The Biggest Roulette Wins of All Time – 2024 Guide

In this article, we will tell you about the huge roulette wins of people who were either lucky or cunning enough to defy the odds. Check out their stories, learn about the way they managed to beat the house and see which are the top roulette games that offer the biggest prizes. Find the biggest roulette wins documented in the gambling history.

About the author

Name	Luke Holmes
Job	Chief Editor
Email	luke.holmes@roulettesites.org

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Luke Holmes, founder of RouletteSites.org, combines his passion for probabilities with online marketing expertise. He created the site in 2011 focusing on roulette strategies and reviews. His mission: to provide a platform that guides you through the online gambling world, starting from the UK to global markets, ensuring a safe experience.

In gambling, math and probabilities are our compasses, transforming luck into calculated risks.

The Biggest Roulette Winners Up to 2024

If there is one certain thing about casino gambling, it is the fact that the house always wins in the end. This is especially true about roulette – a game of pure chance that is designed with casino advantage in mind. No matter how well you are doing, in the long run, the casino is most likely to take back what it gave you. Despite all that, we play roulette to win. And yes, some people do win at the game. Some people win quite a lot. Here’s a summary of some of the biggest roulette winners ever documented:

• 🥇 Charles Wells – 2 Million Francs (1881, Monte Carlo)
• 🥈 Ashley Revell – $270,000 (2004, Las Vegas)
• 🥉 Chris Boyd – $440,000 (1994, Las Vegas)
• 🏅 Pedro Grendene Bartelle – $3.5 Million (2017, Rio de Janeiro)
• 🏅 Sir Philip Green – $2 Million (2004, London)
• 🏅 Mike Ashley – £820,000 (2008, London)
• 🏅 Joseph Jagger – $375,000 (1873, Monte Carlo)
• 🏅 Sir Sean Connery – $27,000 (1963, Saint-Vincent)

Which Online Roulette Games Could Offer The Biggest Win?

As you probably already know, there are many variations of roulette that can be found both online and at land-based casinos. Picking the right game for you is very important, so you should always consider exploring different roulette variants. Some roulette titles might offer rewarding side bets, while others may have higher RTPs, reducing the house edge to a minimum offering the best roulette probability. Check out the table below, as we have listed some of the most popular and played roulette games, along with information about their RTP percentages, different betting ranges and biggest roulette wins.

As you can see, there are more than enough great roulette games that you can choose from. The most popular titles are obviously European Roulette and American Roulette, but there are many more variations that stand out with their lucrative side bets options and interesting themes and designs. Playing on a roulette table online brings many more advantages than playing at a brick-and-mortar casino, and that’s why many of the best US online casinos have extensive roulette libraries with both RNG and live dealer titles.

Which Is the Biggest Roulette Winner in the History?

Now that we have listed some of the most popular online roulette games, it is time to turn our attention to the main focus of this article, and precisely, the biggest roulette winners. Some of the names you will find in this review are successful businessmen and famous celebrities. Others are normal people who like to play gambling games and have enough guts to play with large amounts of money. You will even read about players who have literally gone all in on the roulette table.

In any case, playing roulette with such high bets is not for anyone. Not only you must have a massive bankroll and be brave enough to play with high stakes, but you must also know what you are doing. The game of roulette offers hundreds of betting opportunities, and there are many different payouts and odds. Knowing how to play and learning the rules of the basic game are literally your first priorities if you want to start playing roulette games online.

Of course, it is hard to become one of the biggest roulette winners with only skills and game rules knowledge. Just like most other top gambling games, the luck factor has its role. After all, the bets made by some of the representatives in our list of roulette winners offer nearly 1 to 1 odds, meaning that the chances for a win were pretty much 50-50. If you’re a mobile player who wants to try and join the hall of fame, you can learn more about the best iPhone roulette casino here.

And before we go into details about the biggest roulette winners and their stories, we want to say a few words about responsible gambling. Even though paying the devil’s game can be quite exciting and entertaining, you should always gamble responsibly and play with only what you can afford to lose. The following roulette stories might sound appealing and easily achievable, but trust us, that’s not totally true. You should always play responsibly and have fun, and if you feel like the funs stops, you should stop too.

