Chicago Bears fans have long disliked and distrusted George McCaskey ever since he took over as team chairman in 2011, and one of his first significant acts was firing GM Jerry Angelo. Just over a year later, he also fired Lovie Smith. The two men who'd gotten the Bears to a Super Bowl were gone, replaced by Phil Emery and Marc Trestman. That, of course, was a disaster. Fast forward to a brutal night at Soldier Field against Seattle, where the Bears lost 6-3, and fans serenaded McCaskey with chants of "Sell the team!"
Thanks to a brutal exposé from Kalyn Kahler of ESPN, things have only gotten worse for him this week. In her article, she wrote about a small group of agents' overwhelming power over the NFL head coach cycle every year. No team has felt the string of this more than the Bears, who have been at the mercy of Trace Armstrong going all the way back to 2018.
Since 2018, agent and ex-Chicago defensive end Trace Armstrong and his agency, Athletes First, have represented two fired Bears head coaches, Matt Nagy and Eberflus; three fired offensive coordinators, Mark Helfrich, Luke Getsy and Shane Waldron; as well as current general manager Ryan Poles.
"I've never seen one agent have so much influence on one team and had so little success, but they keep going back and taking his guys," said one coaching agent, who requested anonymity to speak freely on the topic. "And we all kind of shake our heads like, have they not figured this out yet?"
The rest of the NFL sees what the fans see.
Armstrong might be a former defensive end for the team, but he has zero loyalty to the organization. His job is to get his clients work, and it didn't take him long to realize McCaskey would be an easy one to trick.
"Armstrong has had more influence with the Bears than any other team," a coaching agent said. "That's because he was dealing with an accountant that really didn't know football people, and he took advantage of that, and I give him credit for that."
People were surprised when former head coach Ron Rivera got an interview with the team.
He had plenty of experience and ties to the organization. It was logical the Bears would do this despite how things ended in Washington, right? Nope. In reality, Rivera likely got his interview because Armstrong once again worked over McCaskey.
When Ron Rivera was looking for new representation at the end of his tenure as coach of the Commanders in 2023, he said he hired his former Bears teammate Armstrong because it seemed like every time he'd interview assistants for a position, most of them were represented by Armstrong.
"The guy had a lot of connections, and that's what you look for, is a guy that can get you in front of other people," said the two-time NFL head coach, who interviewed for the Jets job in December and the Bears job Jan. 12. "The guy's a hustler. The guy works really hard."
George McCaskey isn't a leader. He's a weak link.
There is no other way to put it. He might be the chairman of the organization, but it is clearer than ever that he is not respected by actual football people around the league. They know he's in over his head and aren't surprised he is so easy to take advantage of whenever tough football decisions must be made. This is why the Bears have floundered so miserably for over a decade. The man making the most important choices inside the organization is like asking Homer Simpson to run a nuclear reactor. Disaster always follows.
Only a stroke of remarkable good fortune will save the Bears from this nightmare. GM Ryan Poles and team president Kevin Warren, both of whom are George McCaskey hires, somehow get the head coaching search right. Then again, we shouldn't act like this is anything new. George's brother, Michael McCaskey, also stumbled through the wilderness for over a decade. Dave Wannstedt and Dick Jauron were his two big hires after firing Mike Ditka in 1993. He mercifully stumbled onto Lovie Smith in 2004.
That should give you an idea of the Bears' quagmire and why fans desperately want this team sold.
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