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Looking back on the Theo Epstein Era

Posted by Tony Massarotti, Globe Staff  October 21, 2011 09:44 AM

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The Theo Epstein era was never solely about Theo Epstein, of course, because it was really about the system. And so when Epstein finally walks out the door, whenever the Red Sox and Chicago Cubs settle the never-ending issue of compensation, the real question will not concern whether the Red Sox can replace Epstein (they can) but how.

Will general manager-in-waiting Ben Cherington merely implement the same methods Epstein did? Or will Cherington do things his way, emphasizing things Epstein did not and eschewing others?

With regard to general managers, evaluating them can be a tricky business. Since the start of the 1998 season, six of the 13 World Series championships have been won by Epstein or Brian Cashman, who have had the highest (or among the highest) payrolls in baseball during their respective tenures. During that same period of time, the Atlanta Braves have won only four fewer regular season games than the Red Sox have – no world titles, mind you – but the Red Sox and Yankees have so dominated the conversation that maybe we have lost sight of how general managers should be truly evaluated.

In the end, this is all really about the draft and player development, because that is the one area in which teams are generally operating on an even playing field. The free agent market – domestically and internationally – comes down to money. Executives like Epstein and Cashman can make multimillion dollar mistakes that other executives cannot. And more often than not, they can endure them.

So are Epstein and Cashman truly among the best general managers in baseball, more capable than Terry Ryan (former) and Bill Smith (current) of the Minnesota Twins, Andrew Friedman of the Tampa Bay Rays, or Jon Daniels of the Texas Rangers? Or are they just more talked about?

We suggest the latter.

That said, no one is suggesting Epstein is a bad GM, either. But he is hardly irreplaceable. (When you get right down to it, who is?) Under Epstein, the Red Sox drafted and developed, among others, Jon Lester, Jonathan Papelbon, Dustin Pedroia, Jacoby Ellsbury, Daniel Bard, and Clay Buchholz, among others. Why the Red Sox hit a developmental gap in recent years is as much a part of their 2011 story as anything else, and the truth is that we won’t be able to get a real read on Epstein’s tenure until a few years down the road, after his final draft classes have played out, one way or the other.

Remember: the Red Sox won 93 games in 2002, the season before Epstein was elevated to the role of general manager. They won 90 this year. Epstein made some shrewd maneuvers and acquisitions during his tenure, but he also made some bad ones. Every general manager does. The net result was a darned good run during his tenure, including two world titles that will define Epstein’s legacy in Boston.

Was he a good GM? Of course. But he was never, ever irreplaceable.

Let’s make something clear here: Epstein is an extremely intelligent, level-headed, and hard-working young man, but his entire career has been shrouded in an extraordinary level of hype. Because of his local roots, he was written about here when he was an intern with the San Diego Padres. He eventually became the general manager of the Red Sox at the age of 28, his status as a hardball prodigy only fortified when he took his first two teams to Game 7 of the American League Championship Series and then a World Series sweep.

And yet, during his time in Boston, Epstein’s major free agent signings have included Julio Lugo, Edgar Renteria, Matt Clement, J.D. Drew, John Lackey, Daisuke Matsuzaka, and Carl Crawford. The Red Sox are now trying to explain many of these maneuvers by suggesting that major free agent signings almost always fail, though it’s worth noting that Manny Ramirez (Red Sox), Randy Johnson (Diamondbacks), Greg Maddux (Braves), CC Sabathia (Yankees), and Mark Teixeira (Yankees) all turned out quite well.

Know what those players all have in common? They were all bona fide, indisputable superstars. This cannot help but make one wonder if the Red Sox merely have extended themselves on the wrong kind of free agent, stopping short on someone like Teixeira, then paying out the nose for players like Drew and Crawford.

In baseball as much as any other sport, it is nearly impossible to overpay a superstar. During his time in Boston, for example, Ramirez was worth every cent. But players like Drew and Crawford look more like supporting actors by comparison, neither having been able (at least thus far) to fill a role the Red Sox had earmarked for him.

All of this brings us to Cherington, who actually preceded Epstein in the Red Sox organization. Cherington served as an intern with the Red Sox while a student at Amherst College and was later hired by Amherst alumnus Dan Duquette, then the Sox general manager. Cherington is regarded as a good evaluator, a skill that undoubtedly will serve him well, and, like Epstein, he is smart and level-headed. Now we just need to find out if John Henry, Tom Werner, and Larry Lucchino regard Cherington as the fuse to replace Epstein in the fuse box, or whether they will actually allow him to make independent decisions on independent factors.

And we need to find out whether Cherington even wants to, or whether he merely will continue to run the existing operation.

In the end, without question, Epstein had a hand in two world championships during his time in Boston. But it was only a hand. Duquette left him Ramirez and Pedro Martinez, among others. Bill Lajoie acquired him Josh Beckett and Mike Lowell. Cherington would be wise to preserve the elements of Epstein’s operation that worked during Epstein’s tenure, and he would be wise to alter those which left the Red Sox, to be kind wanting.

The Red Sox, after all, did well during Epstein’s time here.

But they were hardly perfect.

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Updated: Mar 1, 07:24 AM

About Mazz

Tony Massarotti is a Globe sportswriter and has been writing about sports in Boston for the last 19 years. A lifelong Bostonian, Massarotti graduated from Waltham High School and Tufts University. He was voted the Massachusetts Sportswriter of the Year by his peers in 2000 and 2008 and has been a finalist for the award on several other occasions. This blog won a 2008 EPpy award for "Best Sports Blog".

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