Winnings: $31 million
Time until bust: 20 months
Billie Bob Harrell, Jr. thought his problems were over when he won the $31 million Texas Lotto jackpot in June 1997. Nearly broke and constantly moving between low-paying jobs, with a wife and three children to support, the first of his $1.24 million annual payouts seemed like the light at the end of the tunnel. Instead, it was the beginning of an annus horribilis for the 47-year-old Texan. It started out joyful: he quit his job at Home Depot, took his family to Hawaii, donated tens of thousands of dollars to his church, bought cars and houses for friends and family, and even donated 480 turkeys to the poor. But his lavish spending attracted unwanted attention, and he had to change his phone number several times after strangers called to demand donations. He also made a bad deal with a company that gives lottery winners lump-sum payments in exchange for their annual checks that left him with far less than what he had won. When Harrell and his wife Barbara Jean separated less than a year later, it was the straw that broke the camel’s back. His son found him dead inside his home from a self-inflicted gunshot wound on May 22, 1999, shortly before he was set to have dinner with his ex-wife. While family members disputed the idea that Harrell could have committed suicide, he clearly wasn’t happy with his life; he’d told a financial adviser shortly before his death that “Winning the lottery is the worst thing that ever happened to me.”