4 Questions the Chicago Bears Must Answer in the 2026 NFL Offseason

There are a few things the Bears can do this offseason to set themselves up for sustained success.

Oct 19, 2025; Chicago, Illinois, USA; Chicago Bears head coach Ben Johnson against the New Orleans Saints during the second half at Soldier Field. Mandatory Credit: Mike Dinovo-Imagn Images | Mike Dinovo-Imagn Images

The Bears are coming off their most impressive season since 2010. The 2018 squad may have been great, but they fell flat in the playoffs. This team certainly didn't, and they wound up being one play short from being one game away from the Super Bowl.

Some argue they were far too reliant on miracle finishes, though. Seven come-from-behind victories, with many of which coming in the waning moments of their respective game. They don't see their incredible season as anything more than a one-year wonder.

How can the Bears prove them wrong?

There are a few key questions they must answer inside Halas Hall to put themselves in position for sustained success. They have some difficult decisions to make on a few key players, and their back is against the wall when it comes to the salary cap (they're currently roughly $15 million over the cap).

I could make a list of 20 questions if I wanted to. I'm curious whether they'll view D'Andre Swift as expendable and how much value they put into Austin Booker. What they decide to do with DJ Moore will be a major topic of debate, too. However, I think those are secondary conversations (mainly because I think Moore will be back) compared to a few others to keep an eye on.

For this list, I focused on four of the most important questions on the docket this offseason.

1. How much do they trust Tyrique Stevenson?

Nov 23, 2025; Chicago, Illinois, USA; Chicago Bears cornerback Tyrique Stevenson (29) takes the field prior to a game against the Pittsburgh Steelers at Soldier Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Tyrique Stevenson's disappearance down the stretch was one of the more surprising (and disappointing) developments of the season. He provided the team with their first big defensive spark of the season after ripping the ball out of Cowboys running back Javonte Williams hands in Week 3, and continued to make splash plays over the next few weeks. He wasn't dominant by any means, but he was playing well early on.

Unfortunately, his role was limited down the stretch and became somewhat nullified after Jaylon Johnson returned from injury. Even when it looked like Johnson wasn't healthy enough to be out there, he played over Stevenson. Nahshon Wright held down the fort on the other side, and he experienced his fair share of struggles in coverage at times. Still, his playmaking potential made him a full-time player on defense, while Stevenson was on the bench.

With Wright set to hit the open market, and the Bears not really being in a position to hand him the bag that he earned this season, they have an interesting decision to make on Stevenson. He still has one more year left on his rookie contract, but do they have enough belief in him to give him back the starting outside corner job opposite Johnson? That I don't know. I'd also be surprised if he's in their plans beyond the 2026 season as it stands right now.

I know the cornerback position isn't really talked about as much as some of the other glaring weaknesses on the defensive side of the ball, but that's largely dependent on how they view Stevenson. With Johnson and nickelback Kyler Gordon having their fair share of injury issues this season at the same time, the cornerback spot would be my dark horse selection for their first-round pick in the 2026 NFL Draft. That would surely upset some pass-rush hopefuls, but the defensive line class is loaded. They might feel like it would give them the most bang for their buck.

2. Can they easily replace what Tremaine Edmunds brought to the defense?

Dec 20, 2025; Chicago, Illinois, USA; Chicago Bears linebacker Tremaine Edmunds (49) poses for a television camera with cornerback Jaylon Johnson (1) after recovering a fumble against the Green Bay Packers during the third quarter at Soldier Field. Mandatory Credit: Mike Dinovo-Imagn Images | Mike Dinovo-Imagn Images

Tremaine Edmunds is another interesting player to keep an eye on this offseason. Personally, I think he's the strongest cut candidate on the roster. They'll save $15 million by getting his contract off the books, and that might be too tempting to pass up for a team in dire need of cap relief. It's especially tantalizing because he's in the final year of the four-year, $72 million deal he signed in the 2023 offseason, and would probably walk after the '26 season with a few key offensive contracts (namely Caleb Williams and Darnell Wright) on the horizon.

