The Bears forced Caleb Williams to contemplate losing for the first time in his career

As a high school football player in the Washington, D.C., area, Caleb Williams took his team to a championship. While in college with USC, Williams never quite took the Trojans to such lofty heights, but he did win 23 of 33 career games while also taking home the 2022 Heisman Trophy.

The Bears are a different story. The Bears, led by overmatched general manager Ryan Poles, are a poorly-oiled machine that only produces pain and angst. The Bears — and their rampant losing in the most preventable ways — are something that Williams apparently wasn’t prepared for.

You gotta feel for the kid for clearly having more hope coming into the league.

Alas, the Bears will do that to you.

On Thursday, Williams expressed unique candor about what it’s been like to suffer through the Bears’ current seven-game losing streak. They have not won a game since mid-October. Taking it a step further, they haven’t won stateside since early October.

All of this is uncharted territory for Williams. Even he couldn’t have seen the Bears’ penchant for futility coming:

“I’ve never had a streak like this of losing.”

Caleb Williams on the Bears’ 7-game losing streak. pic.twitter.com/RL0rXmGtdb

— Marquee Bears (@BearsMarquee) December 12, 2024

To Williams’ credit, he does show a lot of maturity here.

Characterizing this whole lost Bears season as a worthy learning experience for someone who expects to be a great quarterback in the NFL one day is exactly what you want to hear. It’s the cookie-cutter explanation, but it’s the right one. You hope Williams can grow from this challenging situation and learn how to channel this mess into sustained success.

Still, by that same token, if Williams is showing this much public honesty about the Bears’ failures, he’s also showing cracks in his armor. It doesn’t seem like he understood just how deep the Bears’ frustrations really went before they made him a No. 1 overall draft pick. That’s quite troubling, to say the least.

Let me help him out.

The Bears have had one winning season since current chairman George McCaskey took the team over in 2011. Including 2024, they have finished in last place in the NFC North six times in that same span. When we expand this purview, the Bears have just six postseason appearances and only three playoff wins this century.

Put another way: the Bears have a well-worn reputation as an NFC cellar dweller.

Maybe Williams will be the player to change that. He definitely has the requisite game-changing ability to transform an afterthought into a marquee NFL franchise. But for now, all of the Bears’ failures sure seem like a shock to his system.

For a quarterback as talented as he is, I don’t blame him.