Our Kind of Town: Talking Chicago, the Bears and Caleb Williams

“My Kind of Town, Chicago is,” once crooned Frank Sinatra.

It truly is one-of-a-kind. From its phenomenal food scene, to its dive bars and its meticulously laid out architecture and geography, Chicago is no one’s “Second City.”

Least of all, to the people that live there.

But there’s another thing that Chicago is known for: it’s sports teams and the city’s loyalty to them — with or without success.

Recent years have been lacking pretty much across the board, but with the arrival of Caleb Williams, and general manager Ryan Poles before that, there might not be a better time to be a Chicago sports fan.

As the Bears get set to kick off the much-anticipated 2024 season, I kicked off Week 1 by having a conversation among Chicagoans, right here at FOX. Danny Parkins went from the radio booth to the studio booth in New York, now appearing daily on FS1’s daily morning show “Breakfast Ball,” repping Chicago on the East Coast.

I reside now near FS1’s headquarters in LA, putting on for the city every chance I get in the Pacific Time Zone. Now that we have the whole country covered, Parkins and I decided to have a chat about our favorite city and that city’s new favorite son.

Parkins: The only thing that unifies Chicagoans is a belief that Chicago is the best city in the world … and the Bears. That’s pretty much all we can all agree on. The Cubs and Sox is split. Even in winter sports, right? You’re either a bigger Bulls fan or a bigger Blackhawks fan. But everyone in Chicago cares about the Bears and the ‘85 Bears still have media gigs in town. They still eat and drink for free, and the city’s never had a good quarterback.

They’ve never had a 4,000-yard passer. They’re the only team that can say that. They’ve never had a 30-touchdown passer —only team that can say that. So it’s just, it’s a huge, passionate, unified fan base that also has never experienced greatness at the most important position in pro sports. A superstar quarterback of the Chicago Bears would be one of the biggest sports figures in that city’s history.

Vitali: I think that it’s also just a perfect storm of opportunity for having a guy like Caleb Williams, who’s coming in no stranger to the spotlight at this point in time, where NIL is a thing, and he’s used to doing all of this kind of stuff. He’s used to budgeting his time and focusing on football when he needs to. And that, I think, uniquely equips him to handle what he could be and what he could mean for Chicago. Because, I have to think that five years ago, even if there’s a rookie that comes into this city, you’re not this optimistic. I mean, we’ve seen it. We saw Mitch Trubisky, we saw Justin Fields. And the weight of these expectations can be absolutely crushing if you’re not ready for them. But I think that not only on the field, has Caleb been one of the most talented prospects we’ve seen, but he’s uniquely equipped to handle the actual city and the expectations.

Parkins: Yeah, I tend to agree. I don’t think that Mitch Trubisky would have been great though, if he went somewhere else. I don’t think that the weight of Chicago crushed Mitch Trubisky, nor do I think the weight of Chicago crushed Justin Fields, but Williams is, I think, because of everything that you said, uniquely prepared to succeed, period. And so if he would have been the first pick of the Patriots and the Tom Brady comparisons would have been there, or Washington’s savior of the franchise with new ownership, right? All of those places would have come with pressure. Now, as much pressure as Chicago? That’s tough to quantify, but I do think because of everything that you said, Caleb is the modern athlete, right? They had NIL money and all that, like, if they are being better prepared to handle that side of things than in the past. There’s no question about that. But I don’t think that the success rate will necessarily increase all that much, because it’s still just really hard to go from college to the pros as a quarterback. It’s just like the weight of the city, the pressure, the money, those things that sunk guys in the past, that those stories should be rarer going forward.

Vitali: Yeah, I’m also in the camp of being cautiously optimistic just because of what I witnessed my entire life. I want to make sure that we’re not going to turn on Caleb, if things don’t immediately click, because not only is Caleb new, Shane Waldron is new, there are so many new offensive pieces. Basically, the only thing that stayed the same, relatively, and that’s not even true for the center, is the offensive line. So, regardless of how talented the quarterback is, how much talent there is around him, and there’s plenty, this still might take a little bit of time, and I just want to make sure that if we have these lofty expectations, we’re not having immediate lofty expectations. If that makes sense.

