1 – Billie Bob Harrell, Jr.
In 1997, Billie Bob Harrell, Jr. won the Texas Lotto jackpot for $31 million. He decided to take the money in annual payouts, and he quickly quit his job and headed off to Hawaii with the family. He spent money on homes and cars for family and friends, donated money to his church, and purchased 480 turkeys, donating them to poor individuals. Strangers started calling his home for donations, which prompted him to change his phone number, and then he made a bad deal with a company that provides lump-sum payments to lottery winners. After his wife left him the next year, he shot himself. Shortly before his suicide, he commented to his financial adviser, “Winning the lottery is the worst thing that ever happened to me.”