Caleb Williams is set to make a fashion statement on Monday Night Football.
The Chicago Bears quarterback plans on wearing his controversial Caddix cleats in the team’s Monday Night Football game against the Seattle Seahawks. Williams has been fined $35,823 for wearing the cleats in each of the Bears’ last two games. But that isn’t stopping him from committing to the bit. And in doing so, he is giving me flashbacks to the stories I heard as a kid growing up about Jim McMahon spitting in the face of authority and taking the fine for wearing a headband that had NFL Commissioner Pete Rozelle in a tizzy.
For what it’s worth, we are not alone in feeling that way. Check out the lead in NFL insider Ian Rapoport’s story on the situation:
The “Punky QB” known as Caleb Williams is at it again, vowing to not only wear his banned cleats that he believes are safer but also refusing to cover up the logo.
His iconoclastic actions call back to another great Chicago Bears quarterback, Jim McMahon, whose famous battles with the NFL were a major storyline before and during Super Bowl XX.
Williams has been warned by the NFL and fined a total of $35,823 over the past two weeks. As one source close to Williams explained, it’s a matter of principle more than anything. Williams believes in his cleats and wants to spread the word.
I love a good commitment to the bit.
Oct 22, 2026; Chicago, Illinois, USA; Chicago Bears quarterback Caleb Williams (18) passes against the New England Patriots during the first half at Soldier Field. Mandatory Credit: Patrick Gorski-Imagn ImagesCaleb Williams Is Committing to the Bit on Monday Night Football
What’s next in this saga is anyone’s guess. Will the NFL turn up the heat on Williams? This anecdote from Jonathan Jones (The Athletic) suggests the league could stop Williams from entering the field of play if he doesn’t cover up the Caddix logo on his shoes (bold emphasis mine):
A Caddix spokesperson told me this week that there “are no financial ties between Caddix and Caleb Williams. Caleb is solely wearing Caddix because he chooses to do so; Caddix is not paying him.”
So if he’s not getting paid, why is he doing this? You’ll recall the pre-draft process where Williams decided to do things his own way. He didn’t have an agent, didn’t submit to combine medical testing, didn’t sign a shoe deal, etc. He enjoys being a bit of an industry disruptor. He’s not harming anyone doing it, and so perhaps he’s testing the boundaries simply for sport.
But Nike, Under Armour and Adidas pay millions of dollars to have their logos shown on the most-watched television broadcasts in the country. The NFL must protect those interests. Now that this has become a definitive “thing,” I suspect Williams — and perhaps others around the league who wear the cleat — will be forced to cover the logo or not be allowed to enter the game.
The NFL is petty enough to have someone inspect Caleb Williams’ cleats to the highest degree. Or the league could keep increasing its fines. But if the increased fines aren’t enough to stop Williams, then I can see the league going to ridiculous lengths for the sake of keeping its financial partners happy.
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