15. Jack Whittaker Jr.
Jack Whittaker Jr. was already doing pretty well for himself as the head of a successful business when he won $315 million. At that point, though, common sense seemed to go out the window. For starters, he took the prize as a single payment, which stripped it down to just under $115 million after taxes. Then he proceeded to blow the lot. In fact, over the course of a single evening he spent $100,000 on strippers before having another $500,000 robbed from his car. In cash. Ouch.
14. Jonathan Vargas
Jonathan Vargas was only 19 when he won $35 million on the Powerball, and being young and impressionable probably didn’t help him when considering investment opportunities. That might explain why he ended up handing his money over to a man named Jimmy “The Mouth of the South” Hart. Hart planned to create a bikini wrestling league called “Wrestlicious” – and Vargas is reported to have subsequently lost everything in the deal.