Jack Whittaker is a big proponent of the theory that he was cursed by the lottery. Whittaker won a whopping $315 million in the 2002 Powerball. Whittaker "donated" money to a strip club, which is where his first instance of bad luck took place: his car was broken into and $2,000 was taken. A year later his car was broken into again; this time, the thieves hit the jackpot: $200,000. Then the accidental deaths began. His granddaughter's boyfriend was found dead of a drug overdose in Whittaker's house. A few months later, his granddaughter also died of a drug overdose. Five years later, his daughter was found dead.