8. Jack Whittaker
Full name Andrew Jackson “Jack” Whittaker Jr., Jack won over $314 million in the 2002 Powerball Jackpot. At the time this was the largest jackpot to be won by a single ticket in American history, a feat that prompted several issues with the law and even some personal tragedy. He spent his money on multiple things including strippers and philanthropic efforts. In 2003 outside of a strip club in Cross Lanes, West Virginia Jack Whittaker’s car was robbed of over $500,000 that he kept in a suitcase at all times. Another incident at the club got two employees arrested for plotting to drug Whittaker and take his money, and in even another car robbery he lost $200,000 in cash that was later recovered. In a strange turn of events the boyfriend of his grand daughter was found dead on Whittaker’s property in the Fall of 2004. A couple of months later his granddaughter was found dead and wrapped in a tarp, he took her death very hard and received a DUI a couple of years later.
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