5 craziest roulette stories of all time

Roulette is one of the most popular table games enjoyed at both land-based casinos all over the world. While some people think the odds of winning roulette or the winnings themselves are not as attractive as some other games, there have been some massive collects combining strategy and luck throughout history.

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Below we have re-lived some of the most exciting wins imaginable and, who knows, if you are lucky enough to strike a big win at the Roulette table, perhaps we could be writing about you in the future.

The man who broke Monte Carlo

Charles De Ville Wells - top 5 craziest roulette wins

The Man Who Broke the Bank.

Charles De Ville Wells is often regarded as being one of the greatest roulette cheaters of all time, and is well-known for being the man who broke the bank at Monte Carlo back in 1891.

Whilst the term ‘breaking the bank’ at a casino doesn’t mean bankrupting it, it does mean winning every chip on the table which is an astonishing feat.

His story is hard to fathom, having taken £400 pounds from different investors at a time which he claimed was to fund a musical jump rope – but instead Wells pocketed the cash and set out to have some fun at the Casinos along the French Rivera.

Wells headed to the Roulette tables and remarkably played the game clean, collecting over 1 million francs during a monster 11-hour gambling marathon.

His exploits saw him become globally famous and he even inspired a song sung by Charles Coborn titled ‘The Man who broke the bank at Monte Carlo’.

Wells’ luck did eventually catch up with him, losing all his winnings in the Casino de-Monte Carlo, while he was also arrested several times and served eight years behind bars for fraud.

Wells died in Paris in 1922, penniless, but what a run he’d had.

Philip Green gets richer

Phillip Green - most insane roulette wins

The rich get richer!

Retail billionaire Philip Green, who owns fashion outlet Arcadia, is often regarded as one of the most erratic gamblers of all time.

In 2004, Green visited the Les Ambassadeurs in Mayfair, winning more than £2,000,000 playing roulette during one session on one night. He followed his winning escapade up by winning a further £1,000,000 during subsequent betting sessions.

His win was enough to trigger a profit warning by the casino, with Green saying of his lucky run “I had a fantastic night at the tables”. Now that’s an understatement.

Green is said to be a fan of playing a mixed system of even-money bets such as red-black alongside straight up bets on particular numbers.

Sean Connery and the number 17

Sean Connery - famous roulette wins

The original James Bond and a roulette champion – jealous?

Sean Connery, the original James Bond, appears on our list – but not for his character’s trademark game, Baccarat. In 1963, Connery visited the Casino de la Valee in Saint Vincent, Italy, where he stepped up to the Roulette table to place five bets on the number 17.

The first two bets lost. However, Connery got lucky on the third spin, with the number coming up at odds of 37 to 1. Rather than walking away a winner, Connery placed all his winnings back on number 17 and, against all odds, he won again.

Unbelievably, Connery risked all his winnings once again, putting all his cash on 17 for a fifth and final time. Once again, the number came up, with Connery leaving the table $27,000 in front.

The win seems even bigger when considering the odds of the Roulette wheel landing on number 17 three times in a row are more than 50,000 to 1.

Mike Ashley – 1.3 million in 15 minutes

Mike Ashley - lucky roulette winner

Ashley was in and out with his big win.

Perhaps gaining inspiration from Connery was billionaire Mike Ashley, who also cleaned up betting on the number 17 back in 2008. The high-rolling gambler, the owner of the Newcastle United Football Club, was ranked as Britain’s 54th richest man at the time.

Ashley headed to the exclusive Fifty London casino in Mayfair, where he placed a series of bets totaling £480,000 on his lucky number, 17. He walked away from the table just 15 minutes later with a staggering £1.3 million.

Ashley placed a complex bet known as a complete bet which means he bet on every successful combination including the number 17 itself – i.e. the ball falling on an odd number, betting on black, and betting it would fall on a number between one and 18.

Notoriously shy, it is reported that following his win, Ashley stood up and calmly said to the croupier “That’ll do me, thanks very much,” before collecting his winnings and walking away to the sounds of cheering from other punters.

Ashley Revell – your whole life on red

Ashley Revell - most insane roulette winner of all time

How many of you would bet your life savings on red?

The story of Ashley Revell started one night over drinks at a pub with his mates. In their drunken state, one friend mentioned the idea of betting everything on a single spin of the roulette wheel. The next day, despite the conversation having taken place while he was inebriated, the idea was set in Revell’s mind.

The 32-year-old sold all of his possessions including his BMW car, a Rolex watch and golf clubs, as well as all of his personal and sentimental items. During his quest, a television crew from the UK heard about his plan and created a mini series called Double or Nothing, while Revell was also sponsored to change his name to “Ashley Blue Square Revell” by a UK online bookmaker.

Once tallied, Revell made the flight to Las Vegas with £76,840. Stepping into the Plaza Hotel and Casino, Revell still had no idea whether to bet on red or black, only making his decision to go with red when the ball began to spin.

The ball eventually landed on number 7 – a red number – with Revell doubling his money to £153,680.

He used his money to take a motorcycle trip around Europe. Whilst on his trip, Revell met a woman in Holland who he took back to England with him and married. He is now a father of two with quite a story to tell the kids.