You may have heard of the phrase ‘the house always wins’ when it comes to gambling in a casino or online. For most people, this is true, especially when it comes to playing roulette. Winning is considered pure luck, with the payouts built to favor the casino.
And no matter how long you play for or how well you think you are doing, you will always pay back what the casino gives you, and more.
For the people included in this article, it’s certainly not the case.
Whether it was down to luck alone or they had strategies to give them an edge, these big winners prove that it is possible to come away from the roulette table with a lot more money than what you started with – and then some.
These are the biggest roulette wins ever recorded, with the numbers guaranteed to make your head spin. From movie stars to businessmen and Knights, these people defied the odds and rode off into the sunset, winning more money than they could have thought possible.
Charles Wells, 2 Million Francs [$10+ million] In 1891
Charles Wells was a small-time criminal who enjoyed gambling more than the average Joe. However, he certainly made more money from roulette compared to his shady dealings.
One night in 1891, Wells ventured down to the Monte Carlo Casino Resort, one of the most famous casinos in the world. He hit the roulette table and the rest is history.
According to sources at the time, Wells went on one of the most incredible winning streaks of all time, claiming that he won 23 out of 30 consecutive spins on the wheel.
In fact, Wells was winning so much money that he actually managed to ‘break the bank’, ie the table he was playing at could no longer afford to pay out as it ran out of money.
It’s reported that Wells won almost one million francs in that single night. It was this mighty triumph that went on to inspire the song ‘The Man Who Broke the Bank at Monte Carlo’.
One million francs in 1891 was a hell of a lot of money… but evidently not enough for Charles Wells.
Later down the line, he returned to the very same casino in Monte Carlo and tried his luck at the roulette table. As it turned out, Wells had not yet lost his rabbit’s foot, going on to win another one million francs.
According to sources, it was all down to luck too. They say there was no funny business going on, and that he won the money fair and square.
These claims should be taken valid too; after all, considering that Wells was a known criminal, the casino would have been keeping a close eye on his actions on both nights.
The second they thought he was cheating, they would have either thrown him out of the property, called for the police to arrest him or, considering the era the game was played, perhaps something more serious than that.
Converting that amount of cash into modern currency is no easy task, but if it was to be done, it would be in the tens of millions of US dollars today.
But even with this enormous wealth, it apparently was not enough for Charles Wells to leave his days of breaking the law behind him. He continued his scams before being thrown into jail for 8 years.
In 1922, some 30 years on from his incredible win, Wells died in Paris with nothing more than a nickel to his name.
It’s not known how or why he lost all of his money but considering he continued his shady ways, it’s likely they played a part.
Joseph Jagger, $375,000 [$2+ million] In 1873
Now, while Wells didn’t use any tricks to make his millions, the same can’t be said about Joseph Jagger. Nevertheless, he took his chance and it paid off and becomes one of the biggest roulette winners of all time.
Jagger had a mechanical background, with a knowledge of how machines worked and, importantly, how they failed.
One day, Jagger visited a Monte Carlo casino. He bribed six of the clerks in return for writing down every single result of every spin of the roulette wheel for a few weeks.
After analyzing the results, Jagger realized that one of the wheels in the casino was biased towards a few numbers, namely 7, 8, 9, 17, 18, 19, 22, 28 and 29. These pockets were hit more frequently compared to all the other numbers on the wheel.
On a regular roulette wheel, this is something that should never be able to happen.
So with this knowledge, Jagger entered the casino and set his sights on the biased wheel. Over the course of several days, Joseph Jagger won more than $375,000, which when translated into modern currency would have made him a multimillionaire.
The casino eventually found out what was going on and removed the biased roulette wheel from play. But Joseph didn’t mind too much; he didn’t even enter another casino again.
Instead, he quit his job and used his winnings to invest in a business of his own.
Sir Philip Green, £2 Million [~ $3.6 million] In 2004
Sir Philip Green, famous fashion mogul, has been known for spending his time – and money – in some of London’s biggest casinos. However, not even he could have expected to win such an extraordinary amount of money from one of his typical sessions. He sits comfortably in second place for the biggest roulette wins ever.
One night in 2004, Green went out with his wife Tina, owner of Bhs and the Arcadia group, to Les Ambassadeurs casino in Mayfair.
In just under a few hours, Green managed to rack up a huge win of £2 million. After leaving the table, Green was quoted as saying, “I had a fantastic night at the tables” – quite relaxed for a guy that has just won a fortune playing a game of chance.
