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Theo Epstein discusses his Red Sox legacy

Theo Epstein, the president of baseball operations for the Chicago Cubs, helped guide the Red Sox to two World Series titles.
Theo Epstein, the president of baseball operations for the Chicago Cubs, helped guide the Red Sox to two World Series titles.File/Jonathan Daniel/Getty Images/Getty

At 28 years old, Theo Epstein was the youngest general manager in baseball history when he took over the Red Sox before the 2003 season.

A lot of great things happened to the Sox while Epstein was general manager. The team won two World Series, made the playoffs six times, and averaged more than 94 wins per season. Scouting and player development improved dramatically, and the Sox won that second championship with home-grown talents Dustin Pedroia, Jon Lester, Jonathan Papelbon, and Jacoby Ellsbury leading the way.

In Epstein’s later years, the Sox signed numerous free agents for huge amounts of money, and some flopped famously: Julio Lugo, John Lackey, Mike Cameron, Bobby Jenks, and (thus far) Carl Crawford. Lackey was signed for five years and $82.5 million. Crawford signed a seven-year deal for $142 million.


Carrying 15 All-Stars and the third-highest payroll in baseball, the 2011 Red Sox were projected as a serious World Series contender. They went 81-42 over a four-month stretch, but collapsed in September, losing 20 of 27. Two weeks after the season ended with the Sox missing the playoffs, Epstein accepted a five-year, $18.5 million offer to become president of baseball operations with the Cubs.

Epstein was under contract to the Sox for 2012, but they allowed him to go to the Cubs in mid-October, agreeing to work out compensation at a later date. It took more than four months to resolve the compensation issue. The Sox finally settled for minor league pitcher Chris Carpenter. One month after Carpenter joined the Boston organization, he underwent surgery to remove a bone spur in his elbow.

The Red Sox are in Chicago this weekend to play three games against the Cubs at Wrigley Field. Both teams are in last place. While the Sox have struggled to get over .500 all season, the Cubs have been bad all season. Epstein’s team went into Wednesday night’s action with the second-worst record in baseball, 21-40.


Epstein’s wife and young son have remained in the Boston area while his son finishes preschool. They plan to move to Chicago soon. Last Friday, wearing a C.A.I. soccer hat pulled down over his forehead, Epstein sat down with the Globe for an in-depth interview at Starbucks on Route 9 in Chestnut Hill.

Q. Could you talk about the state of the Cubs?

A. “We’re certainly struggling to compete in 2012. I do think, despite the record, some positive things have happened this year. As a staff, we’ve established a nice culture of accountability and preparation, and that’s going to serve dividends for many years to come.

“We had some young players step forward that will probably be core pieces. Most notably, Jeff Samardzija has transformed from an up-and-down reliever to a front-of-the-line starter and has a chance to be a front-of-the-rotation guy. That’s big.

“Anthony Rizzo, we acquired this winter. We traded a really good pitcher - a guy that throws 100 - for him. It was nice to get him back [the Sox had traded Rizzo to the Padres in the Adrian Gonzalez deal]. He’s shortened his swing, changed his approach, and established a really good routine at Triple A. He’s got a chance to be a good big leaguer for a long time.

“We’ve had some things happen positively. And behind the scenes, we’ve tried to establish a whole Cubs way of doing things in player development. We’ve adopted a new scouting philosophy, implemented new systems in the front office.


“We’re trying to be transparent with our fan base - that there are no short cuts. There was a bit of a talent deficit throughout the whole system when we got there. So rather than look for quick fixes in free agency, we’re trying to build a foundation through young players that will get us to a point where we can contend every year.

“It might be tough sledding along the way, but we’re being open about it and I think our fans understand. As patient as they’ve been for 103 or 104 years, I think they appreciate the emphasis on young players and I think they can be patient a bit longer. When we get there, it’s going to be a lot of fun.’’

Q. The Chicago Sun-Times ran a cover photo of you walking across Lake Michigan Opening Day. Your thoughts on that?

A. “Beyond ridiculous. It reinforced the lesson that needed no reinforcement, which is that you can’t attach any meaning to it. It’s so obviously setting one up to fail in every possible way. When people you don’t know say nice things about you, if you allow yourself, even subconsciously, to attach a shred of meaning to it, when the opposite happens, when people you don’t know say bad things about you, you can’t attach that same meaning. To be human and live the life you want to live, you have to protect yourself and be completely removed from that type of stuff, so it didn’t really bother me.’’


