‘Wait for my dresses’: Caleb Williams is the Zoomer QB to shake up the hidebound Bears

Among the NFL’s heirloom franchises, the Chicago Bears are the still living in the last century – the pride of George “Papa Bear” Halas, a league founding father. From their neoclassical stadium to their 101-year-old owner-matriarch to their stubborn reverence for “Bear Weather” (ie: lake-effect winter conditions that only affect the other team), everything about the franchise is old-fashioned. Even the Bears being in position to select a quarterback with the first pick in this month’s draft has arrived about 30 years too late in a league where the passing game dominates. What’s notable is that the passer in their sights isn’t the second-coming of 1940s hero Sid Luckman or a Harvard man or some other statuesque golden boy. It’s Caleb Williams, Gen Z’s poster boy quarterback.

On paper, Williams would appear to possess precisely the resume that Virginia McCaskey, the owner-matriarch in question, might describe as “the cat’s pajamas.” He went to USC – a college football program that Chicagoland’s many Notre Dame fans at least respect. He won the Heisman trophy, putting him in a league with early Bears two-way star Johnny Lujack. And Williams played most of his college games in the LA Memorial Coliseum, one of the few stadiums left that can rival Soldier Field’s antiquity – so he shouldn’t be a snob about the patchy quality of the Bears natural home turf.

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Thing is, paper is a relic of the analog world, the world the Bears lorded over once, when they won eight championships before the Super Bowl era. Williams, on the other hand, is a product of our perpetually online age. He wasn’t even born when Tom Brady was drafted, and he marches to the beat of his own drum. The 22-year-old psyches himself up for games by listening to the very un-Zoomer John Legend’s Ordinary People, which is … a choice. He pushes the fashion envelope, infamously posing for GQ in a red dress with white gym socks and sneakers. That didn’t sit well with old-school football fans. “I’m not taking him with my no1 pick,” one Barstool sports commentator posted on TikTok. “I’m not even gonna explain it. I’m trading the pick.”

And keyboard crusaders lost their minds again when Williams turned up to a USC women’s basketball game this month with fingernails painted to match his pink iPhone and wallet – which some predictably took as a sign that Williams might be gay and, thus, unfit to be the face of an NFL franchise. (Never mind that Williams has a girlfriend and that, besides, Carl Nassib proved how few people actually care about pro footballers’ sexuality.) “The most important qualities in a leader are being confident, being secure with yourself, being bold and having everyone you’re leading want to follow you,” the NFL Network’s Kyle Brandt said in Williams’s defense.

Like many modern paragons of manhood, Williams often paints his fingernails for a bit of extra flair, sometimes with subtle messages meant for his opponents. FUCK UTAH, which he wrote for a 2022 game against the Utes, was less subtle, however, and was doomed to live in infamy after Williams left USC without even once beating the Utes. It makes Bears legend Jim McMahon’s commissioner-taunting headbands look quaint by comparison.

Williams isn’t just irreverent. He’s irrepressible, taking to social media to dunk on writers who have the temerity to suggest he “has never experienced adversity” – which is their way of suggesting he plays against the Black athlete stereotype. Williams was also among the first college football stars to take advantage of the transfer portal, moving to USC from Oklahoma expressly to continue developing under coach Lincoln Riley and also prime himself for the pro game under QB whisperer Kliff Kingsbury, the former Arizona Cardinals head man now running the Washington Commanders offense. Until a few months ago, the speculation was that Williams was tying his fate to Kingsbury and DC – his hometown franchise who will pick second in this year’s draft – was a more likely landing spot than Chicago, where he allegedly had no interest in playing.

All of this deepened the loyalty Bears fans had for Justin Fields, the quarterback the team drafted with the 11th pick just three years ago. When Chicago played host to Atlanta on New Year’s Eve, 62,000 fans at Chicago’s Soldier Field chanted: “We want Fields” as he led the Bears to a 37-17 victory. The route to the Bears’ suburban practice facility was lined with campaign signs that read “In Justin We Trustin’”. But in March, Chicago shipped Fields to Pittsburgh, essentially clearing space to bring in Williams – who even makes Fields, your typical young footballer with a point to prove, look like an old curmudgeon.

Williams could have turned pro at the end of his Heisman season in 2022, but opted to remain in school to avoid being picked first by Carolina – the Clampetts to the Astor-like Bears. (And given the mess the team turned into last season, who wouldn’t say it wasn’t the right call?) He was slammed for the decision, taken on the advice of father, Carl – who, among other things, has been quick to point out that his son, already college sports’ top NIL earner, will be motivated by more than just money. In fact, rumors last July that Carl had asked prospective agents if they’d feel comfortable negotiating with NFL teams for ownership stakes were all but confirmed when league owners voted to prohibit “non-family employees” from taking equity in teams. “He’d almost be better off not being drafted than being drafted first,” Carl told GQ in February. “The system is completely backwards.”

Ever since, league insiders have dismissed Carl as a bad influence – no surprise given that the NFL draft is, essentially, a lurid TV show about Black fatherlessness. And for too many armchair pundits, his Zoomer son seems bound to be as out of place on the Bears as a 90in plasma screen inside a Victorian drawing room (over the fireplace, where the Rembrandt once had pride of place), with some fearing Williams may actually turn out to be as big a bust as USC lab project Todd Marinovich.

If Williams is being overly nitpicked, it’s because there isn’t much to criticize when it comes to his actual talent. Time and again during his college career, he was touted as the second coming of Patrick Mahomes, adept at executing plays as they were drawn up, and improvising when things broke down. Like Mahomes, Williams can make every throw you can think of and a fair few you can’t – or, as one scout calls them, the “holy shit” throws. As the draft draws near, pro talent evaluators have taken to comparing him to Aaron Rodgers – another QB known for, ahem, doing things differently, and a man with whom the Bears are hauntingly familiar.

Maybe a decade ago, when Bears football was still built around bellcow runners, hero linebackers and other Monsters of the Midway, they would have been the last team to use a top pick on a generational passer – let alone one with Black and Native American ancestry. (Some of us Bears fans are old enough to remember the slim margins Black stars like Vince Evans and Kordell Stewart were given among the team’s wider support.)

But while football fans outside Chicago weren’t looking, the Bears did something many never thought possible: they evolved. They stopped letting family members run the franchise or get taken in by the hot young GM prospect and turned the reins over to Chiefs front-office grinder Ryan Poles – who, incidentally, is also Black. (Egads, what would Papa Bear think!) Poles has been given unprecedented authority to move the team on from Fields and other popular players and rebuild around new faces like Williams and Keenan Allen, a sure-handed receiver who arrived via a trade with the Los Angeles Chargers last month. It’s almost as if Poles knows what he’s looking for in a championship team, something Bears fans haven’t experienced since Mike Ditka and Buddy Ryan were both carried off the field after a near flawless 1985 season.

What’s most encouraging: Williams, despite reports to the contrary, doesn’t just want to be in Chicago; he hasn’t hesitated to laugh at the outlandish outfits fans speculate he might wear on draft day. “Wait til; yall see draft day suit and my ladies dress,” he wrote in response to one outfit guess, the geisha-evoking cover image from Young Thug’s 2016 mixtape.

The world may not be ready for a perception-bending star QB who’s so supremely self possessed. But the league’s most hidebound franchise has only gotten so far hewing to tradition. Williams, at least, points them in a direction that’s the closest they’ve come to the future.