Phillips was named team’s President and CEO in 1999, and he first joined Chicago’s staff in September of 1983, when he worked as the team’s controller. He worked his way up over his 39 years with the organization, also serving as Director of Finance and Vice President of Operations during his time with the franchise.
“I came to the conclusion that, my gosh, almost 40 years is a long time,” Phillips told Pompei about his decision to retire. “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.”
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Potential In-House Replacements for Phillips Named
Since he was named President of the team in 1999, the Bears amassed a record of 177-192, which ranks 17th-best out of 32 NFL teams. The Bears had three playoff victories and no Super Bowl championships over that span.
“The reality is the team wasn’t a consistent winner,” Phillips admitted to Pompeii. “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.”
So, who could succeed Phillips as the team’s fifth President in history, while also taking over the overseeing of the team’s new stadium construction in Arlington Heights?
“Potential in-house replacements may include senior vice president of marketing and communications Scott Hagel and senior vice president and legal counsel Cliff Stein,” Pompeii revealed, also noting that team Chairman George McCaskey “would not identify possible candidates at this time.”
McCaskey did tell Pompei that “the new president likely will be in charge of the new stadium pursuit but not necessarily. It depends on that person’s skill set.”
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Don’t Count Trace Armstrong Out, Either
Another name to consider as Chicago’s next President and/or CEO is Trace Armstrong, who played defensive end for the Bears from 1989 to 1994. Armstrong, who has spent over a decade working as a professional agent for Athletes First, represents both Bears general manager Ryan Poles and head coach Matt Eberflus. His ties to the team still seem relatively strong.
Pro Football Network’s Adam H. Beasley reported in January of 2022 that Armstrong “convinced the McCaskey family to take a chance on Poles, but he also persuaded them to make Eberflus part of the package deal.”
It’s far too early for the team to name its next President, but Armstrong has both business savvy and football acumen. If the Bears really do want to bring a more football-oriented replacement in to fill Phillips’ shoes, Armstrong may be the perfect choice.
In the meantime, some are celebrating Phillips before he rides off into the sunset at season’s end.
Team owner Virginia Halas McCaskey said the following about Phillips in a statement shared by ESPN’s Courtney Cronin: “He started out with us as a financial expert. Anything that he was ever asked to take care of, he came through and did it very well. We’ve been very blessed to have him.”