Winnings: $315 million
Time until bust: 4 years

Whittaker may have been the wealthiest man ever to win a major lottery jackpot. When the 55-year-old West Virginia construction company president won a $315 million Powerball jackpot in December 2002 — at the time, the largest jackpot ever won by a single ticket — he was already worth some $17 million. And Whittaker knew to distribute his new mega-wealth, pledging to give 10 percent of his fortune to Christian charities, donating $14 million to his Jack Whittaker Foundation, and even giving a $123,000 house, a new Dodge Ram Truck, and $50,000 in cash to the woman who worked at the convenience store where he had purchased his winning ticket.

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But even Whittaker couldn’t escape his own demons. Beset by legal difficulties and personal problems, he began drinking heavily and frequenting strip clubs. On Aug. 5, 2003, thieves stole $545,000 from his car in a West Virginia strip club parking lot while he was inside. In January 2007, Whittaker reported to the police that thieves had completely emptied his bank accounts. On Jan. 25, 2004, robbers once again broke into his car, stealing an estimated $200,000 in cash that was later recovered. And a string of personal tragedies followed. On Sept. 17, 2004, his granddaughter’s boyfriend was found dead from a drug overdose in Whittaker’s home. Three months later, the granddaughter also died of a drug overdose. Her mother, Ginger Whittaker Bragg, died five years later on July 5, 2009. Whittaker himself is alleged to be broke — a claim he made as early as January 2007 for failing to pay a women who successfully sued him. He’s also being sued by Caesars Atlantic City casino for bouncing $1.5 million worth of checks to cover gambling losses. “I wish I’d torn that ticket up,” he sobbed to reporters at the time of his daughter’s death.

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