William "Bud" Post won $16.2 million in the Pennsylvania Lottery in 1988, paid out in installments of roughly $497,000 a year before tax. Almost immediately, a former girlfriend sued him, claiming he'd promised to split any lottery winnings with her — a promise made before he ever bought the ticket.
In the first year alone, Post bought a twin-engine airplane he never learned to pilot, sank money into a restaurant and bar venture that failed, and handed out loans and gifts to family members that were never paid back. He also faced a string of lawsuits from people claiming a share of the winnings.
Within about a year, he was roughly $1 million in debt — on a jackpot most people would assume was impossible to lose. Things then turned genuinely dangerous: his own brother was later convicted of hiring a hitman to kill Post and his wife, hoping to inherit a share of what was left of the remaining annual payments.
Post eventually sold off his remaining future lottery payments for a lump sum just to cover debts and stay afloat, and spent his final years living on food stamps and disability payments — at one point in a truck.
He died in 2006, having gone from a $16.2 million jackpot to functional poverty in under two decades.
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