How the NFL's Hardest Schedule Could Impact Caleb Williams' Contract Extension

The strength of schedule for each team ahead of the 2026 NFL season has been unveiled, and the Chicago Bears stand at the top with the hardest expected schedule. That alone shouldn't concern Bears fans, but perhaps an odd bit of NFL history should. NFL analyst John Breech of CBS Sports posted on his X account that the team with the hardest first-place schedule has regressed by an average of four games.

How a 2026 regression could put Caleb Williams' future with the Bears in doubt

Caleb Williams' breakout season in 2025 was exactly what Bears fans had been dreaming of for years, even decades. For the first time in living memory, the Bears had a quarterback who could lead a team and be the reason why they're winning. Indeed, Williams' seven fourth-quarter comebacks, including that triumphant Wild Card win over the Packers, surpassed the great Peyton Manning for the most ever in a single season by a quarterback younger than 25-years-old.

Poles has already said the Bears are digging into an extension for their superstar passer. "Matt Feinstein is digging into it now," Poles told assembled media in February. "We’ve had some preliminary conversations because we want to take some of these things into consideration as we build the team.

Nearly everyone, even sports writers and analysts who are not necessarily Bears fans, expects Williams to continue to grow into a superstar. But what if they're all wrong? John Breech's note on the history of teams with the hardest strength of schedule suggests that they are. A four-game regression for the Bears would drop them to 7-10 in 2026, a losing record, and potentially last place in the NFC North.

If that comes to fruition, then Williams will have almost certainly regressed hard into his old, bad habits. In this scenario, Williams would be going into Year 4 still having to prove that he's a capable NFL starter.

Ryan Poles has said he's awaiting a green light to sign Williams to a massive contract extension. A regression in 2026 would not only table that discussion, but suddenly the Bears would find themselves in the discussion for teams looking to draft a quarterback in Round 1 of the 2027 NFL draft, which is expected to feature as many as six first-round quarterbacks.

Why Bears fans don't need to worry (too much) about the strength of schedule

Before any Bears fans lose all hope of a successful 2026 season, remember one thing: preseason strength of schedule is almost entirely meaningless. It's based on the winning percentages of every team from last year, and as we all know, teams often undergo radical changes from year to year. Just look at the Bears, who went from a 5-12 season in 2024 to 11 wins in 2025.

This also isn't the first time the Bears have been pegged to face a daunting schedule. Last year, the Bears ranked near the top of the preseason 2025 strength of schedule. By the end of the year, it turned out to be one of the easiest schedules in the league.

Additionally, as Breech explains in his full article on the 2026 NFL strength of schedule, the Bears are currently hurt by virtue of being in the NFC North, a division that saw each team finish 2025 with a winning record. According to Breech, this is just the second time in the Super Bowl era that any division has had every team finish above .500 in one season. That greatly inflates the Bears' strength of schedule compared to teams from other divisions.

Chicago Bears quarterback Caleb Williams watches a USC Trojans basketball game. Mandatory Credit: Kirby Lee-Imagn Images | Kirby Lee-Imagn Images

The Bottom Line

It's unnerving to see NFL history stacked against the Bears like this, especially when you consider Chicago's own history. After a dominant 2018 season that included an NFC North division title, the Bears regressed to just eight wins in 2019 and 2020. But these Bears are not your father's Bears. They've already proven to have a stronger foundation than the one-and-done teams of the past, and that's thanks in large part to the fact that they have the right head coach and quarterback for the first time since Mike Ditka and Jim McMahon were in the building.

Breech's fun fact about teams with the hardest first-place schedule is nothing more than that. A fun little anecdote that has absolutely no relevance to the 2026 Bears. Will they likely face some very good teams? Of course. They may even have to play the defending Super Bowl champions in the NFL season-opening game. But the Bears expect to be much improved in 2026, and they'll be ready for the challenges ahead.

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