Sometimes, we gamblers need a little inspiration to remind us why we bother to bet at all. Especially after a losing streak, stories about roulette winners can remind us why we love the game and why picking ourselves up and trying again is just what we do. These are the stories of the biggest roulette winners of all time. These roulette stories remind us that with guts comes glory, often in the form of life-changing wins.

These are the stories of the biggest roulette winners of all time. These roulette stories remind us that with guts comes glory, often in the form of life-changing wins. The Biggest Roulette Winners of All Time Charles Wells – 1891. Charles Wells may have been a petty crook and conman, but he earned his place in the roulette history books back. Winner Stories December 20, 2017. Hip Hop, “Rhythm Roulette,” and More With Peter Bittenbender, CEO of Mass Appeal. “We want to be telling the best and most authentic stories.” Rhythm Roulette is a perfect example of that focus. Conceived by Director of Content Development Matt Lubanksy, the show came about in the early.

The Biggest Roulette Winners of All Time

Charles Wells – 1891

Charles Wells may have been a petty crook and conman, but he earned his place in the roulette history books back in Monte Carlo in 1891. Because of the events that transpired that night, he’s known as “The Man Who Broke the Bank at Monte Carlo.”

Wells went on the lucky streak of a lifetime, winning 23 out of 30 spins of the wheel. This win scooped him one million Francs and broke the casino. He cleaned them out so that they couldn’t continue to let him play.

As if that wasn’t enough, Wells later returned to the same casino and pulled off the same insane winning streak. Did he cheat? It’s hard to rule it out, but the casino could never prove it if he did. This is one of the luckiest roulette stories of all time.

Ahsley Revell – 2004

There are defining moments in every person’s life when things could go either way and make or break them. Most of us encounter these moments through no choice of our own, but Ashley Revell decided to walk up to the line, stare fate straight in the face, and dance.

Mr. Revell sold all of his worldly possessions including his house, his car, any cash he had saved, and just about everything else he owned. In total, he had $135,000 US dollars when he entered the Plaza Hotel and Casino in Las Vegas.

Tossing all bankroll management advice aside, Mr. Revell waged the full $135,000 on red. Moments later, he had doubled his net worth.

While this isn’t the biggest roulette win of all time, it’s certainly one of the ballsiest. We don’t know what drove him to do it, and we don’t necessarily recommend such drastic action, but in this case, a tip of the hat is due as a gesture of respect.

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Mike Ashely – 2008

Mike Ashley is better-known as the boss of Sports Direct, a successful sports equipment franchise in the United Kingdom. He’s a billionaire, so it’s only fitting that he’d be a high roller roulette player.

In 2008, Mr. Ashely entered a Mayfair casino and wagered £480,000 on a “complete bet” on the number 17. For those who don’t know, this means he covered every bet that could lead to 17, plus a few extras.

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Mr. Ashley walked away with £1.3 million. That’s only a fraction of his net worth, but we’re sure it still gave him a thrill nonetheless!

Chris Boyd – 1994

This story is probably where Ahsley Revell got his inspiration from, and the similarities in the two stories are uncanny. Since this one happened a decade before the other, we think it’s safe to say that this was the original.

Chris Boyd was a 40-year-old computer programmer who had collected $220,000 over a few years of coding. He walked into the Binion’s Horseshoe Club and wagered the lot on red. Rumour has it that several other casinos had refused him, but that Binion’s had decided to entertain him and had covered up the extra zero pocket as part of the deal.

They probably wish they hadn’t, because Boyd’s bet came good and he walked away twice as rich. What a guy!

Pedro Grendene Bartelle – 2017

It’s no secret that the bigger your bankroll is, the bigger the risks you can take, and the larger the payouts you’ll win tend to be. Such is the case in this story about the biggest roulette winner on this list.

Pedro Grendene Bartelle is a successful Brazilian businessman who placed a $35,000 wager on a single number: 32, at the Hotel Conrad in Uruguay.

Experienced roulette players will know what straight bets pay. He walked away with $3.5 million, and it was all on film!

Biggest Roulette Winners – Summary

We don’t recommend selling everything you own and wagering it all on the roulette wheel. Remember that for every success story like this, there are countless untold stories of players who lost it all on the wager of a lifetime.

We suggest studying the most successful roulette strategies and trying your luck with more conservative bets. If you even triple your money with some big roulette wins while having some fun, that’s about all you can hope for, isn’t it?

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 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

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

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.

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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

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

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.