10 People Who Won the Lottery — Then Lost it All

55-year-old Jack Whittaker ran a successful contracting company in West Virginia when he won a $315 million Powerball jackpot. At the time, it was the biggest amount ever won by a single ticket.

Whittaker, who already had a net worth of $17 million, received a $114 million check after taxes. He gave money to Christian charities and a personal foundation supporting low-income families.

Whittaker did some good, but his bad deeds make his story. He was arrested twice, once for drunk driving and once for threatening a bar manager followed. A woman sued him after he groped her at a dog racetrack. Thieves took $545,000 in cash from Whittaker’s car while he was visiting a strip club. About a year later, thieves again stole $200,000 from his car. Caesars Atlantic City sued him for bouncing $1.5 million in checks. His wife divorced him.

Then, there were the dead bodies. In 2003, Whittaker’s granddaughter’s boyfriend was found dead of an overdose inside Whittaker’s home. His 17-year-old granddaughter, whom he had been giving a $2,100 weekly allowance, fatally overdosed months later, at a different location. His daughter—mother of the dead granddaughter—died this year of as-yet-undetermined causes.

In this messiest of lotto stories, nobody seems to have won.