Natural Selection: Red Sox Officially Replace Theo Epstein with Ben Cherington as GM

You know the saying. Be careful what you wish for, because you just might get it. In Red Sox Nation, diehard fans such as myself wanted longtime General Manager Theo Epstein to move on from his hometown franchise. Unexpectedly however, it was manager Terry Francona who left, upsetting many who thought he was the fall guy for a team that underperformed for him and that was curated by the now ex-Sox GM. However, Francona’s exit a few weeks ago apparently expedited Epstein’s own eventual exit a year ahead of schedule, as he talked of possibly moving on once his contract expired at the end of 2012 and having his assistant Ben Cherington succeed him.

This afternoon, Cherington will indeed be officially introduced as Red Sox GM, while Epstein, who officially resigned from the Red Sox last Friday (October 21), will be officially introduced as President of Baseball Operations of the Chicago Cubs (a reported $18.5 million job), the same position his one-time mentor Larry Lucchino is in with the Red Sox.

Epstein’s time with the Red Sox lasted 10 years, the last nine as GM. Under him (2003-2011), the BoSox won two World Series, made four trips to the ALCS, and made the playoffs in six of the nine seasons in an extremely competitive AL East division. He was also named one of the top executives of the 2000s by Sports Illustrated and The Sporting News.

That’s the great part of his resume. The bad part? Free agency, especially in recent years. Names like Edgar Renteria, Julio Lugo, Wade Miller, David Wells, Brad Penny, Matt Clement, J.D. Drew, Bobby Jenks, John Lackey, Mike Cameron and plenty of others all come to mind as veteran acquisitions that made little to no positive impact on the Red Sox during Epstein’s tenure (to be kind). At least Lugo, Drew and (the expensive) Daisuke Matsuzaka had some memorable moments during the 2007 championship run. But the rest? Forget ’em.

But this is the same GM who signed key members of the ’04 World Series title, including Curt Schilling, Bill Mueller, Kevin Millar, Mark Bellhorn, Bronson Arroyo, Dave Roberts, and of course, David Ortiz. And let’s not forgot the Nomar trade that brought Orlando Cabrera to town for some shining moments and stability at shortstop during the ’04 title run. He also drafted Dustin Pedroia, Jonathan Papelbon, Daniel Bard, and other key Sox players in his tenure.

True, trading Arroyo for Wily Mo Pena was a bad deal, and though it was the right move at the time, the Eric Gagne trade with Texas just didn’t work out well (even though the Sox still won with him in ’07). And even more true, Ben Cherington and Jed Hoyer traded for Josh Beckett and Mike Lowell during the three months in late 2005 that they were co-General Managers of the Red Sox when Epstein had briefly resigned. And though the Carl Crawford deal looks bad now, few quarreled with it before the 2011 season started, and he can only do better going forward.

On the other hand, Epstein did bring Adrian Gonzalez to town via a big trade with San Diego last year. The Sox may now be without its top pitching prospect Casey Kelly because of that trade, but Epstein has left a good farm system behind, though not as great as it once was. Otherwise, he and Francona would’ve had much better options than to have the Kyle Weilands of the world pitch important games in a playoff run as was the case during the “September Collapse.”

But the good free agency signings, draft picks and key trades Theo Epstein made outweigh the bad in my view. And of course, his front office team (including Cherington) got Boston two titles it hadn’t seen since 1918. Thus, even though his teams haven’t done well the last three years, Theo Epstein will eventually go down as one of the greatest GMs in Red Sox history (and not just a “good” GM, as ex-Red Sox utility great Lou Merloni said this morning on sports talk station WEEI).

Now Cherington, who has been with the Red Sox since the Dan Duquette era (when he was a just a lowly intern in 1997 in his early 20s), has some big shoes to fill as Epstein’s successor. He has his work cut out for him, starting with finding a new manager. And with that, I wish him good luck. He’s gonna need it.