Chicago has its next Michael Jordan in Caleb Williams ... at least that’s the hope

It’s the kind of photo that, years from now, might decorate a hundred Chicago sports bars: Cubs, Bulls and Bears, all coming together like some kind of Windy City Avengers. There’s the Cubs Pete Crow-Armstrong in the midst of a likely MVP season; two on-the-rise Bulls in Caleb Wilson and Matas Buzelis; and in the middle of it all, the guy who carries the hopes and dreams of an entire city on his shoulders. 

At the start of his third season, Caleb Williams stands on the doorstep of glory. He’s already given Chicago Bears fans the kind of hope they haven’t had in decades. And if he’s able to keep the reigning NFC North champion Bears on their current trajectory, well — immortality awaits. Nobody loves a hometown hero quite like Chicago.

These are exciting days in Chicago, the kind of days when you know you’re at the start of something special. Crow-Armstrong should soon steal his way to the first 40-40 season in Cubs history and, with it, the National League MVP. Both the Cubs and White Sox are currently in postseason position. The Bulls, particularly Wilson, have potential. The Blackhawks’ Connor Bedard is one of the most exciting players in hockey. Heck, even the pope is a Chicago sports fan.

But with all due respect to the other franchises, the Bears control the conversation, and it’s on Williams to run the Bears. “The entire city of Chicago is behind Caleb Williams in a way that I’ve never seen us get behind a Bears quarterback,” says Kevin Kaduk, author of the Bears By 7 newsletter. “It’s just a different feeling of confidence when he goes out there and works with Ben Johnson. What’s also cool is that he’s out and about around town. … When he goes to Wrigley Field to watch (PCA), he sits in the stands, not a luxury box.”

Granted, the bar for Williams when he arrived was on the floor. At this point in their Bears tenure, previous quarterbacks Justin Fields and Mitch Trubisky were already hopeless. Indeed, since the fabled ‘85 Bears won Super Bowl XX, Chicago has started an astounding 45 quarterbacks, virtually none of whom left any lasting impression. Don’t believe me? See how many you can name in Bears By 7’s quiz. (We’ll spot you Jim McMahon and Jim Harbaugh.)

When Chicago selected Williams with the first pick in the 2024 draft thanks to the generosity of the Carolina Panthers — the Bears’ Week 1 opponent, coincidentally enough — no analysts questioned Williams’ innate talent. Most, though, rightly questioned the Bears’ ability to unlock that talent for the good of the team.

That proved a valid fear; although Williams himself set multiple rookie records, the Bears as a whole finished the 2024 season at 5-12, costing Matt Eberflus his job. Chicago snagged Johnson from division rival Detroit, and the results were immediate: a six-win improvement, a division championship, the franchise’s first playoff victory since 2010 … and that intoxicating, unfamiliar feeling of hope.

So what do Williams and Johnson do for an encore? Work on fine-tuning an already fast machine, to start.

Williams set the franchise’s single-season passing record with 3,942 yards — yes, Chicago still has never had a 4,000-yard quarterback — and a 27-to-7 touchdown-to-interception ratio. But he did so by slinging hero balls; his completion percentage of 58.1 ranked 32nd in the league, ahead of only Minnesota’s J.J. McCarthy. A second season under the tutelage of Johnson ought to help Williams manage the little things — footwork, timing, communication — to go along with his TikTok-worthy highlights. 

“Late in some of those (2025) games, we were making some heroic plays . . . but it wasn’t necessary if we execute in the first quarter and second quarter,” Bears quarterback coach J.T. Barrett told Chicago media earlier this offseason. “We might be up two touchdowns by the time we get to the fourth quarter. We can be efficient and take what the defense is giving. You don’t necessarily have to put the cape on and make those crazy plays because you already were killing them in the first three quarters.”

Off the field, Williams is saying and doing all the right things to endear himself to Chicago. He sang the city’s praises during a sweaty appearance as he devoured blazing-hot wings on the YouTube series “Hot Ones.” And he surely lowered some blood pressures around town when he framed his future contract negotiations in terms of his love for the city.

"I obviously want to be here forever," Williams said last week, via the Chicago Sun-Times. "That's a goal of mine: to be at one place until I'm done, until I decide that it's over for me and I want to go home and ride off into the sun. ... I'll be here. "

Analysts expect Chicago to post another playoff-worthy year, potentially even another division title. However, the Bears will face the toughest schedule in the NFL in 2026 based on opponents’ winning percentage in 2025. It will be on Williams to succeed against that daunting slate.

If he’s able to lead Chicago back into the playoffs, Williams will get standing ovations at every Cubs or Bulls game he attends next year. And although we’re getting ahead of ourselves … what if, one day, he’s able to do even more than that?

“I don’t think there’s any doubt he’d be at the top of the pantheon with people like Michael Jordan, Walter Payton and Patrick Kane,” Kaduk said. “We’ve been talking about the Super Bowl XX Bears for more than 40 years, and if he finally delivered another one, we’d be talking about him for at least another 40.”