Jack Whittaker

Andrew Jackson “Jack” Whittaker, Jr. (born c. 1947 in Jumping Branch, Summers County, West Virginia) is a West Virginia businessman who became famous when he won US$315 million in the Powerball multi-state lottery. At the time it was the largest jackpot ever won by a single winning ticket in the history of American lottery.

Whittaker, who already had a net worth of $17 million, received a $114 million check after taxes(!!! wtf $201 million?!). 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 Whittakers 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, Whittakers granddaughters boyfriend was found dead of an overdose inside Whittakers 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 daughters mother of the dead granddaughter died this year of as-yet-undetermined causes.

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