Bears land aggressive Super Bowl take that will shock NFC North fans

Imagn Images

Bears land aggressive Super Bowl take that will shock NFC North fans

Originally posted on ChiCitySports | By Matthew Schmidt | Last updated Jun 3, 2026 11:18 AM ET

The Chicago Bears appear to be one of the top up-and-coming teams in the NFL right now. They won 11 games last season and captured the NFC North division title, ultimately winning their first playoff game since January 2011.

Naturally, spirits are pretty high amongst Bears fans, and why wouldn’t they be? Chicago has been starving for success for years, and now, the Bears are finally getting a taste of it.

Chicago is widely viewed as a Super Bowl contender in the NFC heading into 2026, thanks much in part to the progression that Caleb Williams showed during his sophomore campaign. But just how seriously should we be taking the Bears?

Well, Marshall Harris of 104.3 The Score doesn’t seem to believe Chicago is in great shape right now, specifically referring to the timeline of Williams’ rookie contract.

In fact, Harris thinks the Bears might have already blown their opportunity with the former No. 1 overall pick.

Have the Chicago Bears already failed Caleb Williams?

Dec 7, 2025; Green Bay, Wisconsin, USA; Chicago Bears quarterback Caleb Williams (18) reacts in the first quarter against the Green Bay Packers at Lambeau Field. Mandatory Credit: Jeff Hanisch-Imagn Images

Harris feels that Chicago hasn’t exactly put the best team possible around Williams on his rookie deal, and he thinks it will come back to bite the team.

“I don’t see, as of right now, them taking advantage of this rookie contract in the way that I had hoped. And I feel like the door has closed already, on that specific window of the Bears being Super Bowl contenders,” Harris said.

Wow. Williams hasn’t even yet started his third NFL season, and Harris feels Chicago’s Super Bowl window has already shut?

Harris’ point is that by the time the Bears are ready to win, Williams will already be making big money, and it will then be more difficult to surround him with the appropriate pieces necessary to make a Super Bowl push.

Williams becomes eligible for a contract extension after 2026, but the Bears can push it through 2028 if they so please. That would be the year Chicago would exercise his fifth-year option. But even then, Williams’ cap hit would increase each season, giving the Bears less and less financial flexibility.

I understand the general theme, but even so, it seems pretty wild to already rule out any chance of Chicago winning a Super Bowl over the next few seasons.

This article first appeared on ChiCitySports and was syndicated with permission.

More must-reads: