The stories originate from everywhere, from one shining sea to the other. Local SoCal legend, for example, says that there once was this USC quarterback who threw for so many touchdowns in one game—in one half!—that a cheerleading Trojan horse who gallops down the sideline after each score missed a lap because he required a breather. Thousands of miles away in D.C., meanwhile, the cherry trees of our nation’s capital whisper about a teen who clinched the Washington Catholic Athletic Conference championship with a 53-yard, on-the-nose Hail Mary. (The play even made SportsCenter, as if God’s grace weren’t reward enough.) Some of the most enduring lore springs from the losers: In certain parts of the Lone Star State, haunted memories remain of an Oklahoma true frosh who was spirited straight off the bench and into a rivalry game, turned a 28-7 deficit into a frenzied 55-48 win, and proved that one sure can, and should, mess with Texas.
So many tales of nigh-unbelievable achievements! And as it turns out, they’re all about the very same guy.
That would be Chicago Bears rookie quarterback Caleb Williams, who, in addition to all of the above, has also won a Heisman Trophy (and displayed it alongside his finest Legos); surfed the first wave of the collegiate athlete marketing and compensation movement; and, oh right, been selected first in the NFL draft. That’s not all! Sure, Williams has yet to take a single regular-season NFL snap, but the 22-year-old has inked a four-year, $39.4 million contract with Chicago; amiably butchered John Legend karaoke on Hard Knocks; appeared onstage at a Drake concert and on the mound at MLB games; modeled Gucci bags and mani inspo; and established himself—and, by extension, his new teammates—as compelling dudes to follow this season.
“The opportunity is through the roof for him,” veteran receiver Keenan Allen declares in the locker room following a preseason win over the Bengals, in which Williams threw for 75 yards in limited minutes and ran in a touchdown. “We’re all learning together, and it’s been great.” Allen is part of a trio of talented wide receivers (DJ Moore and rookie Rome Odunze being two others) that the Bears hope can help ease Williams’s transition to professional life—and help Chicago do something it hasn’t done since the (first!) Obama administration: win in the playoffs.
“With all the guys that we’ve got around Caleb, I think, just, everyone’s going to feed off one another,” tight end Cole Kmet—who was drafted by Chicago in 2020 and is somehow one of the three longest-tenured Bears players—tells The Ringer. “I know as an offense, we’re really excited about it.”
And so are football fans throughout Chicago, especially those gathered at one end of a cul-de-sac surrounded by pharmaceutical corporate campuses in Lake Forest, Illinois, all of whom are screaming for one man:
Caleb! Caleb! Caleb!!!!!!!!!!
Yes, it’s the end of another August day of training camp at the Chicago Bears practice facility, and the field is quite literally buzzing: The sonic landscape generated by the cicadas hidden up in the trees is so loud and insistent that I initially mistake it for some kind of move-along-now security alarm. And competing with the cicadas in volume is the unlikely, and only slightly unholy, harmony of Sharpie-clutching, predominantly tweenaged autograph seekers who are waiting for Williams.
Every now and then, someone’s voice rises over the clatter. “Caleb! Tell Madden to stop playin’ ya!” someone hollers in reference to the recent release of Williams’s 76 score, which is in line with other top NFL rookies but is below Williams’s personal 81-99 target range. “Did you say thank you?” scolds a kid’s mom as he shows off the other signatures he’s gotten; the boy whines that he did. “Calebwegottabirthdayboyhere!” begs a loud dad. Another voice near the sideline rings out, loud and very performatively falsetto: “CAAAAALEBBB!!!! CAAAALEBBB??!” That’s offensive lineman Braxton Jones, who’s giggling and signing some autographs of his own. Williams, from the far side of the practice field, waves and cheerfully, expertly declines to take his teammate’s bait.
Instead, the Windy City’s newest sportsman-in-the-spotlight climbs into the shotgun seat of a golf cart, fashions a heart with his hands in the direction of the mostly understanding, only slightly disappointed crowd, and is whisked away to face his next big challenge. If his fans and critics are hoping to see him really sweat, they may find themselves waiting awhile.
“Here’s what I want to know,” longtime Chicago sports radio host Laurence Holmes says on a recent Friday morning, pausing for effect like the broadcast professional he’s been for decades. “How can we balance excitement about Caleb Williams with coverage of Caleb Williams—honest coverage?”
