GOD HELP THE BEARS IF CALEB WILLIAMS DOESN’T WIN IMMEDIATELY IN CHICAGO
Before the NFL draft, he says he likes the team, the legends of Payton and Jordan and deep-dish pizza, but if the Bears clog around the competitive NFC North, Williams will beg out of town in no time
Pinned at the top of his social media page, Caleb Williams announces who he is and what he desires. “I’m Not a Businessman; I’m a Business, Man!” he said, and it remains there about 2 1/2 years later, after he won the Heisman Trophy and made $10 million in NIL money and awaits an NFL draft in which he’ll be drafted first.
He has a father, Carl, who is a prominent reason why he won’t obtain an agent for his continuing professional career. And his dad is a potential pain for his next team, likely the Chicago Bears, who have had too many pains in the four decades since winning one Super Bowl. Carl has made it known in league circles that his son might like to own a piece of the franchise that drafts him, an issue joined by Hall of Famer Aaron Rodgers, both of whom were shot down when owners banned “non-family employees from taking equity in teams.”
It should be known by now, among various McCaskeys in Chicago and Josh Harris in Washington, that the team drafting the quarterback also will be drafting Big Carl. Are the Bears ready for this curiosity, if not total tumult? For now, as Caleb graces the NFL combine in Indiana, he says all the complimentary things about Chicago, the Bears, Michael Jordan, Walter Payton and deep-dish pizza. Speaking to ESPN, as he awaits a news conference Friday, Williams says he’s intrigued about a new life in the land of double-digit-loss seasons and polar vortexes.
“If I get drafted by the Bears, I'll be excited," he said. “If they trade the pick, and I get drafted by someone else, I'm just as excited. Speaking about Chicago, they have a talented team, a talented offense and defense. For anyone to be in that situation, I think they'd be excited.”
So no active pushes on his part to coax the Commanders into a trade for the No. 1 position, in his hometown, where he played high-school ball and could enlighten fans as one of their own? “I’m not pushing any agenda," Williams said. “At the end of the day, the Bears have the last say. Regardless of how I feel, I'm not pushing an agenda of, ‘Yeah, I want to go. Or no, I don't want to go.’ I'm excited for whatever comes.”
Regardless of “how I feel,” he mentioned. Would he prefer to be in Washington? It’s a comment to be pulled from many over the next several months.
He even has dreamed about becoming the next Jordan or Payton. “I'm 22. I didn't really get to see those players. As the saying goes, the legends live on. That's my goal of playing football — it's not money, it's not fame, it's to be immortal,” Williams said. “I want to reach that sense of being a legend. Being at the table and having a rightful seat through hard work and energy and time I've put into this game that we all love. It's appealing to be in a city like that. With legends that you've looked up to ... reach for the standard they set and try to do anything to get there.”
But the question becomes how this aspiring immortal deals with the possibility of losing in a town that sulks in misery, not just in the NFL but all sports. His dad not only is a bold newbie, so are other representatives — including Cody Boulware, who has worked with Caleb for six years, and entertainment executive Phil Crimaldi of Smith & Company, known as “a strategic advisory firm of creative storytellers, crisis managers, proven strategists and digital specialists driven to create dynamic solutions for our partners.” They aren’t to be confused with Drew Rosenhaus, Chris Cabott, Todd France, Joel Segal, David Mulugheta or other major agents, as The Athletic pointed out.
Those folks are running Caleb’s World. That includes a GQ article, featuring Caleb wearing an orange shirt and a skirt by Jil Sander and sneakers by Givenchy, in which Carl suggests he won’t be long for any franchise he doesn’t like — such as the Bears, who never have developed a superstar quarterback in 104 years of trying and blew it lately by missing on Patrick Mahomes and C.J. Stroud. Again, because this can’t be repeated enough in behind-the-scenes conversations, Carl observed: “The funky thing about the NFL draft process is, he’d almost be better off not being drafted than being drafted first. The system is completely backwards. he way the system is constructed, you go to the worst possible situation. The worst possible team, the worst organization in the league —because of their desire for parity — gets the first pick. So it’s the gift and the curse.
“The organizations matter. He’s got two shots at the apple.”
In the same article, Caleb says, “I’ve had a plan for treatment, I’ve had a plan for workouts, I’ve had a plan for eating, I’ve had a plan for nutrition and things like that. Vitamins. A lot of shrimp and chicken breasts and fish. But now, going into this next part of my career, it’s weird ’cause it’s so uncertain. You don’t know anything. You can’t control anything but you and how you act. That’s honestly the weirdest part for me, is the uncertainty.”
Well, nothing is more uncertain in his next life than a trip to the Bears, the sulking dogs of Halas Hall, training in a northern suburb as eroded fans ask why 13 years have passed without a postseason victory. They’ve had two winning seasons since then and have gone 0-2 in the playoffs. They’ve tried building a stadium and gulped. This is not only a weird team, it’s owned by mom-and-poppers, meaning Caleb will have to meet Virginia McCaskey and realize she’s the principal owner at age 101. They are run by people like George McCaskey, who used to be the ticket manager. They are generally managed by Ryan Poles, who missed last season on Stroud and has tried to build a team without a reliable quarterback. They are coached by Matt Eberflus, who should be dumped today and replaced by Mike Vrabel. They are in a division with the Detroit Lions, who should have played in the Super Bowl, and the Green Bay Packers, who have developed a quarterback specimen in Jordan Love and will make more postseasons, and the Minnesota Vikings, who will be in the hunt if Kirk Cousins returns with good health. The Bears are improving at 7-10.
How would Caleb Williams, who cried in his mother’s arms after a defense-less USC season, deal with going 7-10 with the last-place team in the NFC North?
Worse, he isn’t fond of dealing with the media, preferring gatherings to promote his endorsements with Nissan, Wendy’s and Dr. Pepper. When he refused to show up after an early-season romp over Nevada, he looked like a kid bigger than the college story. “LeBron James talks after every game. Matthew Stafford talks after every game. Justin Herbert talks after every game,” Bill Plaschke wrote in the Los Angeles Times. Not Caleb Williams, who cannot pull that stuff in any NFL town. When asked about Carl’s “two shots at the apple” remark, he said, “The main goal is to go out and beat Stanford. … That would be the answer toward all questions about the NFL.”
With Eberflus a mamby-pamby as Poles grows into the job, while McCaskey goes to owners’ meetings without much to add, the Bears have no idea how to handle the 2024 concept of personal empowerment. “No concerns about that at all,” Poles said of Williams, in general. “I would love to know why, if that was the case. I think for a young quarterback — I have been around it — the infrastructure is important. I think we have made really good progress in terms of having a really good infrastructure.” Like no rookie we’ve seen of late, Williams must win big instantly. It will be difficult from the outset. Otherwise, his father might point out why four years is too long for a first-timer’s contract, with a fifth as a team option.
And what did Caleb tell ESPN about the Commanders, in a town where he went to Gonzaga College High School? “It'd be really cool because it's so familiar," he said.
Really cool, he said. It probably beats matching Chicago legends he never has watched. This is one of the biggest moments in Bears history. Nervous already?
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Jay Mariotti, called “without question the most impacting Chicago sportswriter of the past quarter-century,’’ writes general sports columns for Substack while appearing on some of the 1,678,498 podcasts and shows in production today. He is an accomplished columnist, TV panelist and talk/podcast host. Living in Los Angeles, he gravitated by osmosis to film projects.