Chris Chelios

In 1999, Chelios was traded to the Detroit Red Wings, the division rival team that he had learned to hate as a boy cheering for the Chicago Blackhawks and as an adult playing for them. He was sorry to leave his hometown, he said, but if he had to be traded he wanted it to be to a team that had a chance of winning the Stanley Cup. Fitting in with his new team was tough at first—"It's sort of like letting Public Enemy No. 1 free and telling his enemies that they have to make friends with him," Chelios said to Sporting News reporter Larry Wigge in 2000—but eventually it all came together. In 2002, Chelios achieved his goal, winning his second Stanley Cup at the age of forty.