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10 Biggest Gambling Losses Of All Time Charles Barkley’s gambling habits can’t even be called an open secret, as he’s never tried to make a secret of them at all. But now, Barkley says, he’s learned to control his gambling habits at least by his standards. Those losses, along with a debt dispute with the Wynn. The gambling escapades of Charles Barkley are not a secret. Barkley projected that he had lost a million dollars on 30 separate occasions. But I've also went to Vegas and lost a million probably three times as much," Barkley said. A group of Vegas casinos announced a ban on Barkley from their “All You Can Eat” Buffets. A representative of the Wynn Casino's said, “I don't.