One of the most underrated decisions thus far by GM Ryan Poles was turning over salary cap control and contract negotiation to Cliff Stein. While he’s hardly a household name among casual Chicago Bears fans, the man is among the most respected in the NFL. A former agent, he was hired by the organization in 2002 to take over those same duties. From there, he became arguably one of the best negotiators in the league. Somebody that both NFL people and player agents respected in equal measure.
Stein was a rare breed. Somebody that could see from both sides of the table. That is often why he could get players signed so much faster and efficiently than other teams. It was so confusing when Ryan Pace decided to move him out of that role in favor of Joey Laine. It felt like he was just getting a buddy of his from New Orleans a job rather than employing the most qualified. It spoke to how much the ownership favored Stein that they kept him on in a different role.
Now he’s back where he belongs.
The question moving forward is how much longer he stays there. It isn’t because the Bears have any plans to fire him or anything like that. Instead, there are rumblings that the McCaskey family might have bigger things in mind for him. A few months ago, rumors began to percolate that team president Ted Phillips is contemplating retirement in 2023. If so, that would leave a question of who will succeed him. Jeff Hughes of Da Bears Blog, who’s been on top of this from the beginning, believes there is growing momentum for Stein to fill that void.
“Yes, Cliff Stein is back running contracts and cap for the Bears. But he is also the in-house frontrunner to replace Ted Phillips in 2023. There are many strong outside candidates – including Trace Armstrong – but Stein has a lot of support in the McCaskey family.”
Something like this makes plenty of sense. The McCaskeys aren’t known for having the strongest connections around the NFL. Researching outside candidates is something they will consider, but it’s more likely they’d prefer somebody they’re familiar with. Somebody they’ve known for 20 years now. Stein would make an excellent choice given his business background coupled with loads of experience working with football people.
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Cliff Stein would undoubtedly be the most seamless transition.
If the timeline rumored with Phillips is correct, that means he will be gone after the 2023 season at the latest. Smart money says both Poles and head coach Matt Eberflus will still be employed at their jobs during that time. Under such circumstances, it might not be wise to bring in a brand new team president from outside. Such a person might have ideas about forging football operations of their own.
On the other hand, promoting Cliff Stein would be far simpler. He already had a relationship with Poles going back to when they first connected in 2008. The latter was an undrafted rookie out of Boston College at the time. They are now working closely together in contract and cap discussions. That connection should only strengthen over the next two years.
Stein would make a perfect intermediary between the GM and ownership.
Whether he’ll be an improvement on Phillips is anybody’s guess. He will be different. At this point, Bears fans would welcome that. Truth be told, this is something the man has deserved for a long time. His work speaks for itself. If anybody has been groomed to become president of this franchise, it’s Stein.