Parkins: Yeah, you and I are different here. For me, I do have immediate lofty expectations, but if he doesn’t meet them, I also don’t think that the city will turn on him. We’re not New York, we’re not Philly, we’re not Boston, kind of like the we’re like the big brother and the biggest, baddest city of all of the other cities. But Chicago had a huge percentage of people that were still defending Justin Fields and wanted him back, and chanted his name at Soldier Field at his last game. So even to the very end, when it was absolutely inevitable, according to anyone that you’ve talked to in league circles, that of course the Bears were going to move on from Justin Fields and draft the quarterback with the number one pick, Bears fans were still very split and believing in Justin Fields. So I don’t think it’s a fan base that like turns on guys quickly or lacks loyalty because they are so addicted to the hope of this next guy can be our guy. So I think you’ll have plenty of leash from Bears fans, and then in terms of what’s reasonable on the field, I think there’s just a ton of reasonable X’s and O’s football points to suggest that he is going to be good and potentially very good sooner than later. And I mean, I can go through them. All of the best rookie quarterback seasons in NFL history have happened in the last 12 years. It’s just getting easier. Again, not that it’s easy but now, Andrew Luck, RGIII, Cam Newton, CJ Stroud, Justin Herbert, those are the best rookie quarterback seasons ever, and they’ve all happened since Andrew Luck’s rookie year. So it’s just, it’s just easier to do because the NFL offense more mirrors the college offense. Now it’s not like you must be under center, seven-step drop, pro-style, you know, like that. The NFL has gotten smarter in that regard. So that’s just like a league-wide trend.

But then we’ve never seen a No.1 1 pick quarterback go to a situation this good in NFL history, because they didn’t earn the No. 1 pick themselves, right? The Bears won seven games, and so they got to then be a seven-win team with a good, potentially great defense, and add Rome Odunze to it, and add Keenan Allen to it, and add D’Andre Swift to what they already had. This is just an excellent situation for an excellent talent in a time in league history that is excellent for young quarterbacks to have success. So all of those factors lead me to believe that he’s going to be really damn good, really damn soon.

Vitali: The perfect storm aspect I think applies to this too, just given the fact that, for all the reasons you just said, this was a very unique situation for a No. 1 overall pick to come into I’ve been saying I think it’s the best situation a quarterback taken number one overall has ever come into—

Parkins: Because of the fact it is. I think that’s an objective fact.

Vitali: Totally and on top of not warranting the first overall pick, they had a ton of cap space, and had spent multiple years reconstructing a roster, and saw the defensive success turn, and now you have that to rely on, on top of all of this now offensive talent, and you’re also set up in a way cap wise and just kind of contracts wise, where this is sustainable now. And that’s new, I think for Chicago in general.

Parkins: Ryan Poles seems to be doing a great job. It’s a great situation. Of course, there’s holes on the team. Every team has holes. Of course, Caleb will have his struggles. C.J. Stroud, he had games with zero touchdowns last year. He had 23 touchdowns and he had five in one game. So, you know, I’m not, I’m not saying it’s going to be a 5,000-yard perfect season right out of chute, but he’s in a really, really good spot to be successful. The biggest thing that we don’t know, other than Caleb, is Shane Waldron, right? He was there in Seattle with Geno Smith, and he’s called plays before, but Williams is not a guy being drafted to Kyle Shanahan or Andy Reid or Mike McDaniel. That is the only thing that could have made this situation even better on paper is if he was going to, we know beyond a shadow of a doubt that this guy knows how to coach offensive football and call plays at a high level. We can’t say that about Shane Waldron. He doesn’t have a large enough track record, so that’s the only thing that stops me from saying it’s a perfect situation for Caleb.

Vitali: But even if Waldrom doesn’t have a long track record, though, if you look at the Bears’ hires the last few years, he has a track record, which is an improvement over someone like Luke Getsy who only coached in one system, only really coached one guy who didn’t really need a lot of coaching and didn’t call plays before that. So if you weren’t gonna get a McVay, a Shanahan, even a Kevin O’Connell, this, I think, was probably your best option that you had available.

Parkins: Once they decided to keep Eberflus, this was probably their best option available. And I said, before the hire, or before they even interviewed him, we did a thing on the show of like, who would your top five candidates be? And Waldron was on my list, right? So I liked the hire, but I also was on the record at the time of saying I would have fired Eberflus. Because I think that to pair coach and quarterback on the same timeline, they would have lost continuity and yes, the defense got better, and I know Poles loves him and the leadership and the culture and all that stuff, but I’m just, I’m not convinced that Jim Harbaugh doesn’t coach the Bears if Caleb Williams is here. I’m not convinced that Ben Johnson is still in Detroit if that job is open. So I think you would have been able to get the absolute best offensive minds available to line up to interview for that job. And I thought that that was a misstep. But I do trust Ryan Poles in the macro sense. He’s earned the right to make that decision.

Vitali: I think it’s going to be really interesting, though, to see then, all right, does this how much of a leash does Eberflus now have? Because you don’t want to continue the cycle of what you’ve done with the last two quarterbacks in firing their head coach and turning everything over a year after they get into the league. That hasn’t proved to help anybody. And so I wonder if there is no chance that Eberflus will be fired this year, because you’re going to give it at least a year to take hold, barring an absolute like catastrophic meltdown.

