The Most Epic Wins in Roulette History

by Enrico
Updated Roulette strategy guides and tips how to win

biggest roulette wins
Everyone says they are aware of the classic casino tricks, no matter what games they play, at the end of the day, casinos themselves are always the ultimate winners. Remember the old phrase, the house always wins. Curiously, this banal fact has never stopped players from trying to bag big prizes. Roulette is actually one of the most difficult, yet favored casino games, around, but it’s also become home to some of the most casino bank-busting wins of all time

A fortuitous group of enthusiasts who are fascinated by roulette made themselves rich overnight by besting the odds. For your pleasure, and ours, we have summarized the biggest roulette winners in recorded history.

These men have become true roulette legends, so it’s time to hear all about how they cashed-in on one of the world’s most famous casino game.

Joseph Jagger

Total win: $375,000
How he did it: Exploited an uneven wheel

Joseph Jagger is arguably the first-ever recorded famous roulette player who made his mark all the way back in 1873. He was an engineer who was certainly very good at mechanics. Besides the bulky machines, Jagger also loved playing roulette. He had a unique belief that nothing is perfect, everything has a slight imperfection. Most importantly, he believed that not all roulette wheels are made perfect, there will always be an uneven element somewhere to be exploited. Jagger decided to prove his theory by going to Monte Carlo and hitting the roulette wheels hard.

He asked 6 people who worked at the casino to watch and record the results of every spin. A secret unknown bias was found out after his thorough analysis, one of the wheels had a certain favor to the designated numbers: 7, 8, 9, 17, 18, 19, 22, 28 and 29, meaning the ball fell into these slots more frequently than others. Joseph went into the casino and took advantage of this wheel’s tendency and cunningly won more than $375,000 – an amount that would equal millions nowadays.

After three days, the casino became more and more skeptical about Jagger due to his large sum of winnings. They decided to change the positions of all the roulette tables, following that the wheels started to fall off Jagger’s epic winning streak. Finally, he realized the scratch mark had disappeared and went to look for the biased wheel. As expected, he discovered the marked wheel and started winning again for a few more days.

The casino eventually removed the imperfect wheel. He left Monte Carlo with no further greed and invested all of his winnings into his business, and made the determination of never stepping into a casino again. We can’t say for sure that he kept his word, but given how much cash he banked, we like to think that he did.

Charles Wells 

Total win: 2 million francs
How he did it: Breaking the bank in Monte Carlo

Back in the 1890s, Charles Wells was rather a dishonest conman who relished gambling. He started playing roulette in the world-renowned Monte Carlo Casino, somehow managing to achieve a then-unheard-of winning steak by winning 23 out of 30 spins consecutively. He played until drain the casino of cash, to the point where they couldn’t even afford to pay off Mr. Wells’s winnings. Over one single night, Charles won around a million francs. Interestingly enough, a song was inspired by his drama called “The Man Who Broke the Bank at Monte Carlo”.

Once is purely beginner’s luck, what if the same thing happened the second time? Obviously, the first win could not satisfy his want for more money, Wells went back again to Monte Carlo after some time to once again challenge the odds. Out of surprise, he won a million francs again, while being closely monitored and thoroughly checked by the casino for how he played – they certainly suspected that he was cheating, but couldn’t quite figure out how. Nobody could spot any irregularities in how he played, but he was a crook after all.

Based on current modern currencies, it’s not easy to tell about the sum of all his winnings, but putting it in the tens of millions of dollars bracket is a fair assumption. Once a cheater, always a cheater, as the saying goes. He couldn’t stop with his con tricks though, which saw him spend 8 long years in jail. In 1922, Wells died in Paris stone-cold broke, leaving the vanished millions of francs as a mystery.

Sean Connery

Total win: $27,000
How he did it: James Bond’s consecutive winning bets on 17

Sean Connery was the original and the greatest James bond in our opinion. However, before he began his acting career, he had a strong passion for playing roulette. He had his favorite betting strategy, the ever-popular “Lucky Number“ system, a very high-risk method of betting on the same number persistently.

