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Lions defensive end Marcus Davenport (92) sacks Bears quarterback Caleb Williams (18) in Week 2. Junfu Han / USA TODAY NETWORK via Imagn Images

3 reasons why Sunday vs. Cowboys is biggest game of Bears QB Caleb Williams' career

Originally posted on Chicago Bears on SI
By Richie Whitt | Last updated Sep 18, 2025 3:49 PM ET

The record. The opponent. The backup. Add it all up, and Sunday against the Dallas Cowboys will be the biggest game of Chicago Bears' quarterback Caleb Williams' young NFL career.

For the former No. 1 overall draft pick with immense it certainly isn't do-or-die but ... an underwhelming performance punctuated with a loss could have analysts and fans alike calling for Williams to be benched.

The three reasons Williams will be under even more scrutiny than usual Sunday afternoon at Soldier Field:

1. THE RECORD

With a loss to the Cowboys, the Bears would fall to 0-3 with two home defeats in the NFC. We already know that no team in franchise history has rallied from 0-2 to make the playoffs. Falling into an 0-3 hole would feel like the season is over before it really even began.

It would also mean Williams would have lost 13 of his last 14 starts, with the one victory coming in a meaningless 2024 regular-season finale in which the Green Bay Packers rested most of their starters for most of the game. Caleb's last legitimate win came in Week 6 last season over the Jacksonville Jaguars, 11 months ago.

2. THE OPPONENT

Williams couldn't ask for a more vulnerable defense to face with his Bears' career potentially on the line.

The Cowboys, who have a defensive coordinator named Matt Eberflus (ring a bell?), were shredded last weekend by New York Giants' quarterback Russell Wilson. Just days after NFL analysts were collectively saying he was "washed," the 36-year-old threw for 450 yards and three touchdowns. He also ran three times for another 23 yards as the Giants - a week after being held without a touchdown in their opener - put up 37 points.

Eberflus' defense is stagnant, with minimal pre-snap movement or disguise. Without Micah Parsons, the Cowboys generate no consistent pass rush. And their secondary is compounded by cornerbacks who aggressively bite on play-fakes and safeties who lack the speed to cover deep routes on the back end.

The Cowboys' pass defense ranks 30th in yards per game (301) and 31st in completion percentage (76.6) If Williams can't exploit this team, doubts will arise about him not being able to do it all.

3. THE BACKUP

It's not only the two-year, $10 million contract the Bears gave to Tyson Bagent in August that should have Williams hearing footsteps, it's the way head coach Ben Johnson talks about his No. 2.

"He and I are wired very similar," Johnson said Aug. 20 when explaining the rationale behind Bagent's new deal. "When he enters a room, he's all business. He's always locked in, and I appreciate that about him. I can relate."

That's some serious, public flirting. And it resonates even louder when this week as Johnson has spent time criticizing the Bears' offense - led by Caleb - and its lackadaisical practice demeanor.

Said Johnson, "I think our practice habits are yet to reflect a championship caliber team."

While Williams' strength is being Superman, Johnson cherishes being simple. Back in August one Bears insider predicted this crossroads would arrive at some point in 2025.

It's here sooner than we all expected. Sunday is indeed the most important start of Caleb Williams' career.

This article first appeared on Chicago Bears on SI and was syndicated with permission.

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