Q. Regarding reaction to your teams, compare the day-to-day noise of Boston vs. Chicago.

A. “It is a little calmer [in Chicago]. I think there’s an understanding that no matter what we do, it will be hard to get immediate results at the big league level despite our efforts to do so. I think there’s some optimism there. I think people want the Cubs to succeed, and by extension, they want people associated with the Cubs to succeed.

“From what I can tell, in that market, there’s a real appreciation of things that go well, whether it’s one well-played game or a young player who plays hard and is growing on the job, or even a nice rendition of the seventh-inning stretch.

“Maybe it’s a Midwestern sensibility. There’s a real-time appreciation and enjoyment of things that go well and less of a sense of overall doom and cynicism. I love both markets. Maybe it reveals two sides of my personality.

“I’m pretty in tune with the Boston vibe, too. I appreciate it, and feel part of it, and I get it, and it makes sense, and I love the Boston fans.’’

Q. Might the Cubs be “sellers’’ at the trading deadline?

A. “I think we have to be realistic about where we are, because we have to consider the long term and build around a core of young players. We can’t look past any opportunity to acquire a potential core piece for the future.’’


Q. What about the notion that the Cubs are cursed, just as it was believed that the Red Sox were cursed before they finally won?

A. “I’ll just say that when we won in Boston, the drought added layers of meaning to the victory that were kind of indescribable. Winning a World Series in Boston impacted so many people in such a deep and positive way, in part because we hadn’t won in so long.

“I try to look at it as a positive in Chicago, too. There’s a lot of resonance to what we’re doing. There’s so much passion in the fan base for it. Generations are connected by the experience of going to Wrigley Field, but also in part by the frustration of not winning it all. If working hard helps us get closer to giving millions of people satisfaction that way, then it’s great.

“Let it serve as inspiration. It will make the champagne that much sweeter.’’

Q. Was the Cubs’ drought part of what drew you to Chicago?

A. “Yes. The challenge is a primary part of the draw, and the fact that it was a challenge with great meaning. After you work somewhere like the Red Sox, it’s really hard to go to - insert generic franchise here. That was one of the coolest parts of working for the Red Sox. What we were doing mattered in a very personal way to so many people. Had I gone someplace where that didn’t exist, there would have been a feeling of great loss. Clearly, this is one place where I can replicate that feeling, and it’s a great part of the daily motivation.’’

Q. How closely do you follow the Red Sox?

A. “I watch them a lot. I guess I have an excuse because maybe they’ll be a buyer later in the summer. But I watch it for personal reasons as well. I care very deeply about so many people who work there. A lot of them are on a short list of the closest friends in my life and I want them to succeed.

“And I’m a Red Sox fan. I still have an American League team. And they will be it. I’m not going to try to deny that I’m a Red Sox fan. I grew up a Red Sox fan, had a great decade here that I really enjoyed, and that will always be a part of me. Especially now while Ben [Cherington] and the crew are running things.’’

Q. Were you actually working out of the Red Sox offices for a while after you took the job with the Cubs?

A. “Yes, from time to time. I was working for the Cubs. I didn’t ask the suits upstairs. It was for a month or so. We had a nice insulated environment down in the basement. There were times I needed a computer, or to print something out, or to make a few calls. I’d be in the area and I’d pop in and say hi to everyone and there was an empty office and I’d say, ‘Do you mind if I make a few calls in there?’ ’’

Q. It seemed like things got testy regarding the issue of compensation to the Red Sox.

A. “It wasn’t testy with the people that I interacted with on a daily basis.’’

Q. But the Sox seemed to lose all leverage by letting you go without settling that issue. Isn’t it a little like letting someone move into your house before the closing settlement?

A. “This was truly an issue where the ratio of debate and words spoken and ink spilled was in a ratio of 10,000 to 1. That’s media vs. actual operations. It wasn’t that significant a deal. It was hard to work out because I think both parties came at it from opposing angles. But it wasn’t all that contentious, at least with the people I was speaking with. It was a hard riddle to solve and eventually it got done.

“For years, I’d been having conversations with John [Henry] and Tom [Werner] about my future with the Red Sox and I was up front with them and they were up front with me. They told me they really wanted me to stay and they’d be sort of flexible about my role and that meant a lot to me. But I was open to them about the fact that I wasn’t sure if I could, for a lot of reasons that I put in the editorial I wrote in your paper. I was open to them that I wasn’t sure if I could stay.

