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

4. Generous to a Fault

Janite Lee won $18 million in 1993. Although her gambling habit reportedly cost her more than $300,000 per year, she may have spent more on charitable and political donations. Her generosity included $1 million for Washington University to build a new library. In 2001, she filed for bankruptcy.

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