1. Evelyn Adams
Winning the lottery once is one thing. The odds are astronomical at best, and it's sort of like being hit by lightning (with a pot of gold at the end of it or something). Normally, if it does happen to a person, it never happens again.
For Evelyn Adams of New Jersey, however, it did happen twice, in 1985 and 1986. She won about $5.4 million total and, instead of thinking that maybe it was a sign that she should put it away or invest it or something, Adams thought it'd be a great idea to spend it all gambling in nearby Atlantic City. A little over 20 years later, she found herself broke and living in a less-than-lavish trailer park.
The moral of this story, guys? If you're batshit insane lucky to win the lottery twice, at least only blow one of the checks on whatever stupid shit you want.