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Cliff Stein’s rise and fall and what led to his dismissal

After 22 years, Cliff Stein is out with the Chicago Bears organization, what led to such a significant change?

Twenty-two years is a long time. Sometimes it’s long enough where change is needed, but even if that is the case, change can be jarring.

For many in and around the Chicago Bears organization, there was plenty of surprise that the Chicago Bears have moved on from Senior Vice President and General Counsel Cliff Stein.

There has been no change to the Chicago Bears website about Stein’s position with the organization but Stein did announce that his time with the Bears had ended on his personal LinkedIn page.

After speaking with multiple sources, we looked back at Stein’s tenure in Chicago and examined why such a massive change took place at Halas Hall.


When Jerry Angelo was hired as the Chicago Bears General Manager back in 2001, after his first season finished, he realized that the organization could use an upgrade in contract negotiations and someone with salary cap expertise.

Angelo knew of an up-and-coming young agent named Cliff Stein. He had his law degree from Temple and had a strong grasp in contract negotiations so in January of 2002, shortly after Donovan McNabb and the Philadelphia Eagles defeated the Chicago Bears in the Divisional Round of the playoffs, Angelo brought Stein aboard as their chief contract negotiator.

Stein’s early work was impeccable. He earned the reputation as a firm but fair negotiator. Stein was incredibly smart and did extensive homework before entering negotiations with agents. He would examine previous contract structures from particular agents to see where their preferences lay and would do plenty of background research with his negotiation “opponent” to know them better.

A perfect example of this was when Stein entered his first negotiation with NFL super agent Drew Rosenhaus. He read his book that had been released a few years earlier looking for tells.

Stein was also at the forefront of what we all now accept as the standard 4-year rookie deal, but rookie deals weren’t standardized for years; Stein helped bring the 4-year deal to the league and helped standardize rookie deals, which was a huge step forward for the league in general and led to more franchise stability.

Beyond his work with the cap and contracts, Stein’s legal background became invaluable for President Ted Phillips. Phillips was a businessman, and Stein’s knowledge of the law allowed him to become a key advisor to Phillips which led to his expanded role in the organization.

When Phil Emery took over as general manager in 2012, he kept Stein in the same role as the cap expert and contract negotiator. When Ryan Pace took that same job in January of 2015 after Emery’s dismissal, he did the same. However, after their first offseason together, Pace made a change and brought in Joey Laine from the New Orleans Saints in May of 2015.

Pace had previously been with Laine in New Orleans, but he wasn’t brought over immediately. While sources wouldn’t clarify if it took Pace a few months to get Laine over from New Orleans or if there was an issue with Stein and Pace during their first offseason together, it didn’t appear that Stein was going to be a good fit for Pace’s football operations.

Stein remained with the Bears as their general counsel. His relationships with Phillips and the McCaskey family were strong, and they were committed to keeping him a part of the organization.

But like all NFL franchises, change is a constant. In January of 2022, Ryan Poles was brought in as the team’s new general manager. Poles, at the suggestion of George McCaskey and Phillips, reinstated Stein in his previous role prior to Pace’s arrival. A year later, the Bears started the process of replacing Ted Phillips who had announced his upcoming retirement. Kevin Warren was hired in January of 2023 to replace Phillips and started officially in April of that year.

Warren had previously stated that he was going to take the first several months and examine the Bears franchise from top to bottom. He would evaluate all aspects of the organization and make any changes he saw fit.

Roughly eight months into his tenure as President, Warren (and this decision was Warren’s) decided to relieve Cliff Stein of all his duties with the Bears. This was a move that also shows that George McCaskey has given Warren significant power in the organization to make serious change if he deems it necessary.

The news surprised multiple people in and around the organization. Letting someone go after more than two decades of service isn’t a decision that you come to lightly, so how did Warren get here?

Multiple sources said that Stein’s reputation as a firm but fair negotiator had tilted too far in one direction. Many agents felt that Stein had started driving too much of a hard bargain during negotiations which led to some relationships being damaged with player representation.

One source cited a particular issue with Jaquan Brisker’s contract negotiation that resulted in Brisker missing rookie minicamp (previously been reported by Pro Football Focus’ Brad Spielberger).

Another source discussed that Warren felt that Halas Hall was a “leaky ship” and that too much information had been reaching the media before it should have been reported. While the source didn’t directly link any information leaking to Stein, he did say that Warren needed to “clear out the old Oak Trees” to help tighten up things at Halas. Whatever information has leaked from Halas Hall to the media, a different source said he would be shocked if one of them was Stein, considering his legal background and how keeping client information under wraps is a critical aspect of a lawyer’s position within an organization. One source suggested that there may be other high-level executives within the organization that could be let go in the coming weeks.

The Bears are entering possibly the most important offseason in the history of the franchise and have several decisions to make, especially the one at quarterback, that will determine the future direction of the team. They certainly don’t want any potential leaks out of the building that could damage what they want to do and what they want to accomplish this offseason.

The Bears want to avoid the same issues the Chiefs faced in 2017. The Chiefs fired general manager John Dorsey in June of that year. There was a long-standing rumor that it was because Dorsey leaked information to the media of the Chiefs’ intention to trade up for Patrick Mahomes, which led to the Chiefs needing to give greater draft capital to make the move. That rumor was confirmed on Parkins and Spiegel a couple years ago by CBS Sports’ Boomer Esiason.

Last, but certainly not least, is the issue of the new stadium. As we all know, a large piece of Kevin Warren’s role as Team President was to lead the way in building a state-of-the-art stadium for the Chicago Bears. That task started prior to Warren’s arrival and was largely handled by both Phillips and Stein.

One source mentioned that Warren wasn’t thrilled with some of the work that was done prior to his arrival, particularly with the town of Arlington Heights. Those issues have led to a stalemate between the Bears and the town and may ultimately impact what location the Bears eventually finalize as the home to their new stadium.

Warren said there would be changes. It started small with things like better food in the press box, but this is the first major change, and some others could be on the horizon. There was always a strong possibility that Warren was going to want his own people as his top lieutenants in the organization and Stein’s departure shows that possibility is now becoming a reality.