Winnings: $16 million
After he was arrested for stealing a sandwich, you can almost call Michael Carroll the modern day Jean Valjean. Except that he didn’t steal to feed his family, but because he blew all his lottery winnings. Oops.
Ten years after winning a hefty $16 million prize, he was living off government benefits. Where did all the money go? He basically tried to become Leonardo DiCaprio in The Wolf of Wall Street, spending it all on drugs, pricey cars and risky investments. His partying persisted until he was more broke than he was before winning the lottery. Note to self: if you ever win the jackpot, PLEASE get a financial advisor.