Cubs News

Theo Epstein’s World Series dreams

3 years agoTony Andracki

In many ways, Major League Baseball executives are just like fans, living and dying with every pitch.

The only difference is general managers and team presidents have some amount of control over the outcome, even if they’re not the ones on the field directly affecting the game.

So it should be no surprise that Theo Epstein was just like every other Cubs fan in that he dreamt — literally — of what it would be like to win the World Series before the magical 2016 fall.

As he steps down from his position as president of baseball operations with the Cubs this week, Epstein took some time to reflect on what was undoubtedly his greatest accomplishment during his nine-year tenure in Chicago.

When Epstein joined the Cubs front office in the fall of 2011, he set forth high expectations — to bring a World Series trophy to the franchise for the first time in over 100 years. All the time, energy and effort he and his colleagues poured into that goal were realized five years later on a rainy night in Cleveland.

It was a moment Epstein had long since dreamed about.

“Before we won during the rebuild and up through when we started to become competitive, I would occasionally wake up in the middle of a dream where we had just won the World Series and that moment after you win where you realize that the World Series flag is gonna fly forever, that the curse is over and that we can all rejoice and that so many people’s lives would be forever transformed,” Epstein recounted. “And in my case, this great relief that I will have accomplished what I set out to do here and then could be free moving forward.

“Only to wake up to the realization that it was just a dream and no, we’re in fifth place and have a lot of work to do. And so when we did win and flew back the next morning to Chicago from Cleveland, I passed out on my bed and woke up to that same familiar feeling of, ‘oh, we just won the World Series’ and then had a brief second where I wasn’t sure if it was a dream or not.

“And then realize it was real life and felt this incredible rush of just joy and pride and accomplishment and collective accomplishment and freedom realizing that I had done what I set out to do and could be free from that burden going forward.”

For every Cubs fan alive, that championship meant so much on so many different levels. After more than a lifetime without a World Series title, the Cubs hoisting the trophy became the exclamation mark on the greatest pursuit in American sports history.

That moment was just as special to Epstein, as was the pride he felt knowing it was a collective accomplishment for everybody involved — players, coaches, ownership, front office executives, fans.

In the four years since that feat, Epstein is constantly reminded of how much that World Series run meant to the community.

“It’s just an honor to be associated with that,” he said. “And a privilege because as was the case in Boston, here, virtually every day, somebody will come up to me — strangers — and share what the World Series meant to them and their family and start sharing intimate details of relationships in their family, growing up watching the Cubs together, what it meant to them.

“That is such a privilege. Where else in life can you get that where you run into a stranger and then all of sudden, they’re sharing these intimate details with you and you have this instant connection? It’s just a privilege to be a small part of that.”

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