In an interview with the Telegraph, a friend of Green said, “Like all gamblers, Philip has his losses as well as his wins but he has been on a golden run recently. The real knack is not dribbling back [to the casino] the money once you have had a big win.”
But while Mr. Green was enjoying his winnings, Les Ambassadeurs was not so cheery after that night. London Clubs International (LCI), owners of Les Ambassadeurs, were forced to issue a warning, stating that their profits were to fall “significantly” due to the size of the win.
Mike Ashley, £820,000 [~ $1.5 Million] In 2008
Like Mr. Green, Mike Ashley is another billionaire that managed to add to his incredible wealth with one of the biggest roulette wins in history. Ashley owns Sports Direct, one of the biggest sportswear businesses in the UK, and Newcastle United, a Premier League football club.
Ashley attended a private casino in Mayfair, London, betting on every single possible combination of inside bets that included his favorite number, 17. This type of betting is called ‘complete betting’. It consists of corners, streets, splits, six-line bets, and of course, a bet on the number 17 itself.
Ashley wagered £480,000 on this complex bet. It’s reported that Ashley also made bets on other numbers too, showing that he was attempting to make his own luck to make him money from the game.
At the end of the session, Mike Ashley made £1.3 million, a net profit of £820,000.
While this may not be much money to him, it is certainly one of the biggest roulette wins in recorded history. Knowing him, he probably got more satisfaction seeing that the ball landed exactly where he thought it would.
Chris Boyd, $220,000 In 1994
Chris Boyd was just an ordinary gentleman that just happened to win one of the biggest payouts ever in roulette. He has a similar story to the next person on this list in that he decided to bet big in Las Vegas – except it wasn’t literally all or nothing.
Boyd wagered $220,000 he managed to save 3 years prior. Most casinos balked at this staggering single bet amount, but Binion’s Horseshoe Club decided to take it. In normal circumstances, they would only accept bets of up to $100,000 – but this was no ordinary occasion.
To make it more interesting, since they only had American roulette wheels, the casino agreed to cover the 00, turning it into a European roulette wheel and giving Boyd a slightly bigger chance of winning.
Boyd stuck the full $220,000 on red and you can only imagine how he was feeling when it landed on 7 red. He doubled his money and left with a lot more money than he brought with him.
Ashley Revell, $135,000 In 2004
In the same year that Sir Philip Green won big, Ashley Revell also managed to land himself a spot on the list of the biggest roulette wins ever. But unlike Green and some of the others on this list, there was a little more riding on the outcome it…
In 2004, Revell decided that he wanted to go to Las Vegas and, literally, wager everything he had on roulette.
This really did happen. This story attracted so much attention at the time, a mini TV series documented the entire event.
It’s reported that Revell withdrew his life savings, sold his house, his car, all of his clothes and more. Essentially, he sold everything he could and took it all to the roulette table.
In total, Revell had $135,000 to bet with. In one of the most absurd bets ever made at roulette, he risked it all on red. After the most intense seconds of his entire life were spent watching the ball spin, it finally landed on red 7, doubling his net worth and sending him into utter ecstasy.
Since this fateful day, Revell is now the owner of two thriving businesses. He started the online poker site Poker UTD and I Gaming Recruitment, a business designed to help people find work at online casinos.
This legendary win has been written into online gambling folklore.
Funnily enough, it was red 7 that also gave Chris Boyd his big win too! Coincidence? Fate? Either way, it was a remarkable win.
Sir Sean Connery, $27,000 In 1963
Sir Sean Connery loved to gamble before he became one of the most iconic actors of his generation. He didn’t have it easy to begin with, growing up in working class Edinburgh, Scotland and working multiple manual labor jobs to help feed his family.
In 1963, Connery visited a casino in Saint-Vincent, Italy. He decided to make multiple bets on the number 17, profiting more than $27,000 in the process.
Now, while compared to the others on this list of biggest roulette wins, it’s not that big of a deal. What’s most astonishing is how unlikely the result was to occur.
Connery’s first bet on 17 didn’t come in so he decided to bet it again. This second bet also didn’t win. But Connery is a persistent man and bet the number 17 for a third time in a row.
This time proved far more profitable as he won. Feeling lucky, he let it ride and wagered his winnings on 17. The wheel span and once again, the ball landed on 17. Connery decided to try his luck for a third time and wagered it all on 17 – and sure enough, the ball landed on 17!
If you were to translate this into odds, the chances of this happening are 1 in 50,653!!
Connery would later go on to star as the original James Bond, starting the beginning one of the biggest movie franchises in history.
Which do you think he considered the bigger win? Either way, he did pretty darn good for himself, wouldn’t you agree?