Theo Epstein Had the Same Dream About the Cubs for Years. Then It Finally Came True.

Theo Epstein spent years waking up disappointed. Not because the Cubs lost, but because they hadn’t won yet — at least, not in real life.

The former Cubs president of baseball operations told ESPN’s Jesse Rogers this week that he used to have a recurring dream where Chicago finally broke the 108-year curse and won the World Series. It felt so real every time. Then he’d open his eyes and remember none of it actually happened.

“It was such a letdown every morning,” Epstein said.

That dream didn’t stop after 2016. But somewhere along the way, the letdown turned into something else. Epstein still has the dream sometimes. Now it’s just a memory of something that actually happened.

The Cubs celebrated the 10-year anniversary of that title on Saturday at Wrigley Field. They beat the Twins 6-2. First baseman Michael Busch hit a home run in the first inning. Anthony Rizzo, back in town for the festivities, actually recovered the ball in the bleachers after it bounced off the concrete. It was one of those moments that felt almost too perfect, like something out of a script nobody would’ve believed a decade ago.

Rizzo spoke before the game along with former manager Joe Maddon and team owner Tom Ricketts. The organization also unveiled “Champions Gate” on the West Side of Wrigley Field, a permanent tribute to the 2016 title that ended more than a century of futility.

An executive’s obsession

Epstein is one of those rare baseball figures who’s been on both sides of history. He ran the Red Sox front office when they ended their 86-year drought in 2004. Then he did it again with the Cubs, a franchise that hadn’t won since 1908. Two franchises. Two century-long curses. One guy in charge of breaking both.

But the Cubs one was different. The weight of it was heavier. The city had been waiting longer. The jokes were older. The scar tissue was thicker.

So maybe it’s not surprising that Epstein’s subconscious kept playing out the moment before it actually happened. He’s not the first person to dream about something that felt impossible. He’s just one of the few who got to wake up and find out it wasn’t a dream anymore.