We are seated up high in a beautiful downtown Chicago skyscraper that houses the sports radio station 670 The Score. Out in the hallway, confetti is scattered everywhere, hundreds of little festive, crumpled, hard-to-sweep vestiges of two big on-air moments from earlier that morning: (a) the conclusion of a 24-plus-hour Cubs-sponsored radiothon that raised more than half a million dollars for cancer research and (b) a farewell show for Danny Parkins, a 670 The Score vet who recently took a new morning TV gig on FS1. (Parkins’s first-day segment at the new job: a change-my-mind argument in which he declared that Williams ought to already be considered the GOAT Chicago Bears quarterback despite having appeared in zero pro games. A+, no notes.)
“Every one of our bosses … they have figured out, if we talk about it from an algorithm standpoint: Caleb Williams equals great,” Holmes tells his listeners and his recurring guest cohost, sports anchor Leila Rahimi. “It equals eyes. It equals clicks. Like, all of those things.”
The reason for a great many of those things and clicks and eyes is, naturally, Williams himself. He is, after all, a player who has been tracked and lauded (and self-promoted) since he was still in braces. He is a talent whose cold-blooded I got this style of quarterbacking is nearly impossible not to enjoy; he is a personality who has zero qualms about painting f-bombs on his fingernails, or talking openly and repeatedly about immortality, or saying things like “some opinion of a sheep, lions don’t worry about that stuff” with both a straight face and a chill demeanor that somehow don’t wind up at odds with each other.
But the reaction to Williams also has a lot to do with the history of the franchise that drafted him—and with the departure he might represent from the organization’s status quo. “The history is the history. I’m kind of done talking about it,” Bears general manager Ryan Poles said on draft night. “Obviously, we love our history here, but it hasn’t been smooth recently.”
Much like the New York Knicks or the Toronto Maple Leafs, the Chicago Bears have long been a premier yet puzzling franchise. The team has an iconic legacy, but it is rooted in successes from a distant past. Traditionally, the Bears’ finest seasons have stemmed from good old-fashioned “Monsters of the Midway” defense, because many of the team’s legends—like Dick Butkus and Brian Urlacher and the whole 1985 Super Bowl champion defensive corps—have lined up against quarterbacks, not alongside them. On the offensive side of the ball, meanwhile, the Bears have spent the past 100 years accumulating a pretty illuminating and/or upsetting collection of trivia and stats.
For example: The last time Chicago drafted a quarterback that it actually developed and stuck with—in this case, Sid Luckman—the United States had still yet to enter World War II. And the last time the Bears had an All-Pro quarterback? The 1950s! The Bears are the second-oldest organization in all of professional football, preceding a number of NFL franchises by some 70 years, yet they are also the only team that has never, ever had a quarterback throw for 4,000 yards for them in a season. (Nor have they had a QB throw for 30 touchdowns; grump-king Jay Cutler came closest to the mark, with 28 in the 2014 season.)
“There’s been a long trail of tears when it comes to quarterbacks and Chicago,” former Bears quarterback Cade McNown told the L.A. Times earlier this year; ask him how he knows. Still, once or even twice in recent seasons, many Chicago fans have gone ahead and talked themselves into believing that, for once, the team had found someone legit; that Mitch Trubisky’s ball placement or Justin Fields’s wheels distinguished them; that this guy, this time really was different. The result? One playoff win in the past 17 seasons.
On the bright side, though, that long journey has now brought them to Caleb Williams. This guy, this time? He really is different. That’s what I, and much of Chicago, have been talking ourselves into believing, anyway.
As the story goes, when Williams was 10 or 11, he and his dad identified his life’s stretch goal—to be a top NFL player—and they put together a multipronged action plan to make it happen. The first couple of steps wound up being, in practice: (a) Quit being a linebacker who had the Waterboy-inspired nickname “Bobby Boucher,” and (b) start being a quarterback who got called Superman instead. Simple as!
Since then, Williams’s journey has been one of private quarterback coaches from a young age; performance training facilities financed by an extremely invested father; 4:30 a.m. wake-ups on Saturday mornings; spreadsheets with tabs for things like “hot yoga”; a “no summers off” policy; Washington Post photo shoots; medicine balls; public speaking consultants; and personalized, optimized, specialized everything.
