In 2002, Jack Whittaker won a $314 million Powerball jackpot which, at the time, was the biggest lottery prize in history. The West Virginia construction worker, known for his outsized cowboy hats and even bigger personality, remains one of the most extreme cautionary tales about the lottery’s power to ruin lives. Whittaker reveled in the ability to give handouts, which he did until the money ran out, donating stacks of cash to churches, diner waitresses, family members, strangers and his local strip club.
His life turned to turmoil, according to ABC News. His wife left, his house burned down, he ran afoul of the law, he lost a daughter to cancer and a granddaughter to drugs. In 2020, Whitaker died at the age of 72.