Top 10 Biggest Wins in Roulette Throughout History

Throughout history, a casino game like Roulette has always attracted gentlemen who appreciate the finer things in life. The “win big or nothing” straightforwardness nature of roulette has not only managed to make big news but has also carved a few lucky names in the chapters of the world’s entire roulette game history

Through the course of this article, I’ll be throwing light on some of these popular names, which are cemented in the history books for betting big and winning even bigger. 

So, let’s quickly get started with the list of top 10 biggest roulette wins.

1. Charles Deville Wells

  • Bet Won: 2 Million francs
  • Year of Winning: 1891

Charles Deville WellsImage Source

A devil indeed when it comes to winning big, Charles Wells, a petty thief who spent most of his time committing small-time robberies and loitering around the streets of France, one night walked into the world-renowned Monte Carlo Casino Resort to play roulette. 

Little did he know, on a particular night in 1891, he would be on a winning streak of his lifetime. Wells won 23 out of the 30 rounds of roulette he played and ended up breaking the bank. The term breaking the bank is when the casino runs out of money to pay the winners. 

This winning streak, later on, went on to inspire the song “The Man Who Broke the Bank at Monte Carlo.”

After winning a staggering 1 million francs, Wells comes back later the very night and doubles his money by placing a single bet. A scam artist by profession, the casino kept a close eye on Wells and ensured there was no foul play in his winnings. 

And according to witnesses and sources, Charles Deville Wells won 2 million francs by pure luck and this money converted to INR and fixed to inflation, today, is a jaw-dropping ₹80 crores. 

Sticking to his old ways of scamming people, Wells was later imprisoned for 8 years and eventually passed away in the year 1922 in Paris. It is believed that he lost the winning money running his cons and schemes. 

2. Mike Ashley

  • Bet Won: £820,000
  • Year of Winning: 2008

Mike AshleyImage Source

The story of Mike Ashley shows that not every roulette story is a rags to riches one.  A billionaire businessman by trait, owner of a world-famous English Premier League football team, Newcastle United, Mike’s vice was occasionally gambling to his heart’s content on a roulette wheel. 

With luck on his side, billions in the bank and a simple betting strategy, Mike goes to a private casino in Mayfair and wagers an amount of £480,000. Placing bets on everything that includes the number 17, Mike uses a strategy of betting called the “complete bet.” 

Including all splits, streets, corners, and six-line bets that include 17, along with a straight bet on 17 itself, Mike was sure that his strategy would pay out well. 

Managing to win a total of £1,300,000, out of which £820,000 was profit, Mike was also seen betting on the first half, middle dozen, middle column, black and odd as well. This may seem like an inconsequential win for a billionaire but hey, it is a handsome profit nonetheless. 

3. Joseph Jagger

  • Bet Won: $375,000
  • Year of Winning: 1873

Joseph Jagger

Image Source

You’ll never know if Joseph Jagger was related to the famous musician Mick Jagger or even moved like him. 

But we certainly know that he’s one of the most famous “Jaggers” from the 19th century because of a savvy technique he used to win against a faulty roulette wheel. 

As you may imagine, mechanical casino games back in 1873 needed much maintenance and there were intelligent people like Joseph Jagger who used simple statistical deductions to win a fortune. 

What Joseph did was nothing short of remarkable for this time period. 

Upon acquiring sufficient knowledge about all the machines and roulette wheels, Joseph noticed that one of the wheels of a roulette game was biased towards certain numbers. 

The pockets 7, 8, 9, 17, 18, 19, 22, 28, and 29 would consistently win a lot more than the others and Joseph quickly picked up on this biased or broken wheel and walked into the casino to play some roulette.  

Not to cause suspicion, Joseph took several days to place bets on the numbers the wheel was biased towards and managed to win more than $375,000. 

Eventually, catching on to this anomaly, the casino replaced the faulty wheel but Joseph had won enough money not to care and did not return to the casino. 

4. Chris Boyd

  • Bet Won: $220,000
  • Year of Winning: 1991

A computer engineer by occupation, Chris Boyd decided to wager a massive $220,000 on a single bet. Saved over a span of 3 years, this was no small amount for a computer engineer in 1991 but he was headstrong to go all or nothing on it. 

Boyd flew to Las Vegas and started approaching casinos that would accept his massive bet. 

After a few days of trying, Boyd made a deal with Binion’s Horseshoe Club, which accepted his deal, despite having a strict betting cap of $100,000 on a single roulette bet. 

The club also changed the American roulette wheel into a European wheel by adding the 00 slots to increase the odds. 

On a single go, Boyd placed a bet of $220,000 on a single color red and the ball landed on the 7 red. While playing with real money, he doubled it in a matter of minutes and returned home a happy, wealthy computer engineer. 

5. Ashley Revell

  • Bet Won: $135,000
  • Year of Winning: 2004

Ashley Revell

Image Source

One of the most famous gambling stories and biggest roulette wins of the modern era took place in the year 2004. Ashley Revell, a gambler from Kent, United Kingdom sells every single thing he owns to bet on a single roulette spin. 

He amassed all the money he had saved, sold his house, his car, watches, and all his clothes and literally took every single penny and flew to Las Vegas. 

Deciding to try his luck on a fateful day, Ashley walks into the Plaza Hotel & Casino in Las Vegas and wagers all his money of around $135,000 on a single bet on a “red.”

To his astounding luck, the ball lands on a red 7 pocket, pocketing Ashley double the money he had wagered, an amount of $270,000. 

