Much of Cliff Stein's early career was occupied by high-stakes bargaining sessions negotiating NFL contracts.
The rest of Stein's professional life has been spent doing, well, pretty much the same thing.
Except now he's working the other side of the table.
Stein, 41, is Chicago Bears senior director of football administration and general counsel, a position he has held since 2002. He is also a former player agent, having represented football clients from 1994 to 2001. In a league that revolves around titles, the lengthy handle assigned to Stein is not that unusual. His background as an agent, however, makes him a curiosity of sorts.
And his track record of consummating contracts while many of his peers are vacationing makes Stein rare indeed. In two of the past three years, the Bears were the first team in the league to have all their draft choices under contract.
"The mentality of most [negotiations] in our league is that it has to be a win-lose kind of thing," Bears general manager Jerry Angelo said. "Somebody's going to get screwed, and somebody is going to come out on top. That's how most people view contract talks. But that's not the case with Cliff. He understands the nuances of [the task]. His firsthand experience on the other side of the table is beneficial, I think, because it gives him more perspective."
Through the years, franchises have employed a number of former player agents as key management officials. Bruce Allen, dismissed by Tampa Bay last year, was a longtime GM. Jack Mula once worked in the Patriots' front office, negotiating some contracts. Until recently, Andy Brandt was point man in most Packers contract negotiations.
According to the NFL Fact & Record Book, Stein is one of only two former agents currently employed full time by teams in any front-office capacity. The other is Redskins VP of football administration Eric Schaffer, who negotiates contracts and manages the salary cap.
Chicago president and CEO Ted Phillips has a strong background in finance. Angelo, at various points in his career, has negotiated player contracts. The Bears' management group has been essentially intact since coach Lovie Smith succeeded Dick Jauron in 2004. The core of Chicago's front-office team has been together for eight or nine years, which epitomizes stability in the NFL. The group provides Stein with directions more than it issues directives.
Said Angelo: "What I ask from Cliff is consistency. If we're going to sign guys to four-year contracts, then they should all be four years. You don't pick and choose."
The Bears have signed seven of their nine picks from the 2009 draft, all to four-year contracts. No other team has signed more than four players, and only 14 of the 256 prospects chosen in this year's draft have reached agreements.
Indeed, part of what makes Stein unique is his uncanny ability to complete contract negotiations before most franchises have even started talks. Given the NFL's deadline mindset, many teams don't even begin discussions with rookies and the players' agents until early July, basically using the impending start of training camps as negotiating leverage. By then, however, Stein typically has completed deals with all of Chicago's rookies.
"We usually start [negotiations] right after the draft," Stein said. "For us, it's a pretty busy time."
Last Friday was indicative of the warp-speed manner in which Stein operates and the positive results he frequently gets. That day, the Bears signed veteran defensive tackle Israel Idonije to a two-year contract extension. Chicago also came to terms with free-agent outside linebacker Pisa Tinoisamoa, the leading tackler in St. Louis last season, who was released recently. Just as impressive, the club announced that it had signed seven of its nine choices from the '09 draft.
Because of the Jay Cutler trade earlier this spring, the Bears did not have a first- or second-round selection. Not having to battle the agent for a first-round choice certainly makes things easier. But this is the first year since Stein arrived in 2002 that the Bears didn't own a pick in the opening round. In 2003, the club had a pair of first-rounders and Stein still finished the deals earlier than most clubs. In 2007, Stein began substantive negotiations with the agent for first-round choice Greg Olsen on a Thursday evening and finished the deal the next day, making the tight end the earliest top pick in the league to sign.
"Cliff is tough but fair, and he's able to better appreciate the job we do because he's walked in [our] shoes," said one agent who has negotiated multiple contracts with Stein. "He's got a great perspective from both sides of the debate."
Stein completes deals long before the market has been set, but his contract numbers hold up when scrutinized.
"We do things the right way," Stein said. "I think my experience [as an agent] has been beneficial because I can empathize with those guys. And I know there are people besides the player to whom they are answerable. But they're also our [vehicle] for interacting with the player at that point. Everything we do, from the first-rounder to the last, is transparent, especially after you get the first deal finished. But you want an agent to tell the client and his family that the team was fair with him. "
The initiative for having the team's draft choices signed early is an organizational philosophy by the Bears, one born of Angelo's time as Bucs director of player personnel. Although the rookie stance is a collaborative one, Stein is the man who implements that philosophy and, in doing so, facilitates the jobs of Smith and his staff.
The early signings mean that most or all of Chicago's rookies are already under contract when minicamps begin and the club starts its organized team activities.
In addition to the draft choices that Stein has signed since joining the team, he has negotiated 31 contract extensions for veteran players. And only once, for defensive end Alex Brown, did he have to go back and readdress the deal. And that wasn't so much that the numbers didn't jibe as it was a case of the salary-cap issues changing and an alteration in the leaguewide model for what defensive ends should earn.
"Whether it's draft picks or veteran guys, he has to look into the crystal ball and make projections about the level of salaries in the future," Angelo said. "That's hard to do. But in that regard, Cliff's batting average is impeccably good."
Len Pasquarelli, a recipient of the Pro Football Hall of Fame's McCann Award for distinguished reporting, is a senior writer for ESPN.com.