Charles Wells

Charles Wells was a small-time crook and an overall shady person who enjoyed gambling. One night in 1891, he went to the world-famous Monte Carlo Casino Resort and started playing roulette. He had the winning streak of a lifetime – sources claim that he won 23 out of 30 consecutive spins. Charles Wells managed to break the bank, meaning that the table was all out of money and no longer available for playing at. Mr Wells won close to a million francs that night, inspiring the once-popular song ‘The Man Who Broke the Bank at Monte Carlo’.

But a million francs wasn’t enough for Wells. He returned to Monte Carlo some time later and tried his luck again. Once again, he managed to win over a million francs – and according to all sources, he did it on pure luck, without cheating in any way. After all, Wells was a known scammer, so the casino would take extra interest in the manner in which he won this fortune. They didn’t find anything dishonest about the way he played.

It’s hard to calculate how much cash he actually won converted in modern money, but it’s in the tens of millions of dollars range. Apparently, this amazing sum of money was not enough for old Charles Wells, since he continued with his scams. He was eventually thrown in jail for 8 years. Wells passed away in 1922 in Paris, broke as a joke. No one knows what really happened with his millions of francs, but we bet he lost it all while running his schemes.

Ashley Revell

Our article about the biggest roulette wins continues with one truly fascinating story. In 2004, Mr Ashley Revell decided to make a change in his life. He took his entire life savings and went to Las Vegas, with the intention to wager them all on roulette. He did not only take the money he managed to collect during his life, he also sold his house, his car, his watch, and all of his clothes. He literally got every single penny that he had and decided to try his luck. The story was so compelling, that there was even a TV mini-series documenting the event.

On the faithful day, Ashley wagered all that he had – $135,000. He bet on red and watched breathlessly as the ball fell in the red 7 pocket. In one spin, Ashley had doubled his net worth and walked out with $270K. The amount is not that big but imagine the guts this guy had. That alone earns him a spot in this list.

Ashley Revell used his winnings to start an online poker site called Poker UTD. Recently, he created another site called I Gaming Recruitment, with the purpose of helping people find jobs at online casinos. Apparently Mr Revell is doing well after his legendary win. Those of you who like playing poker online can find some great operators in our list of the best PayPal casinos in the USA.

Chris Boyd

A similar turn of events occurred for programmer Chris Boyd when he decided to wager $220,000 collected over the span of three years. Just like Ashley Revell, he flew to Las Vegas and started looking for a casino that is willing to take such an enormous bet. Naturally, most casinos he approached refused – but he finally managed to make a deal with Binion’s Horseshoe Club.

Even though Binion had a strict betting limit of $100,000, they decided to make this one exception and let Chris Boyd try his luck. In addition, since they had only American roulette wheels, they agreed to cover the 00 pocket, effectively turning it into a European Roulette wheel.

Boyd wagered the spectacular amount of $220.000 on red and won. The ball allegedly landed on 7 red – the exact pocket that brought Ashley Revell his fortune. According to the roulette rules for online and land-based games, the payout for such a bet is 1:1. In other words, Boyd doubled his money and left Las Vegas a much wealthier man. We couldn’t find any information on his following activities, but we bet he is doing pretty good.

Pedro Grendene Bartelle

After mentioning some average guys who bet all they had and won on European Roulette and other variations, we are moving forward with some different examples of the biggest roulette wins. The next three entries on the list are people who had more than enough wealth at the time they made their huge roulette wins. The first to mention in this group is Pedro Grendene Bartelle, who won the stunning $3.5 million in 2017.

Bartelle is the owner of the third-largest footwear company in Latin America. This seems to be a family trait, as his uncle owns an even larger corporation in the same industry. That said, the lucky winner didn’t really need the money, and his wealth explains why he could afford a $35,000 on a straight bet. The lucky number that put the businessman on our list of biggest roulette winners is 32.

Sir Philip Green

A tycoon owning several fashion retail companies, Sir Phillip Green is another man that could afford to wager obscene amounts of money without thinking of the mortgage. He’s known to be an avid blackjack player, but his bold roulette bets and wins helped him make the news. The billionaire cashed out over £2 million in a single night at the Les Ambassadeurs in 2004. Furthermore, this was reportedly the first of a series of large roulette wins that he made in the same year. He’s said to have made another £1 million in subsequent visits to the same casino on the roulette table.