The issue is that Edmunds finally started to live up to said contract this season. After years of being just a guy on the defensive side of the ball, he showed real playmaking ability this season. He was well on his way to an All-Pro caliber season and was among the league leaders in interceptions (with Nahshon Wright and Kevin Byard III) before suffering a hip injury ahead of the Week 12 matchup against Pittsburgh.

With that said, I personally think they should move on from Edmunds and prioritize resigning D'Marco Jackson, who played extremely well after Edmunds got hurt. He has familiarity with Dennis Allen's scheme after playing under him in New Orleans and would be a great low-cost replacement candidate.

3. How much confidence do they have in Theo Benedet?

Jul 23, 2025; Lake Forest, IL, USA; Chicago Bears guard Theo Benedet (79) and offensive tackle Darnell Wright (58) run a drill during training camp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

Speaking of potential low-cost replacement candidates, it will be interesting to see how they handle the left tackle position this offseason. You could've written Ozzy Trapilo's name there in Sharpie before he suffered a torn Achilles injury in the Wild Card Round matchup against Green Bay. That leaves the left tackle spot as a question mark heading into next season, but they did re-sign Theo Benedet to a one-year, $1 million contract last week.

Bears OT Theo Benedet, who was a ERFA, is officially returning to Chicago for 2026 on a 1-yr, 1M deal, per @kfishbain 👀

Great move and a very affordable price tag for Theo. He’ll have the entire offseason to improve and compete at LT for Chicago. pic.twitter.com/lUPuu5dUGP

— Bearsszn (@bearszn) February 5, 2026

It's so easy to say, 'Well, they obviously don't trust Benedet, considering they moved Joe Thuney to left tackle in the Divisional Round against the Rams instead of playing him'. However, I don't think that's such a black-and-white situation.

Feeling better about Thuney, who played left tackle for the Chiefs over a long stretch last season, being on an island against one of the league's best pass-rushers in Jared Verse (who became the first rookie in NFL history to lead the league in total pressures since the stat was created and finished sixth in pressures this season) seems reasonable to me. I don't think it's as much of an indictment on Benedet as some believe.

Benedet started eight games for Chicago this season, and largely held his own when he was out there. I don't think he would've even lost his job to Trapilo had he not gotten hurt ahead of their game against Pittsburgh. He struggled in pass protection, but was downright dominant in the running game.

I know some might scoff at the idea of Benedet protecting Caleb Williams' blindside, but I don't think it's as crazy an idea as it sounds. We've already seen that this coaching staff values player development, and it's not out of the realm of possibilities for the Canadian Eagle to get much better in pass protection over the offseason. I would much rather them roll the dice there and bring in a veteran tackle as insurance if things go poorly than draft another OT early in April.

4. How are they going to handle the safety position?

Dec 28, 2025; Santa Clara, California, USA; Chicago Bears safety Kevin Byard III (31) and safety Jaquan Brisker (9) tackle San Francisco 49ers running back Brian Robinson Jr. (3) in the first half at Levi's Stadium. Mandatory Credit: Kyle Terada-Imagn Images | Kyle Terada-Imagn Images

This is arguably the most important question the Bears must answer this offseason. All five of the safeties that were on the roster this season are set to his free agency.

Ryan Poles specifically mentioned that they wanted to bring Kevin Byard III back for another run at his year-end press conference. That really should be at the top of their to-do list this offseason, as he showed that he has plenty of gas left in the tank this year. However, it's fair to wonder if they will be able to get it done with their current cap situation.

Even if they can bring back Byard, they still will have a glaring hole at the strong safety spot if they can't bring back Jaquan Brisker. There's simply no chance that they'd be able to bring back both of them.

I think they will ultimately value what Byard brought to the room in terms of his leadership more and find a way to get something done there. Then they will go out and draft Brisker's replacement on day two (or potentially night one) of the draft.

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