3 Chicago Bears Who Came Out Winning After Day One of Free Agency

Ryan Poles and Co. got off to a busy start in free agency today. They landed one of the top safeties in this year's crop of free agents, Coby Bryant, an ascending linebacker who is coming off his best season, Devin Bush, and a rotational defensive tackle who can provide some pass-rush juice, Neville Gallimore.

Notably, they also brought back two of their own players in D'Marco Jackson and Braxton Jones. I've been pining for them to come to terms with the former, and I'm honestly a bit surprised that they were able to do so with the latter. I know there was speculation that they could bring Jones back for another run, but I'm shocked that it actually came to fruition following a year in which he got benched for a former undrafted free agent (who was also re-signed earlier this offseason).

The Bears eliminated a few key weaknesses today and put themselves in a good position to knock out a few more through the draft (and the rest of free agency). This was the first step in the roster taking shape, and a few players will be waking up tomorrow feeling a lot better about their role on next year's squad than they did this morning.

Which players stood out as the biggest winners from day one of free agency?

D'Marco Jackson

I mean, this one's obvious, right? I easily could've included everyone who put pen to paper today (but that would've been really boring). All three outside acquisitions signed for multi-year deals. However, I believe that they would've signed for roughly the same elsewhere, and they'll also provide a similar impact as they would've elsewhere.

D'Marco Jackson, on the other hand, probably re-signed because he has a real chance to make an impact for the Bears in 2026. His two-year, $7.5 million deal might be relatively modest, but it's enough where you can effectively pencil him in as the team's third linebacker (at worst). I honestly don't think he would've had that type of security with another team.

#Bears are bringing back LB D’Marco Jackson on a 2 yr, $7.5 million deal worth up to 10.5 million, sources tell The Insiders. pic.twitter.com/09qRUUsfP1
— Mike Garafolo (@MikeGarafolo) March 9, 2026

Newly acquired Devin Bush will definitely play an every-down role, but I think he has a strong chance to play alongside him. TJ Edwards will still be under contract for at least one more year (barring a surprising trade), but he was already somewhat of a liability in coverage and will be coming back from a fractured fibula. Meanwhile, Jackson was their best coverage 'backer last season. He'll play an important role.

D’Marco Jackson was PFF’s 2nd highest graded LB in coverage this season, min 350 snaps
— Ilan (@ilannfl18) January 20, 2026

Braxton Jones

Again, is this cheating? Like Jackson, Jones was also brought back today. The team re-signed him to one-year deal worth up to $10 million.

The Braxton Jones deal with the #Bears is 1-year, $5M with another $5M in incentives, per sources. https://t.co/xYCoeBomvt
— Jordan Schultz (@Schultz_Report) March 9, 2026

Not a bad pay-day for the former fifth-round pick. Not a bad situation he's entering, either. He has a real chance to reclaim his starting job if he successfully regains his anchor (which was by far the biggest obstacle that saw him get benched last season), being one more year removed from surgery on his broken fibula.

With Ozzy Trapilo suffering a ruptured patellar tendon in the team's Wild Card matchup against Green Bay, his main competition for playing time will be with the man who first took his job last season, Theo Benedet. He's certainly got the leg up on Benedet as it stands right now, as the former undrafted rookie's one-year deal is only worth $1 million.

Austin Booker

Now, this one can still change. I still fully expect the Bears to add some competition to the edge this offseason, and they were reportedly in on Maxx Crosby until the price got too high. However, as it stands right now, they didn't feel urged to overpay for some of the other top pass-rushers on the open market (similar to how many other teams have).

Their lack of movement at the edge today says two things. One, they're not willing to overpay for a quality edge rusher (it was quite a booming market today). And two, they've seen enough Austin Booker to not need to replace everything he provides. A big-ticket free agent signing would've effectively done that. He'd still have a minor impact, but it'd be dwarfed. He'd be relegated to situational pass rush duty.

While I still expect them to draft an edge rusher somewhat early, that's a much greater gamble than a free agent acquisition would have been. Even if they're drafting someone in the first round, there's still a significant amount of projection that goes into that (although a first-round edge rusher would be very bad news for Booker). A big-ticket free agent signing could've spelled disaster for his role on the '26 squad. He's probably breathing a bit easier now that the market has thinned out significantly.