In this way, Williams’s path to pro football has kind of been the ultimate representation of today’s ever-escalating, always-specializing youth sports–industrial complex. His success at every level is less proof of concept than it is cautionary tale for the rest of us: what worked for him probably has far more to do with the “him” than the “what.” For young athletic strivers wanting to learn from the example of someone successful like Williams, it certainly can’t hurt to start eating right, try lap swimming, etc. Less universally applicable is this advice from Caleb’s father, Carl Williams, which is presented in the how-to book Quarterback Dads:
“When a kid decides he has a dream and is willing to work for it, you turn over whatever resources you have,” says Carl Williams. “As a parent you make the investment, you adjust your life. Honestly, it doesn’t matter if you have to refinance or take out a second mortgage. If you want uncommon results, you have to do uncommon things.”
What also stands out about Williams’s uncommon ascent from just-a-kid-out-there to prized college recruit to sophomore Heisman winner to no. 1 draft pick is how remarkably smoothly it dovetailed with some of the most sweeping structural changes to ever hit college athletics.
On July 4, 2020, in a video featuring holiday fireworks, Williams announced his commitment to play football at Oklahoma under head coach Lincoln Riley. Williams and his dad sought out Riley because he’d coached high-profile NFL-bound QBs like Baker Mayfield, Kyler Murray, and Jalen Hurts, although at first the Sooners didn’t seem like the ideal option: Another quarterback in Williams’s same recruiting class, Brock Vandagriff, had been committed to Oklahoma since 2019. But Vandagriff ultimately decommitted to play closer to his home in Georgia, which opened up a spot for Williams behind then-Sooners starter Spencer Rattler.
So it was perfect synchrony when, in the summer of 2021, the new “NIL” rules enabling college athletes to monetize their name, image, and likeness went into effect—just as Williams began a rookie collegiate season in which he would take over the starting role by early October. Between then and now, the L.A. Times reports that Williams amassed a portfolio of endorsements worth an estimated $10 million.
Equally crucial for Williams was the change to the NCAA’s transfer policy. Previous generations of players who wanted to switch programs were required to sit out of competition for a year, even as coaches were able to move freely for greener pastures. But when Riley abruptly left Oklahoma for USC around the Thanksgiving of Williams’s freshman season, the quarterback found himself with options that would have been unavailable to him even a couple of years earlier.
The route he chose—following Riley to USC—boosted his profile, earned him new business deals, and set him on the path to winning a Heisman. And this April, after Williams was drafted by the Bears with the first pick, he described to reporters the hypergrowth mindset that had helped get him that far. “You put dreams and goals in front of you that you aren’t able to reach within a year or two,” he explained, “and you try to go get ’em. You have to consistently not get tired with consistency.” His ultimate goal, he has repeatedly said, is “immortality”—the kind that can be achieved only via an NFL championship.
One realm in which the Bears have been extremely consistent as of late, much to the despair of their biggest fans, has been their lousy record against the Packers. Chicago hasn’t beaten Green Bay since 2018, which means that there is but one (1) player in the Bears organization who even knows how it feels for the Bears to nab a W over the Packers. (And that one player, long snapper Patrick Scales, was recently put on the injured reserve list.) During my week of Bears reporting, one of the things that stood out to me most starkly was just how deeply embedded the Packers are within the psyche of the typical Chicago fan. If I’d had a few more days in town, I might have considered setting a timer every time I met a new Bears supporter to track how long it took for them to mention the Packers in an unsolicited and aggrieved way.
Ahead of a home preseason game against the Bengals in mid-August, one fan who brings an enormous teddy bear to the tailgates tells me that when the Packers last came to town, he’d dressed the bear in an Aaron Rodgers jersey and a giant diaper. At one training camp practice, someone else tells me that someone else once told them that, as an organizational rule, the Bears operations staff never sets out relish next to mustard at Soldier Field, because screw the green and yellow! (This is almost certainly an urban legend, but I find it delightful and choose to believe.)
One friend of mine from Chicago laments the unfairness of how, between 1992 and now, with a tiny handful of one-off exceptions, Green Bay has enjoyed an unusually stable line of quarterback succession, moving directly from Brett Favre to Aaron Rodgers to Jordan Love. I try twice to count how many people lined up under center for the Bears over that same time period but lose track both times; just know that both Kordell Stewart and Jim Harbaugh are on the list. I revisit old Bears stories written by my former colleague and noted Chicago fan Robert Mays, noting his bitter aside at one point that “a certain team from Nowhere, Wisconsin, has become America’s Darlings”—and then realize he wrote that almost 13 years ago.
