The Kid - Theo Epstein
Red Sox Nation can’t resist the boy wonder, Theo Epstein.  He is our Bill Clinton…our Elizabeth Taylor…our Michael Jackson.  Regardless of his relevance in Major League Baseball, we will follow his every move until the day he dies.  Really though, can you blame us?  At 28, he rode into town as a young, strapping, charasmatic Brookline native who pledged to do two things:  bring Boston a long awaited championship and build a “$100M player development machine.”  Though his tenure was rife with ups and downs, only the most pessimistic and self-loathing would consider his ten year tenure (nine as GM) with the club as anything but a massive success.

After a long, torturous 86-year championship drought that brought endless ridicule from our New York compatriots, we tasted the fruits of his methodical, objective approach when the Red Sox reeled off eight straight wins against the Yankees and Cardinals to win the 2004 World Series.  Three years later, he followed up his magnificent 2004 opus with a second championship that was nearly as satisfying.  On the player development side, his approach was nearly as successful.  The steady stream of All-Star caliber talent that emerged from the system became the envy of many teams; including their chief rivals who struggled to match that success.  In fact, many of the players he drafted and developed remain as part of the 2012 roster’s primary core.

Why am I rehashing the Theo-era nearly eight months after his departure?  As many of you know, WEEI’s esteemed Alex Speier dropped an incredibly interesting interview with Epstein yesterday morning where he reveals many eye opening details about end of his tenure with the club.  He starts out being both positive and contemplative about his experience.

“I am genuinely, really appreciative of all the time I spent there, people I remain in contact with, everything that we went through, things that went wrong, things that went right, the World Series, the relationships. It’s a huge source of pride and appreciation and nostalgia for me already,” said Epstein. “It will always be a part of me. I’ll always root for the Red Sox. I’m excited about the next chapter, but that doesn’t mean I will forget how important that was to me.”

From there, the tone of the interview shifts drastically.  In many spots, it seems as if Epstein is filled with much regret about the process in which his Baseball Operations department made decisions and developed the Red Sox major league roster.

Epstein did not want to talk specifically about individual players and deals, but speaking more broadly, it is clear that he became uncomfortable with the decision-making culture that he helped to create and that, ultimately, he felt he should leave behind. He spoke of the “monster” of expectations and the perceived need to get better constantly — a feeling, Epstein suggested, that he and his baseball operations team shared with other departments in the organization — at the expense of a club whose successes are driven by a scouting and player development machine.

“As a leader of baseball operations, it’s my responsibility to manage that [monster] and to be true to our own philosophies and to put the best team on the field and build the best organization so we can succeed year in and year out,” said Epstein. “Our successes were probably well documented, so any failings have to be attributed directly to us in baseball operations.

No one can deny that the Red Sox baseball operations department largely abandoned the philosophy that brought them two championships and four ALCS appearances in six seasons.  Particularly in the early days, Theo Epstein’s calling cards were shrewdly signing “value” free agents to supplement the club in the short-term; brokering clever trades that always seemed favor the team’s immediate needs while giving up little; and drafting proven but high-upside college players to fill-up the farm system.  While many will debate the timing of the front office’s change in philosophy, I tend to pinpoint it to the July 31 trading deadline in 2009.

When the Red Sox acquired Victor Martinez for Justin Masterson and two prospects, it marked a shift in philosophy.  Rather than continuing to build for the future, the Baseball Operations department made a conscious decision to take a stab at a championship.  In most cases, this wouldn’t have mattered, but the Red Sox’s window (once thought to be a long-term window) was rapidly closing under the unexpected weight of injuries and advanced age-related regression.  Although, Nick Hagadone and Bryan Price would not have helped the Red Sox at any point over the next couple of years, Masterson’s presence as a swingman has been missed ever since.  In hindsight, the price seems incredibly high when you factor Martinez was a defensively challenged catcher who only played in Boston for only a year-and-a-half.   This was just the beginning of a string of shortsighted moves.

“For a team like us in a big market that had success, a team that’s admittedly aggressive on the baseball side, there’s always going to be pressures and tensions, and it was a real palpable thing that we talked about, where there was a natural tendency to sort of take, by whatever measure you go by — revenue, attendance, wins, ratings, to look at the successes and the spikes that came with the World Series championships — and assume that’s the new baseline.

“To demonstrate success, you then need to accomplish even more, show continued growth, and at a minimum maintain that. We talked about, how do we maintain this and be true to ourselves? How do we fight the natural tendency and desire, especially in some of the revenue-generating parts of any business, to be bigger and do more? How do we fight the natural tendency that comes after winning to not be arrogant as an organization?”

