The first wave of free agency has passed and with the initial dust starting to settle, the Chicago Bears once again look like the offseason champs of the NFL.
Now, the team still has a long way to go and some more glaring needs to fill but things look promising in Chicago following the recent moves made by the front office.
With that being said, it's time to assess the work that's been done and how it will impact the rest of the team, including the coaching staff. The best way to do so is by breaking down the biggest winners and losers on the team following the first wave.
Bears 2025 Free Agency Winners and Losers
Winner: Caleb Williams
There's no question quarterback Caleb Williams is the biggest winner of free agency so far in Chicago. In fact, I'm willing to say he's the biggest winner in the entire NFL.
Williams was sacked a league-high 68 times in 2024 while working with an incompetent coaching staff. Just a few months later, the Bears gifted Williams the top coaching candidate, a former Pro Bowl guard, a back-to-back All-Pro guard, and the top center on the free agent market.
The only thing that can make Williams' life any better right now is adding another wide receiver option behind DJ Moore and Rome Odunze along with an upgrade in the backfield (which is sure to come in the draft at this rate).
Winner: Ryan Poles
As good as things have been for Caleb Williams this offseason, things might actually be better for general manager Ryan Poles. Poles' seat was really starting to warm up after the 2024 season and many wondered if he'd even see another year in Chicago.
The organization committed to him, and even allowed him to find his next head coach. That process was a homerun in landing Ben Johnson, and Poles' decision to allow Johnson to have a say in player acquisitions is clearly helping the entire team.
Johnson is helping restore the fanbase's trust in their top executive based on the additions they have made to this roster. I mean the level of talent coming into the building this offseason has been vastly different compared to Poles' previous years, especially on the offensive line.
Loser: Zacch Pickens
It seems like the Bears are quickly losing faith in defensive tackle Zacch Pickens. Pickens was expected to have a big role last season as the DT3 but failed to take the next step, forcing the front office to trade for Chris Williams after roster cuts.
Williams received a tender from the Bears to return in 2025 and then the front office brought in Grady Jarrett in free agency. Those two decisions knock Pickens down to DT5 at best on the depth chart.
Pickens was already finishing his sophomore season on the inactives list for gamedays and now the future looks even worse for the 64th overall pick from 2023.
Winner: Richard Hightower
As far as the additions go, no coordinator gained more than Richard Hightower in Chicago. It's pretty telling when the only pending free agents you bring back are special teams players when a new staff comes in.
The Bears ranked 5th in DVOA last season on special teams and Hightower wanted to make sure he got some of his core guys back.
The front office made that happen by re-signing Josh Blackwell, Amen Ogbongbemiga , Tarvarius Moore, and Scott Daly. Daniel Hardy and Ameer Speed also received tenders to return in 2025. It's important to keep that area of the team intact.
Loser: Dominique Robinson
Things already looked bleak for defensive end Dominique Robinson after the Bears signed Dayo Odeyingbo, not that his outlook even looked that great beforehand. It can go from bad to worse if the Bears add another pass rusher to the mix in the draft.
In a scenario in which the Bears have Montez Sweat, Odeyingbo, Dexter, a potential high draft pick, plus Austin Booker off the edge, Robinson will be the odd man out.
By the time cuts come around late in the summer, don't be surprised when the former fifth-round selection in 2022 finds his way off the roster. I'm honestly still surprised he survived the roster cuts last season.
Up In The Air: Gervon Dexter Sr.
The impact the additions of Dayo Odeyingbo and Grady Jarrett have on Gervon Dexter won't be known until we get to training camp. But we do know this, Dennis Allen prefers short/tank defensive tackles and lengthy edge rushers.
That means expect to see Dexter take over that DeMarcus Walker role as someone who could line up inside or off the edge. That's not necessarily a bad thing saying Dexter can shed some more weight and become even more explosive.
For a guy who was able to breakout in 2024, I'm excited to see what his impact can be with more opportunities to move around the formation and attack against different matchups. He's going to be a real chess piece up front if this works out the right way.
