Bears Ownership in ‘Turmoil,’ Multiple Big Changes May Be Coming: Report

Virginia Halas McCaskey

Getty Virginia Halas McCaskey has been the Bears' owner since 1983.

Chicago Bears owner Virginia Halas McCaskey, daughter of legendary team founder/coach George Halas, inherited the Bears when her father died in 1983, making her the longest-tenured owner in the NFL.

According to a new report by top Bears insider Jeff Hughes of Da Bears Blog, the 99-year-old McCaskey is “not well,” and neither are team dynamics.

“Virginia McCaskey is not well. And things inside the McCaskeys are not either,” Hughes wrote on March 11. “The family has rarely been in this much turmoil over the last thirty years and there are some close to the organization who believe a sale might actually be on the table once Virginia passes.”

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Hughes: Bears President Ted Phillips is Retiring in 2023, Team Struggling to Find Replacement

Hughes, who was the only insider to reveal the team was parting ways with both ex-GM Ryan Pace and former coach Matt Nagy, has been correct about the majority of his reports and is one of the most tuned-in insiders covering the team. In addition to revealing the team’s matriarch is currently ailing, Hughes also reported team chairman George McCaskey, son of Virginia, is having a difficult time finding a replacement for team President Ted Phillips, who Hughes says is retiring next year.

“One of the major issues facing George is replacing Ted Phillips, who is set to retire in 2023,” Hughes wrote. “George doesn’t have to plan to do it and is ill-equipped to handle any of the duties currently performed by Ted. (He’s also not particularly interested in doing that much work.) Bears fans have never understood that the team’s connections around the league are Ted’s, not George’s, and ultimately, it’ll be Ted that leads the process of finding his replacement inside Halas Hall.”

Hughes then named a potential front-runner to replace Phillips.

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Cliff Stein Named Potential Replacement for Phillips

If and when Phillips retires, who could replace him? “Look for Cliff Stein to be an internal frontrunner,” Hughes noted.

Stein is currently the team’s senior vice president/general counsel, and has been with the team for 20 years. He serves as the lead negotiator for all player contracts while also assisting the GM  with salary cap management, as well as with all legal issues in the football operations department. Stein, like Phillips, has established many contacts throughout the league.

He is also the liaison between the NFL’s management council and the Bears on all CBA/salary cap compliance-related issues in addition to being the Bears’ general counsel on all general legal matters. Clearly, he wears a lot of hats. He was named the team’s senior vice president in 2016. He received his law degree from Temple University in 1994.

The team has yet to comment on the condition of Halas McCaskey, and so far, Hughes is the only one to report she’s currently unwell.

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