Caleb Williams: Separating fact from fiction as the Chicago Bears prepare for their biggest decision ever

Those with great hype face intense scrutiny. 

For Caleb Williams, this is nothing new. 

Only the hype is as big as it has ever been. As the superstar quarterback inches closer to realizing his dream of being the No. 1 overall pick in the 2024 NFL Draft, each day seems to bring more questions, speculation and rumors. 

The Caleb Williams conversation in Chicago began in September when the Bears got off to an 0-4 start. And now that they own Carolina’s No. 1 pick in the draft, it has divided the fan base and sparked intense reactions from both sides.

Caleb Williams vs Justin Fields. Justin Fields vs Caleb Williams. 

Inside the walls of Halas Hall, the conversation is much more measured. The evaluation of Fields through three seasons in the NFL is done. A new offensive coaching staff led by offensive coordinator Shane Waldron has been hired in a fashion that could easily cater to a rookie starter or pivot back to getting the most out of Fields should they stick with the incumbent. 

As the NFL Draft draws nearer, the Bears are in fact-finding mode. What’s true about Caleb Williams and what’s not? Does he even want to come to Chicago? What do his teammates think of him? What do his coaches think of him?

CHGO has been looking into these same questions over the past few months, trying to separate fact from fiction when it comes to the franchise’s biggest decision this offseason — and perhaps ever. 

In reporting this story, CHGO spoke to numerous sources who have either played with or coached Williams. Some were granted anonymity to ensure candid responses with the goal of painting a full picture.

With that in mind, here are the answers we can provide to some of the most common questions regarding Caleb Williams:

Does Caleb Williams want to be drafted by the Chicago Bears?

Rumors of Caleb Williams not wanting to be a Chicago Bear have existed for months, and that conversation gained steam last week when television host Colin Cowherd claimed Williams did not want to go to Chicago. The very next day, Cowherd walked back that claim after saying he received a phone call from “Williams’ camp.” Cowherd clarified that Williams camp didn’t want to be painted as “anti-Chicago.”

Even before Cowherd’s comments, two of Williams’ former coaches expressed skepticism the quarterback would ever refuse to go to Chicago. But both pointed to Williams’ high school, college and transfer recruitments as evidence that his family — and, in particular, his father — would be meticulous in making sure Williams would be set up for success in the NFL. 

“His family is always looking for the best situation possible to put his talents on display,” one of the coaches said, adding that the Bears’ lack of historical success at the quarterback position, “might be an issue.”

When Williams was in eighth grade, he was recruited by many private schools in the Washington D.C. area. There was an assumption that he would end up at powerhouse DeMatha, but Carl Williams, Caleb’s father, did his homework. Academics were a huge piece of the equation (at one point Stanford was a preferred college destination for Williams) and Gonzaga College High School had the edge on the academic side. But scheme mattered too. Gonzaga ran more of a modern offense that translated better to both college and the pros, which was intriguing to both Caleb and Carl Williams. In the end, Gonzaga got Caleb. 

The college decision was even more detailed. According to the book “Quarterback Dads” by Teddy Greenstein and Donovan Dooley, Carl kept a detailed spreadsheet with four main categories and many sub-categories to help Caleb make his decision to attend Oklahoma. And when Williams chose to transfer when Lincoln Riley left Norman for USC, Carl Williams hosted Zoom calls with at least 25 schools. At that point, NIL money had become huge in the transfer portal, but Carl was more focused on the NFL.

“It’s NFL, not NIL,” Carl Williams says in Quarterback Dads. “The first pick in the draft last year came close to $40 million. And the fact of the matter is, in 2024, there will be a significant bump to the salary cap.”

According to the book, Carl came to that conclusion by analyzing the influx of sports betting revenues and the projected bump in NFL media rights agreements.

As you can probably tell, the NFL has been on the minds of the Williams family for quite some time — which is why doubts about the Bears as a potential landing spot exist. But it’s not just the initial destination that matters, it’s the second NFL contract that is truly generational money. And that’s why you better believe Carl and Caleb Williams will be meticulous in making sure they don’t end up on a team that fails to put the quarterback in a position to succeed. 

Far too often, the Bears are that team. 

