Bears president and CEO Ted Phillips to retire after the 2022 season, ending a 23-year run

After 23 years as president and chief executive officer of the Chicago Bears and 39 years as a member of the team’s front office, Ted Phillips is retiring at the end of the 2022 season, marking the end of an era in which the team thrived off the field but was inconsistent on it.

Last fall, Phillips, 65, told team chairman George McCaskey he was considering retirement. After a series of discussions, the decision was made for Phillips to step down next February.

“When COVID came, it changed a lot of dynamics and gave me some time to reflect on my life, my work life,” Phillips said in an exclusive interview with The Athletic. “I came to the conclusion that, my gosh, almost 40 years is a long time. It’s time to hand over the baton and give myself the gift of time. You know how this business can be, a lot of hours and time away from family. I just turned 65 years old. I feel good. My health is good. I felt it was time to slow down and do whatever I want to do.”

McCaskey said his primary feeling about Phillips’ tenure with the Bears is gratitude.

Asked what stood out about Phillips’ run, McCaskey said, “His humility. His intelligence. His consensus building. His steady hand. His refusal to get too high or too low. He’s been an outstanding leader for the Bears. Peerless is the word that comes to mind.”

The process of finding a successor has begun. McCaskey, Phillips and Tanesha Wade, senior vice president of diversity, equity and inclusion, have been in discussions with the search firm Nolan Partners.

Potential in-house replacements may include senior vice president of marketing and communications Scott Hagel and senior vice president and legal counsel Cliff Stein. McCaskey said he would not identify possible candidates at this time.

Ted Phillips, left, and Bears chairman George H. McCaskey listen to new general manager Ryan Poles during a news conference at Halas Hall on Jan. 31, 2022. (Nam Y. Huh/Associated Press)

The renovation of Soldier Field nearly 20 years ago was Phillips’ crowning achievement. In the 1990s, the Bears found themselves in an antiquated stadium without revenue streams that were competitive with other stadium-team deals. Without a new home, the Bears might have had to take drastic measures to ensure survival.

The Soldier Field rebuild significantly increased the Bears’ profitability and gave the team its first satisfactory football-only stadium in 100 years.

Phillips, known for his people skills and an easy, hearty laugh, approached the stadium dilemma by building trust with then-Chicago Mayor Richard M. Daley. Phillips and Daley found common ground in their love of the Bears. They talked about players, games and coaches, as well as where they would play. Then Phillips asked the McCaskeys to grant him permission to sign a five-year extension on their below-market lease at Soldier Field. On the surface, it was a step back for the Bears — but it paid off because it set the tone for a give-and-take relationship between the team and the city.

Initially, Phillips proposed demolishing old Solider Field while leaving the landmark colonnades and building a new stadium in the south parking lot. Daley rejected that idea but accepted a second proposal to rebuild the stadium in its existing location.

The $630 million Lakefront Improvement Plan that was agreed upon was funded by a hotel tax and more than $200 million from the Bears and the NFL.

“When I think about it, that probably was the highlight of my career,” said Phillips, who accomplished what George Halas and Michael McCaskey failed to in numerous attempts. “There was a lot involved, working with the political strategists, architects, three contractors, politicians, different lawyers. It was an all-encompassing, 24-7 job for a while. When I drive to Soldier Field sometimes, I still look at that place and say I can’t believe we got this done.”

As his career winds down, Phillips spends most of his hours working on the Bears’ next home as the point person for a stadium in suburban Arlington Heights. George McCaskey said when the Bears were approached about bidding on the land formerly occupied by Arlington Park, Phillips researched the value of the land and led the Bears through a complicated bidding process. Since their bid has been accepted and a purchase sale agreement signed, Phillips has been responsible for entitlement due diligence and has engaged with experts in corporate land purchases, stadium architecture, traffic and financing.

The intention is to close on the property before Phillips retires, but Phillips and McCaskey indicated there are too many unknowns and challenges to determine if or when a closing will happen.

McCaskey said the new president likely will be in charge of the new stadium pursuit but not necessarily. “It depends on that person’s skill set,” he said.

It’s also possible Phillips will be retained as a consultant for the project. Both McCaskey and Phillips said they are open to the possibility but have not yet discussed it.

In January, the organizational flow chart changed. In the past, general managers reported to Phillips. New general manager Ryan Poles reports to McCaskey. When the change was announced, McCaskey referenced the Arlington Heights project as a reason.

But there was more to it.

“The reality is the team wasn’t a consistent winner,” Phillips said. “So I talked to George and told him that we need to make some changes in terms of football reporting, and the decision was made to make a change.”

During Phillips’ reign, the Bears have a .480 winning percentage and failed to make the playoffs in 73 percent of their seasons. Phillips called the lack of winning “my biggest disappointment.”

