4 Options to replace Ted Phillips as the Chicago Bears President/CEO

The Chicago Bears might turn to Cliff Stein as the next President and CEO

An obvious option that we might see take over for Ted Phillips is Cliff Stein. Stein is known as the contracts guru. He has been with the Chicago Bears since 2002, and he oversaw the salary cap for a large portion of his career here. He had an inside track to seeing both sides of the coin as a former player’s agent. Ryan Pace changed that in 2015 when he put Joey Laine in charge instead. We saw where that got the team.

Cliff Stein returned to that role again this year and it makes me wonder if the Roquan Smith situation is mostly at the fault of Smith not having a true agent. We will see if Stein can retain his title as contract guru as the team cleared a ton of cap space this season and left the door open for over $100 million in cap space next season. We will have to see how well Stein and Ryan Poles work together and if Stein will retain that role. If Stein replaces Phillips in 2023, they may have to look to replace him anyway.

Ted Phillips and Cliff Stein have worked together for years now and it would make sense for him to be the next in line. Stein is currently a Senior Vice President and General Counsel for the Chicago Bears. Could the Bears and Phillips be grooming him this season for a possible takeover?