Theo Epstein became the youngest general manager in major league history when he was hired, at age 28, as GM of the Boston Red Sox. Epstein, who turned 30 one month ago, now has 14 months under his belt as GM and 11 years in professional baseball. He also has three decades of experience with the Red Sox; Epstein grew up in Brookline, Mass., within walking distance of Fenway Park. As GM, he still walks to the ballpark every day. (Hours after this interview, the Red Sox re-acquired veteran designated hitter Ellis Burks. Burks, when he came up as a rookie with the Red Sox in 1987, was patrolling center field in front of his 13-year-old future GM.) Baseball Prospectus spoke with Epstein at his office inside a snow-covered Fenway Park.

Baseball Prospectus: Your Major League Baseball career started as an intern (at age 18) in Baltimore’s PR department. What were you studying at Yale, and how did you get your foot in the door with the Orioles?

Theo Epstein: I ended up as an American Studies major at Yale, and that allowed me to write most of my papers on baseball, rock and roll–things that I wanted to write about. But I started out first as a psychology major, then as a poli-sci major, then as a philosophy major, then, I think by my sophomore year I was an American Studies major. I got my foot in the door with the cliché approach, I wrote letters to several teams, and then the letter to the Orioles got redirected to the desk of Calvin Hill, who was the VP of administrative personnel at the time–Grant Hill’s father, a former Yalie and NFL football player. So, I think the school connection, the sort of horses*** Ivy League connection that you’re supposed to feel guilty about–and I sometimes do–paid off there. So instead of the letter ending up in the trash can somewhere, Calvin ended up reading it and calling me. He brought me in for an interview and I went down there during spring break of my freshman year; instead of going to Cancun with my buddies, I went to Baltimore. I interviewed, Calvin and I had a good talk and I ended up getting the job. I was in Baltimore for the summers of ’92, ’93 and ’94.

BP: (Current Red Sox President and Chief Executive Officer) Larry Lucchino took you along with him to San Diego, where you got your law degree at USD, while working a reported 70 hours per week with the Padres.

Epstein: Everyone in baseball works long hours. I was working full-time, and going to law school full-time. That meant two things: The Padres were really cooperative with me, and I’m very thankful for that. And it also meant that I was very rarely in class. (Laughing.) I selected the classes based on my best guess on the teachers’ attendance policies. The ones who never took attendance and didn’t care became my favorite teachers.

BP: You’ve said that the law degree got you “a better seat at the table.” What did that mean in real terms?

Epstein: At the time, the Padres were a very small baseball operation. They only had, really, a handful of full-time people involved in the office. Padres GM Kevin Towers did a great job of surrounding himself with people that complemented him, and each brought a different skill set to the table. No one under his purview directly in baseball operations had a law degree. So by going to law school and getting the degree, if there was a negotiation where maybe (Towers) would only have the assistant general manager with him, in this case he would approve me as well–if only do the contract language. Getting that seat at the table gave me the opportunity to be involved, and then my responsibilities grew from there.

BP: And how many law degrees are there here?

Epstein: At the Red Sox? Well, we have a bigger operation. Let me guess. In the baseball operations department itself, I think just one. But we have three lawyers in-house for club counsel, and then Larry Lucchino has a law degree as well.

BP: Headed into your second spring as GM, what’s a typical day for you?

Epstein: We’re in a bit of an atypical time right now because we’re just finishing up some small issues before we head to spring training. One of the best elements of this job, or any job in baseball operations that’s multi-disciplinary, is that our specific responsibilities and our daily life change every couple of months. So in November and December, we’re constantly on the phone with agents, constantly trying to assess the needs and wants of other organizations, constantly brainstorming trades. We’re on the phone with other organizations, agents, figuring out our budget, making moves, setting up for the winter meetings, visiting free agents–or players with no-trade clauses occasionally–things of that nature. So November and December are very hectic and they’re all about player acquisitions and player transactions.

January is typically a month of contract negotiations and arbitration. We spent much of last month preparing for an arbitration case, in David Ortiz, that didn’t come. We were able to avoid it with a settlement–we settled all our arbitration cases–and now we’re working on a multi-year deal or two (Ed note: Soon after this interview was conducted, the Sox inked Trot Nixon to a three-year, $19.5 million contract). So January’s about contract negotiations.

February and March move into spring training, and you take the time to get to know your big league staff and get to know your big league club. It’s also a rare opportunity to see all your minor league players in the same place at one time. You make plenty of roster moves and maybe an acquisition or two as you whittle down from 50-something players in camp down to 25 who break with the big league club.

