William “Bud” Post III: He called his winnings the “lottery of death.” The Pennsylvania man, who died in 2006, won $16.2 million in 1988, but it all went downhill. His sixth wife left him. He spent time in jail for firing a gun at a bill collector. His brother was convicted for hiring a hit man to kill him. In the end Mr. Post declared bankruptcy.
Jack Whittaker: Nothing but trouble followed the West Virginian after he won a record $314.9 million in the multistate Powerball lottery in 2002. He gave away $3 million to local churches. More than $545,000 in cash was stolen from his car while he was in a strip club. His granddaughter Brandi died of a drug overdose. He was arrested twice for drunken driving and ordered into rehab and pleaded no contest after attacking a bar manager. Last year, his daughter, Brandi’s mother, was found dead.

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