Parkins: Listen, I think that if people are talking about Matt Eberflus, first coach fired, that would be the worst bet in the world. The Bears have never fired a coach in the season. And Ryan Poles, if he was going to have that short of a leash on Matt Eberflus, he would have done it in the offseason. So, I mean, Eberflus gets the year at a minimum. And to your point, he probably gets multiple years, because it would just, it also would look terrible for Poles to repeat exactly what happened with Mitch Trubisky, with John Fox, and then Matt Nagy, and then with Justin Fields, with Matt Nagy. It would be criminal to do that to three quarterbacks in a row, even if Poles would not have been the executive that would have done it three times. So I tend to agree with you. I think that this offseason was the fork in the road moment, right? And he chose his path, and Eberflus is comfortably here for, you know, two years now. Shane Waldron, if it’s a disaster, maybe? Or if the defense is bottom half of the league somehow, then maybe you see them gone. But only in the case of true outlier events. I think that they’ve got some continuity here.

Vitali: I find myself in this space now wanting to shed my scars, for lack of a better term, from this team, from growing up watching them and being like, all right, what if this really does work? What if this is really it? What if this does result in really insane offensive football that we’ve never seen in this city, and that leads to actual success and sustained success in the way that they’re planning for it to? The domino effect of that for the entire city is so Incredible. It warms my heart. It makes me emotional. I can’t even imagine what that would look like in this day and age with social media, too. It would be so different even from 1985-86, I don’t know how old you are. I wasn’t born yet, so I have no frame of reference for what this could be. On top of the fact that in the modern NFL, with the modern fan, I can’t even see the ceiling. I don’t even know what it looks like.

Parkins: So I was born in ‘86 and Bears fans, I think sometimes we overstate right, that people watch the rest of the league. Now people watch the rest of the league more in the NFL than any of the other sports. By far. We’re in fantasy. We gamble. There’s Sunday Night Football, Monday Night Football, Thursday Night Football, etc. But a lot of the people that just love the Bears tlak about, ‘Gotta run the ball. Gotta have a great middle linebacker. It’s too windy to throw the ball that won’t work in this city.’ Like, those are things that we would get all the time as callers and texters and social media comments at the radio station. And I was like, hold on a second, guys, it’s cold in Green Bay, right?

Vitali: It’s windy in Buffalo!

Parkins: Right! And it works for Josh Allen, okay? So I think that there is a belief that, like the Bears are gonna “Bears” this up. And my pushback on that is always the Bengals were the bungles, until they got Joe Burrow. He changed everything. I used to cover the Chiefs. This was the craziest stat ever: until Patrick Mahomes, the Chiefs hadn’t won a single regular season game with a quarterback that they had drafted since Todd Blackledge in the 1983 NFL Draft. Now they had good quarterbacks, Trent Green, Joe Montana, Alex Smith, but they were always someone else’s quarterback.

And then they drafted a guy named Patrick Mahomes. But the belief in Kansas City was, “We can’t draft a quarterback.” So like, we have these scars, but you have to actually believe that the laundry is cursed, to believe that Caleb Williams can’t be great because he’s in Chicago. That doesn’t make any sense, or else the stink of the Chiefs’ draft history would have rubbed off on Patrick Mahomes, or the stink of the Bungles would have rubbed off on Joe Burrow. And that’s just not the way it works.

Vitali: I just cannot fathom, from the sports bars that are ubiquitous throughout the city to the neighborhood watch parties, I feel like the entire economy in Chicago changes, if this works. If they can count on their football team being good, and they can count on their football team being not only good, but very visible and relevant, like they’re not doing it the hard way, which I feel like is always the Chicago way, to your point, they’re shedding that identity and being like, “No, we’re fun, we’re flashy and we’re successful,” and what that looks like for the city itself? It is something that’s going to be tough to imagine.

Parkins: But we are a city that has had sports icons before, right? Walter Payton, Michael Jordan, Frank Thomas, Ernie Banks. We’ve had sports icons before, and they’re all a huge deal, and the city loves them and embraces them, and the nation embraces them, and in some cases, the world embraces them. So you know, there, there is something to it being a little bit more special if this happens in Chicago. There just is. Sure, you and I are biased on that, but we can point to the history of the city with true superstars, and that’s what Caleb is gunning for.

And that’s not us putting unfair expectations on the kid. He’s like, “Yeah, I study Tom Brady and Michael Jordan and Kobe Bryant and Aaron Rodgers. That’s what I’m trying to be.”

It’s like, okay, well, one of those guys was in Chicago, and it was the biggest deal in the world.

Vitali: Literally, in the world.

Parkins: That’s what I’m saying. So if that happens, that level of talent does happen, it’s gonna make an impact on everyone in the city. I mean, everyone is not to be taken literally, because there are obviously some people who don’t love sports, but it is the thing that unifies Chicagoans. The Bears are the single thing that unifies Chicagoans. So it’s hard to overstate how massive it would be for Chicago.

Carmen Vitali is an NFL Reporter for FOX Sports. Carmen had previous stops with The Draft Network and the Tampa Bay Buccaneers. She spent six seasons with the Bucs, including 2020, which added the title of Super Bowl Champion (and boat-parade participant) to her résumé. You can follow Carmen on Twitter at @CarmieV. 

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