“It was hard to sort of find that right balance,” said Epstein. “I think in a big market, the daily struggle is how to balance the here and now with legitimate plans for the future. It’s a difficult thing to reconcile. … You have to start thinking about now at the expense of the future sometimes. Those are realities.

“I think the realities of building from within and being patient and developing prospects, there’s going to be an ebb and flow of success. There’s going to have to be bridge years mixed in. But that doesn’t always match with the overall goals of the organization as a whole. That’s something that has to be managed. To everyone’s credit, we managed that really well for a long time. Winning makes that a lot easier.

As card carrying members of Red Sox Nation, I’m sure we can all sympathize with Theo’s sentiments regarding his struggle to balance short and long-term goals and expectations.  We’ve all read Dan Shaughnessy and Tony Massarotti.  We’ve all listened to Boston sports radio.  We’ve all talked to RSN’s lunatic fringe.  The concept of “The Monster” is very scary and very real.  As a high revenue club that lives in ESPN’s backyard, and has to compete with the Yankees and their seemingly unlimited stream of revenue the pressure the Red Sox face at building a winner year-after-year is unfathomable.  Just look at the reaction all three aforementioned groups had to Ben Cherington’s offseason inaction in the wake of last September’s collapse.  With a roster bloated with expensive contracts, it’d never been more clear that the Red Sox needed to take a step back from the free agent buffet table.  Yet for some reason, the calls for C.J. Wilson, Prince Fielder, Albert Pujols, etc. remained.

After much initial success in free agency with “value” players, Epstein’s received mixed reviews for his forays into that realm starting around 2007.  Julio Lugo, J.D. Drew, John Lackey, and Carl Crawford have widely been panned as Theo’s biggest and most expensive mistakes.  While one could make a valid argument for Drew and possibly Crawford (he’s only 30 and in the second year of his deal), it’s painfully obvious that Lugo and Lackey will go down as colossal missteps.

Why did the front office feel it necessary to overpay in the inefficient free agent market?  Well, in the case of Lackey and Crawford, it’s pretty clear.  Their farm system stopped producing talent as expected.  In lieu of young, cost controllable talent capable of filling major roles on the roster, the allure of the free agent market forced their hand into making deals they might not have normally made.  These short-term quick wins have quickly clouded the club’s short-term future.

Let’s take a look back at the players that graduated from the system:  Kevin Youkilis (2004); Jonathan Papelbon (2005); Dustin Pedroia and Jon Lester (2006); Jacoby Ellsbury and Clay Buchholz (2007); Justin Masterson and Jed Lowrie (2008); and Daniel Bard (2009).  That’s a pretty solid group of players; all of whom played key roles on the Red Sox over the past several years.  Who have the Red Sox successfully graduated since 2009?  Not a whole lot.  One could make arguments for Ryan Kalish and Josh Reddick, but neither are currently on the club’s active 25-man roster.  Will Middlebrooks and Felix Doubront are the closest and most promising, but neither even have a full year of service time under their belt.

“I think an objective look at the 10 years we had there showed some things that are not really up for dispute,” said Epstein. I think we did a great job drafting, great job developing players, we did a nice job in trades, we did a pretty nice job on buy-low free agents, and then we had a very spotty track record with higher profile free agents. That’s just the fact of it.

“The organization’s actually in really good long-term shape. With all those pluses and minuses factored in, I don’t think it’s a surprise to see what you get. The farm system, the young players coming on the roster, those who have been part of the core and are wrapped up on longer deals, thats a product of 10 years of being far from perfect but doing a pretty good job in scouting and player development. 

“Some of the bigger names that have underperformed are a product of missing on big-name free agents. It is what it is. People will interpret that however they want, but I think there’s a lot to be proud of, all the people who were involved over the last decade, to take a step back and look at what we accomplished.”

While, at times, it seems easy to believe Theo left the Red Sox as an unfixable mess.  This club has plenty of talent at the major league level, plus a lot of promising talent developing in the farm system.  It may be years before we see another bumper crop of talent like the one we experienced between 2004 and 2009.  Still, a pipeline that includes Ryan Lavarnway, Jose Iglesias, Bryce Brentz, Jackie Bradley, Matt Barnes, Anthony Ranaudo, Blake Swihart, Brandon Jacobs, and Xander Bogaerts (plus Doubront and Middlebrooks), should give Red Sox Nation a lot of hope.  Not all of these prospects will become major league players, but if even two or three of them become impact players; the system will have been successful.