The idea of selling every single thing and betting the amount on one single roulette wheel spin was so ludicrous that the event was broadcast live by the Sky One channel. 

As Ashley exited the casino he spoke to the media and avered “It all happened so fast, it was over before I knew it” and when asked if he wants to try his luck again, Revell wisely said, “No, that is it for me, I don’t want to ride my luck”. 

Ashley Revell now is a professional poker player and he spent his winning money on starting an online poker website called “Poker UTD.”

6. Sean Connery

  • Bet Won: $27,000
  • Year of Winning: 1963

Sean Connery

Image Source

If this name feels familiar, it’s because he is Mr. Bond, James Bond himself. Arguably, one of the most popular James Bond actors of all time, Sean Connery had a taste for occasionally gambling just like the fictional character he played. 

In 1963, Sean walked into a casino called Saint-Vincent in Italy and placed multiple bets on 17. You’d have seen this trend by another high roller before so it must definitely have winning odds in its favour, and Sean was obviously aware of this. 

With his first two bets on 17 not hitting, the odds were no more in Sean’s favour but sticking to his guns (no pun intended), he placed the next 3 bets on 17 as well. Miraculously, all the next 3 bets on 17 hit, back to back. 

I used the word “miraculous” because the odds of 17 hitting thrice is 1 to 50653. 

Would you call this luck coming to Sean’s rescue or his strategy paying him dividends, it is up to you but at the end of the day, Sean walked away with an impressive profit of around $27,000. 

Though it may seem small for James bond, it is a large sum when you convert the inflation amount to today’s value. Sean would bet on 17 again, but this time it is in his classic 1971 movie, “Diamonds are Forever”.

7. Pedro Grendene Bartelle

  • Bet Won: $3,500,000
  • Year of Winning: 2017

Pedro Grendene Bartelle

Image Source

Amidst an anxious, cheerful crowd in the casino, Pedro takes one last sip of his red wine, the roulette wheel stops spinning and boom, he has won $3.5 million and has made a 10 times profit on his initial bet. 

Don’t understand the scenario of this recent, 2017 mind-blowing jackpot of a win? Let me take you back in time to a few hours ago. 

It’s a relatively cold day in Uruguay and in a popular casino, Pedro Grendene Bartelle is playing roulette with his friend, relatives, and siblings and has a roulette strategy attached to his betting. 

Placing a “complete bet,” consistently on the number 32, Pedro bets $35,000 on his initial bet. 

As you would have seen in an earlier scenario, Pedro cleverly places a modified bet on the number 32 that covers the number from every possible combination of inside bets, so the single number bet, the split bets, the square bets, and so on, therefore increasing his odds of winning tremendously. 

It is observed time and again that strategy can play as important a role in a game like roulette as well and when it’s in the hands of ‘happy-go-lucky’ people like Pedro, the win seems nothing short of hitting a lottery. 

8. William Nelson Darnborough

  • Bet Won: $415,000
  • Year of Winning: Between 1904 and 1911

William Nelson Darnborough

Image Source

William Nelson Darnborough is someone who was naturally gifted. 

A player who called in his bet only after the dealer had spun the ball, William is known to have had the unique ability of a “Wheel Watcher” (today known as the Wheel Clockers) who could predict the outcome of the game by observing the spinning roulette wheel and the ball. 

The ability which most definitely worked to his favour made him quite rich between 1904 and 1911, which are known to be his golden years of gambling. 

In 1904, William won a handsome £80,000 while playing roulette and managed to make more than $415,000 in his prime years as a genius roulette player. 

One of William’s famous sessions is documented to be on a French Roulette wheel where he bet on the number 5 and won 5 times in a row and not even James Bond, 5 decades later could beat this spree. 

9. Philip Nigel Ross Green

  • Bet Won: £2,000,000
  • Year of Winning: 2004

Philip Nigel Ross Green

Image Source

In a casino named Les Ambassadeurs Club, in Mayfair, Philip green won a mammoth £2,000,000 playing a high roller stakes at a roulette table. 

Philip Green who is a retail billionaire, Chairman of the Arcadia group which owns Topshop, Topman, Evans, Burton, Wallis and many others had a stroke of luck and won big but what’s even more mind-boggling is the fact that he won another £1,000,000 on a subsequent bet. 

As a caution measure, the casino triggered a profit warning and Philip walked away with his winnings and was later documented saying, “I had a fantastic night at the tables.” 

The business tycoon loves to play Even Money Switcher System, Even-Money bets, and straight-up bets that payout at 35:1 like the other high rollers. 

10. Billy Walters

  • Bet Won: $4,000,0000
  • Year of Winning: 1980

Billy Walters

Image Source

You must have heard the phrase “history repeats itself.” Just like Joseph Jagger won consecutively by betting on faulty wheels, more than 100 years ago, Billy Walters takes the same route to win big in the year 1980. 

Hiring a team of gamblers to scour out defective roulette wheels in casinos, Billy had plans to hit the casinos and win big money. 

With the badge of being a successful businessman from Atlantic City who had a taste for spending big at casinos, Billy manages to persuade the management at Caesars Palace, Las Vegas to let him play the higher stakes. 

Little did the management at the casino know, the gamblers Billy had already found a faulty wheel that was biased towards the number 5 winning more than other numbers or colours. 

Betting within $2,000 to $10,000 on these 5 numbers, Billy had won more anywhere between $3 to 4 million before he decided to stop playing. 

This just goes to prove that despite the time or the advancement of technology, regardless of small or bigger casinos, people with the conviction to find a loop pole in gambling will always find one, and use it to win big. 

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