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In 1996, the Chicago Tribune ran a story on Buddy Post, a lottery winner who is “living proof that money can’t buy happiness.” In 1988, he won $16.2 million in the Pennsylvania Lottery. Since then, he has been convicted “of assault, his sixth wife left him, his brother was convicted of trying to kill him, and his landlady successfully sued him for one-third of the jackpot.”

“Money didn’t change me,” insists Post, a 58-year-old former carnival worker and cook. “It changed the people around me that I knew, that I thought cared a little bit about me. But they only cared about the money.”

Post is trying to auction off seventeen future payments, valued at nearly $5 million, in order to pay off taxes, legal fees, and a number of failed business ventures.

He plans to spend his life as an ex-winner pursuing lawsuits he has filed against police, judges, and lawyers who...

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