#4-Chris Williams 2008, 1st Rd #14, OT
The 2008 draft was very rich in offensive tackle talent and the Bears were desperate for a tackle. I understand the position pick, but Jerry Angelo picked the wrong one. Williams came into the draft with some red flags on his durability and this was confirmed right away as Williams missed immediate time with a back injury. Jerry couldn’t seem to get anything right as there were 8 offensive tackles drafted in round 1. Of the first round tackles that year, 4 became pro bowlers and 6 became solid starters. Then, there was Chris Williams. He’s not lower on this list because the Bears needed an offensive lineman at that time. He also showed flashes when moved to guard and had some contribution, unlike the players lower on this list. Overall, this was a risky pick right away and became another unfortunate memory of the Jerry Angelo era in Chicago.
#3-Gabe Carimi 2011, 1st Rd #29, OT
I have to be honest; I thought this was a good pick that made complete sense at the time. Even with the red flags about his pass blocking ability and lack of athleticism, he had the reputation of a hard working guy which is uncharacteristic for a bust. Carimi’s NFL career started with a major knee injury after 2 games in 2011, which he never was able to recover from. Carimi started 14 of 16 games he appeared in during the 2012 season and may have well just stayed injured as he was graded #73 out of 80 eligible tackles, according to Pro Football Focus. He was traded to Tampa Bay after 2 seasons for a bag of practice footballs, further expanding the long list of Bears 1st round busts. Even though the pick made sense at the time and the Bears did not reach to get him, he lasted only 2 seasons which is dreadful for any 1st round pick. When you have trouble beating out guys like J’Marcus Webb and Jonathan Scott for playing time, you have earned the #3 spot on this list.