According to the Telegraph, these events forced officials at London Clubs International, the company which owns the Les Ambassadeurs, to issue statements about decreasing profits. Evidently, people who are richer than the casino can be a great threat despite the house advantage. To the rest of us, however, the rule that the casino always wins, is still valid.

Mike Ashley

Mike Ashley is not just your average guy. He is a billionaire entrepreneur who owns many business ventures, among which is the football club Newcastle United. In 2008, he decided that his billions are not enough for him, so he attempted to make some more money by playing on roulette.

He went to a private casino in Mayfair, and wagered a total of £480,000 on absolutely every inside bet that included the number 17. This betting style is known as a ‘complete bet’, and includes all splits, corners, streets, and six-line bets that include 17. Plus, a straight-up bet on 17 itself. Reports claim that he also put money on other bets – the first half, middle dozen, middle column, black and odd. It looked like he really knew what he was doing.

In the end, Mike Ashley managed to win a total of £1,300,000. The net profit from all that was £820,000. This may not be a lot of money for a guy like him, but the epic part is that the ball landed right where he wanted it to. And it’s a really big sum, come to think of it.

Joseph Jagger

Now, for something a bit different. Joseph Jagger was a gentleman who worked in the mechanical sector and had sufficient knowledge of machines and such. One day, he went to a casino in Monte Carlo and bribed six of the clerks into writing down all the results of all roulette wheels in the joint for a couple of weeks.

Upon inspecting the results, Joseph noticed that one of the wheels was a bit biased towards certain numbers. The pockets 7, 8, 9, 17, 18, 19, 22, 28 and 29 were consistently hit a lot more than the other – something that is not natural for a completely random roulette wheel.

Joseph took his newfound knowledge and went to the casino once more. Over the next several days, Mr Jagger took advantage of the biased wheel and won more than $375,000 – which in modern-day money would be millions. Unfortunately, the casino caught wind of what was going on and removed the defect wheel from the casino. Joseph didn’t care much about that – he took his winnings, quit his job, invested in a business of his own and never entered a casino again.

Sean Connery

Sir Sean Connery was a gambling enthusiast even before he became a famous actor. He had a rough time growing up in the working class areas of Edinburgh, having to work numerous manual labour jobs in order to support the family.

In 1963, he went to a casino in Saint-Vincent, Italy, where he wagered multiple times on the number 17. Eventually, he left the table with a profit of over $27,000. It’s not that much, but we will tell you about this case because of the astonishing odds that Sir Connery somehow managed to overcome.

His first bet was on 17 which didn’t hit. He then repeated the same bet, but the result was the same. Persistent as always, Connery wagered on 17 a third time – and this time, it worked. He decided to wager his winnings on another 17, and it hit again! Connery wagered his winnings one last time, again on 17 – and he was lucky again. The odds of 17 hitting three times in a row are 1 to 50653. Sean Connery would hit 17 again a few years later – but this time as James Bond, in the classic movie Diamonds Are Forever.

Conclusion: Who Can Win Big in Roulette?

Those were, in our opinion, the biggest roulette winners and the greatest roulette wins in history. Most of them weren’t made at some of the £5 minimum deposit casino sites, but as you can see, anyone can win at roulette – from people who wager their life savings, to successful billionaires. Keep in mind that none of them used a particular strategy (except for Joseph, who was exploiting a biased wheel), they were just plain lucky. However, bear in mind that the quickest way to such a massive roulette win is through playing high stakes roulette online.

If you want to be a part of the list of the biggest roulette winners, you need to start playing. Our website contains plenty of information on the best online casinos where you can start winning. You can check which are the top gambling sites and give them a try. A great alternative is also joining one of the fast withdrawal casino UK sites. Good luck!

The Biggest Roulette Wins FAQ

In the following paragraphs, you are going to find the most frequently asked questions about the biggest roulette wins in history. We’ve done our best to provide you with answers that you are going to find both interesting and informative.

Written by: Luke Holmes