Chuck Howley
This might be the only trade on the list that can be deemed “excusable.” Chuck Howley was no doubt a gifted linebacker. The Bears thought so, making him the seventh overall pick in 1958. Unfortunately the first three seasons of his career were ruined by injuries. Experts weren’t sure he’d ever be able to play after after missing all of 1960. That didn’t stop the Dallas Cowboys from dealing for him. They desperately needed talent for their young roster and felt it was worth the risk.
They were absolutely right. Howley became a pillar for the eventual Doomsday defenses of the late 1960s and early 1970s. In addition to reaching six Pro Bowls he also won a Super Bowl title and remains the only player in NFL history to win Super Bowl MVP as part of the losing team. It’s hard not to think about what might’ve happened had the Bears held on just a little longer. They could’ve teams him with Dick Butkus, who arrived a few years later.
Sigh.