Nothing stirs the blood quite like tales of legendary gamblers and their big wins. Horse racing, the sport of kings, has been woven deep into the fabric of British cultural life for centuries. A “tilt at the ring” has long been a phrase to excite a player’s imagination; the brave betting soul heading into the bookie’s den at a racetrack and trying to outfox them all. Or landing the football acca that pays a life changing amount. Online gambling, in all its glorious forms, has captivated Brits like almost no other leisure pursuit, revealing a Dostoevskyite tendency the persists to this day.
UK gambling history is full of poor boys made good, usually on the bookmaking side. Names like Victor Chandler and the Bet365 suprema Denise Coates have amassed huge fortunes, but their stories aren’t the ones to stir the blood. UK gamblers prefer poachers, not the game-keepers, to win and the following three characters have all won (and often) lost vast sums, but never took a backward step. Legends all!
Best Known and Richest Gamblers in the UK
1. Terry Ramsden
Why Netflix are yet to make a series about the life of Terry Ramsden is a mystery. Son of a humble postal worker, he starting betting on the horses as a boy and by his late teens, had made a small fortune. His most famous win came in 1984, when he bought the horse Katies only a few days before she was due to run in the Irish 1,000 Guineas. He backed the filly at 20/1 and won over £2.5 million when she duly romped home (a whopping £7.7 million in today’s money). Bookmakers trembled whenever he entered the betting ring and he became one of the best known “faces” on UK racetracks. At his peak, he was worth £150 million, but sadly it all came crashing down and he ended up in jail, owning £100 million. Like Icarus, Ramsden may have sailed too close to the sun, but his betting exploits in the 1980’s have guaranteed him punting immortality.
2. Barney Curley
Another imposing figure in the mythology of UK gamblers, Barney Curley was known as the king of the coup and loved for nothing more than to plot and strategise how to take money off the enemy (bookmakers, naturally). His most infamous victory was the Yellow Sam betting coup that occurred at Bellewstown racecourse in Ireland in 1975. Underhand tactics had been used to sting the bookies, including cutting one of the only two telephone lines from the course, so bookies couldn’t lay off some of their liabilities when the money came flooding in for “no-hoper” Yellow Sam, at 20/1. Curley also had an army of punters putting bets on for him in betting shops across Ireland. All told, Curley scooped £300,000, which is £2.4 million in today’s money. He vowed to be up front with his betting after that and spent a good part of his fortune on the charity he set up to help the poor of Africa. And yet…betting coups in 2010 and 2014 had the Curley imprint all over them, suggesting that this legendary punter never really have lost his hunger for the big win.
3. Harry Findlay

A gambler of immense proportions, Findlay is most famous as the owner of Gold Cup winner Denman. His first love is greyhound racing and he has won a king’s ransom on the dogs over the years, as well as being an enthusiastic owner. As he outlined in his best-selling memoir “Gambling For Life”, Findlay has always been obsessed with punting and has made many millions from it. When his horse Denman was the overwhelming 1-12 (1.08) favourite for a race early in its career, Findlay marched into the betting ring and had £360,000 on the horse. It sluiced up by 17 lengths. He also famously wagered over £2.5 million on the New Zealand All Blacks to win the Rugby World Cup in 2007, only to see them lose to the French in the quarter-final. Even today, aged 61, Findlay still loves a flutter and is happy to regale listeners with the punting war stories that have cemented his position in the UK betting hall of fame.
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