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Jon Gruden sends Caleb Williams a warning Bears fans should hear

ByChris Pownall
Jon Gruden during the Vol Walk before a football game between Tennessee and Kentucky at Neyland Stadium in Knoxville, Tenn., Nov. 7, 2026
Jon Gruden during the Vol Walk before a football game between Tennessee and Kentucky at Neyland Stadium in Knoxville, Tenn., Nov. 7, 2026 | USA TODAY Network via Reuters Connect

The Chicago Bears escaped Tampa Bay with a 27-24 victory despite Caleb Williams throwing four interceptions. Former NFL head coach Jon Gruden liked how the young quarterback responded, but he also had a warning that Bears fans probably don't want to hear.

During Monday's appearance on Wake Up Barstool, former NFL head coach Jon Gruden discussed Williams' performance and the problems Chicago could face if those turnovers continue.

Jon Gruden warns Caleb Williams about costly mistakes

"I give Caleb Williams a lot of credit, man," Gruden said. "He overcame a lot of adversity and found a way to make plays at the end of the game, which is what the great quarterbacks do."

That's certainly one way to look at it.

Williams deserves credit for delivering when Chicago needed him. Four interceptions, however, are four interceptions. There's no getting around that, regardless of what happened in the final minutes.

Gruden wasn't about to overlook them, either.

"We all know you're not going to win a Super Bowl or a championship turning the ball over at that rate," he said.

And there's the warning.

Chicago survived Sunday night because its defense kept the game within reach. Williams eventually made enough plays to finish the job, but expecting that kind of escape every week is asking for trouble.

Gruden also offered an explanation for why young quarterbacks sometimes get themselves into these situations.

"When you get hot early, sometimes it can have a negative toll," Gruden explained. "You start thinking, man, maybe I can make all the throws."

Williams has the arm talent to attempt throws most quarterbacks wouldn't even consider. That's part of what makes him dangerous. It's also how a promising possession can turn into an interception when he tries to do too much.

The Bears need more from Williams moving forward

There's something encouraging about a quarterback who can throw four interceptions and still have enough confidence to lead his team to victory.

There's also something concerning about needing to overcome four interceptions in the first place.

Gruden believes Williams will benefit from the experience, saying he expects the Bears quarterback to learn from his mistakes.

Chicago certainly hopes he's right.

The Bears have shown they can win games in different ways, and Williams has repeatedly demonstrated his ability to respond under pressure. But the postseason won't offer much forgiveness for careless decisions.

Eventually, Chicago will encounter an opponent that turns those interceptions into touchdowns rather than missed opportunities.

Williams doesn't need to stop taking chances. He needs to get better at recognizing which chances are worth taking.

Gruden sees a quarterback capable of making winning plays. His warning was about everything Williams does before those moments arrive.

The Bears got away with it against Tampa Bay. They shouldn't count on getting away with it again.

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