Roulette is one of those casino games that never seems to lose its allure. Despite its mysterious origins, it has captivated gamblers for years, and in modern times it continues to be the game of choice for many. It is also frequently represented in popular culture, most notably in hundreds of films throughout the last century.

There are several reasons why it remains much loved by professional and amateur gamblers alike. It is a straightforward game that offers players multiple ways to wager. There are nuances, of course, but the actual gameplay is not overly complicated and is fairly accessible. 

Another reason why this casino game is so popular is because it has a strong social component, bringing people together around a table. After they place their bets, players have to wait with bated breath to see who the lucky winner could be, and because it is a game of chance, no one has an edge or leverage over the others. 

Although substantial winning amounts don’t happen very often, there are quite a few examples throughout history of players walking away with rather hefty sums after a very lucky stint at roulette.

It is important to keep in mind that roulette wins are a multiple of how much a player bets, so those substantial winnings tend to be based on rather large initial wager amounts. Starting out in the game with an above-average budget can sometimes boost a player’s advantage.

That being said, small bets can turn into sizable wins that the player can plow back into the game. With some strategic wagering, patience and a lot of luck, there’s nothing to stop a small wager from turning into a substantial win. 

In this article, we take a look at those lucky roulette winners who walked away with some of the biggest prize amounts in history. We’ll also delve into the most notable events that took place during those games, as well as the roulette strategies that they reportedly used. 

Looking online, you will find that there are some players who are listed as big winners but who aren’t included in this list. This is because they exploited a bias at the table. This isn’t unusual; many players set out to look for roulette tables that can be exploited. 

Charles Wells – 2 million francs in 1891

This is an interesting case because, in today’s terms, this certainly isn’t the biggest roulette win of all time. However, looking at when the game took place, it is certainly one of the largest roulette wins – based on the exchange rate, the total works out to about $77m. 

How did Charles Wells pull it off? The first thing to note about Wells is that he wasn’t an expert roulette player – he was simply a person (some might say with a not-so-good reputation) who enjoyed gambling. 

One night, he decided to go to the Monte Carlo Casino for a game of roulette and got extraordinarily lucky. It’s reported that he won 23 out of 30 consecutive spins and the table ran out of money, which meant that he could not continue playing. 

Having ‘broken the bank’ (he was celebrated in the song ‘The Man Who Broke the Bank at Monte Carlo’), he walked away with a little under 1,000,000 francs. Not long afterwards, he decided to go back to the same casino, walking away a winner for the second time with more than 1,000,000 francs. 

Needless to say, the establishment did everything that it could to find out how he was winning and whether he was cheating. As mentioned previously, he was known to some as a bit of a crook, so it only seemed logical to investigate how he could possibly be so lucky twice in a row. 

After extensive investigations, the casino couldn’t find any evidence that Wells had cheated or used any underhanded tricks. It was all pure luck, and he walked away with enough to live on very comfortably for the rest of his life. 

Unfortunately, even after such a lucky streak, Wells committed some acts of fraud that landed him an eight-year prison term. He died in Paris without a cent in 1922, and no one can say for certain what he did with all the money that he had won.

Pedro Grendene Bartelle – $3.5 million in 2017

Pedro Grendene Bartelle is the nephew of one of the richest men in Brazil and is worth $1.1bn, according to Forbes. He is the co-founder of one of the biggest sandal manufacturing companies in the world (Grendene) and is an avid investor in footwear companies. 

In 2017, while he was visiting Hotel Conrad in Uruguay, he decided to play a game of roulette, betting on 32 numbers with a wager of $35,000 with a potential payout of 35:1. He won $3.5m, which was reported as the biggest roulette win of modern times. 

Some skeptics have said that he would have needed to have bet $100,000 to win $3.5m, but on closer examination, it emerged that there were four piles of chips around the 32^nd slot, and this is what possibly led to the huge payout. 

Not much is known beyond this. There are several clips of bystanders celebrating, but we don’t know much else about his win. 

Sir Philip Green – £2 million in 2004

If we take inflation into account, this win works out to about £7.9m today, which is a lot of money. 

Sir Philip Green, who was born in 1952, is a British businessman and chairman of Arcadia, an umbrella company that owned top clothing brands such as Topshop, Topman and Miss Selfridge. 

Although he is an avid blackjack gambler, he indulges in roulette from time to time, and back in 2004, he placed a wager that netted him more than £2m at Les Ambassadeurs Club in Mayfair. 

On a subsequent trip to the same casino, he won another £1m, making him one of the biggest roulette winners of all time. 

His win had such an impact on the casino that it shortly thereafter issued a statement about shrinking profits. The event brought home the fact that big wins can cripple a casino, and the house edge isn’t always an advantage for the establishment. 

When the COVID-19 pandemic caused a drop in sales in most high street businesses, his companies took a hit and eventually went into administration. Despite this turn of fortune, he is widely recognized in the roulette world as a very lucky man. 

Mike Ashley – £1.3 million in 2008

Again, this is a case of money following money because Mike Ashley is a British billionaire and former owner of Newcastle Football Club. One night in 2008, he placed a roulette bet of £48,000 and in one spin won £1.3m. Ashley had bet on 17, which he considered to be his lucky number, and the ball landed on a black 17. 

It is said that as he watched the ball settle on his lucky number, Ashley looked the croupier straight in the eye, said “That’ll do me, thank you”, collected his chips, and left the table. He had been at the table for just about 15 minutes, but luck was on his side, and he walked away with more than £1m. 

Since then, this sort of strategy – where a player bets a huge amount in one go and hopes to win – has been associated with his name. 

Ashley’s wager included every inside bet and his lucky number, splits, corners and six-line bets. According to some, he also put money on the first half, middle column, middle dozen black and odd. If it is true, then his chosen strategy allowed him to cover as much ground as possible. In light of this, there was very little chance that his bet wouldn’t be successful. 

Chris Boyd – $440,000 in 1994

Chris Boyd is a British programmer who had an avid interest in casino games, and in 1994, he decided to take money that he had been setting aside for three years ($220,000) with him on a trip to Las Vegas to see whether he could multiply it. 

When Boyd arrived in the city, he had to look for a casino that was willing to take such a big wager – naturally, many refused. 

Eventually, he was able to strike a deal with Binion’s Horseshoe Club and he was allowed to play in the establishment. The casino had a strict wager limit of $100,000, but it decided to make an exception for Boyd. Because the establishment had only American roulette tables, it also agreed to cover the 00 pocket, effectively converting the table that he would be using into one suited for European roulette. 

Boyd bet all the money that he had saved on red and won. According to the accounts of those who were present, the ball landed on a red seven. This resulted in a payout of 1:1, which meant that Boyd had doubled his wager. 

There have been other notable roulette winners, and they include Joseph Jagger who won $375,000 in 1873, Sean Connery (yes, the actor best known for playing James Bond) who won $27,000 in 1963, and Richard Jarecki who won £1,280,000 in 1971. 

Paul Newey caused the Star City Casino in Birmingham, England to issue a profit warning after he won £3m, and Billy Walters, through a syndicate, won $3.8m in 2007. 

While it is true that most big wins are enjoyed by players who have large amounts of money to bet, roulette is a game of luck, and even those with small bankrolls could potentially win substantial amounts at the spin of a wheel.