Sunday, May 31, 2026
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Five Moves The Chicago Bears May Regret Not Making This Offseason

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The Chicago Bears had themselves a pretty good offseason on paper. They got younger and faster on defense, headlined by the arrivals of 1st round pick Dillon Thieneman, safety Coby Bryant, and linebacker Devin Bush. They also added some extra firepower with Sam Roush and Zavion Thomas, improving both their blocking and vertical speed. Not to mention their return game. This feels like a team that got more explosive, which is not what opponents want to hear.

That said, not everything went according to plan. There were some moves made, or rather ones not made, that lots of experts believe could come back to bite the Bears at some point this season. Here are the five that stand out the most.

The Chicago Bears may soon regret some moves they didn’t make.

Signing a mid-tier edge rusher

It was never feasible for the Bears to go hunting for a true difference-maker at edge rusher this offseason. They’re way too expensive, and the odds of a good one falling to them in the 1st round weren’t likely either. Yet for them to ignore the mid-range of the free agent market entirely was a bad decision. Their explanation was that they want to give Dayo Odeyingbo and Shemar Turner fair shots to get going once they return. The problem is that both are coming off very serious injuries. Meanwhile, the Bears watched guys like Arnold Ebiketie ($4 million), D.J. Wonnum ($3 million), and Dante Fowler Jr. ($2.5 million) sign for highly affordable prices elsewhere. Any one of them could’ve been great depth at the very least. Big missed opportunity.

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A stronger push for Taylor Decker

The explanation here is that Decker is reluctant to join any other NFC North team because of his loyalty to Detroit. Perfectly admirable. At the same time, the Lions aren’t showing him the same courtesy. The Bears seem content to leave the second-most-important position on their roster in the hands of Braxton Jones or Jedrick Wills. Neither has been healthy for at least the past two seasons, and they weren’t playing anywhere near Decker’s level even when they were. In a season where your expectations are a Super Bowl, one would think adding a good left tackle is a high priority.

Finding insurance for Kyler Gordon

Fourteen games. That is how many Gordon missed last season with a slew of different injuries. In truth, the cornerback has never played a fully healthy season since being drafted in 2022. Sure enough, he was dealing with another injury before the start of OTAs. As good as Gordon can be, he’s not reliable. The Bears had to think there was a strong possibility the same problems would crop up again this season. Opponents killed them in the slot last year, which was Gordon’s area. Yet the only notable addition they made at cornerback was 4th round pick Malik Muhammad, and he doesn’t have much experience in the slot. That feels like an unnecessarily dangerous risk.

Being more serious about running back depth

D’Andre Swift and Kyle Monangai made for an excellent pair last season, guiding the Chicago Bears to the #3 rushing attack in the NFL. One can understand why the team would be content to, pardon the pun, run it back for another year. The problem is that no position in the NFL suffers attrition greater than running backs. Expecting Swift and Monangai to stay healthy for a full season feels a little too iffy. Right now, the depth situation behind them isn’t great. Roschon Johnson has health concerns of his own. Brittain Brown has minimal experience. Coleman Bennett is an undrafted rookie. If one of them goes down, the Bears could be in big trouble.

Not adding serious competition for Tory Taylor

This one isn’t talked about enough. Nobody wants to address the fact that Tory Taylor has largely been an entirely average punter since the Bears drafted him. That was no different in 2025 as he failed to crack the top ten in any of the major stat categories.

  • Gross Punting Average: 47.8 yards (13th)
  • Longest Punt: 69 yards (Tied-12th)
  • Total Punts: 60 (Tied-14th)
  • Inside the 20 (IN20): 21 punts (Tied-21st)
  • Total Punting Yards: 2,870 yards (16th)
  • Net Punting Average: 40.4 yards

The Bears drafted Taylor in the 4th round. They clearly believe in his talent. Unfortunately, it hasn’t translated to NFL success. He’s pretty much the same as most other punters. To not at least bring in some competition feels like a decision they’ll regret at some point.

Erik Lambert
Erik Lambert
I’m a football writer with more than 15 years covering the Chicago Bears. I hold a master’s degree in the Teaching of Writing from Columbia College Chicago, and my work on Sports Mockery has earned more than twenty million views. I focus on providing analysis, context, and reporting on Bears strategy, roster decisions, and team developments, and I’ve shared insight on 670 The Score, ESPN 1000, and football podcasts in the U.S. and Europe.

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