Jeffrey Dampier

When Jeffrey Dampier won $20 million in the Illinois state lottery in 1996, he spent it well. He shared it generously, buying a house for his parents, cars for his siblings and a seven-day Caribbean cruise for 38 family members. But Dampier was also having an affair with Victoria Jackson, his sister-in-law, according to Time. But Jackson was after the money. Victoria and unrelated-boyfriend Nathaniel Jackson robbed Dampier, but then Victoria ordered Nathaniel to shoot Dampier. He did, and both were subsequently sentenced to life in prison without parole.