27. Chicago Bears – Trading For Quarterback Jay Cutler
The Chicago Bears thought they had a steal after then-Denver Broncos head coach Josh McDaniels had essentially run Jay Cutler out of town. After all, Cutler had just thrown for over 4,500 yards in 2008 and looked like he would only get better. Thus, the Bears traded Kyle Orton, two first-round picks, and a third-round pick to get Cutler.
But the Bears ended up being terribly wrong. Cutler ended up spending eight years in Chicago, with the Bears reaching the playoffs just once in that span. The longer Cutler remained with the Bears, the worse things got and the worse that trade looks.