On December 25, 2002, West Virginia building contractor Andrew Jackson "Jack" Whittaker Jr. (pictured above right) won $315 million in the Powerball multi-state lottery, at that time the largest jackpot in history won by a single person. Whittaker, already worth an estimated $17 million at the time, famously pledged 10% of his winnings to various Christian charities and created the Jack Whittaker Foundation with another $14 million.
But with immense wealth also came legal problems. By 2004, Whittaker had spent $3 million fending off suits against his business, according to one of his attorneys. Whittaker became depressed and began to drink to excess. In 2003 he was arrested for DUI.
On August 5, 2003, thieves smashed the driver's window of his SUV, which was parked at the Pink Pony strip club in Cross Lanes, W.Va., and stole a briefcase containing $245,000 in cash and three $100,000 cashier's checks belonging to Whittaker. Whittaker, who had been drunk at the club and allowed to stay past its 3:00 a.m. closing time, notified police of the loss at 5:20 a.m. He claimed that he had been drugged and provided deputies with a urine sample to back his claim. Kanawha County Sheriff Dave Tucker noted that it was widely known that Whittaker routinely carried large amounts of cash with him, frequenting similar clubs and casinos. The stolen briefcase, cash and checks were found behind a nearby trash bin. Two club employees were later arrested for the theft. On January 25, 2004, thieves again broke into Whittaker's vehicle, this time taking an estimated $200,000 in cash that was also later recovered. And again in March 2004 his house was robbed of $85,000, a Rolex watch and an ostrich-skin jacket.
Things deteriorated further for Whittaker in September when the boyfriend of Whittaker's granddaughter (pictured above second from left) was found in Whittaker's home, dead from an apparent overdose. Soon after, the granddaughter herself went missing; she was found in December, concealed under a van near her new boyfriend's home, also dead from an apparent overdose. His granddaughter's boyfriend pleaded guilty a year later to hiding her body, to manufacturing a controlled substance, and to possession with intent to deliver.
Six weeks after the discovery his granddaughter's death, Whittaker's wife Jewell (pictured above next to Jack Whittaker) filed for divorce.
In January 2007, Whittaker reported to police that thieves had emptied his bank accounts through a series of fraudulent withdrawals. In March, Whittaker settled a wrongful death suit in the case of his granddaughter's first boyfriend. Whittaker had admitted to giving his deceased granddaughter a $2100 per week allowance and to only minimally supervising her even though she was in his custody.
In July 2009, Whittacker's daughter Ginger Whittaker Bragg (pictured above left), the mother of his dead granddaughter, was also found dead in her home of an apparent overdose. Authorities conducted an autopsy, though foul play was not suspected. When reached for comment, Whittaker, now with no family and no fortune, said "I wish I'd torn that ticket up."