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John Daly: I lost $55 million gambling In a recent interview, John Daly said he's lost $55 or $57 million gambling. Here's why that might mean he actually has the addiction under control. John Daly ( – April 26, ) was an American sportsman, professional gambler and A protege of John Morrissey, he was involved in illegal gambling on Broadway and in Midtown Manhattan for. John Daly Relied On Tax Records To Figure $90 Million Gambling Losses. You don’t think tax returns are handy? Tell that to John Daly.