When Ben Johnson became the Chicago Bears' head coach, after being a hot candidate for head coaching jobs in prior years, getting to work with Caleb Williams was a clear differentiator for him. The young signal caller's raw talent was not in question, but now he'd have someone who could mold him into a quarterback.
Williams made some noticeable strides last season, but there's more work to do as he eyes taking another step in 2026.
With that next step, Williams would put himself in a position for a nice contract extension when he's eligible for one next offseason. The Bears could kick the proverbial can down the road a bit by picking up his fifth-year option, but waiting will just make a long-term deal more expensive as other quarterbacks get new contracts.
Bears are entering unchartered territory with Caleb Williams
The last time the Bears had someone who looked like a legit long-term franchise quarterback.....well, failure to reach a particular statistical benchmark tells us all we need to know there. Williams looks poised to put an end to both of those concerns,
In the wake of the notable contract adjustment the Kansas City Chiefs gave Patrick Mahomes, Eva Geitheim of SI.com pointed to four quarterbacks who are next in line to get paid. Williams rounded out the group.
"Like (Drake) Maye, Caleb Williams will become extension eligible next offseason. Also like Maye and the Patriots, the Bears can wait until the 2028 offseason to re-sign Williams if they so choose, though the price tag will likely be even steeper by that point."
"Williams is on the path to superstardom. Though he still needs to find greater consistency on the gridiron, if he continues on his current trajectory, he could be in for a stellar season and one worthy of a top-10 quarterback payday."
Williams would not be at all likely to reset the top of the quarterback market with his second contract, but landing in the top-10 based on annual average is certainly in play.
Geitheim also noted how the Bears are headed toward unchartered territory with Williams.
"There is little indication for how the Bears will go about Williams’s eventual extension. The Bears have not signed a quarterback to a second contract since Jay Cutler in 2014, who they inked to a seven-year deal through 2020. Cutler was on a new team by 2017. Overall, the Bears have not signed a first-round pick to a second contract since 2014 first-round pick Kyle Fuller, who they didn’t re-sign until after placing the transition tag on him. The Bears will certainly extend Williams at some point, the questions will be when and for how much."
Beyond not having signed a quarterback to a second contract since Cutler, the Bears' first-round picks haven't proven worthy of second contracts lately. Of course, the latter thing is set to change soon, when right tackle Darnell Wright gets a contract extension, but overall that run of not being in a position to dole out big second contracts stands out.
Read more: 5 Chicago Bears who could easily be first time Pro Bowlers in 2026
Barring something absolutely unforeseen, the Bears will gladly pay Williams what the market says he's worth when the time comes. It's just a matter of time/timing, followed by the length and cost of the contract.
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