The Chicago Bears, as we know them, don't get many Super Bowl chances.
Up until recently, the Bears have been futility personified. Over the last 40 years, the NFL's charter franchise is best known for one-off playoff campaigns, a random run to Super Bowl 41 in 2007, and otherwise for being one of the NFL's most popular laughingstocks. So when they feel like they have a real chance not only to end their Lombardi Trophy drought, but to open an extended window to potentially stack a few championships, it makes sense to go all-in.
NFL contention windows don't last forever. You either finish the job, or you're left with regrets forever.
That's what happened in 2018 when the Bears made a blockbuster move for all-world defender Khalil Mack. The superstar
defender would, unsurprisingly, change the dynamic of the team en route to a 12-win NFC North division title campaign. There was just one problem. While those Bears pushed their chips in with Mack, their quarterback was the uninspiring and ultimately underwhelming Mitchell Trubisky. Their lofty Mack bet was built on faulty logic about who Trubisky was. It ended with just two postseason appearances and no playoff wins because, of course, it did.
That's not the case in 2026 with All-Pro interior pass-rusher Jeffery Simmons. With the Bears, once again, swinging for the fences by trading two first-round draft picks for the mammoth defensive tackle, they're taking a bold but calculated risk on much more solid ground. This time around, the foundation they're standing on is Caleb Williams, a genuine superstar quarterback. Williams is the kind of quarterback who may have turned in a Herculean effort to put the Bears in Super Bowl contention even without Simmons' game-wrecking services.
But here, Simmons is now a Bear, expressly because of Williams. And the quarterback knows it:
Caleb Williams reaction to the Jeffery Simmons trade 😂
— Bearsszn (@bearszn) October 29, 2026
“🫣Goodmorning world ” pic.twitter.com/wMd508Sgjk
The Simmons trade represents an exciting distinction for the Bears and their fans. Simmons is in Chicago now because the Bears recognized the player they have under center and the unique moment they can take a firm grasp of. For the first time in the Super Bowl era, they have a bona fide franchise quarterback who makes it worth mortgaging future assets to surround him with core stars like Simmons. They have a guy like Williams, a player primed to be one of the faces of the NFL for the foreseeable future, whose mere presence makes it so you don't even bat an eyelash about giving up valuable draft capital to help him try to add to the Bears' considerable trophy case (pre-Super Bowl era).
That's exactly what general manager Ryan Poles and head coach Ben Johnson signaled to the football world by acquiring Simmons on Thursday. They paid the price to make Simmons their defensive centerpiece through 2030 because Williams is on his rookie contract (and therefore at his cheapest). As such, the next few years may be the best opportunity to be the last NFL team standing in February, several times.
Put another way: These Bears are ready to reach football's tallest summit because they believe Williams, specifically, is ready to go the distance.
The best part? Even if the Bears don't win a Super Bowl with Simmons, the 24-year-old Williams will afford them the chance to open at least another major contention window down the line. That's the sort of comfortable margin for error presented to you when you have a difference-making quarterback. You can take big trade swings at the plate like this knowing your quarterback will ensure the current iteration isn't going on a Last Dance-esque journey. You are afforded that sort of roster construction breathing room by default.
Thursday's Simmons trade was a seminal, turning-point moment in Bears history. It was the day they shouted from the rooftops about their special quarterback and what he's capable of to the entire football world. Soon enough, with one of the best defenders of his generation buoying him, everyone who follows the NFL might just do the same thing about Williams.
This article originally appeared on For The Win: Jeffery Simmons trade marks Bears' first Super Bowl swing with legit QB
