Rumors have persisted for months now that Chicago Bears president Ted Phillips is approaching the end of his tenure with the organization. Pushing into his 60s now and having run the team for 23 years, expectations are he will likely retire as soon as the end of 2023. This explains why the organization has begun researching possible candidates to replace him. It was a big reason they met with Pittsburgh Steelers director of football and business administration Omar Khan in January.
According to Jeff Hughes of Da Bears Blog, who has been on top of team news since the offseason began, it sounds like ownership hasn’t put much time into lining up a successor. Part of that is George McCaskey being distracted by other issues. Namely, getting Ryan Poles and Matt Eberflus’s new regime and the health of his mother, Virginia. However, another part is the family may feel they already have Phillips’ replacement in-house.
“One of the major issues facing George is replacing Ted Phillips, who is set to retire in 2023. George doesn’t have a 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. (Also look for Cliff Stein to be an internal frontrunner.)”
This idea makes a ton of sense.
Stein has quietly been one of the unsung heroes of the Bears organization for two decades. He joined the team as their chief contract negotiator in 2002 after serving as a player agent from 1994 to 2001. He would hold that job until 2015, becoming one of the most respected men in the business. His ability to swiftly bring deals together before everybody else earned him a strong reputation. A big reason for that success was his unique background as a former agent, allowing him to see things from both sides of the table.
He has several contacts around the NFL and understands the Bears’ inner workings better than almost anybody else. In terms of qualifications, there are few better suited for the job of team president. His football background is far stronger than Ted Phillips’ was when he took over back in 1999. The McCaskey know and trust him. If they can’t find somebody they deem better in the next calendar year, don’t be surprised to see Stein promoted when Phillips finally steps down.
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