9. Billie Bob Harrell Jr.
When Billie Bob Harrell Jr. won $31 million in the Texas lottery back in 1997, he was a former Pentecoastal preacher working as a bag boy in a Home Depot. The win seemed, for lack of a better term, heaven-sent, but the outcome was hardly that.
He bought himself a few things, like a home and cars and things of that nature, but he ended up loaning out a lot of his money to so-called friends and family who came out of the woodwork upon hearing of his newfound riches. No surprise, he never received any of the money back, and he was broke within two years. Sadly, Harrell committed suicide in 1999, only 20 months after initially winning the lottery. Hopefully his "friends and family" feel some guilt about it.