When Chicago Bears President and CEO Ted Phillips announced last week he will retire at the end of the 2022 season, it created more change for a franchise that already is eyeing a lot of it.
In the middle of the Bears’ exploration of building a new stadium and entertainment complex in Arlington Heights, the team also is searching for a new president.
Here are some of their answers on what the Bears are looking for in the next president, how the Arlington project will be handled as Phillips prepares to depart, how Phillips reflects on his tenure and more.
The interview was edited for length and clarity.
The search for a new president
How far are you in the search process for a new president? Who’s involved and what will it entail?
George McCaskey: We’ve had plenty of discussions. We’ve got the search firm on board. The internal team consists of Tanesha Wade, Ted and myself. We’ve had good discussions with Nolan Partners. We established a rapport very early on with them. We feel good about the decision to have them assist us in the process. And we’re looking forward to a good result.
What are you looking for in the next president?
McCaskey: Leadership, vision, humility, consensus building. You look at the qualities of outstanding leaders, and we think we’re going to be able to bring in an exceptional candidate to succeed Ted and lead the Bears.
What sort of consideration will be given to people inside the building and is there an appeal to going outside the building?
McCaskey: We’re open to all possibilities. I would compare it to a head coach search. There’s no limitation on college or pro, offense or defense. The same principle applies on a broader scale to this position.
When you had a GM search recently, what did you learn about the way organizations worked around the league, if anything, that might inform your president search?
McCaskey: Well, one benefit of that type of experience is you get a little intel on how other organizations work, so that’s helpful. I’ll leave it at that.
You said in January that you didn’t get the appeal of a “football czar.” Does that hold here and can you say with certainty you’re looking for a business person as opposed to a football guy to fill the president role?
McCaskey: We don’t anticipate any change in the structure, but we’re not locked into a business or football person.
So general manager Ryan Poles would still report to you?
McCaskey: It would depend on the candidate.
Would you like someone with a balance of football and business expertise or does that not matter to you?
McCaskey: Again, we don’t want to get locked into a quote-unquote football person or a quote-unquote businessperson. What we’re looking for more are the qualities I recited just a moment ago.
A lot of teams have built stadiums recently. Would someone who has experience in this huge undertaking of building a stadium have an appeal to you?
McCaskey: Not necessarily. If that person didn’t have that type of background, we would count on him or her to find the right people with that expertise.
Ted, what do you think the Bears need in your replacement?
Phillips: Besides what George has said, I would say someone that can make tough decisions. It’s very important. Someone who can handle a lot of different balls in the air on a daily basis because every day is different. Someone who understands what it means to be a Bear. Culture here is important. You don’t have the right fit, you can be the smartest person on Earth but won’t get it done.
Someone that’s able to deal with different personalities from politicians to business leaders to the media. It’s not easy, so we need someone who can understand all those different dynamics. Someone who can groom younger people. I think about that because I got a lot of great opportunities when I was younger and through my whole career. So I love that, and I think that’s important for someone to be able to come in and be able to listen more than they talk and learn from others, including those who aren’t at the same level as them. It’s important.
Do you need to find the right personality match for Halas Hall?
Phillips: Not so much for Halas Hall but for the family, I do, yes. I do think that’s important. Because without that, you’re just another corporation. And that doesn’t work.
Ted, when are you retiring?
Phillips: Feb. 28.
George, when would you like a new president in place? Would you like him or her to spend a few months with Ted?
McCaskey: Just like the broad scope of the search, we’re not going to be locked in by someone’s availability. It’s going to be whenever the timing is right. If we find somebody in late February and Ted has to stay on for another six months…
Ted, will you consult with the Bears on a stadium project?
Phillips: George and I have just touched on that idea and have left the door open if it makes sense at the right time and it makes sense for the Bears and for me. I’d consider it. It’s hard to say no when you’ve been somewhere for 40 years.
McCaskey: It makes sense for the Bears.
The Arlington Heights stadium project
What steps are you doing to assure the handoff of the Arlington project to the next president goes smoothly?
Phillips: That’s going to be a big component of my successor’s role. What I’m happy about is that we have good people here internally who have been involved in the Arlington project, so assuming we close, assuming we develop it, there are a lot of people with expertise here, and obviously whoever that new CEO is, I’ll sit down with him, talk to him, explain all the ins and outs of what we’ve been going through. So I don’t see it being a difficult transition at all from that standpoint.
Ted, how much of your life has been devoted to the stadium the last 18 months? Is it exhausting?
