Winnings: $16.2 million
Time until bust: 3 months
William Post III proved Notorious B.I.G.’s adage true: more money, more problems. After Post won $16.2 million in the Pennsylvania lottery in 1988, he fell victim to crime, bankruptcy, tragedy and simply poor spending habits. In the two weeks after he received his first annual payment of nearly $500,000, he had already blown two-thirds of it, purchasing a restaurant, a used-car lot, and an airplane. His reckless spending continued; within three months, he was $500,000 in debt. But numbers were the least of his problems. According to Yahoo News, Post’s brother was arrested for hiring a hit man to try to kill him and his sixth (yes, sixth) wife; his relatives convinced him to invest in worthless business ventures; and his landlady duped him into handing over a third of his cash. He ultimately filed for bankruptcy, and faced a stint in jail for firing a gun at a bill collector.
“Everybody dreams of winning money, but nobody realizes the nightmares that come out of the woodwork, or the problems,” Post said in 1993, according to the Washington Post.
It seemed unlikely that the windfall could do anything but good for Post, who had already endured a hard-knock childhood in an orphanage and a nomadic young adulthood. According to the Post, he told reporters that he was surviving on disability payments and had a mere $2.46 in his bank account on the day he won millions. Still, the win did little improve his lot in life, and Post allegedly claimed, “I was much happier when I was broke.” Post died of respiratory failure in 2006 at age 66, leaving behind his seventh wife and nine children from his second marriage.
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