With Caleb Williams making magic, Chicago Bears will be NFL's Cinderella team of 2024

The NCAA men’s basketball tournament is rocking and rolling. The ink is finally dry on the contracts that drove free agency frenzy. And that means it’s time for one of my absolute favorite annual columns: announcing my Cinderella squad for the upcoming NFL season, the team that will embody the rags-to-riches ethos of March Madness with an eye-catching rise to prominence.

In the seven previous years that I’ve done this, I’ve made selections that look good (the 2017 Jaguars, 2018 Bears, 2019 Bills and 2022 Dolphins all went on to make the playoffs) and, well … not so good (the 2020 Cardinals, 2021 Chargers and 2023 Saints did not). But one thing I’ve never done before? Choose a squad that is likely to be helmed by a rookie quarterback.

This is partly because of timing. It’s not always possible at this juncture of the calendar to say with much certainty where the top quarterback prospects will end up. And when it is possible to project a pairing this far ahead of the draft, it’s usually because a team played its way to the No. 1 overall pick in the preceding season, which usually indicates the roster isn’t ready to support a Cinderella-esque run right away.

This year is, shall we say, different.

But before we get to the good stuff, let me take a second to remind everyone of my criteria. To be eligible for Cinderella status, a team must not have made the playoffs in the previous season, and it shouldn’t be widely considered a Super Bowl contender.

The Chicago Bears currently meet both requirements, as their fans definitely know. When next March rolls around, though, my 2024 Cinderella team will not be in the running for repeat honors, because the Bears are about to win a minimum of 10 games and make the postseason.

Yes, I know this column is not meant to be a playoff prediction; I don’t usually lock those in until after Labor Day. I just have to get this bold with Chicago, because of how much I love what the Bears have done — and what they’re about to do.

First, let’s consider what they’ve accomplished so far.

I still cannot believe general manager Ryan Poles nabbed Keenan Allen from the Chargers in exchange for a fourth-round pick — that was an amazing steal. Allen might be about to turn 32, but he’s still a great receiver coming off a monster season (108 catches, 1,243 yards, seven receiving TDs). He’s an experienced, ultra-reliable veteran with great hands, route-running skills and leadership capabilities. I love how he’ll mesh with DJ Moore, a king of yards after the catch and highlight-reel plays. The Allen-Moore pairing is going to be a terrific, dynamic 1-2 punch.

The offensive improvements weren’t limited to Allen. Don’t overlook the underrated signing of Gerald Everett, who should make a solid partner for budding stud Cole Kmet at tight end. And new running back D’Andre Swift is a good runner with reliable hands out of the backfield — I liked his addition before, but it looks even better now that Allen is in the fold.

On the other side of the ball, Poles smartly retained terrific play-making corner Jaylon Johnson to headline a strong group of defensive backs (which now also includes veteran Kevin Byard). Head coach Matt Eberflus’ defense operated at a different level last season after pass-rusher Montez Sweat arrived via trade; Poles was right to hand Sweat a megabucks extension last November to continue leading Chicago’s excellent front seven. With a full season of Sweat rushing the passer (and Eberflus calling plays), the Bears’ D should become a true force.

One of Poles’ true strokes of brilliance came not this offseason but about one year ago, when he traded away the No. 1 overall pick in the 2023 NFL Draft to the Panthers. Not only did he net Moore in that deal, but he landed Carolina’s first-rounder this year … which, thanks to the Panthers’ two-win season, became the No. 1 overall pick, putting Chicago in position to make a franchise-altering selection.

I like Justin Fields, and I don’t think he was always put in the best position during his time as the quarterback in Chicago. I think he will end up starting and playing well in Pittsburgh. I understand why Poles said trading Fields to the Steelers was “probably one of the harder things” he’s had to do, but to my eyes, in terms of team-building, it was a no-brainer. Because it helped clear the way for them to add an absolute superstar when the draft kicks off in Detroit.

Caleb Williams isn’t just a solid prospect — he’s sensational. Dreamy. He’s the kind of quarterback Bears fans have been waiting on for a lifetime or longer, since the days of Sid Luckman. I interviewed him after he won the Heisman Trophy in 2022 with a college football season for the ages at USC (4,537 passing yards, 42 passing TDs, five picks, 10 rushing TDs), and his smarts, humility, team-oriented nature and leadership skills poured through.

Was his 2023 as stunningly successful as his 2022? No — but he was still fantastic, throwing 30 TD passes against five picks (plus scoring 11 times on the ground), doing his best to compensate for an awful Trojans defense. Watching Poles, Eberflus and Allen (I love that the receiver showed up!) at Williams’ pro day, it was all too easy to envision Williams embarking on a C.J. Stroud-like run of rookie genius for Chicago. (In a juicy twist, Stroud’s Texans will face the Bears in the Pro Football Hall of Fame Game this August.)

In fact, as I’ve written before, I think Williams is one of the best QB prospects of the past 25 years — and I think he’s going to have the greatest rookie season ever by a No. 1 pick at quarterback.

As the Texans did for Stroud last year, the Bears will be able to give Williams another roster-strengthening impact talent in the first round. And they won’t have to force the issue; rather, they can let the draft come to them at No. 9 overall. Might they opt for an offensive lineman? A defensive star? With two to three other QBs possibly coming off the board before that slot, could an elite receiver like Malik Nabers or Rome Odunze be there?

It’s amazing to see how much progress Poles has made following the disastrous 2022 trade for receiver Chase Claypool. Claypool flamed out, but Poles has mostly pulled the right levers since. He and Eberflus have this organization ready to take a step forward — and Caleb Williams is about to change everything.