1) Cliff Stein Jay Cutler contract - possibly the lowest moment in franchise history. Unconscionable.
2) Frank Omiyale - not only did he suck, I remember the year after the Bears got rid of him, he was still counting like $4.5M against the cap. He continued to cripple the franchise even after he left.
3) Phil Emery's hiring - Bears fire Jerry Angelo because of bad drafting...then they bring in Angelo's former chief scout. Makes sense.
4) David Terrell - I can't remember a single thing Terrell did with this organization other than rack up parking tickets. I had a friend who coached at UM when Terrell was there, and he told me that Terrell was the luckiest "right place/right time" player because he had no football ability.