When I enter the stadium for the Bengals game, I see that Simone Biles is on the sideline to cheer on her husband Jonathan Owens and think, “Ah, that’s nice!” Little do I know that in addition to her bucket hat and medical walking boot, she’s wearing a garment that features images of Owens from his time on a former team—you guessed it, the Packers—a choice that triggers legions of Bears fans. A couple of nights later, during the Democratic National Convention that’s being held in Chicago, the United Center crowd boos Wisconsin Governor Tony Evers for mentioning the Packers during a speech.
Of all the Packers-related indignities, though, one that really kinda stung took place during last season’s opening NFL weekend. Following a pleasant 2023 preseason that raised expectations for the Bears in general and for their third-year quarterback Justin Fields in particular, Chicago lost to Green Bay in a game best summed up by the pick-six Fields threw in the fourth quarter. That put the Packers up 38-14—and the fact that the Bears narrowed the final score to 38-20 cheered up exactly no one. The Bears “were telling us the whole time they were good. They weren’t good!” Rahimi reminds 670 The Score listeners about the 2023 offseason, shaking her head at the memory. “I do not want them to get embarrassed again like they did against Green Bay last year!” That game was the beginning of the end for Fields, who is now a Pittsburgh Steeler. And it’s one more strange chapter that Bears fans would like to forget.
These days, Chicago is firmly Williams’s team. And at the combine this spring, when a reporter brought up the fact that the Bears have struggled at QB for ages, Williams—who hadn’t yet been drafted—both did and didn’t engage. “I don’t compare myself to the other guys,” he said. “ I think I’m my own player.” He could have stopped there and been done with it, but instead he continued. “I tend to create history and rewrite history,” he said, sticking to the facts.
Williams tries to do just that during the Bears-Bengals preseason game. With the song “Family Ties” ringing through Soldier Field, he runs onto the field to the cheers of an appreciative, if rain-drenched, crowd. But when Williams and his offense start things off with back-to-back-to-back three-and-outs, the crowd grows vewwy, vewwy uneasy. The intermittent rain adds to the sense of mild gloom, and I start thinking about an earlier conversation I’d had with a fan at the tailgate. “I feel kind of bad in a way for Caleb,” that fan told me, “because at some point he’s going to have a bad game. And if Justin Fields is starting at that same time, and has a great game? It will take this crowd a half hour to say, damn, what do we do?”
It’s true that this threatens to be a Bears season marked by people overreacting in both positive and negative directions to everything that happens. But during the Bengals game, head coach Matt Eberflus resists becoming one of them. He lets the top unit stay in a little bit longer, and eventually Williams and his teammates begin to thrive. “We got settled in and Caleb started to turn it up a little bit,” Allen tells me afterward, “and then everybody just fed off that.”
Williams turns it up incrementally at first, connecting with Bears newcomer Gerald Everett to help set up a field goal early in the second quarter. Then, with a few minutes left before halftime, he goes full volume: bailing out of a second-and-10 broken pocket, rolling left, whipping the ball across his body for a 45-yard completion up the sideline to his fellow rookie Odunze. Three plays later—after a wee rookie “Tony Toe-Tap” mistake by Odunze negates what looked like a sure touchdown pass—Williams takes matters into his own hands, tucking into the end zone for a huge exhale of a touchdown run and exiting the game with a 10-0 Bears lead.
During his postgame press conference, when he’s asked about that cross-body 45-yarder, Williams remarks that it’s a skill he’s long associated with Aaron Rodgers—and then immediately interrupts himself. “And I know, he was a Green Bay guy,” he says dramatically, grinning and rolling his eyes. “Sorry, guys.” For a guy so focused on throwing, Williams clearly also catches on fast.
It’s always difficult to parse the hope from the cope during NFL training camp, that glorious golden season of players who are in the best shape of their lives and coaches who are really connecting with their guys. But to be a Bears fan is to live forever in a state of skepticism—about how long Williams sometimes waits to throw the ball, about this whole oddly handled “new stadium” hubbub, about how many games Nate Davis will play this season, and on and on. (Bears chairman George McCaskey, just the other day, felt the need to ask fans to please be patient with Williams.)
