TopicsCelebrities
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Dispatches from the celebrities desk

Celebrities.

The actors, athletes, musicians, and characters whose gambling lives became their own kind of legend. Some won quietly. Most did not.

27 articlesUpdated Aug 29, 2026
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  1. Famous Sports Bettors Who Changed the Industry
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    Sports BettingCelebrities

    Famous Sports Bettors Who Changed the Industry

    The bettors who changed sports betting weren't famous when they started. They were in back rooms doing math no one understood, making money that casinos couldn't stop, until the casinos finally figured out what they were doing.

    Aug 9, 2026 · Tom Bennett
  2. 50 Cent vs Floyd Mayweather: The Reading and Betting Beef
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    CelebritiesReviews

    50 Cent vs Floyd Mayweather: The Reading and Betting Beef

    Two famous people with public disagreements about cryptocurrency, casinos, and the math of wagering. The architecture of their conflict reveals how culture shapes gambling decisions.

    Jul 15, 2026 · Rachel Monroe
  3. The Real Story Behind the Book Bringing Down the House
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    BlackjackCelebrities

    The Real Story Behind the Book Bringing Down the House

    Ben Mezrich's 2002 book told the story of MIT students card-counting blackjack. It was a bestseller. The actual story was more complicated and less profitable than the book suggested.

    Jul 2, 2026 · Jake Sullivan
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