Windy City Gridiron
The 2026 season will mark Ryan Poles’ fifth season as general manager of the Chicago Bears. Things are trending in the right direction for his regime, seeing as though the Bears won the NFC North last year and won their first playoff game since the 2010-11 season.
There’s been a lot of good to come from Poles’ tenure as Chicago’s general manager, and we’ll break down his best moves in a future article. For the sake of fairness, though, we’re starting off by highlighting some of the mistakes he’s made.
It hasn’t been a flawless tenure for Poles, which could be assuming seeing as though it took him until Year 5 to make the playoffs. Again, it’s worth noting that there’s a lot of positivity around the Bears’ organization right now, as there should be. But as we approach half of a decade with him in the role, it’s fair to provide balanced commentary and analysis.
Amegadjie is an honorable mention because he’s still on the roster, as opposed to the other draft picks on this list (spoiler alert). I’m going to give him one more offseason, though Chicago’s deeper offensive tackle could make it tougher for him to make the 53-man roster in 2026.
Eberflus was obviously a terrible selection to be the Bears’ head coach, but Poles was forced to choose between the three finalists that were identified by Chicago’s search committee before Poles even became hired. Dan Quinn was clearly the best of the bunch, but none of the three were incredibly encouraging. Eberflus’ entry on this list comes with a major asterisk, which is why it doesn’t crack the top five.
Jarrett only had 1.5 sacks in his first season with the Bears, but his contract is slightly cheaper than another disappointing free agent signing from 2025.
Though technically a third-round pick, Zacch Pickens was basically a second-round pick as the No. 64 overall pick in the 2023 NFL Draft, due to a forfeiting first-round pick by the Dolphins. He only lasted two seasons in Chicago, starting in just three games for some bad Bears defenses. He tallied a combined 1.5 sacks and 18 pressures in that time, having been released before the 2025 season in preseason cutdowns.
Pickens was a freak athlete during his time at South Carolina, but he was a raw technician who never quite developed his pad level and pass-rushing diversity properly.
The selection of Velus Jones Jr. in Round 3 was a major surprise to begin with, seeing as though he turned 25 years old just after the 2022 NFL Draft and took until his sixth year in college to put together meaningful collegiate production. The Bears needed contributors at wide receiver, but taking a raw, older prospect that early...
