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Cliff Stein is the Bears’ money man

Bears negotiator salary cap expert Cliff Stein

Bears negotiator and salary cap expert Cliff Stein

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Updated: July 22, 2014 12:56PM



The maitre d’ at the Ritz-Carlton was right: No one could overhear their conversation.

Three men sat in a glass-enclosed room in March at a tapas bar in Orlando, Fla., miles from the fancy hotel crawling with NFL executives and media members.

Bears general manager Phil Emery dined with agent Ken Harris, whose client, defensive end Jared Allen, was a free agent. Harris had been smuggled out of the hotel, whisked behind a pillar at the valet parking station to avoid the eyes of an ESPN reporter and the Cleveland Browns’ staff.

The third man at the table was an essential piece of the Bears’ offseason plan who has — by choice — avoided the spotlight for years: chief negotiator Cliff Stein.

A former agent, lawyer and prosecutor, Stein is the Bears’ vice president of football administration and general counsel. He oversees the Bears’ salary cap and, with approval from president Ted Phillips and Emery, the financial side of player contracts.

‘‘I don’t think any of us were drinking wine,’’ an amused Stein told the Sun-Times in a rare interview, ‘‘but we were in a wine vault.’’

‘Tremendous respect’

The Bears spent a year crafting options for one of the busiest and most important offseasons in their history — ‘‘We always overplan for a number of scenarios,’’ Stein said — but signing Allen seemed implausible.

‘‘That plan always incorporates some things you might not expect,’’ Stein said, ‘‘[such as] when we traded for Jay Cutler or Brandon Marshall or, this year, the signing of Jared Allen. When those things become available, you can’t always predict and plan.’’

Over small bites, the sides laid out their motivations: Allen’s agent said his client wanted to play in Chicago. The Bears wanted him to take less money in the first year in exchange for more guaranteed in the second.

‘‘You don’t always get that flexibility in a free agent that has options,’’ Stein said.

Eventually, they had a four-year, $32 million deal.

‘‘A lot of that is Cliff’s understanding of the cap and all the consequences of where we were at and where we could go with it in the proceeding years and the amount of guarantees,’’ Emery said. ‘‘That’s just a credit to his ability to make that all come together.’’

Stein, a 47-year-old father of two, communicates with the NFL about rules, waivers and employee contracts in addition to negotiating deals.

‘‘Once the plan is laid out, I get a tremendous amount of autonomy,’’ said Stein, who was born in Philadelphia and graduated from Temple. ‘‘I’m really fortunate to work with some great leaders.’’

His dry wit is legendary at Halas Hall. He sums up tense negotiations by sending video clips from the ‘‘The Sopranos’’ or ‘‘Goodfellas’’ to Bears staffers.

‘‘He’s got a tremendous amount of respect throughout the NFL,’’ Emery said, ‘‘both from personnel people — in terms of his knowledge base and what he accomplishes with contracts — [and] among the agents. Because Cliff was one of them, they all recognize that.’’

A dealmaker

If signing Allen was a surprise cap to the Bears’ offseason, the cornerstone was Cutler, whose seven-year, $126.7 million contract is the largest in team history. The deal was finished four days after the 2013 regular-season finale.

‘‘When you have two sides highly motivated, it’s really not that difficult,’’ Stein said. ‘‘None of these have to take months, and none of these have to take weeks. All of these can be simple when you have both sides with a shared interest and one side’s not trying to do something unreasonable.’’

Cutler’s contract ‘‘had ramifications on everything else,’’ Emery said, because it ‘‘gave us a road map as to what was possible’’ with other free agents.

From the last week of the regular season to the start of training camp this week, the Bears signed 40 players — not counting draftees, rookie free agents and reserve/future deals — and gave Marshall an extension.

‘‘That’s why we were able to get all those contracts done at the end of the year,’’ Emery said. ‘‘He’s relentless in his effort.’’

Before being hired by then-GM Jerry Angelo in 2002, Stein described himself as a ‘‘no-name agent’’ for eight years. He said his wife, a lawyer at a large firm, took on the role as breadwinner while he pursued his agent ‘‘dream.’’

Stein, then, can sympathize with agents. About 55 percent of them don’t have an active player.

‘‘Coming to each situation with the understanding of their role is helpful, having done what they’re doing and understanding the challenges and difficulties in their life,’’ Stein said.

Stein ‘‘doesn’t try to embarrass you,’’ a prominent agent said. ‘‘He tries to make you look good in front of your client. He’s all about the win-win.

‘‘Some teams want to crush you. Some guys, it’s like playing tennis and they want to beat you. Cliff is more like playing in a best-ball golf tournament.’’

Sense of fairness

Angelo tells the story with wonder and respect. Before draft-pick salaries were codified by the collective-bargaining agreement, the Bears agreed to terms with a high selection who had a relative serving as his agent.

After other picks in his round had signed, it was clear the Bears were paying about $200,000 below market value. They knew the agent would look bad and the player would be shorted.

‘‘Cliff came to me and said: ‘Jerry, we gotta do something about this. We cannot embarrass this guy. We certainly can’t make the player feel like we took advantage of him,’ ’’ Angelo said.

The Bears didn’t have to do anything — the agent wouldn’t represent another player — but Stein suggested the contract take on a different structure to make up the difference.

‘‘Ninety percent of the teams would never have done that and just would have let it go,’’ Angelo said. ‘‘That was the integrity he had when he did contracts. That’s where he got that trust level.’’

Years later, that trust still is paying dividends.

‘‘That’s why he’s the best in football,’’ Angelo said.

Email: pfinley@suntimes.com

Twitter: @patrickfinley



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