Commentary

Here's looking at you, Theo

As Boston's Boy Wonder moves on, the Sox are left with their own drama

Updated: October 24, 2011, 9:21 AM ET
By Gordon Edes | ESPNBoston.com

BOSTON -- And so, the ending is different than the one penned by his grandfather and great-uncle, the Oscar winners.

This wasn't Casablanca. This was Yawkey Way, and this time the hero, Theo Epstein, took the letters of transport and boarded the plane.

(Although that may well have been Larry Lucchino as Major Strasser, taking a couple of plugs to the midsection on Epstein's way out of town.)

The Red Sox and Chicago Cubs, with a push from commissioner Bud Selig, set aside their differences long enough Friday night to confirm with a joint press release a transaction that seems as if it has been around almost as long as Babe Ruth's sale to the Yankees.

Epstein is going to Chicago to become president of baseball operations for the Cubs, a position created just for him. That will be announced officially on Tuesday, the same day the Red Sox announce that Ben Cherington -- a longtime Epstein sidekick with Sox roots that began with Dan Duquette -- will be Epstein's successor as Red Sox general manager. By then, the World Series will either be over or in travel mode before a possible Game 6 on Wednesday, giving the Sox and Cubs a Selig-opened window to go public with their business.

[+] EnlargeBen Cherington
Darren McCollester/Getty ImagesLike Theo Epstein, Ben Cherington is a native New Englander who has plenty of experience working in baseball operations.

The Sox have not confirmed that Cherington is their man, but he has been operating as de facto GM ever since the Cubs and Epstein struck a five-year deal for a reported $18.5 million nine days ago, and has told members of his baseball operations staff that he's the new boss.

Epstein will not be going to Chicago alone. He is reassembling much of his dream team of advisers that helped him win two World Series in a span of four seasons in Boston. Jed Hoyer, one of his closest friends in the game, is swapping his job as GM of the San Diego Padres for the same position in Chicago. Jason McLeod, who in his first draft as Sox scouting director selected Dustin Pedroia, also is leaving the Padres to go to Chicago. It remains to be seen whether Dave Finley -- who has served Epstein for a decade as a trusted talent evaluator and played a huge role in the Adrian Gonzalez deal -- will leave his post as special assistant to the GM here to follow Epstein to the corner of Clark and Addison.

It was Hoyer, you may remember, who accompanied Epstein to the desert in 2003 and Thanksgiving dinner with Curt Schilling to persuade the pitcher to accept a trade to the Red Sox -- as rewarding a trade as any Epstein made in his nine years as Sox GM. The day after Shonda Schilling cooked the turkey, Epstein and Hoyer were in their hotel room, hustling to pack so they could return to the Schilling manor and close the deal, when Hoyer became violently ill and vomited. Epstein tried to clean up the mess, despaired of the task, and flung $20 bills all over the room for the poor housekeeper who would inherit the job.

Epstein never lost his talent for throwing around money, the biggest blemish on an otherwise gold-plated résumé being the millions squandered on the free-agent likes of Edgar Renteria, Julio Lugo, Matt Clement, Daisuke Matsuzaka and John Lackey, with Carl Crawford building a compelling case in his first year that his name belongs on that list, too.

But those misfires have done nothing to temper the anticipation of Epstein's arrival in Chicago, where the only evidence of restraint is that they have yet to erect a statue of Theo next to the one of Harry Caray outside of Wrigley Field; 103 years since the last World Series parade can do that to a fan base that has been whipped up to a fever pitch by the hope of deliverance from the man who will be forever remembered in his hometown as the Wonder Boy who ended 86 years without a World Series title, then won another one just three years later.

With deep-pockets Cubs owner Tom Ricketts, Epstein will have the same resources and mandate to build the scouting and player-development machine that regularly churned out star quality during his tenure in Boston -- Pedroia and Jacoby Ellsbury, Jonathan Papelbon and Daniel Bard, Clay Buchholz and perhaps the next A-list candidate, Ryan Lavarnway. It will take a little time for Epstein to come out from under some of the unwieldy contracts on his big league roster in Chicago, but as team president he can be expected to act boldly, knowing he will have to answer only to Ricketts in the team's internal chain of command.

His first order of business, though, borders on the surreal: He is expected to take over as point man on the Chicago side in negotiating what is a fair price to pay the Red Sox for ... Theo Epstein. That puts him directly in the crosshairs of the elephant gun wielded by his old mentor, Larry Lucchino, whose long-held credo of "contest living" means that he is likely to offer little quarter to his former star pupil. The only thing saving this from becoming steel-cage material is a pledge by both clubs that they have agreed to a mechanism to determine the compensation, a process that presumably will include Selig's intervention if no agreement is struck before Tuesday's dueling press conferences.

There is growing sentiment that the Sox will wind up with just a couple of lesser minor league prospects; if that was the case, this would have all been wrapped up Friday night in one tidy package. But there's still a divide, so don't be surprised if the Sox may yet be rewarded with a prize more to their liking.

Epstein's activity on his own behalf is not without precedent. The hero of "Moneyball,'' Billy Beane, was knee-deep in negotiating the compensation Oakland would get for losing him to the Red Sox in 2002 until he changed his mind and decided to stay with the Athletics, a decision that permanently altered the life of the 28-year-old named to the job instead ... Theo Epstein.

Now Epstein steps aside to make way for the 37-year-old Cherington, who has the mien of a long-distance runner but will be thrust into sprinter's mode as the new GM, charged with turning around -- and fast -- the image of a franchise that has taken a fearsome beating in the wake of September's historic collapse.

Cherington is another native New Englander, hailing from the tiny New Hampshire village of Meriden. He has served in just about every facet of baseball operations since Duquette reached out to his alma mater of Amherst and tapped Cherington as a student intern before hiring him full-time after he'd done another internship with Cleveland.

Cherington's résumé is solid, but he's facing a gauntlet of skepticism and mistrust fostered by the implosion of a team regarded in the spring as a virtual lock to make the playoffs. A tough sell for anyone, especially if the Sox replace manager Terry Francona with another unproven entity.

In the meantime? Well, as Theo's grandfather, Philip Epstein, and great-uncle Julius, might have put it, "We'll always have '04 and '07.''

Gordon Edes covers the Red Sox for ESPNBoston.com.

Gordon Edes

Red Sox reporter, ESPNBoston.com

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