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7 Biggest American Blackjack Wins

Blackjack is a game of skill and bankroll management. It takes intentional practice to commit basic strategy charts to memory and move on to rules-specific strategies.

Don Johnson’s win of $15.1 million in blackjack was the result of his impressive mathematical strategies and card nuances. His success even led to the Netflix USA documentary The Player.

1. Shoeless Joe

When Shoeless Joe entered the casino at Treasure Island in 1995 with a $400 government social security cheque to cash, he was able to build a blackjack kitty of $1.5 million. His clumsy strategy of reckless splitting and doubling meant he ended up losing most of his winnings soon after, but he has the distinction of being one of the biggest blackjack winners in history.

Jackson was a baseball player accused of taking part in the 1919 Black Sox scandal and was banned from the game, but he still has a place in history for his incredible blackjack win. The man has since faded back into poverty and anonymity in Greenville, South Carolina.

2. Don Johnson

Johnson won millions by exploiting the crucial connection between blackjack house edge and game rules. He used this to his advantage and conquered the gambling system. He is a member of the Blackjack Hall of Fame, an elite club that celebrates and honors the best players and contributors to the game.

Johnson’s winning streak didn’t come from luck or wealth; he played the game for years and developed spectacular card nuances and mathematical strategies. He won about $15 million in Atlantic City casinos over a six-month stretch. His calculated bets, which included loss rebates, helped him maximize his gains.

3. Kerry Packer

Kerry Packer was a billionaire media mogul who loved to gamble. He was so good that he had casinos running scared. They had to ban him and he was known for bankrupting many of them.

He would show up with a posse of seven or eight men and play big. He also showed his generous side. On one occasion he paid off a waitress’s mortgage.

He was also a huge tipper. He was once known for winning $20 million in a night playing blackjack six hands at a time at $200,000 a hand.

4. Dana White

Dana White is known for running the biggest MMA promotion in the world, but he’s also quite skilled at blackjack. The UFC president has won and lost millions of dollars in casinos, even to the point where he’s been banned from some places.

When he’s not working as the president of UFC, the 53-year-old spends his time playing high stakes blackjack. He once won $2 million in just three months at the Palms Casino Resort in Las Vegas, prompting the casino to ban him. White is so fearless that he’s been known to bring a suitcase with him when visiting casinos in case the casino kicks him out.

5. MIT Blackjack Team

The MIT Blackjack Team proved that the cliches about casinos being unbeatable aren’t always true. The team used card counting and more sophisticated strategies to beat the casinos, making millions of dollars in the process. Their success inspired a best-selling book (Bringing Down the House), movies (21), and other media coverage.

While their profits continued to grow, the casinos began to take action. Eventually the casinos tracked down team members and barred them from playing at their establishments. In 1984, Kaplan was so well known that he decided to focus on his real estate investment and development company and stopped managing the MIT team.

6. Don J

Blackjack is one of the most popular casino games ever invented. It has also become a target of many gamblers who believe that there are ways to beat the odds and walk away with huge payouts. Several players have mastered the game, leading to some of the biggest blackjack payouts in history.

Ken Uston was a card counter who led a team around casinos in the USA to place huge bets and rake in millions of dollars in winnings. He is credited with pretty much inventing card counting. He is also a famous gambling author who regularly contributes to blackjack message boards and helps players with their questions.

7. Shoeless Joe

The story behind the biggest blackjack win is quite a fascinating one. An unkempt bum referred to as Shoeless Joe (not the baseball player) walked into Treasure Island Casino carrying a $400 government social security cheque and sat down at the $5 blackjack tables. Within a week, in an extraordinary run of luck that few at the time could have believed, Joe built up his kitty to $1.6 million.

He brought his winnings to Charlie Comiskey, but was turned away by the old man’s secretary. Eventually, Shoeless Joe faded back into poverty and anonymity and the dream that anyone might turn a $400 cheque into millions disappeared with him.