Jason Parkhurst-USA TODAY Sports

Reports of Caleb Williams’ doubts about the Chicago Bears continue to persist despite his camp’s denials. Even NFL insider Jay Glazer is trying to sell the team and city to him.

Unless you’ve been living under a rock, you know that the Chicago Bears have a huge decision to make this offseason. They have the #1 pick in this April’s NFL Draft. Everyone around the league is interested in finding out what general manager Ryan Poles does with the pick.

Will Poles trade the pick for a treasure trove of picks? Some are saying he can get three first-round picks, and multiple other picks in this draft, as well as a good veteran player for the pick. Acquiring all of that could go a long way to filling the holes that remain on the roster.

Poles can also keep the pick and use it on a prospect some say has generational talent, Caleb Williams. Williams draws comparisons to Peyton Manning, Andrew Luck, and Patrick Mahomes. Having Williams could help the offense in a big way.

If Poles does keep the pick, that means he would have to trade the current starting quarterback, Justin Fields. Fields has had a rocky three years in Chicago. However, he has shown flashes of greatness. Whether it is enough to stay is the key question Poles has to answer.

Williams may not be a sure thing

While many in Chicago Bears Nation are eager for the team to select Williams, there are some questions, on both sides. While Williams won the Heisman Trophy in 2022, that is not a guarantee of success on the professional level. Plenty of Heisman winners struggled in the NFL.

The 2023 season was not a repeat of WIlliams’ Heisman season. The USC Trojans finished 7-5 and questions were asked. He seemed aloof and detached. His play declined as the season progressed. He threw 9 touchdown passes in his final seven games. Also, half of his touchdowns came against three weak teams — Nevada, Colorado, and San Jose State.

Poles has to do his due diligence and find some answers to whatever questions there are on Williams. He already knows what he has in Fields so once he compares the two he can make an informed decision.

Williams has questions about Chicago

There are;t only questions about Williams. Williams and his camp have questions about Chicago as well. Ever since it became apparent that the Chicago Bears would have the top overall pick in the draft, there have been nagging reports that Williams didn’t want to go there.

Williams’ father, Carl Williams, went so far as to say that his son could return to USC next season if the situation was not right.

He’s got two shots at the apple. So if there’s not a good situation, the truth is, he can come back to school…The organizations matters.

Of course, Williams ultimately decided to forego his final season and he entered the draft. Now it is a matter of whether or not he ends up in Chicago.

The reports about Williams not liking Chicago continue to come out, however. Last week, FOX Sports host Colin Cowherd ruffled more than a few feathers when he said on the air that Williams did not want to go to Chicago.

I do think it’s possible that Washington trades up and Chicago allows Washington to trade up. Because Caleb (Williams) and his group do not want to go to Chicago. The big concern for Caleb Williams, and you have to admit this, where you land matters. Chicago has never developed a star quarterback.

Cowherd received a call from Williams’ camp to have Cowherd clarify that statement. Cowherd said that the Williams camp did not want to be perceived as the villains or anti-Chicago.

While everyone seemed to think that Cowherd was backtracking his words, he really didn’t. Cowherd did say that Williams has concerns about Chicago. Williams and his camp want to have their cake and eat it too. They still don’t like the Chicago Bears but don’t want that fact to be leaked for the world to know.

Williams’ doubts about Chicago continue

While Williams and his camp continue to try to picture themselves as not being anti-Chicago Bears, reports of their doubts continue. Recently, NFL insider Jay Glazer stepped into the Williams/Chicago fray.

In an interview with NBC Sports Chicago, Glazer said that he tried to sell Williams on Chicago.

“I told his people, you have a chance to go to Chicago, go to Chicago. If you win in Chicago, they will erect bridges for you, streets for you, tunnels for you. Are you kidding me? You’ll be forever golden in that city, and it’s a great city. You want to go to a place like Chicago… Chicago is one of those rare places, man, where you have a chance to change your life forever by being engrained in that city.

Of course, Glazer is correct. We see how every Chicago Bears player from the Super Bowl-winning team is still revered today. There are as many Walter Payton jerseys in Chicago as there are Fields. If you win with the Chicago Bears you reach legendary status.

That raises a big question — if Williams is not anti-Chicago and Chicago Bears, why is someone like Glazer trying to convince him that being in Chicago is good for him? Besides winning and becoming a legend, he will also be in the third-biggest market in the NFL. The endorsement opportunities will be plentiful.

If Williams indeed likes Chicago then Glazer would not feel the need to sell the city.

More must-reads:

TODAY'S BEST
Mavericks advance to Western Conference Finals aided by controversial call late
Connor McDavid, Oilers hammer Canucks to force Game 7
Tyson Fury-Oleksandr Usyk epic increases excitement for potential rematch
Seize the Grey wins in muddy Preakness
Even Mike Budenholzer admits the Suns need a point guard
Watch: Juan Soto's first multi-homer game as a Yankee
Xander Schauffele, Collin Morikawa lead at PGA Championship
Knicks could get major boost for Game 7 showdown with Pacers
Giants All-Star pitcher suffers setback in recovery from injury
Panthers star named winner of 2024 Selke Trophy
WNBA to investigate $100,000 sponsorship deals for Aces players
Tiger Woods blames one big factor for missing the cut at PGA Championship
'Ain't good enough': Draymond Green claims Celtics must 'win it all' or it's a 'failure'
Blue Jays GM wants struggling club to feel 'massive sense of urgency'
Raptors expected to flip former NBA champion during the offseason
MLB insider reveals Mets' massive extension offer that Pete Alonso turned down
Celtics legend provides update after gruesome finger injury
Bulls hire former NBA head coach as top assistant
Chiefs move on from young running back
20-year MLB veteran working out, unsure about playing future