The Biggest Wins in History

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Call it luck or good strategy, some people manage to leave the casino with tons of money in their pockets. Those payouts tend to come from higher bets and veteran gamblers, however, it can also happen to ordinary people. Here are four stories about the most prominent casino payouts of all time.

Arch Karas: Poker and Craps

This is the story about the infamous “king of casinos” who famously earned $40 million in Las Vegas after coming in with just a single 50-dollar bill. This player has never been afraid of losing it all. Moreover, he used to be one of the best high rollers in the world. He lived a risky life outside of the casino as well — he went from millionaire to broke in a matter of days.

In December of 1992, Archie started the famous lucky streak that created his reputation of one of the best high rollers in the world. In LA, he lost around $2 million during a high-stakes poker game and was left with his last $50-bill. He believed that this was all he needed to turn the situation around. Luckily, he ran into an old friend who lent him $10,000 so that he could play high-stakes Razz, similar to poker but with one difference — the smallest hand wins. Given his recent bad luck, he believed that this game would be the perfect choice for him. Within 3 hours, Archie repaid the loan and accumulated $40 million in the process.

After that, his luck struck again, so he started circulating through the Horseshoe casino games selection. Karas didn’t learn his lesson from the previous loses and managed to lose terribly in craps, spending over $11 million over the course of three weeks. He couldn’t deal with that loss properly, so he continued to play and lost another $17 million. The king of gambling didn’t stop there — he borrowed another $40,000 and turned it into $1 million within three weeks. In total, Karas ended up both spending and earning over $30 million in just three weeks. So where is Archie today?

Unfortunately, he was caught cheating at a blackjack table in 2013 and is currently facing charges of burglary and fraud. The king who has gambled with more money than anybody in the history of casinos is yet to prove his innocence. In the meantime, he remains a legend.

Elmer Sherwin — Megabucks Slots

Elmer Sherwin, a WWII veteran, has been enjoying slot machines his whole life, and he considered his Megabucks Slot at the Cannery Casino and Hotel particularly lucky. He had played on the same machine for years, with nothing but small winnings. However, Merwin believed that his persistence would pay off. In 1989, he managed to beat the odds and won an incredible $4.6 million at this very slot machine and set the record for one of the biggest slot wins. After Elmer had won the top prize, he believed that he should play on the same slot for the rest of his life in order to hit the jackpot one more time. Sherwin’s win came during the casino’s opening event, which confirmed people’s belief that the biggest wins happen during opening nights.

Elmer Sherwin — Slots

Sherwin continued to impress in his persistence and continued playing the same slot for years to come. In 2005, at the age of 92, Sherwin managed to defeat the odds of 1 in 50 million and won another jackpot of $2.1 million.

It took Merwin 16 years of playing the same slot to win another jackpot. Such cases are truly rare but not impossible, as Sherwin’s feat has since proven.

Mike Ashley — Roulette

This billionaire owner of Newcastle United Football Club stunned everyone when he hit $1.3 million on one single spin on the roulette wheel. This high-rolling gambler played for three hours at the London Casino roulette game, after which he insisted on betting on his lucky number — 17.  However, this was considered a highly risky shot, especially since his initial bet was around 480,000 pounds. But Ashley was convinced that his lucky number would defeat those odds. And as luck would have it, the ball landed on 17 and made this billionaire even wealthier.

His initial bet went from 480,000 to triple that amount. In a composed fashion, the lucky winner kept his cool, took his winnings, and left the premises. Later that year, he tried to repeat this lucky feat and bring another $1.4 million home. However, luck failed him that time, and he lost $1 million in the span of a little more than two hours. Ashley’s luck has been easy come and easy go since then.

Sean Connery — Roulette

Sir Sean Connery has always enjoyed gambling challenges even before he became a famous actor. Connery once visited a casino in the Italian Alps where he played in true Bond fashion. He decided to bet it all on his favorite number, same as Ashley. However, what is interesting is that he chose to bet on it multiple times. He wagered on what he considered his lucky number — 17. The ball missed the 17 slot two times, but the third time it landed on it. Although, what is even more exciting, or even borderline ludicrous, is that the famous James Bond decided to leave his winnings and try again. So he wagered another three times on the same number. However, the odds of hitting the number 17 another three times were 1 to 50,000. But James Bond got it right all three times and collected around 10,000 pounds, which amounts to almost 163,000 pounds today.

Since then, Connery decided to ignore the house edge and place his bet on the same number on the roulette table.

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Charlie Wells — Roulette

This man who broke the Monte Carlo bank, costing them more chips than they had available, had an incredible gambling career. He used to play roulette for more than 12 hours straight at a time. He was already used to great winnings before he set foot in Monte Carlo and decided to test his luck once again. He raised 4,000 francs in chips and managed to turn them into huge winnings.

During that 12-hour play, Wells had won 23 out of 30 successive spins. In today’s money worth, Charlie took home a fortune of $20 million. What is more, he managed to leave a mark in gambling history once again several years later, but in a much different manner.

Wells was known for his strategies, inventions, and sometimes, fraudulent actions. He invented a fuel-saving device for steam chips, which attracted people’s attention. This invention cost investors a lot — they found themselves fooled and lost a fortune while gambling. Wells was finally sentenced for fraudulent activities in England and France where he spent his next 16 years. In 1922, his adventure finished, and he passed away in a French prison.


Lady Luck has been bringing incredible winnings to the brave ever since the beginnings of the world’s gambling scene. All in all, there were those who were brave enough to test her and score insane winnings. Just like that one anonymous man who waited for a basketball game to start and killed his time at the Excalibur Casino. He killed it all right — with $39 million!

Want to see if Lady Luck is on your side? Just be brave, relentless, and enter gambling history.


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