Memorable Cheltenham Festival Gambles That Hit Bookies Hard

by , 8 March 2024

The Cheltenham Festival, an undisputed kingmaker, is jump racing’s Holy Grail. Not only does this annual four-day treat regularly crown champion racehorses that earn legendary status, but down the years, it has produced gambles so large or unusual they have earned their place in racing folklore.

High-street bookmakers, their modern-day cousins, the online sportsbooks, and traditional men with satchels – better known as on-course bookies – have all been on the receiving end of a wrecking ball result at the Festival at some point. The adage, ‘the bookmakers always win,’ does not ring true at Cheltenham.

Owner JP McManus and his jockey, AP McCoy.

JP McManus is the Festival’s most successful owner and the man behind many successful Cheltenham gambles dating back to 1982. ©Getty

From a successful £50 accumulator that smashed through its £1 million payout ceiling to the public gamble that saw Unsinkable Boxer start 5/2 in a 23-runner handicap that he officially won in a canter, the Cheltenham bookies have spilt blood and tears down the years.

JP’s First Winner and First Gamble Landed

Approaching 80 Festival winners as an owner, JP McManus’s green and gold colours are synonymous with Cheltenham. It all started when Mister Donovan won the 1982 Sun Alliance Hurdle and, fittingly, the former bookmaker’s first Festival winner landed a celebrated gamble. The story is an excellent place to start a list of memorable Cheltenham betting coups.

Irish trainer Edward O’Grady had placed Mister Donovan to win two bumper races. But three runs over hurdles suggested he had limited ability. Only on his fourth jumps start – over an inadequate trip at Naas – did the colt show promise. He ran on late to finish third at odds of 25/1. However, the outing was merely a prep race for the Sun Alliance Novices’ Hurdle (now the Ballymore).

McManus knew the plan, and ahead of the 1982 Festival, he stepped in to buy the horse aimed at the contest, worth around £16,000 to the winner. As the Racing Post reported: “We loaded up on him,” McManus has said. “I hadn’t owned the horse for very long, but he had been laid out for the race. I don’t remember quite how much we had on, but it was important at the time anyway.”

Betting the Old Fashioned Way

Placing bets in person with on-course bookmakers, McManus backed his horse into 9/2 – a remarkably short price considering he was beaten at 25/1 in a relative egg-and-spoon race at Naas beforehand. By the off, McManus stood to win a reputed £250,000 (the equivalent of £1 million today).

The gamble was landed, but bookmakers had a chance of keeping JP’s money until the closing yards as Mister Donovan – ridden prominently and leading turning for home – was pressed all the way to the shadow of the post by Spider’s Well. After this performance, it is fair to say McManus was hooked on the Cheltenham Festival.

Sixty-Four Thousand Reasons to Celebrate

Cheltenham 1982 was a springboard for the Festival’s most successful owner. Thirty years later, Cheltenham 2012 proved a launching pad for stable-hand Conor Murphy to start his career as a racehorse trainer. With one of the most outstanding bets of all time, the Irishman parlayed £50 into £1 million on a bet placed four months before the Festival began.

Then, at age 31, his winning bet was an accumulator placed on horses trained by his boss, Nicky Henderson. The winning selections were Sprinter Sacre (6/1 in the Arkle Chase), Simonsig (12/1, Neptune Hurdle), Bob’s Worth (6/1, RSA Chase), Finian’s Rainbow (8/1, Queen Mother Champion Chase) and Riverside Theatre (10/1).

His first two selections, Sprinter Sacre and Simonsig, never gave Murphy an anxious moment by winning easily on the Festival’s opening day. Bob’s Worth and Finian’s Rainbow had to work considerably harder for their victories on the Festival’s second day.

Murphy probably had a sleepless night heading into day three with four winners down and a single runner to go. One more winner would put him in the millionaire’s club. The miracle happened, but not before Albertas Run led his selection, Riverside Theatre, over the final fence in the Ryanair Chase.

In a pulsating finish, Riverside Theatre, owned by actor James Nesbitt, got up to win by half-a-length under Barry Geraghty. Murphy had successfully found five big-priced winners at accumulative odds just shy of 64,000/1. Such were the prices; our betting calculator shows his £50 bet should have returned £3,153,100 but his bookmaker had a £1 million win limit.

Helped by his winnings, Conor Murphy fulfilled his dream of training racehorses in America. Two years later, he enjoyed Graded race success and a visit to the Breeders Cup courtesy of the former British-trained Dimension. And what did he name his Louisville, Kentucky, training establishment? Riverside Stables, of course!

All Furlong’s Christmases Came at Once

The 1991 Cheltenham Festival got off to a spectacular start when Destriero landed a massive gamble by winning the Supreme Novices Hurdle. The horse was Irish-trained, and, given that the Irish had left the Festival empty-handed in 1989 and had just two winners in 1990, few had any interest in the lightly-raced horse from a little-known stable.

