The most recent player selected at number 39 is offensive tackle Teven Jenkins in 2021. Time will tell if this was a good selection or not but with the struggles of the offensive line, Jenkins will get enough playing time to show what he can bring to the table.
James Daniels was also selected at number 39 by the Bears in 2018. The product out of Iowa was recently signed by the Steelers in free agency. Tough loss for the Bears as the young guard was a very young and versatile player.
In 2015, the Bears selected defensive tackle Eddie Goldman at that same spot. Goldman had some good years in Chicago but was recently released.
Other players we can mention are Mark Bradley (Wr, 2005) and Mike Brown (S, 2000). Bradley wasn't a big contributor in Chicago and his NFL career lasted only 5 years. Brown was however a much better player. He played 9 seasons in Chicago and was a first-team All-Pro selection in 2001 and a Pro-Bowler in 2005.
Let's see who the Bears draft with that selection in 2022!