5 Moves the Chicago Bears Must Make This Offseason

In his season-ending presser this week, Chicago Bears head coach Ben Johnson acknowledged that the season did not end the way anyone on the team wanted it to. The goal was a Super Bowl, and a heartbreaking Divisional round loss to the Rams blocked them from reaching that goal. "We go back to square one. We're back at the bottom," Johnson said.

It's back to square one for Ben Johnson and the Bears. pic.twitter.com/8S0q9ufGYd
— FOX Sports: NFL (@NFLonFOX) January 21, 2026

He's right. He put it bluntly, but Johnson is right. Despite a smashing success of a season, one that saw Caleb Williams set franchise records and included a miraculous Wild Card win over the Packers, the page has turned, and everyone will start at 0-0 in September. That means there is no more chest-beating to be done regarding what the Bears accomplished in 2025. The focus now turns to 2026 and what the Bears need to do to get better.

Towards that end, here are five moves the Bears must make this offseason if they're to have any hope of delivering on their promises and taking the next step towards Super Bowl contention.

1. Extend Darnell Wright

Darnell Wright's All-Pro breakthrough this year has silenced any debate on whether the Bears should offer him a contract extension. He's been one of Ryan Poles' best draft selections and has developed into one of the game's top right tackles. His extension should be a no-brainer.

Darnell Wright sent Shemar Stewart to the afterlife on 4th and 1 and took a teammate with him at the end. pic.twitter.com/lBIqlekZGf
— Goodberry (@JoeGoodberry) November 3, 2025

2. Re-sign Kevin Byard III

Both of the Bears' starting safeties, Jaquan Brisker and Kevin Byard III, need new contracts in 2026, and both of them are worthy of an extension. However, the Bears will likely bring back just one of them, and we got a hint at which safety the Bears will prioritize in Ryan Poles' season-ending presser. Spoiler alert: it's Byard.

It may be a tough break for Brisker, but it's what's best for the Bears. Byard is a three-time All-Pro who led the league in interceptions this season and has said that his first choice in free agency is Chicago. He may be slightly older at 32 years old, but the leadership he brings to this team is invaluable.

3. Aggressively address the defensive line

I'm not going to go so far as to say that the Bears have to swing a blockbuster trade for a pass rusher, but 2025's performance in that department was inexcusable. The Bears were one of the worst teams in the league at bringing down the quarterback, and a team that can't register sacks without sending extra rushers is one that will not advance far in the postseason.

Their first-round selection in the 2026 NFL draft should almost certainly go to the best available defensive lineman, and they need to be ready to pounce in free agency if a big name comes available. The Bears have been linked to Maxx Crosby, a five-time Pro Bowl defensive end, and a trade for him might be just what Chicago needs. Whatever they do, the defensive line must be a priority.

Maxx Crosby talking about Bears QB Caleb Williams on the Let’s Go Podcast:

“He’s a hell of a player. He’s ultra competitive. You can tell when he’s out there he’s trying to will his team to win. When you have a guy like that at QB, it permeates through the whole team.”

👀👀👀 pic.twitter.com/UBkZuWZGQK
— Bearsszn (@bearszn) January 22, 2026

4. Find a capable left tackle

In a season full of bad injury luck, none were more devastating than Ozzy Trapilo's ruptured patellar tendon at the very end of their Wild Card game. It was bad enough that this injury came so late in the season, making it unlikely that Trapilo will be able to play until halfway through the 2026 season, but it's such a catastrophic injury for a big man like Trapilo that he may never return to his pre-injury form.

Just as it seemed that the Bears had their left tackle position figured out for the next ten years, they're right back at square one. Ryan Poles needs to operate as if Trapilo isn't even on the roster at this point and aggressively seek a short-term replacement. It also wouldn't hurt to spend another Day 2 draft pick on a left tackle that could be developed into a starter.

5. Prepare for a brutal cap situation in 2027

If all goes well with Caleb Williams' development in 2026, and the 2025 season makes me believe that it will, then the Bears are going to have to reset the quarterback contract market in 2027. This is a position in which the Bears have never found themselves. Their biggest quarterback contract ever was to Jay Cutler in 2014, when he signed a seven-year deal for $126.7 million. That's a measly $18.1 million per year.

Williams' extension will blow that out of the water. There's a very good chance it ends up in the neighborhood of $260 million for a four-year deal, or $65 million per year. Make no mistake, this is a good problem to have. But it is a problem nonetheless, and Ryan Poles needs to spend this offseason positioning himself for this potentially historic contract.