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There Is A Fun Wrinkle To Caleb Williams Vs. Drake Maye Bears Fans Haven’t Noticed

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For his first two seasons, everybody considered Caleb Williams the most disappointing quarterback of the 2024 class. Despite going #1 overall, he had to watch as fellow classmates had greater success. Jayden Daniels went all the way to the NFC Championship as a rookie. Bo Nix made the playoffs. The next year, he and Drake Maye played each other in the AFC Championship, with Maye advancing to his first Super Bowl. As frustrating as that must’ve been for Williams, it wasn’t the worst part.

No, that was losing to those same classmates in head-to-head matchups. The first was the infamous Hail Mary game against Washington in 2024. Then, Maye and the New England Patriots stomped the Chicago Bears at Soldier Field. The next season, J.J. McCarthy engineered a wild opening night comeback to win 27-24. Just like that, Williams was 0-3 against the other 2024 draft quarterbacks. The narrative was getting worse.

Apparently, that must’ve flipped a switch. Since then, Williams is 4-0 in his last four games against them, with Maye on deck.

DateMatchupClass OpponentResult
October 27, 2024Chicago Bears 15, Washington Commanders 18Jayden DanielsLoss
November 10, 2024Chicago Bears 3, New England Patriots 19Drake MayeLoss
September 8, 2025Chicago Bears 24, Minnesota Vikings 27J.J. McCarthyLoss
October 13, 2025Chicago Bears 25, Washington Commanders 24Jayden DanielsWin
October 19, 2025Chicago Bears 26, New Orleans Saints 14Spencer RattlerWin
November 16, 2025Minnesota Vikings 17, Chicago Bears 19J.J. McCarthyWin
October 18, 2026Chicago Bears 31, Atlanta Falcons 23Michael Penix Jr.Win

Caleb Williams has something to prove on Thursday night.

When he says he has much love and respect for Maye, it’s probably true. He and Williams developed a friendship coming out of college. However, the best way to describe that is like Michael Jordan with his friends in the NBA. Sure, he’d hang with them away from the court and have fun. However, once they hit the hardwood, he became a stone-cold killer. It didn’t matter what their relationship was. Jordan was going to win and would do anything and everything possible, whether his friends liked it or not.

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That is how Caleb Williams will approach this game. He knows what the media is saying. They all believe Maye is the superior quarterback. He’s had to listen to that narrative for the better part of two and a half years. Beyond that, Williams almost certainly hasn’t forgotten the last time Maye visited Soldier Field. Losing to your draft classmate while getting sacked 9 times is not an experience that just goes away. The Bears’ quarterback is plenty eager to show how much has changed.

The entire country will be watching.

If ever there was a time for Williams to stake his claim as the actual best quarterback from the 2024 class, this is it. He conquered the Daniels ghosts, sent McCarthy packing, and outdueled Michael Penix last week. Maye is his true final boss in many ways. He’s thrown 10 touchdowns in the last three games, playing some great football after a rocky start to the season. Taking him down in primetime would leave the critics nowhere left to run and nowhere left to hide. To quote Roman Reigns, they would have no choice but to “Acknowledge him.”

The biggest hurdle won’t be Maye himself, though. It will be that Patriots defense. It’s once again top 10 in the league, headlined by a strong defensive front and playmaking secondary. Williams must be on full alert against them. New England can take over games quickly if you’re not careful. They’ve allowed more than 20 points only twice in six games this season. That has to change.

Erik Lambert
Erik Lambert
I’m a football writer with more than 15 years covering the Chicago Bears. I hold a master’s degree in the Teaching of Writing from Columbia College Chicago, and my work on Sports Mockery has earned more than twenty million views. I focus on providing analysis, context, and reporting on Bears strategy, roster decisions, and team developments, and I’ve shared insight on 670 The Score, ESPN 1000, and football podcasts in the U.S. and Europe.

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