Theo Epstein ’95 made baseball history when he was hired as the general manager of the Boston Red Sox in 2002 at the age of 28. After winning two World Series trophies with the Red Sox and breaking the 86-year Curse of the Bambino, Epstein has set his sights on ending another curse: that of the Chicago Cubs, for whom he now serves as team president. During spring training, Epstein spoke with the News about his time at Yale, his own career and what he would tell future generations of Yalies looking to break into professional sports.

Q: How do you feel like being at Yale and your Yale education prepared you for working in baseball?

A Well, the most direct answer to that is that without Yale, I probably wouldn’t ever have gotten an opportunity in baseball, because Calvin Hill ’69, who went to Yale, was the one who hired me initially with the Orioles. He’d been working as their VP of administrative personnel, and in my freshman year, I wrote letters to every team, and he was one of the only ones to respond; he called me. I remember when he called me, on a Friday afternoon … the weekend had already started in our suite, but he invited me down to interview over spring break. I did, and we connected over Yale and had a lot in common to talk about. So that was great to get that opportunity. I grew up a lot there and saw a different side of sports, working for Steve Conn and the Sports Information Office and through writing at the Daily News. It was a great experience.

Q: Perhaps your most famous column for the YDN was the one in 1993 asking if [longtime Yale head football coach] Carm Cozza should go. How did you feel when he gave you the game ball afterward?

A: He didn’t give it to me, technically. I thought it was funny. It was good insight into the way that the media world can work sometimes. I think I learned a lot from that. We sat around discussing what the different angles would be about our game coverage, and we decided let’s have one person write that it’s time to move on, and one person write in support of him. I guess that was a pretty immature approach, and I hope that I would know better now, and it made me realize that I didn’t want to work on the media side.

Q: So is that what made you realize you didn’t want to work in journalism?

A: No, no. Through my internships with the Orioles I realized that journalism can be a little bit of a lonely pursuit, observing the sportswriters, and I really like working with a group of people, and I’m really competitive, so working in a front office is perfect because you get to work really closely with others, and you get a daily referendum on how you’re doing in the standings that can impact how things go with your franchise. I think I look back on that and [I’m] pretty embarrassed that I was part of it, and at the same time it was part of the experience of growing up. I haven’t read that column since I wrote it, but I guess I learned how not to go about it.

Q: Do you still follow Yale sports?

A: Yeah. Not probably as closely as I’d like to because baseball keeps me busy, but through Steve Conn and through some friends of mine, I’ll stay up to date. I watched a bunch of the playoff games that the hockey team had in that run to the championship a few years ago.

Q: Right after school, you pursued a law degree while working with the Padres. Are you glad you did that? What did that give you in baseball front office experience?

A: At the time, there was a bit of a glass ceiling in baseball if you hadn’t played the game at the big league level. It was hard to break in. One path that was available was to go be an area scout for five or 10 years. My boss at the time, Kevin Towers, he was getting pressured — we had a real small inner circle there, in the Padres’ small front office, he was getting pressured to hire a lawyer on the baseball side, and he didn’t really want a lawyer around. He and I had a great relationship, and he had the idea, why don’t you go to law school and we’ll see if that’s good enough? People ask what you take out of law school, and it did help cement a way of thinking. But all of the technical legal stuff, you jettison from your mind the day after you take the bar exam.

Q: What was the biggest challenge of being a GM at such a young age, and what was the biggest benefit?

A: The biggest benefit was that it gave me some really cool experience. To be in a position like that and to have a chance to work with great people and be around world-class athletes and be a small part of some special things happening was just a dream come true. I had great timing, great luck and great mentorship, to be able to be in that position. The challenge is that I think I didn’t have much rope with expected credibility. If things didn’t go well quickly, it probably would’ve been a really quick fall from grace. I was fortunate that I caught some breaks early, and some of the initial decisions that we made worked out. When we won the World Series my second year, that bought me more rope so I could do the job the way I wanted to, gave me time to build up the farm system and everything. But it was funny, being so young, watching other GMs smelling blood and try to take advantage of me. And the media would always add my age into things. It was really a novel concept initially, so it gave them something to talk about. It raised a lot of antennas, people watching closely, waiting for me to do something really young and immature. So I had to make sure all of the immature things I was doing were behind closed doors.

Q: How do you combine analytics and statistics with scouting?

AIt’s really natural for us to do in this organization because that’s been our approach all along. My personal philosophy is the way to assess baseball players is to use both lenses. When I was growing up in the Padre organization, I had the office between the scouting director and the statistical analyst. There were both really single-minded about their approaches. The scouting director didn’t want to hear anything about performance or stats, but he was a great scout. The analyst didn’t want to hear anything about [how a player looked], he just wanted to work with the numbers and he was great with that. They hated each other but they both liked me. So since I was the young guy, and they were living vicariously through the young guys in the office, I realized there was merit to both approaches. Because they were so single-minded, maybe they ran up against some limitations, so I just started to see through trial and error that maybe the best way to do it was to look through both lenses. The decisions that we made that satisfied both criteria ended up being the best decisions. All the way back to my first day at the Red Sox and straight through, we’ve tried to build organizations that embrace both doctrines and combine them.

Q: What advice would you give to Yale students looking to get into baseball or professional sports?

A: I think the key thing is to get your experience really early. Right now, there’s so much more supply than demand in the entry level sports marketplace. Probably 500 people apply for one full-time job. Because of that, teams don’t pay well early on. You have to work really hard for not a lot of money for several years until you can make a career of it. There becomes a point where you start thinking about getting married and having kids, and it’s almost too difficult to work in sports on an entry-level basis. So I think you have to try to get a lot of experience while you’re in college. Write for your school paper, work for your school’s sports information office, become the manager of the team, play the game as long as you can — because that gives you a really unique experience — and work on gaining enough experiences so that when you do get that opportunity to apply for an internship, you do get that opportunity to interview for an internship, you can distinguish yourself from the 499 others applying.

There are informal ways of doing that too. Go to as many games as you can. If you want to work in baseball, go to 100 minor league or college or big league games a year. Get there early, watch batting practice, talk to the scouts, take your own notes on players, see what you’re good at evaluating and what you need work on, and when you go into an interview, you’ll be able to bring your own scouting reports. That can help you distinguish yourself from the other candidates who say, ‘Oh, I like watching baseball on TV.’ It’ll get someone’s attention when you say you’ve gone to 100 games and you’ve taken your own scouting reports. At the same time, you can also familiarize yourself with modern analytics. Go to Fangraphs, Baseball Prospectus, all [of] those sites. You can go to an interview and say, ‘I can work with metrics, I’ve developed a few of my own, here’s what I think is valuable and here’s what’s not. And I also have written 100 of my own scouting reports and I can hand these to you and see what you think.’ That presents a really balanced view of the game, demonstrates your genuine interest in the game and you’re willing to work hard.

Q: I know the baseball season is long, and I know it keeps you busy, but when can we expect to see you back on campus?

A: That’s a great question. I don’t know the next time I’ll get there. Maybe the next time I make a trip to play the Mets. But I’m a Midwesterner now! I don’t spend as much time on the East Coast as I’d like. I miss it, I haven’t been back on campus in a long time. I’m overdue.