Epstein lived out a literal dream during his Cubs tenure


Theo Epstein opened his eyes, the warmth of a World Series victory, a broken curse, a promise fulfilled still coursing through his veins. 

Then, he realized it was just a dream.

“And no,” Epstein recalled, “we’re in fifth place and have a lot of work to do.”

Long before the Cubs won their first World Series in over a century, Epstein dreamt about that moment. He’d wake up just after the fanciful victory had sunk in and have to remind himself that in reality, he was leading the club through a rebuild, or that the Cubs’ young core was just beginning to show their potential.

On Tuesday, during Epstein’s farewell press conference, he brought up those dreams. The story of them was the only way he could think to explain what winning the 2016 World Series meant to him personally.

On Friday, Epstein’s Cubs tenure will officially end, and Cubs general manager Jed Hoyer will step into his position.

As Cubs fans reflect on the Epstein era, they have nine years’ worth of memories to dissect: From Epstein’s 2011 arrival as a proven winner, to the Cubs’ past three years of underperformance in October. But he will always be the man who broke the curse.

“When I think about the World Series, I think about all of us doing it together,” Epstein said Tuesday. “The lines are blurred – front office, ownership, players, coaches, managers, fans – that's what made it so special.”


Aside from the Cubs’ on-field accomplishments, Epstein said the depth of connection with the fans stands out to him when he thinks back on his time in Chicago.

“I really feel like this journey has been something we've taken on together,” Epstein said. “That's how it's felt. Maybe my perspective in Boston (as the Red Sox GM from 2002 through 2011) was different because I grew up a Red Sox fan, so I already felt that way and it was already part of who I was.

“But getting dropped into this situation nine years ago, feeling like a stranger; Chicago, the Cubs, Cubs fans all being foreign to me. And now I look nine years later, and I feel like it's in my blood too. And I don't think that would have been possible elsewhere.”

So, when the Cubs finally did win the World Series in 2016, Epstein understood the gravity of the accomplishment.

He remembers flying back to Chicago the morning after Game 7 and, exhausted, heading to bed.

Epstein woke up with a familiar feeling. It took him a moment to realize that it hadn’t been a dream.

“And felt this incredible rush,” Epstein said, “of just joy and pride and accomplishment and collective accomplishment and freedom realizing that I done what I set out to do.”

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