From Rags to Riches to Rags Again: 21 Winners Who Lost It All

21. A Millionaire Wins the Lottery

Jack Whittaker was already a millionaire when, on Christmas of 2002, he won $314.9 million, the biggest single-person lottery win in history. He opted for a lump-sum payment, which after taxes, left him with $93 million. His contracting business, which employed over 100 people, provided a great living, but his humble lifestyle meant few people knew how much he made. The lottery winnings were apparently a different kind of income.

Whittaker spent money at strip clubs and casinos. He gave millions to charities. His habit of leaving cash in his car resulted in thefts of $545,000 one time and $100,000 another, and his house was robbed. He showered gifts and cash on his beloved 16-year-old granddaughter, who spent much of the money on drugs. A year later, she was found, apparently murdered.

Whittaker rarely speaks to the press now, and some reports say he is broke. When asked if life was easier before his big win, he said, “Yeah, it was a lot easier then.”

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