But it’s hard not to feel the excitement generated by a player like Williams. Safety Kevin Byard, one of several key new Bears acquisitions this offseason, tells reporters, “You don’t really see that type of moxie, that type of, you know, poise, from a rookie quarterback.” Kmet shakes his head with a mixture of appreciation and disbelief when a reporter asks whether the experience of playing with Williams feels distinct from what it was like to work with past Bears QBs. “Oh yeah,” the tight end says immediately. “He’s different. For sure.”
This summer, whenever Williams has been asked about how he handles the pressure that accompanies his skill and his position, he has rejected the premise again and again. “Pressure isn’t a word that I use in my vocabulary, really,” he said on SiriusXM Radio. “Pressure comes from not being ready. Pressure comes from not having confidence.” When athletes say this sort of thing, it’s usually total bullshit or braggadocio—or, more charitably, an attempt to trick oneself into confidence and/or serenity. But as Williams says it, I believe it, in large part because he has historically been open about the way he thinks and feels and operates.
In November 2023, when he went viral for crying in his mother’s arms on camera after one particularly dispiriting USC loss, various people tried to get in their swipes. “How are you gonna come in the huddle as a rookie?” snarked Amani Toomer. “You got your nails painted, you got your tissues in your back pocket. You know where your mom is in the stands, you go crying to her. Come on, man!” The OC Register quoted an anonymous NFL scout who scoffed: “Can you sit here and say [Williams] has 12-out-of-10 mental toughness after seeing that? I don’t think you can.” Another anonymous scout compared Williams to Prince, as if that were even remotely an insult.
The way Williams sees it, this sort of reaction is a sign of someone who must not have that dawg in them. “When you spend so much time on something or someone, when you feel as if you’ve lost or lost someone,” he told The OC Register, “I’d hope and expect that you show some emotion. And that’s what I do. And I don’t see any—I don’t have no shame about it.” When it comes to the subject of his painted nails, Williams has the same knack for disarming by downplaying. “I think it’s just something cool that I do,” he told The Washington Post. In a conversation with GQ, he pointed out that with all the noise and trash talk that takes place around him in a given week, sometimes it’s just nice to go to the nail salon, throw on some headphones, “and kind of just let the nail tech go at it,” Williams said.
In the locker room after the Bengals game, corner Jaylon Johnson, who by virtue of being drafted waaaaay back in 2020 has now played for the Bears for longer than all but two of his teammates, buckles up his chunky Prada sandals and tells me that he’s noticed a broad sense of growth and momentum within the franchise that goes beyond just Williams. “When you’ve been around long enough, you get to see the change, the transformation, certain things,” he says. “Addition, subtraction, the change of culture. For me and some of the other guys who talk about it, you definitely kind of feel it, just throughout the building sometimes.” Kmet, who was also drafted in 2020, seconds this assessment, even if it sometimes rattles him that at the tender age of 25, he’s now considered a wise veteran on the team. “At heart, I’m still a kid, you know?” Kmet tells me. “I’ve been through a lot these past four years, but definitely excited about the direction that we’re heading here.”
The next day, I stop into the Art Institute of Chicago—yep, that very one!—located between 670 The Score’s confetti’d studio and the Bears’ embattled Soldier Field, a powerful trio of cultural monuments indeed. I’m there to check out a collection of Georgia O’Keeffe’s cityscapes, most of which were completed in the 1920s, and as ever, I cry a bit, or maybe a lot.
Spending all this time around the Chicago Bears has turned me into someone extra-keenly attuned to the glorious wonders of days gone by (ha, “turned me into”).
Showcased on one wall in the O’Keeffe exhibit is a remark that the artist made about how she managed to drum up attention in her artwork back in those days. “I’ll make them big like the huge buildings going up,” it reads. “People will be startled; they’ll have to look at them—and they did.” Spending all this time around the Chicago Bears has apparently also turned me into someone who is constantly pondering Caleb Williams, and this quote makes me think of him, too. Over the course of his career thus far, Williams has moved himself through the world with a similar kind of intention. First he makes you look, and then he keeps you watching.
And if it all ends in tears? Well, that will just prove how much you care.