Then, in April and May, you prepare for the draft. Obviously you try to be around the big league team as much as you can at the start of the season, but you focus on the draft for most of April and May. Then, the draft comes the first week of June.

June and July you’re focused on the needs of your big league team, what you need to do to make the right moves. In the last week of July you’re constantly on the phone with all the clubs, negotiating trades. In August, your attention shifts back to the minor leagues–you want to make sure you see all your minor league teams play before the end of the minor league season. In August and September, you’re back for the playoff run, and then October comes around and you’re back looking at minor league free agents and the whole cycle of the off-season starts again.

BP: How much time do you spend in Florida?

Epstein: The whole time. We’re down there just under seven weeks.

BP: What do you do to make yourself better at this job?

Epstein: I think listening is important. And being actively aware, every day, that you want to get better is the most important thing. Then you can’t help but learn from the great people around you. I benefit from having people like Bill James, Bill Lajoie, Craig Shipley, Josh Byrnes, and Mike Port all around me. And they each have an area of expertise. It’s as if I’m at Baseball College–you go to college and you take your classes and get to learn from experts in certain fields. You know, if I want to go watch a game with Bill Lajoie, maybe I can pick something up about a pitcher’s delivery, and then later in the day maybe I’ll have an e-mail exchange with Bill James and learn something about some metric. As long as I’m open-minded I can’t help but get better every day.

And also making mistakes. It’s definitely true that you learn your hardest lessons from your own mistakes.

BP: What are you reading?

Epstein: I just finished the Da Vinci Code, which I thought was great. It was a good quick read and a lot of fun. Oh, and I’m almost done with the Koufax biography, which I highly recommend. Terrific, by Jane Leavy.

BP: You mentioned metrics a minute ago. Larry Lucchino’s “Top 10 Qualifications of the Ideal General Manager,” a document he wrote and used while hiring you, includes…

Epstein: (Laughs)…which he used while determining that I was no better than third, so I can’t say he used them specifically while hiring me.

BP: All right. The number-two qualification was “Familiarity with, and willingness to use, modern quantitative approaches in evaluating players, in addition to traditional methods.” Beyond a cursory explanation of OPS, the papers haven’t dug too deeply into what “modern quantitative approaches” really mean. Can you name the most important measures you look at when evaluating hitting, pitching, and defense?

Epstein: I can. But I never will publicly. It would have the potential to reveal a competitive advantage. There’s no secret formula that we use–we use a combination of things. And we also rely on commonly available formulas as references and quick checks and balances against more proprietary metrics. It’s a combination of things.

BP: I wouldn’t expect you to reveal the secret formula.

Epstein: There is none.

BP: Your father, on the “Cowboy Up” year-end DVD…

Epstein: Oh, no…(Laughing)…which I haven’t seen. This should be interesting.

BP: He said that you are self-described as “risk-averse.” What’s that mean? It surprises me.

Epstein: Well, risk is a funny thing. We talk about it a lot at the Red Sox. You could say our approach is a bit of a paradox, because at the same time we are risk takers and risk-averse. I think we’re risk takers in the sense that we’ll try anything within reason, within moral boundaries, to get a competitive advantage. So if someone has an idea–no matter how crazy, no matter how off-the-wall, no matter how illogical it seems–as long as we don’t have to expend a tremendous amount of resources to try it, we’ll try it. Even if the odds seem stacked against us, we’ll still try an endeavor that in the end, if we’re successful, we think will help us. So in that sense of the word, we’re not afraid to take risks. We’re not afraid something will make us look foolish, or create a bad public perception–that’s fine. We don’t place a lot of weight on that. We’ll take those kind of risks, so we’re risk takers.

Where we’re risk-averse is in situations where there are a lot of resources involved. And when I say resources, I really mean a percentage of our payroll. By design, we’re risk averse with our payroll. We feel that we have tremendous resources, and the quickest thing that we can do to sacrifice that competitive advantage is to take an ill-advised risk with our payroll and have it backfire on us, eliminating that edge. So we are risk averse, because we want to make every single unit of resource count for us; every single dollar on the payroll really counts for us and translates into wins. So I think it is accurate to say that we’re risk-averse and risk takers at the same time.

Joe Sheehan, Dayn Perry, and James Click contributed questions for this interview.

Check back soon for Part II of this interview, including Epstein’s take on the Red Sox’s bullpen strategy, the value of platoons, and why the Sox signed Pokey Reese.

Nathan Fox is a freelance writer living in Boston. He can be reached at

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