As it stands right now, the early part of the Chicago Bears’ 2026 free agency period will be remembered as kind of bland. Through the first few days, no huge trades, no massive contracts handed out, no big surprises. But what the Bears have done so far is add players at positions of need, which helps shape their draft board.
Plus, there’s still time to sign a player or two, and it’s still possible they make a trade.
It’s not like free agency is over!
While there haven’t been any big Bears’ slpashes,
the FanDuel Sportsbook odds for them to win the NFC North have moved to +340 from +400 before free agency opened up. Chicago’s odds to win the NFC are +1300 after being +1500 on Monday. And their Super Bowl odds are now +2500 after being +2700 before they made any free agency moves.
I wonder what Maxx Crosby to the Windy City would do to these odds?
Anyway, here are my Bears’ winners and losers of the first few days of free agency.
Winners
The Quarterback Room: Case Keenum returning on a two-year contract for more money is a great deal for him, and keeping a veteran player as a mentor in the room is good for the two young quarterbacks ahead of him on the depth chart. There was a small buzz about the Bears taking calls on Tyson Bagent, but nothing materialized, so keeping him in the system another year is good for the room in 2026.
Braxton Jones: The 2025 season was supposed to be Jones’ contract year, where he could cash in on four years of starting at left tackle, but a late 2024 broken ankle took away his offseason. He made it back for training camp but was never fully recovered. He gave his all, but was clearly laboring, and was benched. Another injury a few weeks later, and he was back on IR. He’ll now have a chance to win the left tackle job and show the league he’s healthy and worthy of a long-term deal in 2027, while earning up to $10 million.
D’Andre Swift: I never got the rumors about the Bears targeting a free agent running back to replace Swift. He had a productive 2025, and cutting him to spend the same (or more) would have been silly. So far, it seems the Bears are content rolling with Swift in his contract year. And considering he just turned 27, he may be able to cash in one more time in free agency next offseason.
Bears defensive coordinator Dennis Allen: There’s still some work to be done defensively, but considering the holes on the Bears’ defense, the early wave of free agency helped that side of the ball the most. He has more speed at all three levels, which was a must. But again, there’s more work to do.
Losers
Chicago’s 2025 Starting Safeties: Kevin Byard III signed a one-year deal with the New England Patriots, which is a good fit and good money for him, but it seems like he may have left some money on the table by not accepting the Bears’ offer earlier. We’ll never know what deal the Bears had for him, but rumors were that Chicago was offering him a raise over his $8.5M salary, but he wanted to explore all options.
Jaquan Brisker bounced back after an injury-plagued 2024, and he started all 17 games in 2025, but thus far, his market hasn’t materialized. There were projections thrown around north of $10M a season on a multi-year deal, but he may not get that.
Kiran Amegadjie: With Braxton back and the addition of former first-round draft pick Jedrick Wills Jr., Kiran’s path to a roster spot is becoming less likely.
Bears defensive coordinator Dennis Allen: Yep… he’s here too. Even though five of their seven free agents are on defense, the work they still have to do is to find a pass rusher (or more). Until the Bears can find a guy(s) to do that, the defense will be incomplete, and Allen will be forced to creatively get after the quarterback.
Who are your early winners and losers of free agency?
