Most embarrassing moments from Bears Chairman George McCaskey’s press conference

The Chicago Bears fired head coach Matt Nagy and general manager Ryan Pace on Monday morning, which left Bears fans feeling uncharacteristically hopeful that things might actually change.

But much like Nagy’s second-half collapses, Monday went from great to hopeless once Chairman George McCaskey took center stage later that afternoon.

McCaskey met the Chicago media for roughly an hour, where he addressed everything from Nagy and Pace’s firings to the search efforts for a new head coach and GM. But with McCaskey, even a routine end-of-year press conference always seems to develop into an absolute disaster.

While many didn’t think it could get worse than last year’s press conference, it’s right up there with it.

Here’s a look at some of the most embarrassing moments from McCaskey (and Phillips) during their press conference:

Kamil Krzaczynski-USA TODAY Sports

George McCaskey using Jeff Dickerson's passing to chastise Bears fans

Right from the start, McCaskey’s press conference was a disaster. In his opening remarks, McCaskey paid tribute to the late Jeff Dickerson. But instead of stopping there, he used Dickerson’s son Parker as a means to transition to chastising the Bears fans who booed Nagy during his son’s high school playoff game.

While most of us can agree that those fans booing Nagy while he was just trying to be a dad were wrong, it was how McCaskey ultimately turned what should’ve been a nice tribute to Dickerson into something that isn’t on the same level as losing a parent.

George McCaskey calling Olin Kreutz a liar

Whatever you expected to happen during McCaskey’s press conference, I bet you didn’t expect him to call out former Bears center Olin Kreutz as a liar. For context, Kreutz told a story about the time the Bears organization offered him $15 an hour to serve as a consultant for the offensive line with Harry Hiestand back in 2018.

That story was brought up to McCaskey, who could have easily dismissed it as something he wasn’t going to get into. Instead, he used it as an opportunity to take a shot at one of the team’s beloved former players in Kreutz.

“I’ve learned over the years to take everything Olin Kreutz says with a grain of salt,” McCaskey said, before essentially calling Kreutz a liar shortly after.

Ted Phillips still involved in GM search

One of the few good things to come out of Monday’s press conference was news that Phillips won’t be involved with football operations anymore, with the focus being on the business side. The new GM will report to McCaskey.

And yet, McCaskey said that Phillips will be part of the search for the next general manager. Which makes no sense, considering that’s the definition of involving “football operations.”

McCaskey was asked why Phillips will be involved, and he essentially said it has to do with him trusting Phillips and the fact that he’ll be negotiating the contract for the new GM.

Virginia McCaskey was "very, very disappointed"

Patrick Gorski-USA TODAY Sports

The last time the Bears cleaned house, 99-year-old franchise matriarch Virginia McCaskey was “pissed off” following the team’s 5-11 finish in 2014, according to her son.

So the million-dollar question is: What was her assessment of how this year transpired?

“She said, as only a mother can,” McCaskey said, “I’m very, very disappointed.”

George McCaskey is "just a fan, not a football evaluator"

Following the firings of Nagy and Pace, the hope was that ownership would understand the need of having a football guy in place to help find the right fits at head coach and GM.

While Phillips won’t be involved in football operations — other than hiring the next GM — the Bears are still missing a football mind to help right the ship.

Look no further than McCaskey, would himself said, “I’m just a fan, not a football evaluator.” Which would be fine if he was going to bring a “football guy” to Halas Hall to oversee the next GM.

But that’s not the case, as McCaskey said he’ll be responsible for not only picking the next GM, but he’ll be the one the GM reports to.

Basically, Virginia McCaskey let her son keep his job

Given McCaskey hasn’t found success since taking over as chairman — the Bears are 79-97 and have five double-digit losing seasons under him — he was asked about how he’s been evaluated by the organization.

McCaskey said that ownership and the board of directors want him to remain in his position. The only problem is, those people include his mother, Virginia McCaskey, other family and Phillips, who works for him.

Essentially, it sounds like George’s mom is letting her son keep his job.

George McCaskey's free marketing for Bill Polian's book

Perhaps an underrated, yet strange moment during McCaskey’s press conference was the repeated mentions of Bill Polian’s new book. McCaskey referenced Polian’s book on several occasions, which is certainly interesting marketing.

Ted Phillips has no regrets about Ryan Pace and Matt Nagy hirings

AP Photo/Nam Y. Huh

Remember when we were told McCaskey would be conducting the press conference alone? Well, that was only half true, as Phillips was also on the Zoom call. Phillips only got a few questions, which included mostly updates on the Arlington Heights development.

But at one point, Phillips said that he didn’t regret the hirings of Pace and Nagy. In Pace’s seven years, the Bears went 48-67 and had just one winning season. In Nagy’s four seasons, Chicago went 34-33. The Bears made the postseason twice under them, both losses.

To make matters worse, Phillips said they’ll be looking for a new GM and head coach with a lot of the same qualities Pace and Nagy have.

George McCaskey insulting a reporter

There’s a lot of frustration associated with the Bears — and it’s coming from fans, media and even ownership. Still, it’s not a good look when ownership, begin George McCaskey, insults one of the Chicago media members — David Haugh — before he asks his question.

Luckily, Haugh is someone who gave it right back to McCaskey.

Nothing changed from 2015 to now

The biggest thing Bears fans were hoping for on Monday was change. And that extends beyond firing Nagy and Pace. Fans were hoping for an indication that there was real change happening within the organization.

But nothing’s changed.

McCaskey laid out a plan where it’ll be him, Phillips and Hall of Fame executive Bill Polian executing the general manager and head coaching search.

Substitute Polian for Ernie Accorsi, and it’s the same old song for the Bears. McCaskey offered a plan for front office restructure — where the new GM will report to McCaskey, Phillips is no longer in charge of football operations and the new GM will be in charge of all things football operations.

But don’t let it fool you — nothing has truly changed.

George McCaskey stole hope from Bears fans

It’s hard to believe there was a time on Monday when Bears fans were, dare I say, hopeful following the firings of Nagy and Pace. But, just like Nagy’s second-half collapses, Monday soon spiraled into a disaster once McCaskey stepped to the mic.

The hope was McCaskey would be able to inspire some sort of confidence heading into this integral offseason. Instead, you can’t help but wonder if things could actually get worse for the Bears now, especially as we’re back to square one.

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