 His win of US$314.9 million in the Powerball multi-state lottery was, at the time, the largest jackpot ever won by a single winning ticket in the history of American lottery.After winning the lottery, he had several brushes with the law and personal tragedies.Before his lottery win, Whittaker had been the president of Diversified Enterprises Construction, a contracting firm in Putnam County, West Virginia, for 12 years.