Biggest Roulette Wins in History

Roulette, Tables, Coins, Dice, Winner

Reading about the biggest roulette wins ever can be inspirational. Nothing will get us gamblers in the mood to play quicker than reading about the gutsy men and women who took risks and made life-changing money playing roulette.

In this article, I share some of the biggest wins ever on roulette. I also tell you where, when, and how they were won. While it’s true that the house always wins in the end, someone beats the odds and walks away with a fortune every once in a while.

Charles Wells Brings Down the House in Monte Carlo

  • Total: 2 million francs
  • Where: Monte Carlo
  • When: 1891

Some of the largest roulette wins ever are truly legendary, and this is one of them. This one is the stuff of folk tales among roulette players.

Charles Wells was a street hustler and petty criminal in Europe back in the late 19th century. He was also an avid gambler. In 1891, he visited the Monte Carlo Casino Resort and decided to play roulette. Little did he know, his gaming activities that night would be remembered and recalled over a century later.

Wells went on an insane roulette-winning streak. According to the story, he won 23 out of 30 consecutive spins and banked so much money (one million francs) that the casino wouldn’t let him play anymore.

While that story would be good enough on its own, it’s made even better by the fact that Wells returned to the casino and did it a second time. He once again made over a million francs.

What’s this worth in today’s money? It’s difficult to say, but it would be well into the millions of dollars. It is likely the single biggest roulette win of all time that the lucky player got to keep.

Rapper Drake Wins and Loses $25+ Million on Roulette

  • Total: $25+ million
  • Where: Stake Online Casino
  • When: 2022

While the other big roulette wins on this list took place in brick-and-mortar casinos across the world, this one happened at an online casino. Canadian rapper Drake shared footage of playing online roulette on his Twitch Livestream. During it, he won and lost over $25 million.

Futher Info:The stream involved a series of wins and losses. Some wins were as large as $5.73 million. Eventually, his balance swole to over $27 million. However, by the end of the gaming session, he was down to under $2,000.

Some other live streams of Drake playing roulette for real money have shown him winning up to $17.9 million on a single spin. It’s absolutely incredible that anyone can win that sort of money playing roulette online, and all of these wins surely go down as some of the biggest roulette wins in history.

Pedro Grendene Bartelle – A Brazilian Businessman Hits the Bigtime

  • Total: $3.5 million
  • Where: Hotel Conrad, Uruguay
  • When: 2017

Brazilian businessman Pedro Grendene Bartelle was visiting neighboring Uruguay when he decided to go all in on a straight bet at the roulette tables.

Bartelle placed a wager worth $35,000 on the number 32. It came good, and he walked away with a massive $3.5 million win.

While it helps to be the nephew of a billionaire in these situations, that doesn’t mean everyday people can’t place risky wagers at their own comfort level.

Some online variations of roulette offer wagers with returns of a few hundred times your stakes, so even a small bet can lead to a huge return.

Sir Philip Green Shows Who’s Boss

  • Total: £2 million
  • Where: Les Ambassadeurs, Mayfair, London
  • When: 2004

Philip Green is best known as a British business mogul. He was chairman of a huge retail conglomerate known as the Arcadia Group. In 2021, his net worth was estimated to be over £900 million.

Yet, Green is also known as a high roller who frequents some of London’s lavish casinos. It was at one of these, in Mayfair, that he won £2 million playing roulette.

Much like Charles Wells (mentioned above), Green reportedly repeated similar feats, winning well over £1 million as well as several other large sums from the same casino.

Do you know that old saying that it takes money to make money? It certainly seems true in the case of Sir Philip Green.

Mike Ashley Goes Direct to the Cage to Cash Out

  • Total: £1.3 million
  • Where: Fifty Casino, Mayfair, London
  • When: 2008

Mike Ashley is a British businessman who owns Sports Direct. He’s a multi-billionaire, so playing for high stakes probably isn’t that much of a rush for him.

Nonetheless, Mr. Ashley won £1.3 million after wagering £480,000 on a 17 ‘complete bet.’ This means he wagered on every combination that included 17, and he won on black 17.

Like Sir Philip Green, this was yet another case of someone with extremely deep pockets making a colossal wager only to scoop one of the largest known roulette wins in history.

Chris Boyd – A Computer Programmer Bets It All

  • Total: $440,000
  • Where: Binion’s Horseshoe Club, Las Vegas
  • When: 1994

It’s often said that men experience a midlife crisis when they hit 40. I’m not sure if that’s what pushed Chris Boyd, an everyday computer programmer, to bet his life savings of $220,000 on red. Whatever made him do it, he did, and now his wager is the stuff of legends.

Binion’s actually had a $100k table limit in place, but Boyd called ahead and convinced them to make an exception. They also only had American roulette tables, meaning double zeros, but they agreed to cover one up for him.

Boyd walked in, placed his bet, and walked out with double his money. Like Ashley Revell, who I mention next, this man clearly had nerves of steel. Unlike Revell, nobody knows what he did after his big win.

Ashley Revell Goes All In on a Single Spin

  • Total: $270,000
  • Where: Plaza Hotel and Casino, Las Vegas
  • When: 2004

Asley Revell is an English entrepreneur with a few successful ventures behind him. Naturally, to fit into this kind of role, you have to be comfortable with risk.

Futher Info:In 2004, Revell took the biggest risk of his life. He sold all of his possessions, flew to Las Vegas, and wagered his entire life savings on red. How much did he bet? Just over $135,000, which was all the money he had at the time.

Of course, since this post is about the biggest roulette wins ever, you can probably guess the outcome. Lady Luck smiled on Mr. Revell that night, and he doubled up on his even money bet.

Not satisfied with winning by dumb luck, Revell used the funds to start an online poker site called Poker UTD. Clearly, he’s got the risk-taking spirit, and in this case, it paid off.

Where to Play Roulette Online

Thankfully, you don’t have to travel to Vegas, London, or Monte Carlo in the quest for your own big roulette win. Instead, you can play at the best roulette sites online.

These sites offer you welcome bonuses when you sign up, and process wins quickly and efficiently. Be sure to check them out.

Petko Stoyanov
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About Petko Stoyanov
My name is Petko Stoyanov, and I've been a gambling writer for more than ten years. I guess that was the natural path for me since I've loved soccer and card games for as long as I can remember! I have a long and fairly successful history with English Premier League betting and online poker, but I follow many other sports. I watch all big European soccer leagues, basketball, football, and tennis regularly, and I keep an eye on snooker, volleyball, and major UFC events.