Ted Morrison / Gallery Stock

Winnings: $18 million

Time until bust: 8 years

Janite Lee was the rare lottery winner who chose to spend her brand-new wealth on someone other than herself. Lee, an immigrant from South Korea, was working at a wig shop when she hit the Illinois Lottery in 1993. After moving her family into a million-dollar gated community in St. Louis, she spent much of her $620,000 a year on philanthropic efforts. Her political contributions found her dining with Bill Clinton and Al Gore, and her educational donations put her name on a reading room at the Washington University School of Law. But she sold the rights to her annual payment for a lump sum, and in less than a decade Lee was in bankruptcy court to put her debts to rest. When the 60-year-old Lee filed for Chapter 7 in 2001, she had less than $700 to her name and $2.5 million in debts.

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