Examining the Bears’ window to win and how GM Ryan Poles has shaped the roster

To Bears general manager Ryan Poles, it’s as simple as doing what he can to improve the team.

No extra pressure. No specific timeline. Just a combination of resources, needs and available players to help his head coach and quarterback.

That doesn’t mean there isn’t an obvious “championship window.”

The Bears added five starting linemen by the time the 2025 league year began. The offensive line is one of the league’s most improved units with guards Joe Thuney and Jonah Jackson and center Drew Dalman. The defensive line now has a Pro Bowler in Grady Jarrett and an up-and-coming edge rusher in Dayo Odeyingbo.

Last week, Poles was asked about any extra urgency being a factor in the aggressive nature of the additions.

“I think really the focus was, how can we enhance the football team,” he said. “Like I had mentioned with the salary cap and the finance part of it, we have the flexibility to do that and a lot of it has to do with how well (vice president of football administration) Matt Feinstein has kind of structured everything to allow us to … really jump on opportunities.

“Where we had trade options, again, there are two guys we are really familiar with (Thuney and Jackson) that we know can help us not only from a leadership perspective but also on the field. So when that popped open, we were able to jump on it and obviously that wasn’t part of the plan back when we were getting ready for free agency.

“I’ve always learned, over the last few years, you’ve got to be on your toes for those things that pop up so when you match kind of the flexibility in doing good stuff with our salary cap with opportunities, we were able to jump on it.”

It’s all true. The Bears had cap space, draft capital, the needs and the ability to add the players they needed. But looking at quarterback Caleb Williams and the way contracts have been structured, this is the time to strike. The Bears don’t have to be Super Bowl or bust in 2025, but Poles, coach Ben Johnson and Williams have this two- to three-year window in which to take advantage.

Ten starters have contracts that go through 2027, including Williams — who has a fifth-year option — and wide receiver Rome Odunze, who has the same option for 2028. Five more starters have two years left on their deals, while cornerback Kyler Gordon and Thuney are on contracts that expire after 2025, though, it would make sense to extend those before the start of the season.

A new head coach, second-year quarterback, lots of cap space and three top-41 picks could have created an offseason that reflected a longer runway. We’ve heard Johnson talk about stripping the offense down and starting with the fundamentals. No one will be talking Super Bowl for the 2025 Bears. The offseason could have reflected that. How would it have looked? No trades or signings of 30-somethings. Accumulating more draft capital instead of swapping picks for a pair of guards. Spending most of their money on their own, or only 26- and 27-year-old free agents, instead of committing a massive piece of the pie to five new players.

But the NFL is not about five-year rebuilds. GMs and head coaches get replaced too often. The need to be relevant is too pressing. And the Bears haven’t been consistently relevant enough — well, at least for winning.

Look at it as Poles putting together the best team possible for his job security, if you’d like, but there’s strategy here. As long as Williams is on his rookie contract, the Bears have more flexibility. He has the 24th-biggest cap hit in the league among quarterbacks. That could drop to 25 when Brock Purdy gets paid. It’s not worth wasting these next few seasons, because if Williams can finally be the Bears quarterback deserving of a massive contract, the franchise will have financial limitations that it hasn’t dealt with before.

At the 2024 league meetings, Poles referenced his time in Kansas City and the “good problem to have” when sometimes beloved players are traded or not re-signed, all in the name of continuing to contend, only with stricter economic parameters.

“Those decisions will continue to come with success,” he said. “Again, you get to a point where a quarterback starts taking up a lot of cap space or you have a better team … you can’t keep everybody.”

According to Over the Cap and Spotrac, the Bears have five cap hits that exceed $20 million in 2026 — wideout DJ Moore, defensive end Montez Sweat, cornerback Jaylon Johnson and newcomers Jackson and Odeyingbo. Jarrett’s contract has a 2026 cap hit of $19 million. Tremaine Edmunds, who will be in the last year of his deal, will count for $17.4 million of cap space, followed by Dalman at $14 million.

It’ll be an expensive year, but Poles and Feinstein know the salary cap keeps going up, and assuming they can extend Gordon and Thuney, they won’t have any obvious 2026 free agents who need to be re-signed at massive money. They can also restructure contracts and move things around, too, as they buy time before Williams is due for his new deal. A friendly reminder that the Bears haven’t given a quarterback an extension since Jay Cutler in January 2014.

The Bears would love to flip the script and eventually reach a point where they have trouble keeping good players instead of having to spend so much money to find players in free agency. That could come next year, depending on what they do in the draft at safety and on the offensive line, with left tackle Braxton Jones and safety Jaquan Brisker entering the last year of their rookie deals.

This is what happens with good teams. They have players in the pipeline and can reload — the result of that is also compensatory picks.

These are benefits that could come Poles’ way if this thing starts to go in the right direction — winning football games. Financially and draft capital-wise, they’re in a phenomenal position to build around Williams this year, and that’s what we’re seeing.

To make a comparison to 2018 for the umpteenth time, that year, GM Ryan Pace splurged in the offseason on wide receivers Allen Robinson and Taylor Gabriel, tight end Trey Burton, backup quarterback Chase Daniel and kicker Cody Parkey. He traded up in the draft for receiver Anthony Miller. Then over Labor Day weekend, he continued to take advantage of Mitch Trubisky’s contract and took the swing for edge rusher Khalil Mack.

This year’s “haul” is all linemen, and while two are on the “wrong” side of 30, was Poles not supposed to try to add guys who are leaders with Pro Bowls on their resume at positions of need? The Bears don’t need Jarrett and Thuney to dominate in 2028.

The same can be said if they use the No. 10 pick on a running back, a position that often has a short shelf life, or make another trade for a veteran. This is about creating a contender from 2025-27, and, if all goes well, create the “good problem to have” when it’s time to pay the quarterback.

Poles is being honest — he’s focusing on doing what’s best for the Chicago Bears. And what’s best for the 2025 Bears is to build a team that can make the playoffs and recognize the “window.” If the Bears can finally put it all together, maybe it will truly be a “championship window.”

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