From American Studies to Baseball Immortality: How Theo Epstein Carved His Own Path

How in the world did an American Studies major at Yale become the most immortal figure in baseball?

For Theo Epstein, the man who laughs at centuries old curses, his career growth was dependent on two things – goal setting and filling gaps.

Let’s go back to the beginning, long before Epstein led the Boston Red Sox out of their cycle of failure, and to a time where the Cubs were just another perennial loser, a team defined by lost moments. There are insights we can glean from the answer to our original question of how Theo Nathaniel Epstein paved his path to Cooperstown in gold.

It starts with passion and clarity.

While growing up in the Boston suburb of Brookline, just a mile away from Fenway Park, Epstein played baseball but realized if it was to be in his future, it would be behind the scenes of the game he loved. Like President Kennedy declaring in 1961 we will put a man on the moon, Epstein had a clear and stated goal of working in baseball, telling friends in high school and college he would someday be the GM of the Red Sox.

This focus, a personal mission statement of sorts, framed the rest of his decision-making.

When you have a clear goal, everything else falls into place. Decisions become black and white when encircled by your mission statement – does this help me reach my goal, or does it hinder me?

Simplify.

Epstein attended Yale, and while majoring in American Studies may not sound like the logical path to a baseball front office, his extra-curricular activities provided the sports experience he needed. He managed the Men’s Hockey team, worked in the Sports Information department and served as the sports editor of the Yale Daily News.

“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,” recalls Epstein. “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.”

Most people starting out in college are slow to warm up to the concept of networking, focused instead on making it to class, surviving on their own and making new friends. Networking can be daunting, putting yourself out there vulnerable to rejection or disinterest. Many times it is easier to stay in your routine rather than venture outside your comfort zone.

Epstein had no such fear, sending out his resume his freshman year looking for opportunities in the big leagues.

“I got my foot in the door with the cliche 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**t 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.”

After graduating in 1995 Epstein was hired full-time as a public relations assistant. As a full-time staff member Epstein caught the attention of Orioles team president and CEO Larry Lucchino who upon leaving the Orioles for the San Diego Padres, took Epstein with him, this time as Director of Player Personnel, a big jump from the PR department.

In San Diego Epstein learned the principle of filling gaps, and that is when his career really took off.

Lucchino, now a mentor to the young Epstein, suggested the American Studies major get his law degree at the University of San Diego while working full-time with the Padres. There was a gap in the Padres spartan front office staff for someone with a law degree and knowledge of contract negotiations.

“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.”

With a law degree in hand, Epstein became a bigger part of the Padres high-level negotiations.

“By going to law school and getting the degree, if there was a negotiation where maybe GM Kevin 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.”
 

The rest is well known, in 2002 Epstein was named the youngest general manager in baseball history. By 2004 he had assembled a Red Sox team destined to break the curse of the Bambino and then double down in 2007.

In 2011 he left the Red Sox for another curse that needed exorcism, the hapless Chicago Cubs. Five years later he’s a champion again, and a baseball immortal.

From an early stage Epstein had a clear goal that he doggedly pursued, without fear or second guessing. Even after making it to a point some would deem successful or at least comfortable, he pushed again, getting his law degree and filling a gap in the organization that propelled him even further and heightened his contributions.

It's a study of success we can all learn from.