You Win Some, You Lose Some: Lottery Winners Who Lost Everything

You Truly Can’t Buy Happiness

Jack Whittaker’s story might be the saddest of all on our list. When he won $314.9 million in the Powerball, it was, at the time, the largest sum ever won by a single person in American history. But after winning, he had several run-ins with the law and a string of personal tragedies.

His bad luck began a year after his win and is hard to believe. Not only was $545,000 stolen out of his car, but his granddaughter’s boyfriend overdosed and died in Whittaker’s mansion. Soon after his granddaughter succumbed to the same fate and Whittaker turned to drinking over the loss of his granddaughter. He faced a series of lawsuits amidst DUIs and gambling debts before his daughter passed away in 2009. To add insult to injury, Whittaker’s uninsured home burned down in a fire in December 2016.