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The Seven Biggest Gamblers in the UK of All Times

The British have a special relationship with gambling. Taking your first trip to the bookies when you turn 18 feels like a right of passage, and screwing up your failed accumulator every Saturday afternoon is a staple of the British sporting experience. The British love for gambling is as old as time, littered with some brilliant rags-to-riches stories. We all dream of hitting that one big win and changing our lives forever, but in almost all cases, the most successful gamblers are the ones that have dedicated their lives to the craft, building a fortune through cleverly timed bets and well-honed skills. Let’s look at some of British history's biggest and most successful gamblers.

Tony Bloom

You can’t have a list of the UK’s biggest gamblers without mentioning Tony Bloom. Bloom is a man who, fittingly, has always kept his cards close to his chest. His exact worth is unknown, and neither are his collected winnings, but it’s fair to assume that Bloom has racked up quite the treasure chest over his career.

The 51-year-old made his name through his poker performances, taking home millions of pounds through appearances in the World Series of Poker and other major poker tournaments. It’s not just his appearances on the felt that has made Bloom rich, though.

Bloom has used his wealth to build quite an impressive portfolio. He has operated several successful gambling websites and, most famously, is the chairman of Brighton & Hove Albion FC. Bloom’s involvement has helped take the club to new levels, with the team reaching the Premier League for the first time in its history in the 2017/18 season. These kinds of moves would certainly indicate that Bloom has made himself a pretty penny over the years.

Matthew Benham

From one football club owner to another, Matthew Benham is another huge success story from the UK betting scene. Benham’s success has seen him purchase not one but two football clubs - his beloved Brentford FC and FC Midtjylland in Denmark.

Anyone who has followed the meteoric rise of Brentford FC over the years will know all about Benham’s statistics-based approach to the beautiful game, and it is this same approach that saw him build the wealth needed to buy these clubs in the first place.

Benham is an Oxford graduate who spent the early years of his career in finance in the City of London.

In an interesting crossover, Benham was initially hired by Tony Bloom to help with statistics at the club. The two had a falling out, which led Benham to create Statsodd, a decision that would change the course of his career. Benham would make significant amounts of betting on the Asian market and then use this wealth and his money from his finance days to build a betting empire.

This success allowed him to purchase his childhood club, Brentford FC. Like Bloom before him, Benham would find plenty of success, taking the London-based club to the Premier League for the first time in history. Benham’s team have continued to defy the odds, and he has refused to sell, sticking to his unique approach to the game and taking them to new heights.

Everything about Benham’s story is quintessentially British, from his Oxford education to his success at his boyhood football club. He is one of gambling’s biggest success stories, and his impact is still felt today.

Simon McMillan

Simon McMillan is not as successful as other names on this list, but he may be one of the most important gamblers in the UK in recent times. McMillan caused a stir when HMRC investigated him after making much money from sports betting. The size of his winnings is not exactly known, but it’s fair to say it must have been quite a chunk if the tax man decided to get involved.

McMillan had been an active gambler between 1998 and 2010 and had used a complex set-up involving stats to bet on football and his poker skills in high-stakes private games. Gambling winnings are not taxable in the UK, but McMillan’s system saw him taken to court by HMRC.

What followed was an important victory for gamblers in the country. The court ruled in favour of McMillan. It noted that McMillan had used skill to maximise his chances of securing a win but that his earnings had still been earned through gambling and involved risk on his part. It was ruled that it could not be considered a trade, despite his expertise, and that the winnings would remain untaxed.

This was seen as a significant moment for professional gamblers in the UK, with the court ruling that it would not be considered a trade regardless of whether or not there was an element of skill involved.

Harry Findlay

The life of a gambler is full of highs and lows, and few men understand that quite as much as Harry Findlay. The name of Findlay’s autobiography is Gambling for Life: The Man Who Won Millions and Spent Every Penny, which should tell you everything you need to know about him.

Findlay made most of his money through horse racing, arguably one of the biggest British betting sports. His betting stories were often the talk of horse and greyhound racing circles in the 90s and 2000s, with his betting tips being highly sought after. He even found some success on the race tracks, with his horse Denman winning the Cheltenham Gold Cup in 2008.

Findlay is an incredibly British character. He is bold and eccentric and is not afraid to talk about his losses as much as his wins. His winnings are said to have reached up to £20 million, with Findlay also insisting that he lost most of that over the years.

