including footballer who won £900K on 66/1 shot
Cheltenham is no stranger to superstars emerging overnight, but it isn't only those on the track who can enjoy rags-to-riches moments at one of the biggest festivals in horse racing.
Or rich-to-richer tales for that matter, considering some of the biggest bets in the meet's history have been won by those with considerable means. Identifying gaps in the bookmakers' market is crucial when it comes to netting major returns, while other lucrative gains take considerably more luck.
Regardless of how they came to be cashed, Cheltenham has hosted its fair share of six and seven-figure pay days from the most unexpected contenders.
Daily Star Sport breaks down a selection of the most surprising stakes that have made it across the line down the years, including one cash prize won by an ex-Arsenal prospect.
Forgive n' Forget makes £1m memories
Long before the days when tip-offs could cause online ripples overnight, Irish builder and horse owner Tim Kilroe concocted a masterful plan when he purchased Forgive n' Forget with a blueprint in place. Seller Barney Curley was renowned for possessing great gambling guile himself, but it nonetheless took time for the rest of racing to cotton on to just what a talent had traded hands.
By the time the 1983 Coral Golden Hurdle rolled around, Forgive n' Forget was known well enough to be carrying the second-highest weight of 11 stone, six pounds, earning double-digit odds in the process. But that was enough to deter a swell of betting interest, and he went on to run clear regardless, clearing a field of 23 at a price of 5/2.
An emerging Mark Dwyer rode a raucous winner at just 19 years of age to net Kilroe a reported £1million in what proved a birthing point for both jockey and horse. The six-year-old son of Precipice Wood would go on to win Cheltenham's Gold Cup just two years later, but his breakthrough at the Golden Hurdle was the real value bet, billed at the time as a 'licence to print money'.
Ex-Gunner's 66/1 wonder
If ever it was said professional athletes struggle to match the highs of their careers once retired, the trend doesn't apply to former footballer Phil Williams. The Swansea-born starlet started his career on the books at Arsenal before joining Blackpool, Wigan Athletic and Crewe Alexandra, but arguably the best day of his sporting life came after he'd hung up his boots.
Williams - who later worked in the warehouse industry in Dubai - watched as Son of Flicka's price fell from 66/1 on the morning of the 2012 Coral Cup down as far as 16/1 at the post. Much of that might have been influenced by his own bets, which ended up netting him a nifty £900,000 pay-off.
"I have been a punter all my life so pulling something like this off is very special," the former midfielder confessed after the win. "When I was playing for Crewe against Bury, and [manager] Dario Gradi will confirm this, I was in the bookies at five to three in my kit and boots."
The £3million robbery
It's not often one can turn two digits into seven and still come away discontent with the earnings, but such might have been the case for Conor Murphy when he became a millionaire in 2012. That was after the Cork native landed a £50 stake at 64,000/1 odds but was prevented from claiming all his winnings.
Working as a stable hand for esteemed trainer Nicky Henderson at the time, Murphy was ahead of the game when he placed a five-fold accumulator on Sprinter Sacre (6/1), Simonsig (12/1), Bob’s Worth (6/1), Finian’s Rainbow (8/1) and Riverside Theatre (10/1) around Christmas 2011. That ensured the insider snagged premium odds for his picks, though some research into bet365's rules might have altered his selection.
Murphy's winnings amounted to around £3.2million, though he was awarded less than a third of that due to the bookmaker's £1m pay-out cap. He had already decided on a move to Louisville in Kentucky prior to that win given his wife, Julia, is American, but his new life as a trainer in his own right was made all the simpler as he struck Cheltenham gold.
Destriero's dastardly disguise
The bookmakers' balance took a beating in the opening race of the 1991 Festival, where Destriero emerged from obscurity to score a major upset in the Supreme Novices’ Hurdle. Much to the delight of poker player and carpet tycoon Noel Furlong, who owned the horse with wife Betty but tried to keep his talent largely under wraps.
Destriero made a winning debut at Leopardstown in January 1990 but didn't run again December of that year, racking up another victory at the same venue. While much of the racing world remained largely ignorant to his potential - signified by his 7/1 odds ante-post - Furlong was confident enough in his ability to place £300,000 worth of wagers, which returned around £1.5m.
Furlong would have won more than three times that amount if his other runner, The Illiad, followed through in the Champion Hurdle, but it wasn't to be. Asked why Destriero hadn't been more active in the lead-up to Cheltenham, the Irishman revealed he was deliberately held back, explaining: "We didn’t run him [again] because we didn’t want to end up getting 2/1 instead of 6/1."
Crucial cash-out banks £250,000
As sweet as it may be to land that ultimate accumulator, the modern age has given birth to cash-out contentment. And Teesside punter Paul Dean benefited from just such an early exit in 2021 when the decision to bail on his bulked-up bet proved wise indeed.
Dean had already seen four of his five selections come in as Bob Olinger (25/1), Golden Horde (12/1), Hello Youmzain (10/1) and Shishkin (4/1) won their respective races. The £5 ante-post punt moved to Thursday, however, leaving its owner with an awkward night's sleep (or lack thereof) over his fifth and final pick.
Envoi Allen was a strong contender to deliver Dean a £511,000 prize if he scooped up victory in the Marsh Novices' Chase, but he decided to take the £250,000 on offer with Betfair instead. It proved prudent as Envoi Allen went on to fall at the fourth hurdle, saving Dean a lifetime of heartache had he let it run.