Fans and media sometimes blamed Phillips for the Bears’ struggles, but he never made decisions about players and was not a meddler. He hired the people to make decisions about players and then discussed their choices with them.

“My role has been to be a sounding board with the general manager, to provide resources to support the team,” he said. “We have linked on our GMs to put the right structures in place and have the right evaluation processes in place. The Achilles heel of the Bears for many decades has been to have the right quarterback in place who is not only talented but can lead and raise the talent level around him. In my opinion, having the head coach or general manager report differently would not have changed any of that.”

The Bears’ losses could not be blamed on facilities. Phillips was in charge of two significant renovations of Halas Hall that gave the Bears a world-class home. In 2012, 30,000 square feet were added to the Lake Forest building, which opened in 1997. And then in 2019, nearly 200,000 square feet were added.

“Because of Ted’s efforts, we have one of the best facilities in the league,” McCaskey said.

Under Ted Phillips, left, the Bears enjoyed their best years with Lovie Smith as head coach, including a Super Bowl appearance. (Nam Y. Huh/Associated Press)

When Phillips started working for the Bears in 1983, he reported to the original Halas Hall, which cost about $98 million less to build than the latest renovation of the new Halas Hall. It’s one of many ways to measure the organization’s progress during Phillips’ time. In his first year with the team, the Bears employed 50 people, including nine coaches. Now, the team employs about 250 people, including 25 coaches. The Bears went from having one practice field (not counting the public park down the block or the high schools they bused to) to five.

When Phillips became team president in 1999, the value of the average NFL team was $400 million, and the Bears probably were below average because of their stadium situation. Now, Forbes estimates the team is worth $5.8 billion.

“The growth has been staggering,” Phillips said. “It’s fun to have been apart of that. It’s meant that every day my job is different. You never know what’s coming next from finance to football to marketing to public relations to fan experiences to community relations.”

All of it was beyond his imagination when he was hired by the Bears on Sept. 28, 1983. Phillips, a native of New Hampshire, graduated from Notre Dame in 1979 and took a job with the accounting firm Ernst and Whinney in Chicago. He was assigned to prepare tax returns for George Halas, the McCaskey family and the Bears. That’s how Phillips met Bears general manager Jerry Vainisi, who hired him as team controller.

When Vainisi was fired after the 1986 season, a void was created in the Bears’ front office. After several months of conversation, then-Bears director of administration Bill McGrane convinced Phillips to ask Michael McCaskey to make him responsible for negotiating player contracts even though Phillips had no experience in the role. McCaskey took a chance on Phillips, promoting him to director of finance.

Phillips negotiated all Bears’ player contracts from 1987 through 2000 and learned about football management, often consulting with former Bears general manager Jim Finks, who was with the Saints at the time, and Giants general manager George Young. He was promoted to vice president of operations in 1993 and took on the added responsibilities of overseeing football operations.

In early 1999, Michael McCaskey botched an attempt to hire David McGinnis as head coach. His mother, Virginia McCaskey, subsequently decided to replace Michael as team president. In a meeting at McCaskey’s suburban home, Virginia and her husband Ed told Phillips they wanted him to succeed Michael.

On Feb. 10, Phillips assumed the title of president and chief executive officer, making him the fourth president in team history and the first not of the Halas lineage.

During Phillips’ watch, the team hired general managers Jerry Angelo, Phil Emery and Ryan Pace, as well as head coaches Lovie Smith, Marc Trestman, John Fox and Matt Nagy.

Angelo was the Bears’ first general manager in 15 years. Phillips and Angelo worked well together for a decade when the Bears made four playoff appearances and one Super Bowl appearance and had a winning percentage of .540. Phillips called the Angelo years the highlight of his tenure from a football standpoint.

“The fact I had a hand in bringing Jerry aboard, I’m really proud of that,” Phillips said. “I’m forever grateful to Jerry for putting together a really solid team and bringing in Lovie and a good coaching staff. We had some really good years.”

Phillips also left footprints at the league level. He serves as chairman of the NFL’s Employment Benefits Committee and also is a member of the Management Council Executive Committee Working Group, as well as the CBA Player Benefits Plans Committee.

As he prepares for the next phase, Phillips said he treasures his friendships around the NFL and values ​​relationships at Halas Hall. He credits the people he has worked with for all that was accomplished during his tenure.

“I’m so blessed,” he said. “The McCaskey family has been so trusting of me. I feel like part of their family. It’s honestly been a dream come true to work for such a treasured franchise and a family with the most humble people you can imagine but at the same time have a fierce desire to win football games. My career has been a joy every day.”

(Photo: Robin Alam/Icon Sportswire via Getty Images)


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