Phillips: It’s not exhausting. That’s not why I’m retiring if that’s what you’re getting at.
(But) it’s a massive challenge. The idea it might take five years, 10 years if we go forward, more? That played a little bit of a role in my decision to retire. … When I get into a project I go full bore, and I still am full bore.
I believe, I hope, that by the time I retire this project will be in a place where we know if we’re going to close, maybe we have closed, hopefully we have closed. And that there’s a path to where we want to go, either developing or not developing. If I can get to that point, then the rest of it, we’ve got good people that know what’s happened, and I’ll make sure the transition is smooth. I’ve promised George that, so I have no problem doing that.
You said 10 years to complete the project. Is there a world in which this takes that long?
Phillips: Well, the whole development could take 10 years plus, for sure. And that’s just our preliminary guess, estimate, right?
With the stadium, is it more like five?
Phillips: Can’t tell. We haven’t designed it. We haven’t designed the stadium. I think you guys know that now. We’ve still got 12 years, 11 years left on our lease at Soldier Field, so that plays a role in it too.
There’s a way to end that lease earlier?
Phillips: We could reach a settlement with the city. We could.
What are the biggest challenges in getting funding for this project, including public funding, and do you have confidence that funding will ultimately be obtained?
McCaskey: Before we get to that, we have to determine whether we’re going to be able to close on the land. So we’re continuing our financial analysis. It’s not complete yet. But the focus in the short term is the property.
If you close and get funding for the stadium, what happens to PSL (personal seat license) holders at a new stadium?
Phillips: We haven’t gotten to that level of detail because the stadium is not designed. But we think we always take care of our long-term season ticket holders. … And if and when we get to that point, we will come up with a plan that we hope will be beneficial to the long-term PSL holders that we currently have. It’s important to us. But what that is, we don’t know yet.
Last night at the meeting in Arlington Heights, you talked about the 100-year search for a permanent home for the Bears. Have you always felt that way? Did you turn over a new leaf at some point? How did you come to the realization that this might be you fulfilling the dream of George Halas?
McCaskey: Well, George Halas in his book talks about how the Bears came to play at Wrigley, and how he had a handshake agreement. Over the course of the 50 years that they were there, it became less and less workable as a football venue. I mean, one of the end zones wasn’t even 10 yards deep for crying out loud.
… The move to Soldier Field in ‘71 was supposed to be temporary. We played one game in Evanston in 1970. But in each of those situations, the building had been designed and built primarily for other events or another team. This is our 100-year opportunity to design it for us.
Have you believed that for years, that it’s destiny?
McCaskey: No, I would compare it to a homeowner that rents year after year after year. I mean, there are advantages to that, but there are some significant disadvantages to that also.
Ted, as you reflect on your tenure, is there anything you could have done differently to set up the team for better success on the field?
Phillips: I know what’s been said. Obviously. I don’t have regrets. I don’t operate that way. Am I disappointed? Absolutely. We haven’t been able to find a consistently winning team. We’ve had moments of success that have been really fun to be around. But whether or not the structure would have made a difference, I’m not convinced that it would. I think you need a football decision-maker, which we’ve always had. And at some point that person always reports up to ownership.
I think we’ve done a good job here, and I’ll use Ryan Poles and Matt Eberflus as the most recent example of being told, “Put together the structure you need to give yourself the best chance of success.” Evaluating talent, there’s an art to it. It’s a difficult job. You could be wrong 40% of the time and be in the Hall of Fame. I think right now Ryan has put together a really strong personnel department that has layers, not just of soldiers but of leaders, along with himself. And that’s going to be a big help.
So to answer your question: Would I do something differently? No. Maybe encourage past GMs to make sure they’ve got the right people in place who can have a lot of influence and listen to them. Again, we’ve taken the approach that the GM is the final decision-maker. I don’t see that being an issue if they make the right choices going forward.
You said you’ve heard what’s been said. What have you heard?
Phillips: Of course, everyone says I’m not a football guy. It makes me chuckle a little bit. I’m not a coach. I’m not an evaluator. I’ve been in the business for 40 years, and I think I’ve learned a little bit. I’ve never made the decisions of who should coach and who should play. So I guess that’s what I’m saying, the people that write that, I don’t quite understand it. But it’s OK.
Two years ago, when you decided to bring back Ryan Pace and Matt Nagy, you had that quote about everything but the quarterback is in place.
Phillips: It was taken out of context, but that’s OK.
What’s the right context to view that?
