The Biggest Roulette Winners of All Time

Sometimes, we gamblers need a little inspiration to remind us why we bother to bet at all. Especially after a losing streak, stories about roulette winners can remind us why we love the game and why picking ourselves up and trying again is just what we do. These are the stories of the biggest roulette winners of all time. These roulette stories remind us that with guts comes glory, often in the form of life-changing wins.

The Biggest Roulette Winners of All Time

Charles Wells – 1891

Charles Wells may have been a petty crook and conman, but he earned his place in the roulette history books back in Monte Carlo in 1891. Because of the events that transpired that night, he’s known as “The Man Who Broke the Bank at Monte Carlo.”

Wells went on the lucky streak of a lifetime, winning 23 out of 30 spins of the wheel. This win scooped him one million Francs and broke the casino. He cleaned them out so that they couldn’t continue to let him play.

As if that wasn’t enough, Wells later returned to the same casino and pulled off the same insane winning streak. Did he cheat? It’s hard to rule it out, but the casino could never prove it if he did. This is one of the luckiest roulette stories of all time.

Ahsley Revell – 2004

There are defining moments in every person’s life when things could go either way and make or break them. Most of us encounter these moments through no choice of our own, but Ashley Revell decided to walk up to the line, stare fate straight in the face, and dance.

Mr. Revell sold all of his worldly possessions including his house, his car, any cash he had saved, and just about everything else he owned. In total, he had $135,000 US dollars when he entered the Plaza Hotel and Casino in Las Vegas.

Tossing all bankroll management advice aside, Mr. Revell waged the full $135,000 on red. Moments later, he had doubled his net worth.

While this isn’t the biggest roulette win of all time, it’s certainly one of the ballsiest. We don’t know what drove him to do it, and we don’t necessarily recommend such drastic action, but in this case, a tip of the hat is due as a gesture of respect.

Mike Ashely – 2008

Mike Ashley is better-known as the boss of Sports Direct, a successful sports equipment franchise in the United Kingdom. He’s a billionaire, so it’s only fitting that he’d be a high roller roulette player.

In 2008, Mr. Ashely entered a Mayfair casino and wagered £480,000 on a “complete bet” on the number 17. For those who don’t know, this means he covered every bet that could lead to 17, plus a few extras.

Mr. Ashley walked away with £1.3 million. That’s only a fraction of his net worth, but we’re sure it still gave him a thrill nonetheless!

Chris Boyd – 1994

This story is probably where Ahsley Revell got his inspiration from, and the similarities in the two stories are uncanny. Since this one happened a decade before the other, we think it’s safe to say that this was the original.

Chris Boyd was a 40-year-old computer programmer who had collected $220,000 over a few years of coding. He walked into the Binion’s Horseshoe Club and wagered the lot on red. Rumour has it that several other casinos had refused him, but that Binion’s had decided to entertain him and had covered up the extra zero pocket as part of the deal.

They probably wish they hadn’t, because Boyd’s bet came good and he walked away twice as rich. What a guy!

Pedro Grendene Bartelle – 2017

It’s no secret that the bigger your bankroll is, the bigger the risks you can take, and the larger the payouts you’ll win tend to be. Such is the case in this story about the biggest roulette winner on this list.

Pedro Grendene Bartelle is a successful Brazilian businessman who placed a $35,000 wager on a single number: 32, at the Hotel Conrad in Uruguay.

Experienced roulette players will know what straight bets pay. He walked away with $3.5 million, and it was all on film!

Biggest Roulette Winners – Summary

We don’t recommend selling everything you own and wagering it all on the roulette wheel. Remember that for every success story like this, there are countless untold stories of players who lost it all on the wager of a lifetime.

We suggest studying the most successful roulette strategies and trying your luck with more conservative bets. If you even triple your money with some big roulette wins while having some fun, that’s about all you can hope for, isn’t it?