"When You Win, Everything Just Gets Better." Theo Epstein Shares His Thoughts

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“When You Win, Everything Just Gets Better.” Theo Epstein Shares His Thoughts

Chicago Cubs News

I’ll admit it: a small, but certainly non-zero, part of me wondered what would happen – negatively – when the Chicago Cubs finally won it all.

I know many of you never let the thought cross your mind, but I was never able to prevent it from creeping in.

Was it likely that my nearly life-defining fandom of the Chicago Cubs was really rooted in some masochistic desire to forever chase an unreachable goal? No.

But was it possible? Absolutely.

Of course, I sit here now, wearing a Cubs t-shirt, staring at a Cubs banner I have hanging on the wall, and writing for a Chicago Cubs blog with as big of a grin as my face has ever seen: The Cubs are World Series champions, and boy does it feels amazing.

But Theo Epstein knew it would feel this way all along. In fact, he doesn’t have time for the “other” way of thinking – or so he told Joe Posnanski at MLB.com.

Here’s an excerpt from Posnanski’s long piece at MLB.com:

“Yeah, I think the angst people have over that — ‘Will the experience be the same if you win? Will it be ruined once the Cubs are champions?’ — that’s the biggest waste of time ever,” Epstein says. “Are you kidding? When you win, everything just gets better.”

How foolish I was (and I mean that sincerely, because Epstein was right).

It may have taken actually winning for me to realize that it was never about the chase per say, it was about the glory. But now that I’m here, I know that the only thing that’ll quench my third is more glory. Not more history, not more streaks, not more curses … Trophies. Winning all the time. And more trophies.

Either way, that entire idea is just a small part of an excellent interview and article Posnanski put together with and about the Cubs’ President of Baseball Operations in the stands of last week’s exhibition game against Italy. Covering everything from early childhood fandom, to advanced analytics, to art, this interview is yet another peak behind the curtain into the architect behind the Cubs World series.

You’ll want to check it out.


Author: Michael Cerami

Michael Cerami is a Writer at Bleacher Nation, and you can find him on Twitter at @Michael_Cerami.