedly have netted five million if both horses had won.

As it was, The Illiad trailed in last of all behind Morley Street in the Champion Hurdle, though he’d been the medium of some successful gambles earlier in his career, including in Ireland’s richest handicap hurdle, The Ladbroke at Leopardstown, on his last start before Cheltenham.

Destriero, on the other hand, with £300,000 of his owner’s money on him in ante-post bets, was kept largely under wraps before Cheltenham, with his only appearance being a win in a maiden hurdle at Leopardstown on Boxing Day. ‘We didn’t run him [again] because we didn’t want to end up getting 2/1 instead of 6/1’ said Furlong who was only able to attend the Festival – he watched from J. P. McManus’s box – after agreeing to pay a substantial settlement (widely reported to be half a million pounds) to Customs & Excise over an alleged VAT fraud.

The 2/1 favourite was the Martin Pipe-trained Granville Again but the future Champion Hurdle winner was only able to stay on for second after Destriero had quickened impressively into the lead between the final two flights before going on to win by four lengths.

Unsinkable Boxer (1998 Gold Card Handicap Hurdle)

‘This horse is the biggest certainty that will ever walk out onto this racecourse.’ Tony McCoy recalls the words uttered by Martin Pipe as they made their way onto the track before the 1998 Gold Card Handicap Hurdle, nowadays the Pertemps Final. It was a private conversation, of course, though it may just as well have been broadcast over the racecourse PA because the confidence in Unsinkable Boxer seemed common knowledge and he became the subject of a wholesale public gamble.

Unlike the subjects of those Irish gambles, Unsinkable Boxer’s form as a highly progressive novice, despite being a nine-year-old, was there for all to see. Unsinkable Boxer had been dogged by problems in the past (he’d finished down the field as a 150/1 shot in the Supreme three years earlier) but had won all three of his races prior to the 1998 Festival, the first of those at Plumpton from a mark of just 94. He’d missed a run in a Warwick qualifier for the series Final through lameness, though at the time it was sufficient just to be declared for a qualifier to earn a run at Cheltenham.

Backed down to 5/2 – no horse had ever started at shorter odds for that particular race – Unsinkable Boxer won pretty much in the manner Pipe had evidently anticipated. Held up in rear early on, Unsinkable Boxer cruised into contention four out before leading on the bridle with two to jump, enabling McCoy to wave his whip in celebration to a roaring crowd well before the line.

Blowing Wind (1998 County Hurdle)

Just forty-eight hours after Unsinkable Boxer, McCoy had to work a bit harder on an even shorter-priced ‘handicap good thing’ from the Pipe stable. The Festival was still a three-day meeting at the time, and McCoy had the ride on the favourite in each of the last three races on the final day.

Edredon Bleu in the Grand Annual and the Pipe’s stable’s Cyfor Malta in the Cathcart duly obliged before McCoy partnered Blowing Wind in the concluding County Hurdle for which they were sent off at 15/8 against no fewer than twenty-six rivals.

Blowing Wind had already landed some good bets just five days earlier when sent off favourite for the Imperial Cup and his Sandown win under top weight made him eligible for a £50,000 bonus if he proved capable of following up under a 7lb penalty at Cheltenham.

He’d won impressively by four lengths at Sandown but had less to spare at Cheltenham where he became the third horse to complete the Imperial Cup-County Hurdle double, quickening between horses from the last to win by a length and three quarters from Advocat.

Xenophon (2003 Coral Cup)

‘With a horse like this there is no point in going for Mickey Mouse races – one big one like this makes up for ten little ones.’

Tony Martin has earned a reputation as one of the shrewdest of Irish trainers as he has demonstrated several times with well-backed winners at the Cheltenham Festival. Xenophon was a particularly good example, having already won the hugely competitive Pierse Hurdle at Leopardstown before his victory in ‘the big one’ he was referring to, the 2003 Coral Cup.

Xenophon’s 10 lb rise in the weights for his Leopardstown win didn’t please his trainer, but that form worked out really well and there was evidently plenty of support for the theory that, after just five starts over hurdles, Xenophon was still ahead of the handicapper. Available at 8/1 in the morning, Xenophon was heavily backed so that those odds were halved by the time the field of twenty-seven got under way.

Xenophon clearly was still improving as he landed the gamble impressively stepping up in trip, Mick Fitzgerald riding him patiently before making smooth headway into contention and producing him to lead at the last before staying on strongly up the hill to win by three and a half lengths from one of the Pipe runners Samon.

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