Find Out the Most Significant Live Roulette Wins Ever Documented

Roulette is an exciting game where punters predict where the white ball will hit after the wheel stops spinning. Unfortunately, roulette is a game of chance. This means players can do little to ensure they win a wager.

But some lucky gamblers have defied the long roulette odds to register impressive wins that changed the game's history. So, who are some of these roulette players that should inspire you to go for the win?

Drake Wins $27 Million Playing Online Live Roulette

Drake is a famous modern-day rapper currently living in the United States. Although Drake is popular for releasing several hit songs, he also has a reputation for playing roulette and other live casino games. And make no mistake, the Canadian rapper is a serial winner.

In 2022, Drake shared his Twitch live stream playing roulette at a local online live casino. The Toronto native went on to win more than $12 million, betting on the same number. There was a point where his account balance had reached more than $27 million despite starting with $8.5 million.

Charles Wells Beats the House at a Monte Carlo Casino

When speaking of the most legendary roulette wins, the story of Charles Wells in Monaco comes to mind. In 1891, Charles Wells shocked the world after winning 2 million Francs playing European Roulette at Monte Carlo Casino Resort.

This win is even sweeter because Wells was just a mere street hustler before striking luck. The legend has it that Watts won 23 out of 30 spins, with the casino preventing him from continuing to play.

Mike Ashley Wins £820,000 at Mayfair Casino

Mike Ashley is a billionaire entrepreneur from the United Kingdom. He is more famous for his footballing activities and is the former owner of Newcastle United, a top-flight football club in the country.

But Mike Ashley is also famous for playing roulette, winning £820,000 at a private venue in Mayfair. He staked £480,000 on a "complete bet" covering number 17, winning a total payout of £1.3 million. That's not too much money for a billionaire, but it's a win worth writing about.

Besides the three victories above, below are other wins that shaped the general outlook of roulette:

• Pedro Grendene Bartelle - $3.5 million in 2017
• Sir Phillip Green - £2 million in 2004
• Sean Connery - $27,000 in 1963