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Kyle Long (75), Jonathan Bostic

Cap Guru Cliff Stein Keeps the Bears Ahead of the Game

Deep inside Halas Hall is an office belonging to one of the most important members of the Chicago Bears organization. The man occupying it doesn’t throw blocks or make tackles. He isn’t part of the team’s coaching staff. He never holds press conferences or speaks to the media—repeated requests to the team’s PR department for this story were rebuffed.

His name is Cliff Stein, and though he may not be known to casual fans, it’s unlikely the Bears would have a roster with six Pro Bowlers, or a depth chart full of talent that many feel can challenge for an NFC North title in 2013, without him.

Stein’s official job title with the Bears is general counsel and vice president of football administration, but in layman’s terms, he is the team’s capologist. While GM Phil Emery picks the players, and new head coach Marc Trestman and his assistants handle the X’s and O’s, it is Stein who structures the contract’s of the 53 players on the roster, ensuring the Bears are under the NFL salary cap and following all the rules of the league’s Collective Bargaining Agreement. Under Stein’s guidance, the Bears have been able to acquire premier players in trades (Brandon Marshall), in free agency (Julius Peppers) and are often the first of the 32 NFL teams to sign all of their draft choices.

Bears rookies Kyle Long and Jordan Mills shake hands during minicamp.

Bears rookies Kyle Long (left) and Jordan Mills shake hands during minicamp.

Look for Stein in his Halas Hall office and, more than likely, he’ll be talking with someone. Stein is constantly in conversation, speaking with NFL agents, other members of the front office and people around the league. His LinkedIn profile describes his work experience and educational background, but his picture shows him chatting away, a black phone pinned to his left ear.

“I think the world of Cliff,” said longtime NFL agent Eugene Parker. “As a professional, he’s one of the best. He’s always fair, prepared and smart.”

Through the looking glass

A former agent, Stein represented football clients for seven years before he switched to the management side of the negotiating table in 2002; he’s been in his current role as the team’s lead negotiator since 2007. His counterparts in the business say his up-front and direct approach when figuring out contracts is a rarity in the cutthroat world of football deals. Given millions of dollars are at stake—along with only 53 job opportunities on the roster—each contract Stein works out is of vital importance to both parties involved.

“I can say this even more now that I’m a member of the media, but that experience as an agent is invaluable,” said Andrew Brandt, an ESPN NFL business reporter and like Stein, a former agent and front-office exec. “Cliff does a really good job of seeing both sides by being hard-working but fair. He’s very direct and honest, which is huge.”

Parker has worked out hundreds of deals during his lengthy and successful career as an agent for stars such as Deion Sanders and Larry Fitzgerald, and that includes several with Stein and the Bears. He represents Cedric Benson, the Bears first-round pick in 2005 who held out, missed 36 days of training camp and joined the team less than two weeks before their first regular season game. The agent also works for Alshon Jeffery, the team’s second-round pick last spring who signed his contract on May 2, 2012, less than a week after he was drafted to the team. In both cases, Stein was the same, according to the agent.

“Cliff always knows his stuff, and he’s great at separating the personalities from the business,” Parker said. “We may disagree on values, terms and conditions. Cliff can always be taken at his word. He has integrity, which is huge.”

Those adjectives used to describe Stein’s work ethic correspond to his off-field personality as well. Parker spoke of his counterpart’s kindness during the hectic Benson negotiations eight years ago. The two sides met at Parker’s Fort Wayne, Indiana home-office because the agent was simultaneously trying to work out a million-dollar deal with the Bears and care for his under-the-weather wife. According to Parker, Stein was patient and understanding, allowing Parker to come and go from the office as often as needed so he could be attentive to his spouse. As Parker came and went, Stein continued to work. Eventually, the two sides agreed to a deal.

“I remember clearly that Cliff went about it the right way. He was patient with me as I took care of my wife, and we were able to take care of business,” Parker said. “Cedric holding out had nothing to do with Cliff or the angst of the negotiations. The marketplace dictated why Cedric held out.

“Dealing with Cliff, he doesn’t create issues when there are none. He’s always looking to get a deal done quickly, but fair.”

The Bears signed Khaseem Greene (20) within a week of drafting him.

The Bears signed Khaseem Greene (20) within a week of drafting him.

A premium placed on speed

The speed at which Stein works is remarkable. The Bears are always among the first teams to sign all their rookie draft choices. That has proven true in 2013, when the team signed four first-year players to contracts before any of the league’s 31 other teams had signed any rookies. In recent years, they also have struck big deals on the first day of free agency to fill the holes in their depth chart. Part of that is the work of the scouting department, and a huge chunk of the credit goes to Emery and the rest of the player personnel staff. But much of it is Stein, who knows the market value and the league salary cap as well as anybody.

Signing players quickly, to fair deals, has several benefits. Not only does it avoid holdouts and give rookies their best opportunity to learn the playbook and win a starting job in training camp, it also creates an atmosphere of trust in the locker room. Bears players know the front office isn’t trying to screw them, and that they are being compensated fairly compared to the rest of the league. According to peers that know Stein well, he is tough but straight-forward, and lacks a hidden agenda, helping strengthen that feeling of trust during tense negotiations.

“As a former agent, Cliff can really figure out where the other side is coming from,” Brandt said. “He gets past the b.s., past all the games. He’s heard all the lines and said all the lines, and is just looking to get a deal done.”

The unknown maven inside of Halas Hall doesn’t seek the spotlight. However, his presence is well known among those inside the league, and though Bears fans barely recognize his name, Stein’s body of work speaks for itself.

“You want to deal with someone who understands market value and how to get deals done,” said Derrick Fox, an agent for a handful of NFL players. “And that, simply, is Cliff Stein.”

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