But that doesn’t mean they will be this time around. Usually the No. 1 overall pick is owned by a team that earned it with the worst record in the league. The Bears won seven games in 2023 and project to have one of the better defenses in the NFL next season. They own the No. 1 pick because their general manager earned it with a shrewd trade that has the organization on the brink of a significant turnaround. They also boast a true No. 1 wide receiver in DJ Moore and overhauled their offensive staff by hiring Waldron, who has ties to the QB Collective, an outfit that has trained Williams for years.

This last point is very important: If Williams is drafted by a team that gives up a haul to get him, it will hurt that organization’s draft capital for at least half of Williams’ rookie deal, if not longer. Just look at the consequences of the Carolina Panthers’ trade for the No. 1 pick last year. It greatly hurt Bryce Young’s chances to succeed as a rookie. As a result, the Chicago Bears are the only team currently able to draft Williams AND immediately add another highly drafted prospect with the No. 9 overall pick. 

If Carl Williams keeps a spreadsheet on all of his son’s NFL options, you can be sure that reality is listed somewhere on the spreadsheet.

Would Caleb Williams refuse to join the Chicago Bears?

Top college prospects don’t have much in the way of leverage. The NFL Draft is not free agency like a high school or college recruitment, so there’s only so much power the Williams family has in this situation. But an NFL team would likely not want to draft a high-profile rookie who doesn’t want to be there. Still, those who have coached Caleb Williams do not believe he would outright refuse to join the Bears if they choose him No. 1 overall. By all accounts, he is a team player and being the No. 1 overall pick in the NFL Draft has been a goal for the family for a long time. 

On the other hand, that doesn’t mean the Bears are Williams’ top choice. After all, his hometown Washington Commanders own the No. 2 overall pick and the circumstances of Kliff Kingsbury — Williams’ QB coach at USC — backing out of a deal with the Raiders to presumably join the Commanders certainly sent waves through the NFL over the weekend. 

But even if the Kingsbury hire is connected to Williams, it would hardly be the first time a team employed a coach to help impress the Williams family. Two years ago, the University of Wisconsin made a strong push to land Williams in the transfer portal by hiring Bobby Engram as OC. Engram had ties to the family and it gave the Badgers a legitimate chance to land Caleb. Yet it obviously wasn’t enough and Engram only lasted one season at Wisconsin as head coach Paul Chryst was fired months later.

So what does this all mean? Well, if the Bears are serious about drafting Caleb Williams — and the majority of the NFL world believes they are — then they’ll have to at least sell the Williams family on the idea that he’ll be the first quarterback to have legitimate, sustained success in Chicago. 

On the surface, that might be a tough sell, but don’t underestimate the current strength of the Chicago Bears front office. General manager Ryan Poles is highly respected around the league right now, and one source said not to ignore the role of team president Kevin Warren in all this. Warren has friends all over the sports landscape, including LeBron James. That could matter for a young prospect with business interests off the football field.

Compared to this time a year ago, there are reasons to believe the Bears are better suited to support a true superstar quarterback capable of transcending sports.

Wait, so is Carl Williams a problem?

In Quarterback Dads, the chapter on Carl Williams is labeled: “The Quarterback Dad With Answers.” 

By all accounts, Carl is just doing what any dad would — putting his son in the best position to have success in life. A real estate developer by trade, Carl Williams put money into opening a training facility in Maryland, spent $25,000 year on tuition at Gonzaga and did all the homework necessary to send Caleb on a path that culminated in a Heisman Trophy and presumably being the No. 1 overall selection in the 2024 NFL Draft. 

According to one of Caleb Williams’ high school coaches, Carl was very involved, but always let the coaches coach. He never once complained about play calls or the way in which they were coaching his son. Carl is described as the “business guy” who helps Caleb find opportunities, but then gets out of the way. 

Those who have interacted with Carl in the past believe his influence will certainly be felt in the coming months, but if Caleb becomes a Bear, Carl will not be a distraction once his son is on the team. 

Is Caleb Williams a bad teammate?

The overwhelming response to this question is no. Those who have coached Caleb describe him as a great teammate who is always upbeat with a good attitude. They say he doesn’t care about his own headlines, and, if anything, he wants his teammates to look good too. 

“A phenomenal player as we all know, but even better person,” former USC wide receiver Tahj Washington told CHGO’s Nicholas Moreano at the Shrine Bowl. “Having that inside take on him as a person, just being able to see him every day be the person he is with so many distractions around him and still be able to perform. Just take notes from him.” 