Phillips: It’s in terms of the people. They both brought a lot of good things to the organization. Some of the mistakes that were made were high-profile mistakes. Those are tough to come back from. The Achilles’ heel, the one thing I’d change: Get the quarterback right, please. That’s what I’d change. It is. It hurts when you see. I saw it. You’ve all seen the scrolling list. I think since the Super Bowl year there’s been 45 different starting quarterbacks. It’s disappointing. Hopefully, we’ve got that right now.
George, what do you appreciate about Ted’s tenure here?
McCaskey: Well, I’m sorry to be repeating myself. But it’s difficult to put into words my high personal regard for Ted and my high professional regard for him. The way he’s handled the various situations that he just described to you — all the personalities. He touched on just a few of them, and there’s so many more.
When he was my boss, I would look at an issue that faced the organization and think about how I would handle it. And sometimes the path Ted took after he explained it was so clear and made so much sense that I was wondering why I was puzzled about it in the first place.
That’s the kind of leader that he is. He talks about making tough decisions. Not everybody can do that. And when you make tough decisions sometimes you make people unhappy. But he’s always thought about what was best for the Chicago Bears. And just very grateful to Ted and indebted to him for all he’s done for the Bears and all he’s done for our family.
Is this emotional for you, Ted?
Phillips: Of course it is. Forty seasons. It’s a blessing. George used the word that I had in my head. I’m grateful. Grateful for the opportunities. Grateful for all the people here that have made my job easier. It’s been a great team effort. I’ll miss it.
Potential Soldier Field renovations
What do you think of the proposal of putting a roof on Soldier Field?
McCaskey: Our singular focus is Arlington Park.
Have you talked with Mayor Lori Lightfoot or the city about that proposal at all?
McCaskey: She called me shortly before that proposal was presented. We had a good conversation. I have all the respect in the world for Mayor Lightfoot.
What are those talks like? Are they frank, formal, casual?
McCaskey: She just called me up. I’m not going to share the details of the conversation.
Phillips: I can add a little color, from the standpoint of we’ve been very transparent with Mayor Lightfoot and the city. So you ask about the dome proposal. She knows we have an agreement with Churchill Downs. We have a mutual understanding that we will not explore any other site while we’re under contract for that land. She knows that. The city knows it. We’ve been very candid with them. So when they outline that publicly, we haven’t see any of the details because we told them we weren’t engaging in those discussions.
That agreement includes Soldier Field?
Phillips: Correct. We can engage on current operations. But we agreed with Churchill Downs that we would not pursue any other site while we’re under contract with Arlington Park.
That includes renovations to your current site?
Phillips: Long-term renovations, yep. It does.
How do you measure success this year?
McCaskey: Wins are always a gauge of success and progress. Beyond that, I’d like to see some of the themes that Matt has been emphasizing — discipline, smart play, hustle, swarming defense, takeaways, going for the ball. Three-and-outs. Getting the run game going. Minimizing mistakes. And learning from mistakes. He talks about getting better each week, and that’s a good gauge.
What shows you that what needed fixing has been fixed?
McCaskey: In our search for the GM, we relied on Bill Polian and his intelligence network to tell us whether a candidate was a good talent evaluator. I don’t know that there’s any question you could ask or any foolproof research that you could do that would answer that question. We’re relying on his sources for that. And then just what (Poles) conveys in the interview. And what we saw in the interview I think you’re seeing play out on a day to day basis here. His organization, his leadership. His what I would describe as a preternatural calm. Just has a sense about him that when there’s chaos all around him, he’s going to remain calm and make sound decisions.
George, how’s your mom doing?
McCaskey: Doing well. Thank you.
Why the orange helmets? Why mess with a good thing, like the New York Yankees?
McCaskey: That was a consideration. And I think when it comes to uniforms, the Yankees are the Bears of Major League Baseball, if I may borrow from Jerry Reinsdorf. That was a consideration. But we’ve retained the classic look, but over the years we have made minor adjustments from time to time. In ‘62 we added a decal to the helmet. In ‘73 we put the orange in the decal. In ‘84 we added the GSH monogram. In recent years we’ve added the alternate jersey, which is really, in my view, a throwback to the 1930s when we were setting a record for most consecutive regular-season wins. That team was a juggernaut.
We see this as yet another enhancement of a classic look. And I think, like the orange jerseys, people said, “Ugh! That’s too much!” And then we won a few games in them and they became pretty popular. I’m hoping it’s much the same with the orange helmet, orange jersey combination.
Source: Berkshire mont