People Who Landed Big Roulette Wins

Once the wheel spins, all you can do is cross your fingers and say a sweet prayer to lady luck that your bets aren’t far off the mark. Anything can happen and hope can only bridge some of the distance between your ambitions and the odds in store for you - but in some cases, what transpires turns out to be truly awe-inspiring. Getting into the exclusive club of the biggest roulette wins can be exhilarating. Of course, we’re talking about some of the biggest wins in the history of the game. If you’ve ever entered a casino and dreamt of leaving with bags and bags of money, perhaps it’s good for you to know that this dream has become a reality for some of the biggest roulette winners of all time - historical and present.
A group of gamblers playing at a roulette table.
Published on: 23 July 2022

With the stories of these masters of fate, comes the need to ask – how did they pull off these victories? Did they simply evade fate, or defy it with advanced strategies? After all, a good strategy is said to reduce the house’s edge to just 1-2%. Whatever these incredibly lucky individuals did to secure their win, or the lack of any such effort thereof, their stories make for fascinating reading at the very least – for the sheer love of the game. Let’s dive into some of them.

Charles Wells (1891)

Won around 2 million francs

Charles Wells was a con artist who had a weakness for roulette – and with his winning streak, we can’t blame him one bit. Wells was on a streak that became the talk of the town, having reportedly won 23 out of 25 consecutive spins. This was during a night at the Monte Carlo Casino Resort, where he achieved the rare feat of bankrupting the table, which saw him take home close to a million francs that night – and it wouldn’t even be his biggest roulette win. In fact, this was the direct inspiration for a popular song from yesteryear – “The Man Who Broke the Bank at Monte Carlo.”

One would imagine that Mr. Wells would be satisfied with a million francs and walk away with his win. But this story wouldn’t be legendary if that were the case, which it wasn’t. Wells returned to Monte Carlo and tried his luck yet again, and yet again ended up taking home over a million francs. With his reputation preceding him, Wells was the subject of scrutiny at the casino, but was found to be playing fair and square, winning on nothing but luck. The amount he won would amount to tens of millions of dollars today. Sadly, even two million francs wasn’t enough for Wells, who returned to a life of crime, spent time in incarceration, and died in squalor in 1922.

Pedro Grendene Bartelle (2017)

Won $3.5 million

A group of gamblers at a roulette table.

The largest roulette win to date was for $3.5 million.

With the entertaining story of Charles Wells out of the way, we now move on to some of the biggest winners in the modern game – and that undoubtedly needs to start with Pedro Grendene Bartelle, who is widely considered to have the biggest roulette win in history. Bartelle is the owner of the third largest footwear company in Latin America, and the family seems to have a particular proclivity for the footwear business – with his uncle owning another footwear company as well.

Needless to say, Bartelle had no need for the money and could thus afford to place a single bet of $35,000 on his lucky number – 32 – which eventually made him one of the biggest roulette winners of all-time with a hefty payday of $3.5 million. Bartelle, with his footwear empire, is reportedly worth over a billion dollars now.

Sir Philip Green (2004)

Won £2 million

Imagine being a roulette winner on such a streak that you hurt the casino’s balance sheet. Then imagine being a multi-millionaire who’s just 90 million shy of the billionaire club, for whom $2 million is but a drop in the ocean. If you were to imagine that, you’d be imagining yourself as Sir Philip Green, who is always in the conversation when it comes to figuring out the largest roulette win.

Sir Green owns numerous high-fashion retail companies, and could safely bankroll himself without worrying about other financial commitments. While his passion lies with blackjack, roulette has proven to be his cash cow. In 2004, he cashed out over £2 million in a single night, and is said to have won another £1 million in other visits to the very same casino – Les Ambassadeurs.

These events reportedly forced the hand of Les Ambassadeurs, who issued statements regarding a decrease in profits. As one of the biggest roulette winners in the game’s storied history, Sir Green is also the perfect example of how a multi-millionaire’s bankroll can give a player an edge on the house – or reduce the house’s edge at the very least. Sometimes, being a multi-millionaire is simply the best roulette strategy.

Mike Ashley (2008)

Won £820,000

Mike Ashley, like most big roulette winners are, is also a billionaire entrepreneur with several ventures. Until recently, he was also the owner of football club Newcastle United and received a hefty payout after selling it to Saudi Arabia’s Public Investment Fund. He’s also got one of the big roulette wins in recent years to his credit.

However, what stands out about Mike Ashley’s story is that money wasn’t his only superpower. Ashley went to a casino in Mayfair and placed what is known as a ‘complete bet’ on the number 17 – effectively spending £480,000 to cover every split, corner, street, and six-line bets involving the number 17. In addition to a straight-up bet on 17 itself, Ashley is also reported to have placed money on other bets such as the first half, middle dozen, middle column, black, and odd.

The end result of Ashley’s strategy was that he walked out of the casino with a hefty profit of £820,000. While money certainly played a role in his success, it’s also evident that he played an intelligent strategy while spending his money – making his story more than just a tale of money and simple luck.

A group of gamblers beating at a roulette table.

Most of the big roulette wins have been in traditional land-based casinos.

Frequently Asked Questions

We hope that these stories of roulette winners were interesting to read, and that you enjoyed them as much as we did. Here are answers to some questions about roulette and its associated strategies that you may still have.

What is the biggest win in roulette?

The biggest win is $3.5 million won by Pedro Grendene Bartelle in 2017. Bartelle placed a single bet of $35,000 on his lucky number, 32, which eventually made him one of the biggest roulette winners of all-time with a hefty payday of $3.5 million.Follow the link to read about the best casinos for online roulette.

How to win big at roulette?

Winners tend to have varying strategies - ranging from betting strategies to pure luck. One of the more popular mainstream strategies is to place a ‘complete bet’ on a number to cover for all probable outcomes. For a full understanding of roulette and its rules, click here.

Best strategies for big roulette wins?

A complete bet with a mix of diversified bets has worked with the likes of Mike Ashley, but nothing quite works like having big amounts to bet with, since it significantly blunts the house’s edge. For a list of popular roulette strategies, click here.

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