The game of roulette has long been associated with dramatic winning streaks and high-stakes bets. Over the years, a handful of players have recorded larger-than-usual wins. While these stories are widely shared, they don’t reflect typical outcomes. This page looks at some of the most well-known roulette wins and explains what makes them so uncommon.
Why Big Roulette Wins Are So Rare
Although both online roulette and in-person games can produce short-term winning streaks, each spin is independent. This means previous results do not influence future outcomes, even if patterns appear to form. Furthermore, there is no way to improve your skill-level through practice. Though, knowing how to play roulette is certainly still improtant if you plan to hit the tables.
Over time, the built-in house edge ensures that outcomes favour the casino, which is why large wins are typically short-lived rather than sustained. Nonetheless, here are some of the most popular stories of players who beat the odds.
Charles Wells
- Winnings: 2,000,000 Francs
- When: 1891
- Winning Bet: Multiple
Back in 1891, Charles Wells was partaking in a little bit of action at the world-famous Monte Carlo Casino Resort, when he suddenly won. Although the odds of winning in roulette are generally in the house’s favour, 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”.
What made this unusual was the sequence of consecutive wins, rather than any single bet. Streaks like this can occur, but they are unpredictable and tend to even out over time. Stories like Wells’ highlight short-term variance rather than a reliable way to approach casino games.
Ashley Revell
- Winnings: $135,000
- When: 2004
- Winning Bet: Red
Bet it all on black or red is typically shoddy gambling advice. Yet, 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.
Moments like this are memorable because of the risk involved, but they don’t reflect how roulette typically plays out over time.
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.
Bartelle reportedly placed high-value bets over a short period, generating substantial winnings. The scale of the bets increased both the potential reward and the level of risk. Outcomes like this depend heavily on short-term results, which can shift quickly in either direction.
Mike Ashley
- Winnings: 820,000 Pounds
- When: 2008
- Winning Bet: Complete Bet
In 2008, Ashley 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, we checked) 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 asked them to take notes about where the ball was landing with each spin. After they followed it for a couple of weeks, a clear-cut pattern emerged: 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, but it would likely also be more difficult to track down a faulty roulette wheel. This case stands out because it involved physical imperfections in the wheel, rather than standard gameplay. Modern casinos regularly inspect and maintain equipment these days, making this type of situation extremely unlikely.
Cast From MTV’s The Buried Life
- Winnings: $125,000
- When: 2010
- Winning Bet: Red
The cast of The Buried Life attempted a high-risk roulette challenge by placing $125,000 on a single spin, with the aim of building it up to $1 million over multiple bets. Their first wager on red was successful, doubling their money to $250,000. Rather than stopping, they chose to continue and placed the full amount on another spin. This time, the outcome went against them and the entire bankroll was lost.
This example highlights how quickly results can change. While early wins can create momentum, each spin remains independent, and outcomes can reverse just as quickly.
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.
Sean Connery is often associated with casino scenes on screen, but one of his notable real-life wins came from repeatedly betting on the number 17. One day in 1963, this movie star visited a casino in Saint-Vincent, Italy. His first bet didn’t hit, neither did the second, but the third time he bet on No. 17 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.
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. A small team of computer analytics experts. Reportedly, 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. 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. Similar to the story of Joseph Jagger, finding and exploiting this kind of physical flaw is highly unlikely, and not exactly a sustainable betting strategy.
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 is known for high-stakes casino play, including a reported winning streak at a London casino where he accumulated significant winnings across multiple bets. Rather than a single defining spin, this result came from a sequence of favourable outcomes over a short period. These types of high-value bets increase both potential returns and exposure to risk.
Remember that runs like this can occur, but they are typically short-term and can reverse quickly, especially at higher stakes.
Billy Walters
- Winnings: $3-$4 million
- When: 1980’s
- Winning Bet: Various Bets
Billy Walters, best known for sports betting, also applied a structured approach to roulette by identifying wheels with potential biases. Working with a team, he focused on locations where certain numbers appeared more frequently due to imperfections.
Like the other, similar cases, his approach relied on finding specific conditions rather than predicting random outcomes. Casinos have since improved monitoring and maintenance to reduce the likelihood of such advantages.
What These Wins Tell Us About Roulette
While these stories are often remembered for their scale, they are shaped by rare outcomes rather than typical play. Playing roulette can produce favourable results in short bursts, but ulimately, the results remain unpredictable and independent from one spin to the next.
Understanding that difference is key. These wins reflect what’s possible, not what’s likely.
