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We’ve all dreamed of hitting that big payday at the casino and sailing off into the sunset with our millions. For some lucky individuals, this dream has become a very real reality.
Check out 5 of the biggest, craziest gambling wins, and how they did it:
The Blackjack Master
For a 6 month period in 2011, Don Johnson (NOT the Miami Vice star), managed to win $5 million at blackjack from 3 casinos – and he didn’t need to count cards. Rather, he negotiated special rules with the casinos to ensure he would have an edge when playing and could grab more winnings. This edge was a guaranteed 20% payback that he negotiated, meaning that (for example) if he won $100,000 he could keep it all, and if he lost that amount, he would still get $20, 000 back.
He also negotiated the right to bet up to $25,00 a hand, which greatly assisted him considering the edge he already had. Combined with clever strategies he used in choosing the table he played at, Johnson walked away with a huge payday
Betting on the no-hopers

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Nobody thought that English club Leicester City had a chance of winning the Barclays Premier league (BPL) at the beginning of the 2015/2016 season. After all, they had only re-entered the top flight in the 2013/2014 season, and at one point seemed like they would be relegated from the Premier league during the 2014/2015 season. Further, they had never won a top-level football championship, and were not one of the “big-Money” clubs so prevalent in English football, like Arsenal and Manchester United.
Unsurprisingly then, the bookmakers gave 5,000 /1 odds of Leicester city winning the BPL at the beginning of the season. Incredibly, they defied the odds and won the BPL with more than 2 games to spare, in one of sport’s great underdog stories.
Some people were either brave or smart enough to bet on them, and a Guildford-based punter even walked away with a whopping $112,500, having placed a £75 each-way bet on Leicester City when the campaign was only a few weeks old.
Breaking the bank at Monte Carlo
In a run of unbelievable luck, Charles Deville Wells “broke the bank” (won every chip on the table) at Monte Carlo, and managed to win a million francs ($500,000 when adjusted for inflation) in one evening. However, Well’s incredible run wasn’t without deception – he played at the tables with $400 that he had swindled from investors, promising them to use the money to fund a musical jump rope. Eventually, Wells was arrested in England for his trickster schemes, served 8 years for fraud, and was arrested twice more in his life.
James bond wins in real life

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Sean Connery didn’t just hit the casino tables while playing James Bond – he also won a fortune at an Italian casino in the Alps in 1963. At the roulette table, he placed a bet on 17 several times in a row. With 50,000 to 1 odds at one point, Connery eventually cleared over 17 million Lire, which was £10,000 (about £163,000 in today’s market).
Turning $50 into $40 million

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In 1992, Archie Karas lived every gambler’s dream when he went to Las Vegas with only $50 in his pocket and managed to amass a whopping $40 million with that money. Incredibly, Karas had recently suffered a colossal $2 million loss in a Los Angeles high-stakes poker game. How did he turn things around? Well, he did get some help along the way – he ran into a friend who spotted him $10,000 so he could play high-stakes Razz, an unusual poker variant where the lowest hand wins. He subsequently went on a winning run of epic proportions, and eventually won the jaw-dropping amount of $40 million.

