A Cubs win would also bring a twinge of sadness

Nam Y. Huh/ AP Photo

When I daydream about the Chicago Cubs winning the World Series, the first images that come to mind are of joy. Fans hugging each other in the bleachers at Wrigley Field, singing "Go Cubs Go," throwing hats in the air and openly weeping. People pouring out of the bars in Wrigleyville to party in the streets until well after the sun has come up. The grand old marquee flashing "CUBS WIN!! CUBS WIN!!" over and over again.

But then I'm struck by how much sadness sneaks its way in. A second set of images always follows close behind: the smiling faces of Ernie Banks and Ron Santo, two of the greatest Cubs players -- now both deceased -- there ever were, two of the most loyal fans the franchise will ever see. I never met Santo, but often listened to him call Cubs games on the radio. His groans of disappointment and yelps of approval made you feel like you were watching a ballgame with your grandfather, not listening to the call of a future Hall of Famer.

I knew Ernie a bit. For years, he always promised to officiate the marriage of my now-husband and me, an offer he made to quite a few people. He once said it was because as he got older, he wanted to go to as many weddings as he did funerals. In his final years, his mind wasn't always nimble, but he was still just as effortlessly affable, with a smile and a spirit that filled a room. It's gutting to know we'll never see what that smile would look like after the final out of a Cubs World Series win.

And it's not just the Cubs we all know. Many Cubs fans have a personal story. Jamie Baker, a 39-year-old Cubs fan from Lake Villa, Illinois, watched the Cubs' ultimately ill-fated postseason run in 2003.

"We had two friends that had died in a car accident," he says. "While none of us verbally said it during the Cubs' run, when they eventually lost, I turned to one of their brothers. He hugged me, crying, while uttering, 'I really thought [my brother] Danny was helping them win it all.'"

Nearly every living Cubs fan has a Danny, Ernie or Ron -- a grandfather, grandmother, parent, sibling, spouse or friend who didn't make it quite long enough. When the stars finally align for the North Siders, and we all get what Cubs fans waited more than a century for, it will be more complicated than any championship celebration that came before it. There will be incredible joy, yes; the kind of joy that's equal parts elation and relief, which leaves you feeling both full and weightless at the same time. But with that joy will also be tremendous sadness. I'm sure of it.

The climb up the proverbial mountain has been so arduous, it's hard to imagine what awaits us on the other side. Oh sure -- it'll be worth the wait. We'll re-watch the final moments of the win until we've memorized every pitch, every out, every smile and hug. We'll fill the streets of Chicago for history's biggest championship parade and wait as long as we can to wash the champagne out of our clothes. Kris Bryant, Anthony Rizzo, Joe Maddon, Theo Epstein and the rest of the guys will be all but knighted in the city of Chicago, never to pay for a beer again.

But then what? Who are the Cubs -- and Cubs fans -- if not the world's most famous lovable losers? From Johnny to Jay to Jimmy, the most consistent monologue fodder for late night hosts has been the endlessly failing Chicago Cubs. When your identity is so deeply tied to losing, who are you when you win?

I hope this is the year we find out.

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