"Jack" Whittaker Jr - The once biggest lottery winner who lost $114 million in four years

On December 25, 2002, West Virginia building contractor Andrew Jackson "Jack" Whittaker Jr. won $315 million in the Powerball multi-state lottery, at that time the largest jackpot in history won by a single person. At the time, he was the president of a successful contracting firm called Diversified Enterprises Construction. 55-year-old Whittaker was living a successfully comfortable American life complete with a net worth of over one million dollars, a well rounded family, great job and healthy grandkids. After winning the prize, he famously pledged 10% of his winnings to variousChristian charities and created the Jack Whittaker Foundation with another $14 million.

Whittaker did some good, but his bad deeds make his story. He was arrested twice, once for drunk driving and once for threatening a bar manager. A woman sued him after he groped her at a dog racetrack. Thieves took $545,000 in cash from Whittaker's car while he was visiting a strip club. About a year later, thieves again stole $200,000 from his car. Caesars Atlantic City sued him for bouncing $1.5 million in checks. His wife divorced him. Then, there were the dead bodies. In 2003, Whittaker's granddaughter's boyfriend was found dead of an overdose inside Whittaker's home. His 17-year-old granddaughter, whom he had been giving a $2,100 weekly allowance, fatally overdosed months later, at a different location. His daughter—mother of the dead granddaughter—died this year of as-yet-undetermined causes. When reached for comment, Whittaker, now with no family and no fortune, said "I wish I'd torn that ticket up."(Link 1 | Link 2)