However, owner JJ Furlong, an Irish carpet manufacturer better known as Noel (as he was born on Christmas Day), knew how good his horse was. He managed to keep Destriero’s ability under wraps by running him just once over hurdles before heading to Cheltenham.

Furlong backed his judgement and his horse to the tune of £300,000. Most of his guilt-edged investment was placed ante-post, but he also topped up on race day. When Destriero pulled four lengths clear of future Champion Hurdle winner Granville Again, and 20 other rivals at a 6/1 SP, Ladbrokes and other firms were relieved of over £1.5 million.

Successful in business and horse racing – he also owned The Illiad, who won the prestigious Ladbroke at Leopardstown – Noel Furlong certainly had the Midas touch. In 1999, he entered the World Series of Poker and left Las Vegas $1 million richer as the Main Event champion.

Bookies Will Never Forget a Golden 1983

Forgive N’ Forget is a name etched on the illustrious Gold Cup roll of honour. But his 1985 success in the Festival’s showpiece event was not his first appearance in Cheltenham’s winner’s enclosure. In 1983, the horse won the Coral Golden Handicap Hurdle (now known as the Pertemps Hurdle), landing a colossal gamble in the process.

Legendary gambler Barney Curley had a hand – and probably a financial interest – in one of the biggest Cheltenham coups of the 1980s. He had sold the future champion to construction tycoon Tim Kilroe and, along with Forgive N’ Forget’s new trainer, Jimmy Fitzgerald, connections had the utmost faith in their horse.

Despite seemingly anchored by 11-stone 6-pounds, money poured in for Forgive N’ Forget in this traditionally hotly contested handicap. By the time the 25-runner field made its way to the start, Forgive N’ Forget had been backed into 5/2 from the double-digit odds available when the weights were announced – and 9/2 on race day morning.

Looking ready to run another circuit, Forgive N’ Forget won eased down. Bookmakers, on and off course, were left to lick their wounds as the public latched on to the confidence of the Fitzgerald stables. Details were sketchy, but connections alone were believed to have netted £1 million in winning bets – a record at the time.

On the Ball With a 66/1 Ante-Post Score

There is no doubting what Phil Williams, a former professional footballer who played for Crewe Alexandra, Wigan Athletic and Chester, hit bookmakers for in 2012 when his Son Of Flicka landed the Coral Cup. Scoring by three-and-a-half lengths ahead of 27 rivals, the eight-year-old returned at 16/1 for trainer Donald McCain.

Unlike so many owners who reply, “I had a nice bet” when asked if they had backed their winner, Williams confirmed he had indeed backed his horse – at 66/1 ante-post, netting a £900,000 return. The early odds were understandable; Son Of Flicka had not won in 11 previous starts, and his most recent starting prices were 50/1, 33/1 and 66/1.

After the race, the winning owner declared: “I’ll die a happy man now!” Meanwhile, McCain told enquiring stewards: “The gelding appreciated the better ground and comes to himself in the spring.” Afterwards, he stated the obvious to the waiting press: “When he’s on song [Son Of Flicka], he takes some passing.”

Dean’s £5 Losing Accumulator Wins £250,000

Not so much of an orchestrated gamble and certainly not inspired by inside information, but a £5 ante-post five horse accumulator placed by then recreational punter Paul Dean, 40, from Stockton-on-Tees, Durham, on races at Royal Ascot 2020 and the 2021 Cheltenham Festival deserves an honourable mention.

The punter successfully selected Golden Horde to win Ascot’s Commonwealth Cup and Hello Youmzain to land the Diamond Jubilee. Their SPs were 4/1 and 5/1, but Dean had taken ante-post odds of 10/1 and 12/1. After their success, there was a nine-month wait for his final three selections to run.

His third choice was Shishkin at odds of 4/1 in the Arkle Novices’ Chase. No sweat was required as he strolled home a dozen lengths clear of his rivals, priced 4/9. Leg four saw Dean’s money running on Bob Olinger in the Ballymore Novices’ Hurdle. Although the punter had backed him on 25/1 odds, the Irish horse strolled home as the 6/4 favourite.

One day and one race stood between the £5 punter and a remarkable £511,225 win. And, as the final leg hinged on Envoi Allen – unbeaten in 11-lifetime starts and 4/9 favourite for the Marsh Novices’ Chase – most were expected to be raising a glass to the intrepid punter at the end of Festival day number three.

However, a cash-out offer from his bookmaker gave Dean a big decision. At 4/9 odds, Envoi Allen’s probability of winning was just shy of 70 percent. But that meant there was a 30 percent chance of him winning nothing. When his bookmaker offered him £250,000 to close his bet down, with a kicker that he would collect an additional £72,000 if the horse won, Dean took it.

The decision to take half of what he could have won proved an excellent one. Envoi Allen fell at the fourth fence. Technically, it meant a £72,000 loss for Dean. Still, having parlayed £5 into £250,000 and successfully avoided the heartache of rejecting the handsome offer (and winning nothing), Envoi Allen’s first career defeat is unlikely to have left the punter too distressed.

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