William Post

When William Post earned $16.2 million in 1988, he probably felt he had addressed all of his issues. But within five years, he was complaining about how no one understands what a horror of having money is. Post was the only one who knew. After he won, his brother placed hit on him in an attempt to murder him.

Post was sued by his previous landlord, with whom he had made an agreement to split his profits before he won. Post was unable to comply with the court's order to provide her with a third. He'd developed a terrible habit of squandering his yearly installments on frivolous and pointless purchases. He bought a lot of cars for one of his brothers, a restaurant for another, and a jet for himself despite having no pilot's license. He continued accruing debts and then bought more useless things.

To get out of debt, he auctioned off his 17 remaining yearly payments, then spent the majority of the proceeds on additional crap like a yacht, two more residences, and automobiles. As a result, when he passed away in 2006 he was living on disability and poor.

Lottery Winning Year: 1988

Nationality: American