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Deal sending Theo Epstein from Red Sox to Cubs remains virtually inevitable

10.15.11 at 9:38 pm ET

One of the signature moves by the Red Sox under GM Theo Epstein now offers some hint of what to expect regarding compensation talks between the Sox and Cubs about Epstein.

In December 2006, the negotiations between the Sox and agent Scott Boras for the services of right-hander Daisuke Matsuzaka left baseball observers in two countries in a state of suspense. There was plenty of bluster and bluffing, to the point that the Sox said that they would board a plane from Southern California back to Boston without the right-hander.

But as much as it seemed possible, amazingly enough, that the deal might fall apart, it was always going to get done. There was too much at stake, too many parties that wanted the deal to happen for it to collapse.

The Sox needed Matsuzaka to come, both in order to upgrade their rotation and because the negotiation could have significant long-term ramifications for their presence in the Pacific Rim.

Matsuzaka was burning to take his talents to the U.S. and to test himself against the top professional league in the world. Unless the Sox low-balled him, he would have found it nearly impossible to return to Japan.

The Seibu Lions wanted Matsuzaka to go to the Sox so that they could reap the $51.11 million posting fee so that they could apply the money towards heated toilets (among other stadium upgrades).

The only party that didn’t want a deal along the lines of the six-year, $52 million deal offered to Matsuzaka by the Red Sox was Boras, who was frustrated by the fact that the pitcher was not being treated as if he was on the open market. Conceivably, Boras argued, Matsuzaka could return to Seibu and then either be posted again by the Lions or wait until he was a free agent to come to Major League Baseball.

But faced with the reality of sabotaging a deal that everyone wanted or accepting the shared feeling that a deal needed to get done, Matsuzaka and Boras relented, and Matsuzaka became a Red Sox.

The current situation regarding Epstein, the Red Sox and the Cubs features similar incentives.

Sox principal owner John Henry on Friday was already discussing Epstein’s tenure in the past tense; though he also said that he had done everything in his power to try to get Epstein to stay, the team has accepted the fact that he wants to move on, and the club is now ready to do the same and turn over the front office to Ben Cherington, at a time when they can get compensation for their outgoing GM.

Moreover, the Sox would potentially save millions of dollars should Epstein leave, for both his 2012 salary and a bonus he will be owed at the end of his contract. That fact alone helps to underscore why the Sox are interested in prospects rather than money in a deal.

The Cubs and owner Tom Ricketts have already embraced the idea of hiring Epstein — hence the agreement on a five-year deal — and if they believe that he is the right man for the job, they would have no apparent desire to find an alternative head of baseball operations or to waste a year waiting for Epstein’s contract to conclude.

And Epstein is excited enough about a new challenge in Chicago that he negotiated this deal. The idea of turning back and spending another year under contract with the Sox would represent something other than his best-case scenario.

(That said, it is worth noting that Epstein continued to work in the Sox front office — in the interests of a Sox as one of their employees — during the past week. While it is easy to assume that he would be uncomfortable staying in Boston for another year while eying his exit, that may not be true.

After all, he remains close to everyone in the Red Sox front office, and during the months in which Epstein walked away from the job after the 2005 season, he continued to work with members of the front office, including Cherington. And he is familiar enough with failed deals — for instance, the one involving Manny Ramirez and Alex Rodriguez after the 2003 season — that the idea of remaining professional after nearly being dealt away would not be foreign.)

In one sense, every party to the negotiation has significant leverage. In another, no party in the negotiation has significant leverage.

Ultimately, the talks boil down to this: Everyone wants the deal to get done. And so, barring something dramatically unforeseen, it will get done.

Indeed, one source familiar with the negotiations suggested that talks are “progressing” this weekend, and that “all parties expect a deal to occur.”

While there was a report from CSN Chicago that the negotiations had become “increasingly contentious,” in part due to lingering ill-will between Epstein and Sox/CEO Larry Lucchino, the difference of opinion between the sides over the kind of prospect return the Cubs should offer for Epstein is simply a reflection of a normal negotiation in which one party wants to get as big a return as possible and the other wants to give up as little as possible.

The idea that personal animus is confounding the process makes almost no sense; after all, a breakdown in negotiations over a hardline stance would mean that Lucchino and Epstein would have to continue a working relationship at a time when that was in the best interests of neither.

At any rate, the discussions between the sides has focused on the precedents involving trades of managers and GMs who are under contract. To wit:

–Last month, the White Sox sent Ozzie Guillen and minor leaguer Ricardo Ambres (a raw, 20-year-old right-hander) in exchange for 23-year-old right-hander Jhan Marinez — a 23-year-old reliever with power stuff and erratic control in Double-A — and 23-year-old infielder Ozzie Martinez, who profiles as a potential big league utility infielder. Neither is considered a top prospect.

–In 2002, the Mariners sent manager Lou Piniella and second baseman Antonio Perez to Tampa Bay in exchange for 28-year-old All-Star outfielder Randy Winn.

–In 2002, the Red Sox and A’s discussed compensation for GM Billy Beane. While no final agreement was ever reached, future All-Star Kevin Youkilis was a focal point of conversations.

One American League executive suggested that the idea of trading Youkilis — a future MVP candidate who was one of the most valuable players in baseball — as a potential comp for the Epstein situation was likely misleading.

After all, while Youkilis was highly regarded by both the Sox and A’s, no one saw his future blossoming into that of one of the elite power hitters in the game. He was instead viewed at the time as a potential big league regular, though not a superstar.

As valuable as a great general manager can be, even the best GMs are likely more replaceable than the best players. After all, when the Sox did not get Beane, they were able to tab Epstein, who quickly came to be viewed as one of the top GMs in the game. An MVP-caliber player, the source said, has more value than a GM.

–In 1976, the A’s traded manager Chuck Tanner and $100,000 to the Pirates for three-time All-Star Manny Sanguillen.

Those are the precedents in play to guide the process, offering some road map to resolution. There are no doubt variables that remain to be ironed out, whether those whom Epstein can bring with him from Boston to Chicago, or the quality of prospects that the Sox would get for his departure.

But while there will likely be suggestions along the way that the two teams are far from finding middle ground, it is all but inevitable that they do so, because that is the outcome that all involved in the process have now accepted as not just likely but also desirable.

Read More: ben cherington, Billy Beane, Chicago Cubs, Daisuke Matsuzaka
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