Jack Whittaker was already a successful construction company owner in West Virginia when he won a then-record $315 million Powerball jackpot in December 2002 — at the time the largest single-ticket lottery prize in U.S. history. He took the lump sum, roughly $113 million after tax, and immediately pledged large sums to charity and his church.
Whittaker developed a habit of carrying large amounts of cash, which made him a target. He was robbed twice of money left in his vehicle — once outside a strip club — with combined losses reported around $745,000. He was also sued by a casino over roughly $1.5 million in bounced markers, and picked up multiple DUI arrests along the way.
The fallout reached his family directly: his granddaughter, to whom he had given large amounts of cash after the win, died in 2004 in circumstances he has publicly linked to the money itself.
By the mid-2000s, Whittaker said openly that he wished he had torn up the winning ticket. His marriage and business relationships were badly strained, and much of the goodwill from his early charitable giving was overshadowed by the years of scandal that followed.
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