JACK THE TRAGIC
This story may be the biggest tragedy to date. Jack Whittaker won $314.9 million in Powerball, a hefty amount. He may be the richest man on this list, but after a year of winning, bad luck started following him like a shadow. His granddaughter’s boyfriend died of an overdose in his mansion. Then, the same fate happened to the granddaughter. He turned to drinking for comfort and had faced several DUI charges. He was drowning in debt. And that’s not all. His daughter also passed away in 2009. Years later in 2016, his uninsured home was burned down by fire. If you’re talking about the luck of the Irish, Jack certainly had none.
