I would never have guessed that a man with a face tattoo was bad with money, but shockingly it is so. At least, his bankruptcy makes for great entertainment. Unlike others on the list, Tyson lost it all to good ol' fashioned excess. A few things he spent his hard earned $300 million on: Bengal tigers, Rolls Royce's, Harleys, Bentleys, Ferraris (what can we say, the man liked his cars, but don't worry some were for friends), and of course, pigeons. That's right, Mike Tyson loves his pigeons. He's spent hundreds of thousands of dollars on purchasing, caring for and breeding pigeons. He filed for bankruptcy is 2003, owing $10 million to the IRS. But thankfully has made his way back into pop culture with The Hangover movies.