The Casino de la Vallee in Saint-Vincent in Italy was the place where he started the most impressive consecutive win streak in history. One day in 1963, he walked in the Saint-Vincent casino, headed straight to a roulette table, and placed the first bet on number 17. This was a bust, as the ball didn’t fall into this slot, and another failure happened at the second attempt as well.

Two busts didn’t bother Connery though, as during the third game his attempts came up good, the ball incredibly fell on 17. He used all the winnings bet on the same number, lucky him, he won again. At the fifth spin, believe it or not, he made it three consecutive wins on this lucky number. So, over 5 games in only 5 minutes, he earned a staggering $27,000. It was not a huge amount to brag about by other player’s standards, but let’s be clear about the chances of hitting the same number on a roulette wheel three times in a row, it’s 50,000/1 in case you didn’t know.

Interestingly enough, Sean revisited the scene of his big win again in 1971. What’s different this time was that he did it in the role of James Bond because the writer decided to interweave his real-life experience into the movie. Now, isn’t that the best way to immortalize a memorable experience? We certainly think so!

Ashley Revell 

Total win: $270,000
How he did it: Used his all life savings to bet on red

Ashley Revell was a hotheaded gambler who sold his home, car, watch, even clothes, taking his entire savings and heading straight to Las Vegas. He made the decision to change his life by betting everything on roulette. This impetuous attempt was the gamble of a lifetime – go big or go home(less). A short-lived TV series was even based around his attempt to go for it all.

Deep In Ashley’s heart, he must have had immense faith in himself, as in total he bet $135,000 on red. What kind of guts can a person have that he would bet his life on one single spin of the roulette wheel? Fortune favors the brave as they say. After the impatient wait, the ball fell on red 7. He successfully doubled his money and left with $270K. Even though it was not a huge win, Revell has more than earned his place in roulette history.

What did he do with the winnings? Turns out that Ashley is actually doing great, as he invested it in his career path. He set up an online poker site Poker UTD, and opened another site for iGaming recruitment, to help people seeking casino related jobs online. All we can say is good for him.

Chris Boyd

Total win: $440,000
How he did it: Betting on the luckiest number in roulette history – 7 red

Another similar story to Ashley Revell, Chris Boyd is a programmer who decided to bet his three years savings of $220,000 on roulette. He flew to the same place, gamblers’ paradise Las Vegas, and started to seek a casino that could bring him luck. The biggest difficulty he encountered, at least in the beginning, was this rigid rule of restricting the gambling limit per hand in all casinos, the maximum sum a player can bet on one game was $100,000.

Chris asked each casino over and over again to let him bet with this tremendous amount. After Chris was refused many times, he finally worked out a deal with Binion’s Horseshoe Club. Nevertheless, Binion had the same rules, they allowed him to play his way, to bet big and bet on a European roulette wheel. The result would most probably be a big win for the casino anyway, as nobody thought that Boyd could realistically pull out the win.

However, it seems like God favored bold players one more time, Boyd managed to double his bet amount in the same way just like Revell, by falling into the exact pocket, believe it or not, the exact color “Red”, the exact number “7”. What a coincidence! It made 7 red the luckiest combination in roulette history, but do you have the guts to take all your savings and fly to Vegas to try if it for yourself? We doubt it, but that’s okay, as we can all live vicariously through amazing stories such as this.

Pedro Grendene Bartelle

Total win: $3.5 Million
How he did it: A $35,000 bet on a single number

Who says you have to going broke for luck to strike? Only by using money can we can generate more money. You know the old phrase, it takes money to make money. Being wealthy gives you more of a chance of beating the odds because you don’t need to worry about the consequences of losing. Pedro Grendene Bartelle is the perfect example of where wealth alone allows you to best the roulette wheel.

In 2017, Mr. Bartelle made a $35,000 bet on a single number – 32 – and won $3.5 million. To be able to take such a large sum to the casino and wager without a second thought is a luxury that very few of us have. He comes from a wealthy background by owning one of the biggest shoe companies in Latin America, his uncle is also an owner of a giant enterprise, with the family simply drowning in cash.

