Casinos have a reputation for having the upper hand in all the games that they offer, which means they always win in the end. This notion is particularly visible in the game of roulette, even when systems such as the Martingale Strategy are applied to collect payouts. The mathematics of such gameplay does not crash the fact that the game is dependent on luck, and the upper hand of the casino is taken into consideration. Therefore, even with winnings streaming, punters should keep in mind that the gambling platform will end up collecting not only an equivalent of what they have awarded but also some more.

Regardless of the odds standing against gamers, many still hit the wheels for a chance to walk away with winnings. On the upside, some people end up getting smiled upon by lady luck and collect massive payouts. In this review, we touch on some of the roulette winners that have lucked out the biggest in history. No order is used to line up the winners considering some dated wins would translate into bigger amounts with all things considered, such as inflation. Here are the biggest winners that managed to walk out of the casino after playing roulette a lot richer than they were when they walked in:

Charles Wells

  • Wins – 2,000,000 francs
  • How – Pure dumb luck

Charles wells was a criminal of his time, which was the late 1800s. The man was a well-known scam artist that had eluded the arm of the law for the most part. In 1891, Charles dedicated one night to gambling on the roulette tables of Monte Carlo Casino Resort. This gambling destination still stands to date, and it is well-known for its grandeur nature that it had even back in the day.

Wells enjoyed a winning streak that was described by most as phenomenal, with some saying that he only lost seven of the thirty rounds that he played. It got to a point where Charles literally broke the bank, which means that the table lost all its money and no more gamblers could come after him. The lucky punter walked away with close to one million francs, and the events of that day inspired one of the most popular songs of the time.

The big win was far from enough reason to keep Charles away from the roulette wheels, and he went back to the gambling den another day to try his luck. Even better odds were with him on the said date, which saw him collect more than one million francs this time. Considering he was a well-known scam artist, the gambling club did not hold back in airing their scepticism on the payouts collected by Mr Wells. However, no foul play was ever found, and the sequence of winnings was out of sheer luck. When translated into the value of money today, Charles collected tens of millions of francs in Monte Carlo over his gambling period. On the downside, he died as poor as could be in 1922, and no one knows how he spent his fortune.

Ashley Revell

  • Wins – $135,000
  • How – Wagered savings only on red

Ashley’s win is more recent and does not match up to that of Charles Wells. However, it is placed on most lists of big roulette winners due to the massive risk Revell took to collect a fortune in the game. Ashley decided to try his luck by not only gathering his life savings but also selling his car, house, jewellery, and clothing, and taking the money to Vegas. Once there, he singled out roulette as his game of choice, and he placed his bet on the colour red. As luck would have it, the ball spun and landed on the number seven, which is red.

Ultimately, Revell doubled his stake of $135000 since the payout ratio for the even-money bet is one to one. Usually, colour bets have high winning odds that are roughly 50%. Even so, the massive risk the player took cannot be denied, so much so that a television series was created to follow him on his journey.

Today, Ashley is said to be doing well for himself and has gone on to establish websites related to the gambling industry. The player first opened a poker gaming site with his winnings before opening I Gaming Recruitment, which helps people land employment in online gambling destinations.

Chris Boyd

  • Wins – $220,000
  • How – wagered $220,000 on red

Chris Boyd’s story is similar to that of Ashley Revell, where the gambler wagered a large amount of cash on the colour red. Chris did not put all he owned in his life on the line but instead flew to Las Vegas with savings of $220000 that he had put away for three years.

When Boyd got to Vegas, he was first tasked with finding a gambling club that would accept such a large bet in a single round. Most casino terms do not accommodate stakes that high, and he was turned away by many. Nonetheless, he was finally able to strike a deal with Binion’s Horseshoe Club despite the entity having a wager limit of one hundred thousand dollars. Not only did the casino accommodate his high stake, but they also agreed to eliminate the double zero pocket on the roulette wheel he was playing. Binion offers only American Roulette wheels, and this step turned it into European Roulette. Like with Ashley, Chris collected his doubled win on the number seven, which is red. Not much is known of Chris today other than the fact that he left Sin City a much wealthier man than he came.

Mike Ashley

  • Wins – £820,000
  • How – Bet on 17

Mike Ashley is one of the world’s billionaires with his foot in numerous business ventures. In 2008, Mike visited a casino and decided to stake on every possible bet that involved the number seventeen, including straight, split, street, column, and others. The billionaire ended up using a total of £408 000. As luck would have it, the ball landed on the number seventeen, and Ashley left the casino with an impressive one 1 300 000 pounds.

Joseph Jagger

  • Wins – $375,000
  • How – Took advantage of the biased wheel

Jagger is another player that also collected his spoils from Monte Carlo Casino Resort, but unlike Charles Wells, he depended on more than just luck. The man worked in the field of mechanics, which gave him extensive knowledge of the operation of machines. Jagger took his skills to Monte Carlo where he bribed six members of the casino staff to inspect and note down the results of all the roulette games. This went on for a couple of weeks, and when Jagger assessed the outcomes, he was able to single out one wheel that had some bias. The roulette game leaned towards landing the numbers 7, 8, 9, 17, 18, 19, 22, 28, and 29. Such results would be impossible if the wheel was completely random.

With this knowledge, Joseph visited the gambling destination for several days in a row and capitalised on it. However, the casino officials caught wind of what was happening and soon after, removed the wheel from the floor. This was not before Joseph had collected a sweet $375000, which would translate to millions today. The man went on to open his own business with the spoils and is reported never to have gone back to the betting tables again.

Sean Connery

  • Wins – $27,000
  • How – Сonstant bets on 17

Sean Connery is a name that is synonymous with Hollywood fame of both the old and new age, but before his acting success, Sean was an avid gambler. Growing up, Connery experienced a lot of difficulties supporting his family and had to work several manual jobs to keep the ball rolling. In 1963, the gamer met his luck as he placed stakes on the number seventeen several times and walked away with twenty-seven thousand dollars.

This amount is quite shy in comparison to the wins of others on this list, but what makes it interesting is the events that led up to the payout. In the Saint-Vincent Casino in Italy, Sean singled out the number seventeen as his chosen stake. Straight bets have the slimmest odds of being landed, and the first attempt failed. Even so, Sean proceeded to place the stake again, and this time, he won. He repeated this bet two additional times and collected wins with each. The odds of hitting this number three times in a row is one to fifty thousand, six hundred and fifty-three, which makes the case so special.

Final Comments

These few examples of the biggest roulette winners are an indication that anyone can win in the game. Nevertheless, it is recommended to gamble within one’s limits. Also, several strategies can be used to capitalise on the winning chances that come by. These systems of gameplay can be applied in both online and land-based gambling clubs.

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