CHICAGO (WGN) — Esquire’s Brian O’Keefe recently profiled Chicago Bears quarterback Caleb Williams as a part of the fashion magazine’s “Mavericks of Sports” package, where they made him the cover athlete. Williams’ combination of style, business acumen and mystery around his future in the NFL made him ideal for the feature, according to O’Keefe.
“I would say Caleb really fits the profile of an Esquire guy in a lot of ways,” O’Keefe said. “First of all, he’s very interested in style and fashion, which of course, is something that we cover. He’s kind of a renaissance man in certain ways. He’s interested in business as well as being a great athlete. And I think he’s a guy where there’s some tension hanging over him.
“He’s had an incredible college career, went No. 1 overall in the draft. The team and the fans were relying on him to be a franchise quarterback and it was a bumpy ride the first year, as it is for a lot of young quarterbacks so, I think there’s that big question about whether he’s going to be ‘the guy.’
As many Chicago sports fans already know, whether or not Williams becomes ‘the guy’ in Chicago isn’t a foregone conclusion, but something O’Keefe noticed that was unique about Williams took place before he played a single down at Soldier Field.
“He launched an investment firm, a venture capital firm, last summer before he’d ever played his first snap in the NFL,” O’Keefe said. “That really caught my attention because most athletes, these guys who are coming out, they have to really drive themselves to be first-round picks, right? They’re focused on making the team, on establishing their mark in the game.”
O’Keefe pointed out how most athletes don’t think about life outside of or after football until late in their careers, or retirement. They come to a point where they wonder, “What do I do now?”
“They have this void and [Caleb], he’s planning that already, before he steps out on the field,” O’Keefe said. “That is really fascinating, the fact that he would do that. That he would have the confidence to do that.”
Then there’s the fact that Williams spent a large chunk of his offseason outside the United States in Copenhagen, Denmark. O’Keefe travelled to the Danish capital to profile him. In his writing, O’Keefe described how Williams met him at Cafe Side Hustle, a second-story lounge in the city, before the two journeyed to a quieter space down the block to talk.
“He plans to live part-time in Europe in the future because he’s really interested in fashion and culture,” O’Keefe said. “That’s another thing that’s kind of surprising for a young NFL player. He’s not living five miles away from the gym and in there every day. He’s doing his own thing, and at the same time, he’s very confident and very firm about saying he’s all about football.
“He plans to have a long career and he plans to win. But the fact he’s balancing those two things is just really intriguing.”
One thing O’Keefe didn’t include in his profile of Williams is the Bears quarterback’s plans “to step up his fashion game this season.”
“He said, actually, his style game was pretty good this year—his tunnel walk and stuff,” O’Keefe said. “But he’s going to be bringing it to a new level this year because he’s had more time to plan it out and shop so, look for that.”
O’Keefe said he wouldn’t describe Williams as a human being who’s eccentric, as in, unconventional or slightly strange. He said Williams views himself as an athlete who’s a part of a new age that’s completely comfortable in his own skin.
“I think he would say that he’s being his genuine self,” O’Keefe said. “He said that he doesn’t really think about what people say about him. Now, everybody thinks about it a little bit, but I think to some degree, that’s true. I think he’s just not afraid to be himself. He’s not afraid to show some emotion.”
O’Keefe recalled how Williams has received criticism for showing his emotions in the past—his mom shielding his face from cameras while at USC, and a story of how Chicago’s 10-game losing streak broke him down to the point of tears one night. But Williams has never felt that it’s weak to show emotion.
“That’s definitely a different mindset than the NFL has had in the past,” O’Keefe said. “But he’s also from this new generation of players … It’s just in the last few years that these guys, he was really on the cutting edge of this, got this NIL money and became, essentially, highly paid professional athletes—the top ones—in college.
“He was winning the Heisman Trophy and coming back for another year in college, he was making millions of dollars in endorsements. It’s a different generation. They’re encouraged to express themselves and I don’t think he feels self-conscious about it.”
O’Keefe pointed out how Williams’ expressive nature is a part of football catching up with other sports when it comes to the world of fashion, and in doing so, helps add value to football from a social media standpoint.
When hype can be drawn from pre-game tunnel walks and there’s a heightened focus on fashion and culture with players involved, it not only diversifies the content offered when it comes to football, but it also offers a larger volume of content on the sport when it comes to crossing over onto platforms football previously didn’t have an audience on.
For those interested in reading O’Keefe’s full profile on Williams, it can be found by clicking here.
Kaitlin Sharkey’s full interview with O’Keefe can be watched in the video embedded at the top of this article.