
21. Ricky Williams
Williams was the focus of one of the dumbest blockbuster trades in history. Mike Ditka became the Saints’ head coach in 1999 and decided he wanted the Longhorns’ running back. For some reason, the Super Bowl-winning coach believed that Williams was a potential game-changer. That’s why he traded all of the Saints’ picks to move up seven spots (via NBC Sports).

In sum, he handed over eight picks including first and second-round picks for the following season. Even if it worked out, it’s still a crazy amount for a running back. But it didn’t go well and Ditka lost his job after a 3-13 season. Meanwhile, Williams never lived up to his potential. He had a decent NFL career. It’s a shame that he had this puzzling trade hanging over him.