7. Janite Lee

Janite Lee decided to be generous with her money when she won $18 million in the lottery in 1993, which is a nice thought that rarely turns out well. (This is why we don't do nice things!) She donated much of her money to government-related programs and political organizations (Ron Swanson would be appalled), and even broke bread with former President Bill Clinton thanks to her contributions. She dropped $1 million on Washington University in St. Louis, Mo. to allow them to build a new library, which is named after her. 

Lee also gambled a lot, so you can see how this was not a good combination. She blew about $347,000 in a year on her habit, and ended up deep in debt to the point where she filed for bankruptcy in in 2001.