Bears president Ted Phillips will be gone soon. The McCaskeys won’t.

The much-criticized team official will retire in February.

SHARE Bears president Ted Phillips will be gone soon. The McCaskeys won’t.
Bears president Ted Phillips and chairman George McCaskey listening during a press conference.

Bears president Ted Phillips (left) and chairman George McCaskey listen to new head coach Matt Nagy speak during an introductory press conference in 2018.

Jonathan Daniel/Getty Images

Bears fans were celebrating Ted Phillips’ retirement announcement Friday, until it dawned on them that team chairman George McCaskey would hire Phillips’ replacement. Then they went back to their worldview that all hope is lost.

They know from experience that you don’t want a McCaskey, any McCaskey, taking the measure of a prospective employee, in the same way you didn’t want Phillips involved in the hiring of a coach or a general manager. It always ends in something that is not a Super Bowl title.

There are two disparate views of Phillips, who will be retiring in six months. There’s the view of him from ownership, which thinks he’s the consummate professional, if not a member of the family. And there’s the view of him from Bears fans, who think he’s an interfering paper pusher who, if asked to tell the difference between a football and a foot fetish, would request more time.

There is no in-between here, no nuance. It’s one or the other: great businessman or an embodiment of all that is wrong with the Bears. 

His legacy will be that of a person willing to do whatever the McCaskeys asked of him, even when it was clear to others that zigging at the family’s direction was reason to zag immediately. He was their point person on construction projects, from Soldier Field renovations to a new practice facility to a proposed stadium in Arlington Heights. He helped the McCaskeys make a lot of money. 

He took the brunt of the abuse for the renovated Soldier Field, which critics said was ugly and too small. Those shortcomings are why the Bears are now looking to build in the suburbs.

Phillips’ poor public image wasn’t all his doing, at least at the start. Whenever the Bears called a press conference to talk about another failed season or to introduce a new coach or general manager to replace the latest failed coach or general manager, he was front and center. He often had the look of a man who had accidentally swallowed a Swiss army knife, one that had just opened in his large intestine. His presence at these events was at the behest of George McCaskey, who knew he didn’t know anything and wanted to spread the ignorance around. So there was Phillips, a bookkeeper by trade, talking about the elements of winning football to the masses.

I don’t think Phillips was born this way. He’s what happens after prolonged exposure to the McCaskeys. He never should have been one of the faces of the franchises, and he should have begged to stay far away from microphones. Instead, he answered questions, and despite his insistence that he wasn’t involved in the football operation, it became obvious after a while that he certainly was. The Bears had gone through so many coaches and GMs that what you saw was what you got: McCaskey and Phillips by themselves with no one to rely on other than a consultant or two who had time traveled from the 1950s. 

Phillips didn’t know football, but he was thrust into a position in which he was expected to help hire coaches and GMs. Then he started to think he did know football. That’s the Bears right there.

Who to replace him? Despite the public gushing over the job new general manager Ryan Poles is doing — which sounds a lot like the public gushing that once washed over his predecessor, Ryan Pace — I’d like to see a football man as team president. Not an accountant. Not someone with an MBA. Someone to oversee the football department, which is the only department that should matter to a football team.

The problem, of course, is that George McCaskey will make the decision on Phillips’ successor. He’ll surely rely on the opinions of confidantes, but if you question McCaskey’s judgment on hires, then you have to question his judgment on confidantes, too.

If you haven’t liked any of his and Phillips’ other big decisions — Marc Trestman, Phil Emery, Matt Nagy, etc. — why would you like who’s coming next?

Phillips was with the team since 1984, and maybe that’s a clue to what the Bears will look for when deciding on his replacement. The McCaskeys want people owner Virginia McCaskey is comfortable with. It’s how they seem to end up with the same kind of people at Halas Hall year after year, decade after decade — people who think and act like the family does. 

The last, true football bigfoot the Bears had was Jim Finks. He was phenomenal. He was also hired by George Halas, not a McCaskey. 

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