This story certainly won’t be relatable for most, including us, but you can’t take away from the fact that Bartelle swept home a multi-million-dollar payday from a single spin of the roulette wheel. It’s an impressive feat whichever way you look at it.

Sir Philip Green

Total win: $2 Million
How he did it: Broke the bank at one London’s most lavish casinos

Philip Green is a British billionaire and business tycoon who owns numerous trendsetting retail stores, or at least he did once upon a time. As one of the richest people in the country, he is also known as a serial gambler who plays mostly blackjack, yet won the most in roulette. On a night of 2004, he won at least £2 million by playing high stakes roulette at his favorite casino – Les Ambassadeurs in London, an exclusive and luxurious establishment packed with high rollers. Millions are commonly won and lost here, so should you ever step through its doors, you best have a big balance behind you.

Given his successful spins at the casino, among other things, he has been regarded as a noticeable menace to the business. The owner of Les Ambassadeurs had to issue a revenue warning to the shareholders, due to his thrilling wins, purely by his incredible luck. Sadly, while Philip Green’s wins are to be celebrated, the man behind them is not. His aggressive and controversial business practices have hurt thousands of hard-working individuals, to the point where he is considered to be one of the most hated men in Britain.

Mike Ashley

Total win: £820,000
How he did it: A complete bet on lucky number 17

Another billionaire story is about the controversial owner of Newcastle Football Club, Mike Ashley. We’ll address the man himself later on, but let’s start with why he is on this list. He is a regular roulette player at a casino in Mayfair, London. In 2008, he won £1.3 million on a roulette spin by wagering £480,000 on his favorite number 17, the same as James Bond. Basically, he had a really consistent gambling system called “Complete Net” by placing bets on all combinations involving 17.

As a high roller, every time Ashley bets, he does so at the maximum limit £2,000. The odds of landing 17 are 35-1, which could win him £70,000. He clearly knew what he was doing, as he landed several wins on such number across a 15-minute time period. As his last win rolled in, the casino gave him a standing ovation. Following that, he calmly thanked the table and walked out with all his winnings, £820,000 in pure profit.

Number 17 is clearly a lucky number. However, his win doesn’t excuse his general attitude when at the casino. Ashley is known for his drunken, rude, and crass behavior when gambling to the point where he has faced casino bans from some of London’s leading gambling establishments. Like Sir Phillip Green, his win is impressive, but the man behind it often proves to be anything but.

Francis Farrugia, Francesco Baioni and Frank Camilleri

Total win: Unknown (rumored to be in the millions)
How they did it: Cheating through past posting

Who says you have to play fairly to become a big winner at the roulette table? Plenty of crooks have stepped up to the table over the years, yet none have been more organized than Francis Farrugia, Francesco Baioni, and Frank Camilleri. You might not know these three names, but if you spend any time on Las Vegas casino floors, odds are you’ll hear them whispered about, as they are very much the kings of crooked roulette play.

These three men traveled the world, ripping off casinos through the most age-old method of cheating around – distracting the croupier. The idea is simple, one or two players catch the croupier’s eye, while the other fiddles with the chips on the table to create the illusion that a higher bet was placed. This trickery won them huge sums of money rumored to be in the millions, where those millions went or where they are today, nobody seems to be quite sure.

Given their run of dishonesty, you won’t be surprised to hear that all three are banned from practically every major online casino in the world. That certainly didn’t stop them from carrying on their wild scams though. Plying their illicit trade at any gambling establishment that would take them, it was only a matter of time before their illegal efforts caught up with them. And that it did, but not in the way many people thought. Francis Farrugia was eventually sentenced to 9 months in jail for ID, but the sentence was suspended and he was released on supervision. His partners in crime served no time in jail, as they both escaped sentencing.

Will you be the next big roulette winner?

Anyone can play and win big at roulette, and we really do mean anyone. It doesn’t matter about the wagering amount, your favored betting system, if you are on the verge of being broke, or you are a multi-billionaire, whether you are a resourceful engineer or an aspiring movie star. Just pick a favorite lucky number or color, put some money on the table, and you will have the chance of being listed as one of roulette’s greatest ever players.

Today might just be your lucky day, slide on over to the roulette table to find out!

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