Biggest Roulette Wins Of All Time

The roulette table is one of the most iconic spots on the casino floor. You spin to win and when the ball lands in your pocket, you could end up collecting 35 times your money. There have been a number of big roulette wins with this game and bettors that either found an edge or found their luck.

Here’s a look at 10 of the biggest roulette winners of all-time:

Charles Wells

Winnings: 2,000,000 Francs
When: 1891
Winning Bet: Multiple

Back in 1891, Charles Wells, a small-time crook won big…really big.

Wells was partaking in a little bit of action at the world-famous Monte Carlo Casino Resort when he connected on this life-changing win. Although the odds of winning in roulette are generally in the house’s favor, he somehow managed to win on 23 out of 30 consecutive spins. He literally broke the bank as the table was out of money, which would inspire the song ‘The Man Who Broke The Bank At Monte Carlo”.

But, this man didn’t stop while he was ahead; he went even further. He came back another time and again collected about a million Francs. Although he was a bit of a scammer in his day-to-day life, he actually won the money legitimately with just pure luck.

Accounting for inflation and conversions, Wells won in the 10’s of millions of dollars by today’s amounts.

Ashley Revell

Winnings: $135,000
When: 2004
Winning Bet: Red

Bet it all on black or red is typically shoddy gambling advice. It’s not that the odds are against you – it’s actually one of your best chances of winning in a casino – it’s just that it’s typically recommended as a last-resort, let-it-ride type of bet.

That’s exactly what Ashley Revell was thinking of doing when he visited Las Vegas. He took his entire life savings and hit the roulette table, looking to double-up. It was actually more than his life savings as he cashed out his assets too, selling his house, car, watch and clothes. Then he let it ride on red and lucky for him, the No. 7 pocket was red. He eventually used his winnings to start an online poker site called Poker UTD and is apparently doing quite well after his big win.

Pedro Grendene Bartelle

Winnings: $3.5 million
When: 2017
Winning Bet: No. 32

While many of the biggest roulette wins in this article are before the time of smartphones, Pedro Grendene Bartelle’s win was not only recent, it was captured on the camera of a new phone.

The Brazilian businessman went to the Hotel Conrad in Punta del Este in Uruguay to have a little fun. He and his friends crowded around the roulette table as he stacked his chips high on the No. 32. In total, he put $35,000 on the line. As the roulette wheel landed on pocket No. 32, both Bartelle and his posse erupted, dancing and cheering as he won big.

While it’s a big win, it’s mostly peanuts for a man like this. Bartelle’s uncle, Alexandre Grendene Bartelle, is a Brazilian businessman and billionaire and his nephew was the president of the third-largest footwear company in Latin America. In 2014, Bartelle himself reached billionaire status.

Nonetheless, his riches aside, he’s registered one of the biggest recent wins on the roulette table that we’ve seen.

Mike Ashley

Winnings: 820,000 Pounds
When: 2008
Winning Bet: Complete Bet

There are many great rags-to-riches stories in the casino but Mike Ashley isn’t one of them. He did win big with the roulette wheel but let’s just say he was already up in life. Ashley is a billionaire who owns many businesses, including the Newcastle United football team.

In 2008, he felt like getting a taste of the adrenaline, so he visited a private casino in Mayfair. He laid a whopping 480,000-pound wager on a ‘complete bet’. That means he gets any of the splits, streets, corners, and six-line bets. The ball landed on No. 17 and he ended up winning.

Of course, the payout isn’t your typical 35/1 because he didn’t pick just one number. His payout was lessened because he increased his chances of winning. And, winning is exactly what he did as he ended up adding to his epic fortune.

Joseph Jagger

Winnings: $375,000
When: 1873
Winning Bet: 7, 8, 9, 18, 19, 22, 28 and 29

Joseph Jagger, no relation to Mick Jagger, was essentially a mechanical engineer who had a really good understanding of machines and how they work. However, he used a different set of skills to get ahead for his big win on the roulette table.

