Winnings: $20 million
Time until bust: 9 years
Jeffrey Dampier used the $20 million he won from the Illinois Lottery in 1996 to start a popcorn business and to purchase presents for family members — including his sister-in-law Victoria Jackson, with whom he was having an affair. But Jackson turned on him in 2005, when she and her boyfriend Nathaniel Jackson (no relation) plotted to rob Dampier. After the couple bound his hands and feet, Nathaniel forced Victoria to make a choice: “Shoot him or I’ll shoot you,” he reportedly said. Victoria chose to live, and the owner of Kassie’s Gourmet Popcorn in Tampa’s Channelside entertainment district perished from a bullet to the back of his head.