Chicago Bears part ways with senior VP and general counsel Cliff Stein after nearly 22 years with the organization

As the Chicago Bears work to fill out coach Matt Eberflus’ coaching staff — with coordinators needed on both sides of the ball and more — the team is shaking things up outside of football operations.

The team is parting ways with Cliff Stein, a senior vice president and general counsel, after nearly 22 years with the franchise.

On one hand, the news comes as a surprise given that Stein always has been highly regarded within the organization — and the league. On the other, there have been rumblings for months that President/CEO Kevin Warren might have major changes in mind after being on the job for nearly a full year.

GM Jerry Angelo hired Stein in 2002 to manage the team’s salary cap and be its contract negotiator. Stein worked in that role until the arrival of GM Ryan Pace in 2015. Pace brought in Joey Laine to handle the cap and contracts, and the Bears kept Stein because of his legal acumen.

When Ryan Poles was hired in January 2022, Stein was charged with handling the team’s cap and negotiations once again. Poles credited him with helping Matt Feinstein transition into the role.

“We have an unbelievable analytics team, our cap group,” Poles said. “We have Matt and Cliff, who do a great amount of research to kind of keep us in that range in making smart decisions,” Poles said in March.

Stein, who survived thyroid cancer in 2005, broke into football in 1994 as an agent working out of New Jersey. He was considered a shrewd negotiator and years ago, when many Day 3 draft picks would wind up with three-year contracts, Stein was at the forefront of creating a consistent four-year structure for Bears’ picks. That eliminated the possibility they would deal with draft picks that became restricted free agents.

The Bears also became one of the first NFL teams to actively work on late-season contract extensions to exhaust remaining cap space before the league changed rules that allowed teams to roll over unused space from one year to the next.