Boston Red Sox' New GM Faces Tough Road Ahead

BOSTON - FILE: General Manager Theo Epstein and Manger Terry Francona of the Boston Red Sox watch the pre-game action before a game with the New York Yankees at Fenway Park, April 24, 2009, in Boston, Massachusetts. According to reports October 12, 2011, Epstein, who has one-year left on his contract with the Red Sox, has agreed with the Chicago Cubs to a five-year $15 million contract to join their front office, but compensation for the deal has not been reached between the two teams. (Photo by Jim Rogash/Getty Images)

Be it Ben Cherington or an outsider, the next general manager of the Boston Red Sox will face an offseason filled with tough questions and difficult decisions.

On Wednesday, October 12, the Red Sox saw one of the most storied eras in the club's history come to an end.

Gone are Theo Epstein and Terry Francona, the architect and leader of the 2004 and 2007 teams that ended an 86-year period of futility and established an entirely new culture. It would be unfair to call them the "victims" of the 2011 season that, despite 90 wins, was crushingly disappointing due to the way it finished. They were not fired, after all--especially Epstein, who the Sox spent much of Tuesday trying to keep--but that said collapse inspired their departure seems all-too-likely. They needed a new start, and in many ways, so did the Red Sox.

So now they have that "new start"--as clean a slate as can be had without negatively impacting the roster-but where do they go from here?

Obviously the first step is to find and appoint a new general manager. After all, the rest of the offseason will be theirs to run. While it would be great to see the Sox try and poach someone along the lines of Andy Friedman, he seems more likely to move to Houston if he's going anywhere, and the population of smart, available, and proven baseball executives is small without him.

Instead, it seems more likely that they will turn inward to assistant GM Ben Cherington, who at this point seems nearly a lock for the position. While Cherington spent some short time running the show when Theo pulled his quick disappearing act in 2005, there's no question that he will enter his tenure unproven.

The good thing for Cherington is that he's had the best seats in the house to both Theo's successes and failures. He should know the value of a strong farm system, understand the benefit of the Sox' focus on statistical analysis, and hopefully have seen the error of Theo's ways in free agency. There's no way to know for sure whether or not Cherington will prove half as successful as his predecessor, but there's reason to hope, and even a possibility that he could be better. There's no questioning that Theo had faltered in recent years-his biggest free agent signings have been by far the worst performers-so perhaps a new point of view with more to prove will even do the Sox some good.

Either way, though, once Cherington is in place, the Sox will actually have to focus on fixing their other problems, starting with a manager who can hopefully pull the clubhouse together be it with a firm hand, or more of Terry Francona's player-friendly approach. The candidates are numerous-from Ryne Sandberg (who could well find himself following Theo to Chicago) to Tim Bogar (anything to get him away from third-but he's often been named as one of the strongest managerial candidates in the game), it will likely depend on whether or not Cherington is content with the group currently in place, or wants to reforge the organization in his design.

From there, though, the questions don't end. What's to come of the beer drinking clique of Lester, Lackey, and Beckett, featuring as it does both the best and worst pitchers on the team? Can Youkilis still contribute at third, or is it time to call it a day for either him or Ortiz? Jonathan Papelbon is a free agent, Jacoby Ellsbury is an isolated MVP, Marco Scutaro has an option, right field is a question mark, and the rotation needs rebuilding.

Whoever takes over, they have their work cut out for them.

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