A new curse to reverse: Epstein leaves Red Sox, joins Cubs

Theo Epstein joins Chicago after winning two titles in Boston. (AP Photo/Phelan M. Ebenhack)

Effective Friday evening, the man who helped end an 86-year World Series drought resigned from his post as Boston Red Sox GM to join the Chicago Cubs as their President of Baseball Operations. Theo Epstein is headed from Beantown to the South Side.

The two teams had spent nearly two weeks hashing out the details, with disagreements over the Red Sox’s compensation being the sticking point. As they have now put aside those differences, a swap of prospects for the 37-year-old two-time World Series champion will be finalized on Tuesday.

Ben Cherington, who had served as the Assistant GM to Epstein, is expected to be named GM on Tuesday as well, as it is the next off-day of the World Series between the St. Louis Cardinals and Texas Rangers. His introduction will mark the end of an era and the start of a new one. The 37-year-old is about to take over a team that will have plenty of questions to answer this offseason.

Cherington would be hard-pressed to be as successful as Epstein was. Epstein was just 28 when he was hired by Boston in 2002. Putting his age into perspective, prior to his departure from the Red Sox he was still the youngest General Manager in baseball. Less than two years after his hiring, a team he had helped put together ended the Curse of the Bambino. As is superbly documented by the Boston Globe‘s Andrew Mooney, he was responsible for bringing in 17 key pieces to that 2004 team. Among them were David Ortiz, Kevin Millar, Mark Bellhorn, Bill Mueller, Keith Foulke, Curt Schilling, Bronson Arroyo, Mike Timlin, and Orlando Cabrera.

Some may say that Epstein was lucky to be with an organization that had such deep pockets. He could spend as he wished. He sure did over the past couple offseasons, most recently throwing millions at Carl Crawford, John Lackey, and Adrian Gonzalez. Crawford and Lackey have yet to play up to their deals, but Gonzalez has proved to be a wise investment, as have many other Epstein signings throughout his tenure.

How much of Boston’s success since 2002 should Epstein be credited with? A lot, even though he had John Henry writing the checks. Mooney writes:

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“There’s no doubt John Henry’s deep pockets aided Epstein in his tenure in Boston, allowing him to pursue players who were beyond the financial scope of most teams. Any other owner not named Steinbrenner would have laughed him out of the room if asked for $50 million just to talk to a player. But as the Mets, or Epstein’s new team, the Cubs, have shown in the past, a bloated payroll doesn’t automatically translate into a playoff contender. The money has to be spent on the right people, and more often than not, Epstein’s shown an ability to pick them out. This season, the Sox had Pedroia, Jon Lester, Clay Buchholz, Jacoby Ellsbury, and Jed Lowrie under contract for a combined $14.9 million, an incredibly favorable figure. Ellsbury alone was worth that sum and more.”

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Epstein has made his share of mistakes during his nine seasons with the Red Sox. Among them was letting shortstop Orlando Cabrera go after helped Boston to that 2004 World Series championship. The shortstops since: Edgar Renteria, Alex Gonzalez, Julio Lugo, Gonzalez again, Nick “The Pitcher” Green, Jed Lowrie, and now Marco Scutaro. The latter, an impending free-agent, was the only one to put together a solid season. Daisuke Matsuzaka, who, as Mooney alluded to, the Red Sox paid $50 million just to negotiate with in 2007, hasn’t panned out after a superb 2008 season and is currently rehabbing from Tommy John Surgery. Giving a 31-year-old Lackey $82 million and Crawford $142 million this past offseason may turn out to be big mistakes. Then again, they may not.

Epstein did let Jason Bay go after the 2009 season and Victor Martinez go after the 2010 season, but should he be held accountable for poor play and injuries? The vast majority of Epstein’s decisions have paid dividends. Even J.D. Drew’s contract didn’t prove to be all that terrible.

Epstein didn’t just sign players and make trades. His role in player development was under-appreciated. As Mooney writes, there have been few head-scratchers among his draft picks:

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“In case you’re still not convinced about Epstein’s knack for player evaluation, take a look at the players drafted under his watch: Jonathan Papelbon, Pedroia, David Murphy, Ellsbury, Buchholz, Lowrie, Daniel Bard, Justin Masterson, Ryan Kalish, and Josh Reddick. All these players have either made contributions to the big league squad already or served as trade pieces to acquire more immediate needs.”

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Papelbon is one of the best closers in the game. Pedroia is a former MVP. Murphy helped the Rangers reach the World Series this year as a dependable hitter. Buchholz won 17 games in 2010. Lowrie has been solid when healthy. Bard transformed into one of the best set-up men in the game this past season. Masterson won 12 games this season as a starter in Cleveland after being immensely valuable to Boston as a starter and reliever. Kalish has been one of Boston’s top minor leaguers and has contributed in his cup of coffee in the majors. Reddick played a big role with the Red Sox this season and may be the team’s future right-fielder.

All Epstein did was bring in players he thought could be stars in Boston, and he is the best General Manager Boston has ever had. He helped end the curse, added a championship with many more of his own guys in 2007, and continued to build a winner. What he accomplished was incredible.

And now he heads to Chicago, to a team that hasn’t won a championship since 1908. One-hundred and eleven years of misery. The Cubs are a whole new beast, as he inherits bad contracts, a handful in Carlos Zambrano, and fans desperate for a winner. I wish him luck. He has a difficult task ahead, but he’s put curses to bed before. The Cubs should be ecstatic to have him, and no matter what Cherington does, the Red Sox will miss him.