Bears receive strong warning about future contract talks with Caleb Williams

This past winter, Chicago Bears general manager Ryan Poles suggested that he was already thinking about the type of contract extension he would have to hand quarterback Caleb Williams once Williams becomes eligible to sign such a deal after the 2026 regular season wraps up. 

While the Kansas City Chiefs' recent reworking of Patrick Mahomes' contract reset the market for players at the position, it's possible that Baltimore Ravens star quarterback Lamar Jackson could become the NFL's new highest-paid player before the upcoming campaign gets underway. For a piece published on Sunday, Mike Florio of Pro Football Talk sent somewhat of a warning to Poles and Co. regarding how much money Williams' camp may want attached to an extension.

Is Caleb Williams going to want "more than eye-popping" money?

"We’ve already heard talk of Williams having expectations that would be more than eye-popping," Florio wrote. "And we also expect that Williams will make it known that he wants his contract not after the 2026 postseason ends, but promptly upon the opening of the window for a new deal after the Bears face the Vikings in Week 18. Why carry the injury risk into the 2026 postseason? No quarterback on his rookie deal has tried to do that, even though the (collective bargaining agreement) wrinkle has been hiding in plain sight since 2011."

Williams endured a tumultuous rookie season that included the in-campaign firings of both offensive coordinator Shane Waldron and head coach Matt Eberflus. Williams then thrived under first-year head coach Ben Johnson from September 2025 through the postseason. Specifically, Williams tallied seven comeback victories after trailing in the fourth quarter of games from Week 1 through a thrilling wild-card playoff win over the rival Green Bay Packers.

According to Pro Football Reference, Williams ended the 2025 regular season ranked 17th in the league among qualified players with a 58.2 adjusted QBR, 22nd with a 90.1 passer rating, seventh with 3,942 passing yards and sixth with 27 passing touchdowns.

Why Caleb Williams may get more expensive for the Bears

"Williams has been very focused on the business realities of the NFL, from even before he was drafted," Florio explained. "When the time comes for Williams to get a new deal, the Mahomes number will drive the discussion. Especially if Williams continues to be on a trajectory that could put him among the top four or five quarterbacks in football."

It sounds like Williams could want to get paid in a big way come early 2027.