Of course, if you’re going to arrive at a school with an insane amount of hype and your own logo/apparel, some teammates are bound to roll their eyes, too. That has certainly happened over the years, but Williams supposedly never big-timed his teammates, including younger scout team players. 

“He always came off a regular dude,” one of his coaches said. 

So what was up with a USC wide receiver Raleek Brown yelling, “We’re a team now!” while the Trojans beat Louisville in the Holiday Bowl with backup quarterback Miller Moss? 

One of Williams’ former coaches insisted that was not about Caleb. The coach pointed out that Caleb was at the game on the sideline, while other USC opt-outs didn’t even attend the game. If anything, that postgame expression had more to do with the players who were not there, but more than likely was just rooted in the Trojans emphatically ending their three-game losing streak. 

And what about the crying after the loss to Washington?

If you can’t tell by now, goals are a big deal to Caleb Williams and his family. While winning the Heisman Trophy in 2022 was a major milestone, Williams wanted to win a National Championship while in college. USC’s national title hopes were on life support going into the Washington game, but that loss officially ended all hope, which led to Williams crying in his mother’s arms in the stands. 

Many have questioned that emotion, saying it shouldn’t have been public, but as Williams said in the week following the loss, “the touch of a mother” and the reality of a dream ending is what led to him letting it all out. 

The reality is that Williams is known for being ultra competitive. If anything, perhaps he cares too much. 

“He doesn’t want to lose at anything, no matter what it is,” former USC running back MarShawn Lloyd told CHGO at the Senior Bowl. “Very competitive. Dodgeball. Bubble gum chewing. Anything. He’s a very competitive person.”

What’s up with the finger nail polish?

This question is usually followed by some laughter and a simple answer:

His mom owned a nail salon. Williams has been painting his nails since high school. 

Known for having an interest in fashion, one source described it as part of “Caleb’s flair.” In high school, Williams rarely followed the popular trends and instead sought to set his own trends.

On the other hand, painting “F*** UTAH” on his nails was widely viewed as a mistake, especially because USC lost the game. Consider that a lesson learned. But don’t expect the nail polish to go away. 

What about the actual football stuff?

If you can get past all the off-the-field questions, there are many reasons why Caleb Williams is widely considered one of the best quarterback prospects ever. The tape is outstanding, and there are very few criticisms thrown out there by those who have coached him.

In fact, in reporting for this story, the only significant, consistent complaint from coaches is that Williams has a tendency to shut down when things aren’t going well. One of his offensive coaches said Williams has a habit of being standoffish on the sideline when losing.

“Sometimes it’s like talking to a brick wall,” he said. 

As for any other negatives, you really need to squint. One of his high school coaches said Williams was capable of winning every conditioning drill, but he’d sometimes gear down to save his legs.

You’d never see that on game days, though. His coaches would joke: “Superman always has his cape.” 

On the field, the Patrick Mahomes comparisons go back to high school. He can make any throw from any platform. He takes care of his body and only runs when needed. In fact, coaches sometimes get on him for not taking open running lanes when they are there. 

And one more thing… 

Perhaps the biggest reason why those who have coached Williams believe he ultimately won’t shy away from being a Chicago Bear, is because he has never shied away from competition. 

Williams was not handed the starting job at Gonzaga. He had to compete with two upperclassmen (one of whom went on to play lacrosse at Penn State) and wasn’t named the starter until right before his freshman season began. And when Williams went to Oklahoma, he knew the path to starting right away was blocked by Spencer Rattler, who at the time was the Heisman Trophy favorite. Williams started the 2021 season on the bench before taking over for Rattler in the middle of the Red River Rivalry, leading OU to an improbable comeback win over Texas. 

Facing challenging situations is nothing new for Williams, and succeeding as a Chicago Bears quarterback is certainly a challenge. But doubts about Williams wanting to be a Bear are rooted more in the idea of a family doing their due diligence. And given the Bears’ history, can you blame them?

With almost three months until the NFL Draft, there will most likely be more twists and turns in this story. Heck, we don’t even know if the Chicago Bears intend to trade Justin Fields and draft Caleb Williams. 

But if that is the decision the Bears make, those who have been around Williams would be surprised if he does not accept the challenge. 

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