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Kerry Packer takes the crown as the biggest casino winner ever. This Australian media mogul walked into the MGM Grand in Las Vegas in the 1990s with just $250,000. Through intense blackjack sessions, he turned it into a whopping $40 million win. It’s a tale of bold bets paying off big time.​ Archie Karas comes in close with his epic “The Run” from 1992 to 1995. Starting with a tiny $50 loan, he grew it to $40 million across poker and other games in Vegas casinos.