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Charles Barkley on gambling: Lost $1 million 10-20 times A loss resulting from games of chance or wagers on events with uncertain outcomes (gambling). These losses can only be claimed against gambling income. From losing millions to billions at a plethora of casino tables, we count down 10 Biggest Gambling Losses Of. The Man United and England star ran up the bill on roulette and blackjack in Manchester's Casino.