As any good gambler should know, you have to take the rough with the smooth, and he claims to have no regrets about the huge amount of money he has lost. He has truly lived the life of a gambler, and he has earned his place among the most iconic and successful British gamblers as a result.

Patrick Veitch

Patrick Veitch is a Cambridge graduate once dubbed the public enemy number one by bookmakers. Like many of the most successful gamblers, Veitch built his success on maths and statistics. He would spend hours studying the best selections to bet on, devising systems that maximised his chances of landing a big win.

Veitch’s gambling escapades started at Cambridge when he set up a tipping hotline for horse racing. Within three years, Veitch made £10,000 a month from the hotline, let alone from his gambling results.

As a young man raking in this kind of money, Veitch adopted what he described as a ‘playboy’ lifestyle, quickly earning himself a reputation among bookmakers and racecourse owners. No gambler wants this kind of attention, and it quickly becomes difficult for you to accept your bets.

Veitch managed to rack up an incredible wealth of over £10m from his gambling habits, but he has admitted that he has taken a step out of the limelight recently. Veitch became the target of some criminals and realised this was a game-changer for him. Threats were made against his well-being, and he quickly realised that no amount of betting or money was worth his health.

He is still one of the most successful gamblers in the country, though, and occasionally appears as a pundit and tipster. While he does not bet as often as he was at the anger of his powers, he is still said to bring in some significant winnings occasionally.

Terry Ramsden

Many gamblers on this list had a good starting point for success, whether a successful career in finance or a university education from one of the country’s top institutes. Neither of these things applies to Terry Ramsden, a man that has lived the rags-to-riches dream that most gamblers dream about.

Ramsden was the son of a postal worker born in Enfield, London. After working as an insurance clerk for a few years, he realised that working for someone else would never give him the kind of life he wanted. By 19, he was said to earn £25,000 a month through investments and self-employment.

Enfield had a keen analytical eye and quickly built his fortune on horse racing and investment in the Japanese stock market. By the middle of the 1980s, Ramsden had earned over £100m and, at one point, was the 57th richest man in the UK. Not bad going for the son of a postie.

Ramsden’s wealth made him famous in the betting scene, and his tips were highly anticipated. His tips were nearly as famous as his iconic mullet, which would define the sports scene in the UK in the 1980s.

Terry Ramsden is easily one of the UK’s most iconic betting figures, and his lavish lifestyle and extravagant purchases have come to embody the dream many gamblers have.

Jon Heywood

Unlike all other gamblers on this list, Jon Heywood is not a man who has built an entire career out of gambling. He is notable, however, for once holding the World Record for the largest slot win of all time, clocking in at an impressive £13.2 million.

Heywood made the headlines in 2015 when he managed to land his massive win when playing the popular online slot game Mega Moolah. For those who don’t know - Mega Moolah is a popular progressive jackpot slot game responsible for some of the biggest wins in online slots.

What makes Jon Heywood’s story all the more remarkable is that he won the fortune following a £0.25 bet. It’s the kind of win we all dream of and keeps many of us repeatedly going back to our favourite online casinos.

So how has Heywood spent his millions? Heywood had been a soldier in the British army and had returned home to help care for his father, who needed medical attention. Heywood told the media he would spend money helping his father recover.

Heywood’s feel-good story is an example of how gambling can change someone’s life, and while he may not have built an empire like many other people on this list, his selfless acts have earned him a place among them.

Plenty More to Come

The British love to gamble and the success story of these people is why many others will continue to do so. With so many top online casinos and bookmakers available these days, there are more betting options than ever before, and more Brits are taking the slots for a spin or having a cheeky punt on the horses.

Of course, not everyone can hit a £13.2 million jackpot from a £0.25 spin, but the fact that someone has managed to do that suggests that someone else will do it in the future. Who knows? It could end up being you.

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Liam Hoofe
Liam Hoofe
Last Update: 13 Dec 2023
Liam is a skilled writer and journalist, highly regarded for his perceptive examination of the gambling industry. He specializes in online casinos and sports betting, and his work has been published in top-tier publications. Here at GoodLuckMate, Liam covers the latest industry news and has also authored various gambling guides, offering both beginners and experienced players in-depth analyses of games and strategies.
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