7. Jack Whittaker ($314.9 million in 2002)
Unlike other American Dream stories of winning a lottery, Jack Whittaker was already a millionaire even before he won the lottery.
Santa seems to think he was a good boy because in Christmas 2002, he won the biggest single ticket lottery jackpot that time. It was a Powerball’s $314.9 million jackpot. He took the lump sum option and brought home $93 million after taxes.
Before the win, Jack was providing good life for his 100 employees. He was living a humble life himself. But the lottery turned it all upside down. He spent his millions on strip clubs and casinos.
It was a series of unfortunate events for Jack upon winning the lottery. His house was robbed. Thieves took hundred thousands of dollars from him. And his daughter, who was later murdered, was addicted to drugs.