Jagger bribed six clerks that worked the roulette wheel at the Monte Carlo casino and he asked them to take notes and track where the ball was landing on the roulette wheel. After they followed it for a couple of weeks, they reported back to him and there was a clear-cut pattern: the pockets 7, 8, 9, 18, 19, 22, 28 and 29 kept hitting more than any others. Clearly, something was off with what is normally supposed to be a random roulette wheel.

Using the insights he gathered, he hit the casino and ended up winning about $375,000 over the next few days. Nowadays, his winnings would be in the millions, so he took his money and retired. He’d never visit another casino again.

Cast From MTV’s The Buried Life

Winnings: $125,000
When: 2010
Winning Bet: Red

The cast from MTV’s The Buried Life took a ride on the ups and downs of a casino. While many of the players on this list took home their winnings, these guys just didn’t know when to stop.

They put $125,000 on the table with the goal of rolling it over three times and ending up with a million dollars. They looked at each other and decided to bet on red the first and as the wheel spun around, they broke out in sheer euphoria when it landed on what they needed and they doubled up.

While one of them suggested the option of leaving right away and taking home $250,000, they decided to keep going. The $250,000 bet on roulette ended up being the biggest one in Las Vegas casino history.

With their adrenaline still pumping from their big win, the boys settled down and decided to bet on black this time. Unfortunately, they lost. As they say, you win some, you lost some, but this loss will definitely sting for a while.

Sean Connery

Winnings: $27,000
When: 1963
Winning Bet: 17

If you’re thinking this was one of James Bond’s big wins at the casino, it wasn’t.

Sir Sean Connery has always loved to play in casinos but one of his best days came back in 1963. On that day, he went to the casino in Saint-Vincent, Italy and he kept betting on the No. 17. His first bet didn’t hit, then he bet a second time on No. 17, but the third time was the charm. He won on his third spin but instead of taking his winnings, he bet those winnings again on No. 17 and it shockingly hit. He put his winnings on No. 17 a third time and to the surprise of everyone, he won again.

The odds of hitting a single number three times in a row on the roulette wheel is 1 to 50653. Somehow, he pulled it off, though.

Group Of Eastern Europeans

Winnings: Over a million pounds
When: 2004
Winning Bet: Various Numbers

Although the details are scant, one of the biggest roulette winners since the turn of the millennium is actually not an individual; it was a group. It was a small team of computer analytics experts. They used software to record the wheel spin and determine the probability of the different numbers hitting. They actually analyzed the physics of the wheel and apparently found some small imperfections that led to a certain pattern. As a result, they managed to take the Ritz Carlton Casino in the United Kingdom for more than a million pounds before they caught on.

Philip Green

Winnings: 2 million Euros
When: 2004
Winning Bet: Red, Black, Straight Up Bets

Sir Philip Green is a British billionaire and is the chairman of the Arcadia Group. If you’re not familiar with the overarching company, you might be familiar with their fashion brands and retailers like Topshop, Topman, Wallis, Evans, Burton and Outfit.

Green has always been one to hit the tables at some of London’s best casinos and in 2004, he visited Les Ambassadeur’s Club in Mayfair. He didn’t have just one winning bet, though. He went on a hot streak to the point where he ended up setting off a red flag in the casino. That’s because he won over two million Euros, which had a number of people in management a bit nervous.

In terms of what his winning bets were, he prefers to play a mix of red and black, and mix in some straight up bets that payout 35 to 1.

Billy Walters

Winnings: $3-$4 million
When: 1980’s
Winning Bet: Various Bets

Billy Walters is one of the winningest sports bettors of all-time. Sportsbooks are very careful whenever he comes up to place a bet. Although, he’s used runners for years and who knows if he’s actually still betting these days.

Back in the 1980’s, Walters was also a wizard when it came to roulette. He would go on the hunt for biased roulette wheels and hired a team to help him. A group of gamblers would go from casino to casino, looking for defects. Then he’d take the casino for all they had.

One time, he convinced Caesars Palace to up his limits and he specifically wanted to play there as the casino’s roulette wheels seemed to favor five numbers. Playing $1000-$2000 a spin, he ended up cleaning them out for about $3-$4 million.

 

Maple Casino Staff

Maple Casino Staff

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