CHICAGO -- It was not the final note that Theo Epstein wanted in Boston.

The former Red Sox general manager has plenty that is keeping him energized in what he calls the “next chapter” of his baseball life as the president of baseball operations with the Cubs. He is amidst a far-reaching project of rebuilding an organization from the ground-up, suffering through plenty of losses along the way.

Yet as much as that task occupies him, Epstein still remains deeply connected to the team for whom he grew up rooting, and for whom he served as the most successful general manager in franchise history.

On his desk, there is a picture of Epstein holding his 4-year-old son, Jack, at Fenway Park. On his walls, there are framed group photos of Epstein on the field with members of the front office celebrating the two World Series titles he won with the Red Sox.

“Happier times,” he said.

(Adjacent to those photos is another picture frame, this one empty. “Saving a spot for when we win here,” he explained.)

He has been watching the Red Sox -- who will travel to Wrigley Field for a weekend series against his Cubs starting on Friday -- as much as possible, often catching condensed versions of the team’s game on the iPad. His interest is not merely superficial.

“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.”

Even though he has moved on, he remains connected to what happens in his former baseball home. And he remains mindful of not just the achievements en route to six playoff appearances and two World Series in his nine years as GM, but also the failures at the end.

That is true not just of the on-field results -- chiefly, the September collapse that torpedoed a team that had for much of the year seemed like one of the best, if not the best, in baseball -- but also of the way in which the Red Sox had been built in his final years as the head of the team’s baseball operations department. Indeed, with the benefit of detachment, Epstein views those two elements as related.

And with the benefit of hindsight, at a time when he is trying to turn a Cubs franchise synonymous with failure into one primed for long-term success, Epstein recognizes that in his last years in Boston, he was part of the betrayal of core organizational values.

Epstein’s final two offseasons with the Red Sox, in many ways, were unlike any of the previous seven. By and large, the Red Sox had not merely spoken about maintaining financial flexibility by treating free agency as an option of last resort. With the exception of a 2006-07 offseason in which they signed Julio Lugo and J.D. Drew, they had walked the walk.

The team slowly formed the nucleus of a contender on the strength of home grown players. Free agency was treated primarily as a supplement, one where the team was comfortable drawing a line even with players like Mark Teixeira whom it badly wanted to acquire.

But then came the most recent offseasons, when the Red Sox started conferring Scrooge McDuck-sized mountains of gold upon free agents. There was the five-year, $82.5 million deal for John Lackey, and the seven-year, $142 million deal for Carl Crawford. Those represented a change in how the Red Sox did business.

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.

“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?”

Epstein made clear that the so-called monster permeated the thinking of the entire organization, and that his department was not immune from it. As GM, Epstein suggested, he had but did not wield the authority to resist the monster.

He could have eschewed moves that focused on the short-term needs of the team at the potential cost of its long-term well-being. To the detriment of the organization, there were times when he did not.

“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.



“When you don't quite live up to that same standard in the standings, even for a brief period of time, those pressures get magnified, it gets harder to manage, and I think I personally, we didn't do a good enough job certainly of executing our baseball plan, even in a vacuum towards the end. And I didn't do as good a job of managing that.

“Had we been completely true to our baseball philosophy that we set out and believed in and followed, we probably wouldn't have made certain moves that we made anyway, moves that, as I look back on them, they were probably moves too much of convenience, of placating elements that shouldn't have been important,” said Epstein. “Those were my mistakes, and because of that the last couple of years weren't as successful as the previous seven or so.”

The fact that the Sox, for the first time in his tenure, missed the playoffs in back-to-back years in 2010 and 2011 did not make it easier for Epstein to leave. To the contrary, the team’s defeat at the end of last year continues to weigh on the former Red Sox GM, who still admits that the “perfect storm” of forces that led to an epic collapse was mind-boggling.

Even so, he was aware that some of his own actions as GM had played a role in those failures. Perhaps it was complacency borne of years of success, but Epstein recognized that his biggest contributions as a leader of the Red Sox had already been made.

At a certain point, the challenge of managing the organization he had helped to build was less interesting than the more thrilling responsibility of building from the ground up. And so, he embraced the challenge of joining the Cubs.

“I think I had some degree of self-awareness and that led me to the decision to put a cap on my time in that role with the Red Sox, because it would have been really hard to navigate it and still be happy,” said Epstein. “Changing environment is a really helpful tool to get the best out of oneself in a lot of different ways. Professionally and personally, it was definitely time for me.”

Yet while he left at a time that represented the nadir of his nine-year tenure, Epstein still believes that there was plenty about which he can be proud. Obviously, there are the two championships during his time, which offer the ultimate evidence of success.

From a process standpoint, there was the architecture of a successful player development system whose accomplishments Epstein would be thrilled to replicate in Chicago. An there were the moves in which the team made low profile moves that carried tremendous significance, whether the free-agent acquisition of discarded players like David Ortiz and Matt Albers or moves such as the acquisition of a Jarrod Saltalamacchia or a Mike Aviles that looked beyond immediate need.

There were failures, of course, but Epstein feels that despite the fact that the Red Sox missed the playoffs in each of the last two years, and even though the 2012 Sox are in last place, the Boston organization for which he is now rooting from afar is still well situated.

“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.”

He does not feel that he left a bare cupboard. To the contrary, he sees in the Red Sox an organizational model whose successes he hopes to recreate, perhaps without the same monstrous consequences.