Biggest Roulette Winners in History

Although gambling should be all about having fun and experiencing something new, winning is definitely not a burden — especially for these players. Roulette has long been one of the most popular casino games worldwide. With the introduction of live online roulette, more people have discovered the advantages of this game. 

Unfortunately, we do not have much information about online live roulette winners as most prefer to keep their anonymity. Yet, some people have made history with their roulette wins. Whether it’s Lady Luck or something else, the following six people have fascinating winning stories.

Let’s find out more about them.

Chris Boyd’s Lucky Number 7

Lucky Number 7 Although this story dates back to 1994, it’s definitely worth mentioning. Chris Boyd, a programmer, decided to fly to Las Vegas and spend his life savings of $220,000 on roulette. His mission was to find a casino that he felt was lucky, but he kept coming across the maximum betting cap of $100,000.

After being denied by many casinos, Boyd finally came to an agreement with Binion’s Horseshoe Club. The casino allowed Boyd to bet his entire life savings on a game of European roulette. As you might imagine, the casino did not end up taking Boyd’s money, even though that was probably their idea.

Floyd bet all of his chips on red and won $440,000 when the ball landed on 7-red.

Billionaire’s Luck — Sir Phillip Green

Billionaire's LuckWe thought billionaires were already lucky enough, but Sir Phillip Green proved us wrong. The British billionaire made his fortune from retail stores but was also a frantic gambler. Although he preferred playing blackjack, most of his big wins came from roulette.

In 2004, Sir Green visited his favorite London casino, Les Ambassadeurs. The casino is known for its luxurious setting and high wins, so it didn’t come as a surprise that Sir Green walked away with $2 million.

Moreover, due to his many lucky wins, the casino owner had to issue a revenue warning to the shareholders. Unfortunately, this billionaire is proof that money doesn’t always go where it’s needed.

Sir Green is known for his controversial business practices, marking him as one of the most despised men in Britain.

Pedro Grendene Bartelle’s Luxurious Betting 

Luxury BettingYou might not have thought that the wealthy have this much luck betting in casinos, but it’s true. A more recent lucky win occurred in Argentina, where a Brazilian entrepreneur tried his fate on a game of roulette. In 2017, Pedro Grendene Bartelle visited a casino in Rio de Janeiro and undoubtedly earned the title of King of Roulette in Latin America.

Due to his line of work, Bartelle had the luxury of placing high bets, which proved lucrative for him. As not many other bettors share the same luxury, many were envious of his win.

The owner of a giant enterprise placed a $35,000 bet on a single number — 32. That bold move enabled him to put a breathtaking $35 million in his pocket and call it a day.

Unfortunately, this story is not relatable to many of us, but it shows how being bold can sometimes pay off. Naturally, we don’t recommend placing your yearly salary on a single number, but it won’t hurt to take your chances with a smaller sum.

Sean Connery’s Off-Screen Success

Off-Screen Roulette SuccessThis name and story might surprise many readers, but Sean Connery was not only the most beloved 007 but an avid gambler. Before he became an actor, Sean Connery used to visit casinos regularly. Although he came from a working-class family, Connery loved to put some money aside and try his luck on different table games.

While in Saint-Vincent, Italy, in 1963, Connery wagered on number 17 multiple times. Although he didn’t get up with a massive one-hit win, he walked off with more than $27,000 in profits, which was so much more in the ‘60s than today.

What makes this story remarkable is that Connery did not want to give up on the number 17. After multiple failed attempts at winning on that number, Connery finally won. After winning for the first time, he placed bets on the same number until he won the second and third time. What’s intriguing, the odds of hitting the same number three times in a row are 1:50,653.

Ashley Revell’s Last Chance

Last Chance RouletteAshley Revell’s story of winning at roulette is one of the most inspiring and fascinating stories on this list. Namely, Revell was down on his luck in life and decided to make a big change by betting all of his savings on roulette. He also sold all of his clothes, watch, car, and even his house before taking off to Vegas.

Once he arrived, he took all of his money — $135,000 and headed to a casino. Revell bet on red, and guess what — the ball fell in the red #7 pocket. And people say that you shouldn’t believe in lucky numbers!

With that one bet, Revell doubled his winnings and took $270,000 home. It might not seem much to some people, but it was everything for this guy.

Revell invested his winnings in a poker site, Poker UTD, and made a few other successful decisions later on. His story was so compelling and unbelievable that even production houses took note and created a TV mini-series out of it. Revell’s story is a great example of pure luck.

Soccer and Roulette Mix — Mike Ashley

Soccer and Roulette WinningIf you’ve heard of Mike Ashley, you’re probably a soccer fan. More specifically, an English soccer fan. Not only is Ashley a British entrepreneur and billionaire, but he’s also the former owner of Newcastle United. Take that as you may, but it’s evident that billionaires have plenty of luck in roulette.

In 2008, Ashley visited a private casino club in Mayfair. While trying to push his luck, he wagered around $640,000 on roulette.

His idea was to place inside bets on everything that included the number 17. This betting style is known as a complete bet as it contains all splits, streets, corners, and six-line bets with the number 17. On top of that, he also placed a straight bet on the same number. Fellow bettors claimed that he also made numerous other bets.

In the end, Ashley left the table with approximately $1,740,000 in profits. This might not be a lot of money for one of the world’s wealthiest people, but it’s worth a spot on our list, especially since the ball ended up in all the pockets that Ashely wanted.

About the Author

Author Rachel is a law student, and she is helping us out with the legal side of things regarding casino gambling in the US. The legality of gambling in the United States is continually changing, and it has especially been turbulent in the last couple of years, so knowing which states legalized gambling and which are yet to do so is getting a bit difficult. But if you need to know everything about the legality of gambling in your state, Rachel is the person to ask. She keeps track of the latest gambling bills and is ready to bring you news. During her free time, Rachel likes riding her bike and playing video games.