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What is the most money you've ever won in a casino Dec 20, 2007 · And what's the most money you've ever lost? Just want to hear some good stories of people hitting it big and people going bust in the world of gambling. Or you can tell me the story of someone you know or someone you saw. For example, I saw a guy in a casino in Reno hit the jackpot on a slot machine. I asked him how long he'd been at the machine and he said "three days!" …