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Cubs President Theo Epstein On How To Repeat: ‘Remember What Got Us There’

Five years after Theo Epstein was introduced as Cubs president of baseball operations, the organization’s 108-year-long title drought ended.

Prior to joining the Cubs, Epstein helped the Boston Red Sox end their 86-year World Series drought in 2004.

With pitchers and catchers reporting for their first workout of spring training Wednesday, WBEZ sports contributor Cheryl Raye Stout sat down with Epstein to discuss his earliest memories as a baseball fanatic, how he’s put together so many winning teams and what needs to happen for the Cubs to repeat as World Series champions.

Cheryl Raye-Stout: Growing up, were you somebody that read Sporting News or The Boston Globe sports page all the time?

Theo Epstein: Yes and yes. My morning ritual was to sit down at the kitchen table with the bowl of cereal and The Boston Globe sports page and just flip right away to the baseball page and study the box scores. I guess I didn’t look up and converse with my siblings and my parents much during that time. And then yeah, I got the Sporting News and other baseball periodicals. I read a lot of Bill James’ baseball abstracts as well.

Raye-Stout: So you had that appetite and you go to college and then you start pursuing the dream, and you did it by writing letters to different teams. Talk about that process.

Epstein: Well, I played (baseball) through high school and I thought I was pretty good playing at Brookline High School. I would come to later learn, when I moved to San Diego, what real high school baseball was like. I was not very good and wasn’t good enough to play at a Division I school like Yale, where I ended up going. So my career ended early my freshman year, which proved to be beneficial to me because it allowed me to transition to the other side of the game.

Probably the best thing that Yale ever did for me was the good-old-boys network connections. Calvin Hill, the great football player and the father of Grant Hill, the basketball star, was at the time the vice president of administrative personnel at the Baltimore Orioles. He saw my letter and noted that I was going to Yale, his alma mater, and also that I had done some research projects on the negro leagues, and that got his attention. He called me down there so I went down to interview during my spring break during my freshman year. And it ended up working out and he hired me. I got an internship and I worked there all three of my college summers. It was  a great springboard for me.

Raye-Stout: One person who anointed you as “one of the greatest general managers of all time” was Barack Obama. What makes someone a great manager or a great leader?

Epstein: Well, first of all, what makes someone eligible to be called a great baseball general manager really is a function of winning World Series. And a lot goes into that. Any one executive’s individual skill and ability and accomplishment is only a small, small micro-fraction of what goes into it. It’s the collective work of literally hundreds of people in baseball operations working together, sacrificing together, coming together behind a collective vision and then together implementing an effective strategy to get there.

So therein, I think, lies the quality that makes a great leader, which is being able to understand the landscape, understand the challenges, understand obstacles not just now but ones you’ll face in the future, understand the strengths and weaknesses inherent in the organization, and then rally everyone around this vision is a high-bar for the organization but one that’s attainable with collective buy-in and collective sacrifice and collective hard work. Then working with others to plot that strategy and bring people along. That’s part strategic thinking, part analytical thinking, part communication skills. That’s the brunt of it.

Raye-Stout: Now you’re getting prepared for spring training and a new season. How do you maintain the excellence?

Epstein: It’s all mindset at this point and it’s a great challenge. After we won the first time in Boston, I called (New England Patriots head coach) Bill Belichick about how to repeat and how to stay competitive and driven the next year, having just won. He used two words to describe our situation. The first one was “you’re” and the second one I can’t say on the air.

(Laughter) He wasn’t enthusiastic about our chances, let’s put it that way. But I think over the years from watching the Patriots and watching teams like the San Antonio Spurs in the NBA, I think I’ve realized that the very things that helped you win in the first place -- the connectedness of the players, the fact that they are willing to make individual sacrifices for the benefit of the group, the selflessness -- that all creates a dynamic where the whole is greater than the sum of the parts, and it puts you in a position to accomplish things together as a group that you just can’t do as an individual or when you’re motivated by individual concerns ...

Even the most selfless player or any of us in the front office too, there’s always a point in the offseason where you look in the mirror and you say, “Wow, I played a pretty big part in that,” and you puff your chest out a little bit. And that’s fine and it’s natural and it’s human, but it’s really important to remember what got us there. So I think at the beginning of spring training, at the beginning of the season, talking about how the most special part of last year was that we all got  to feel part of something bigger than ourselves, and reminding players that it was the selflessness and the connectedness that got us there, and then asking them to opt-in again. We’re lucky because have players with such great character that I think it’s going to happen naturally, but it’s important to create a culture where you can talk about those kind of things.

This interview has been edited for brevity and clarity. Click the 'play' button to listen to the entire interview. 

Chicago Cubs president of baseball operations Theo Epstein holds the Commissioner's Trophy while son, Jack, right, and Cubs vice president of baseball operations and general manager Jed Hoyer, left, look on during a parade honoring the World Series champions on Nov. 4, 2016. (AP Photo/Paul Beaty)

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