Exclusive Q and A with Chicago Cubs President of Baseball Operations Theo Epstein

Ethan Gainsboro, Sports Writing Editor

Theo Epstein, President of Baseball Operations for the Chicago Cubs, graduated from the high school in 1991.

Do you have any favorite Brookline memories you would like to share?

Growing up at Lawrence School. playing Brookline youth soccer and baseball, running around Amory Park, exploring Hall’s Pond with my brother, walking down Beacon Street to Fenway with my family, taking the Green Line all through Brookline.


What do you remember most about Brookline High School?

Great teachers, especially Mr. Butchart and Mr. Vigliorolo, and having a blast on the soccer and baseball teams.


What lessons did you take from the high school into your career?

Going to such a diverse high school helped me appreciate the importance of respecting and trying to understand backgrounds and perspectives that were different from my own.


What job did you want to have when you were at the high school?

Playing shortstop for the Red Sox.


What did you study in college?

American Studies.


What was your first job out of college?

I started with the San Diego Padres two days after graduation.


How did you first get into baseball?

I interned my three college summers with the Baltimore Orioles.


How/what got you into the front office type of job that you started with the Red Sox?

My experience with the Padres prepared me for my opportunity with the Red Sox.


How did it feel to be the youngest general manager in the history of baseball?

A little surreal. I was comfortable with the baseball aspects of the job, but going from total anonymity to a very public position was unsettling.


How crazy was it to break the Curse of the Bambino?

Very! I still can’t believe it. I watch the highlights from the 2004 postseason every few years just to make sure it really happened.


You recently received a 5 year/ $50 million deal, the largest ever for a non-player. Are you happy that your future is with the Cubs?

Yes. I love the people I work with and we have fun at work every day. The fans waited 108 years for one championship, so we are motivated to work hard and bring them some more.


How amazing is it to have broken the 108 year curse in Chicago and already be heralded as one of the best general managers of all time?

It was incredible to see how much joy Cubs fans experienced after the World Series and how the whole saga connected people with each other and with their families. The city really needed something positive to rally around. Playing a small part in making that happen was exceptionally rewarding.


See also:

Epstein’s legacy now cemented in history” 

Epstein celebrates win