“When the Cubs opportunity presented itself. I was like, ‘Guys, I know there’s one year left on my deal. This is one place that would have a lot of meaning and I’d really like to go there. Let’s try to work it out, rather than stay and then leave at the end of the year. Let’s try to work it out in a way that makes everybody whole. Let’s try to work it out in a way with a smooth transition to Ben.’

“Eighteen months previously, I’d gone to them and said, ‘Look, Ben’s clearly my successor. It doesn’t look like I can necessarily stay until the end of my deal. Let’s be ahead of this and execute a really smooth transition.’

“So that was under way. We were trying to work together to find ways for me to stay, but because of all the reasons I laid out in the editorial, it wasn’t really possible. So then it became a matter of, ‘How do we find a smooth, seamless way for me to move?’ We almost pulled it off, but I think September threw a bit of a bomb on it and it became difficult to reconcile.’’

Q. Do you feel the bad signings at the end damaged your legacy here?

A. “That’s fine. I’ve always admired people who can live more in the moment, who experience life genuinely and organically and aren’t concerned about these things that only exist on paper or in theory. So I try to live up to that, to not be concerned about my own legacy and just to relish the experience that I had.

“I had an incredible decade there, personally. I enjoyed almost all of it. I am really proud of a lot of the things that we accomplished. I know that the people I worked really closely with changed that franchise in a very meaningful way for the better. We left it way better than we found it and played a small part in creating baseball history. So I’m proud of what happened there. I really enjoyed it.

“I think legacies and history books are usually written by those who are still there, not by people who move on, so I’m not going to concern myself with it.’’

Q. But you are the one blamed for Lackey and Crawford.

A. “I think so. In 10 years, you’re going to have misses. I do think this. I think taking a step back, if you take a look at what our baseball group was best at, we were best at drafting and developing young talent and finding some undervalued players. I think we were the best drafting team of the decade and all that. That’s a very patient, organic approach. Pure . . .

“We joked about it all the time in the front office. We’d say, ‘Wouldn’t it be great if we could just say, screw free agency altogether. We’re going with a purely home-grown lineup. We’re going with old-school, Branch Rickey-style, pre-free agency, pre-draft whatever?’

“Middlebrooks at third, Lowrie or Iglesias at short, Pedroia at second, Rizzo at first, Lavarnway catching, Ellsbury in center, Reddick in right, Kalish in left. Wouldn’t that have been fun?

“We kind of clung to that in the back of our minds, knowing it was impossible, recognizing that there was an inherent tension between that approach and bigger business. I kind of kick myself for letting my guard down and giving into it, because that might be a better team in some ways and resonate more with the fans than what we ended up with.

“When you make a mistake in the draft, you just keep drafting. You keep finding another player to develop. When you make a mistake in free agency, you’re stuck with it for the duration of the deal and it can be a real impediment.

“Do I feel bad about that? I really do. But in my mind, it doesn’t take away from everything we accomplished and what we established there. Look at last year’s draft, for example. What’s the lasting impact? What [Matt] Barnes and [Jackie] Bradley are doing down below, and that’s going to impact the franchise in a great way. So that’s my answer for the arc of the career.’’

Q. How long did it take you to recover from September?

A. “In a way, I’ll never recover from September. I don’t fully understand it. It was so disheartening. We were playing, I thought, world-class baseball for 4 1/2 months. I thought we were the best team in the league for a long stretch. Clearly, we had our vulnerabilities. The pitching attrition was real, and we were walking a tightrope.

“But for the wheels to fall off the wagon the way they did, for us to lose not only our competitiveness and our place in the standings, but our identity as a team, was painful to watch. I’ll never really ever get over that. But a few weeks later, I was embroiled, I was forced to have to make a really tough decision.’’

Q. And what of the immediate fallout, that which John Henry termed a “media riot’’?

A. “It was sad. It probably said a lot about a lot of things - human nature, the media dynamic in this town, the bubble we created through success for a long period of time. Once that bubble burst, there was sort of a lot of residue for people to sort of muck around in.

“But the bottom line is, we brought it on ourselves. If we win nine games in April, none of that stuff happens. If we collectively handle ourselves more maturely, more professionally, none of that happens. So we brought it on ourselves.

“It was just unfortunate to experience. But I do think what we accomplished for a decade there really meant something and I think will continue to mean something, and will continue to last and will be a part of the identity of the franchise. The things that happened in September were antithetical to that, so it’s uncomfortable to even think about.’’

Dan Shaughnessy is a Globe columnist. He can be reached at dshaughnessy@globe.com.