Jack Whittaker
Winnings: $315 million
It’s always nice to get money as a holiday gift, but Jack Whittaker (literally) hit the jackpot when he won over $300 million on Christmas morning in 2002.
Sadly, the most exciting moment of his life quickly turned into a series of loss, tragedy and heartache. Despite being a millionaire even before winning the lottery, he quickly became financially irresponsible. He gave over $50 million, became a heavy gambler and was robbed of nearly $600,000 when his car was broken into. His response when asked why he would carry that much cash? “Because I can.”
Whittaker’s personal life was even more heartbreaking. His marriage fell apart, while his 18-year old granddaughter and 42-year old daughter both tragically passed away under bizarre circumstances. His uninsured home was also destroyed in a fire in 2016, though fortunately nobody was hurt.
“You know, my wife said she wishes she’d torn the ticket up,” Whittaker said in 2018. “Well, I wish I would’ve torn the ticket up too.” The good news is that he says his losses have taught him the most (ironically) valuable lesson – money isn’t everything, family is.