At Eastbay, we are surrounded by sports 24/7. Following the best athletes and checking out the latest scores aren’t just something we do during breaks—they are crucial parts of our job. So it goes without saying that our employees love sports and are big-time fans of their favorite teams. Nowhere is this more evident than with Taylor Wroblewski, our Cleated Marketing Manager, who is a diehard Chicago Cubs fan. So, with her beloved Cubbies possibly days away from breaking their 108-year title drought, she chronicled what this moment means to her, her family, and millions of Cubs fans throughout the world.

I am a 28-year-old woman, the Marketing Manager for baseball here at Eastbay, and a Cubs fan in the family line of my father, grandfather, and great-grandfather. And of course, never in my lifetime or theirs, have we seen the Cubs win the Series. There is no person in my life who can even describe to me what that moment would be like. So here I sit, in front of my television for a World Series game at Wrigley Field. It’s a feeling that I can only describe as hope beyond reason, nausea, and a paralyzing fear of my lovable team losing, right at the end. Because as my dad has reminded me so many times (most recently during the NLCS hitting slump), “You’re prepared for the worst, I hope. This isn’t going to end well.”

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The 1940s

I called my grandfather this week. The man has had bypass surgery, a stroke, and both knees replaced but he’s still kicking—I assume waiting around for a winning end to the season. When I tell him I want to talk about the Cubs, I get a general, “Well…I’m not sure what to tell you.” He’s cautious, a little unsure of how to feel at this point, and you can imagine why. But when he talks about growing up with the Cubs, and how his own father introduced him to the team, I smile at his nostalgia. And then I think of what it would do to my sports-loving soul if my 85-year-old grandfather doesn’t ever see the Cubs raise the Commissioner’s Trophy.

The 1960s

While for my grandpa it seems like a pipe dream almost realized, my dad still can’t get past the love/hate dynamic after the consistent disappointment the Northsiders have given him. He had big hopes for Rick Sutcliffe, Nomar Garciaparra, and Alfonso Soriano over the years, but none of them ever quite got our Cubbies there. This, I guess, is why he’s still trying to prepare me for the worst at this point. “It’s never easy being a Cubs fan.”

The worst moment of his Cubs fandom, he can describe explicitly. It was 1969, which makes my dad 13. “We had those guys like Ron Santo and Ernie Banks, and we were the best team. There were no playoffs back then so if you won the NL, you went to the World Series. The Cubs were way ahead and kind of like this year’s team with domination. Then all of a sudden, the Mets got really hot. Their record in October was just unbelievable. And I can tell you the exact moment, and where I was standing when my dad and I heard that the Mets caught us and we weren’t in first place anymore. Duffy Dyer. Practically no one has ever heard of him, but he hit a home run against us, and the Mets won the game. That’s when they passed the Cubs in the standings. I still remember it. We were going to the World Series. And then we weren’t. For any Cubs fan who lived through that, it’s by far the biggest disappointment.”

The best moment? He sighs because, that’s harder to come up with. He eventually settles on, “My best moment probably was getting to go to my first game at Wrigley. I went with my dad’s dad. Back then, you took sack lunches in a brown paper bag. I was only 7 or 8, but you could watch BP from right behind the dugout, no problem. There was a popup that landed right behind me. It was just sitting under the chairs, but some other kid ran down and grabbed the ball before I could get to it.” That’s my dad. Even his best moment with the Cubs always comes with a tinge of disappointment.

But if they won the Series, what would he do? “Um… I don’t know. I may not survive it. I have a limited edition bottle of rum from years ago. You can’t get it anymore. And I’m only opening it if the Cubs win the World Series. But I don’t know… it’s never happened. I think that’s part of what I’ve seen from watching TV. We’ve never been here. We don’t know what to do or how to act. It was weird when they won the Pennant. People went crazy, and then you looked at them in the stands and they were like, ‘Well, what do we do now?’”

This is the guy who taught me how to keep my eye on the ball in our backyard. Who was intolerant of seeing his daughter not run all the way through first during softball. Who squatted down on the sidewalk a kazillion times to catch each pitch I threw in junior high. And who took me for ice cream after every home run. He taught my brother and I to love baseball in a way that’s uncommon for our generation, and he taught us to be winners. I cannot watch him on the losing side of the league for another year.

The 1990s

When the men who made me a diehard fan describe their relationship with this team, I think back to my own childhood and what that meant. I think of playing youth softball, the only girl with a boy’s glove. But because it was embossed with Ryne Sandberg’s signature, I loved it. And then I think of how we’d play street baseball, me yelling “I’m Sammy Sosa!” only to hear back from my neighborhood best bud, “I’m Mark McGwire!” We clipped out the newspaper headlines every time our player hit another homer and had so much fun keeping tally that yea.

I didn’t yet realize the struggle I was in for. That I’d say aloud, more than once, sentences like, “I think we might be able to squeak out 60 wins this year.” And that as I got older, I’d fall more and more in love with a team that always let me down.

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October 2016

At this point in my life, on the brink of historic greatness, I also happen to be close with a couple Cleveland fans. And they like to talk about how great this win would be for the city of Cleveland, how they’ve waited so long.  They don’t get it.

My mother has watched these playoffs with hope for her family’s happiness but describes my dad as “so negative, I want to gouge his eyes out.” (They have a special bond.) She grew up a St. Louis fan though, so she doesn’t really get it.

And I am only 28, which means I’ve only suffered through about a quarter of this ‘curse.’ And that means I can’t really get it, either.

But they’re so great this year! The starting rotation is awe-inspiring. The relievers have really come into their own. The offense works… on most days. And I am absolutely chugging the Bryzzo Kool-Aid. Watching this pinstriped group has been so exhilarating that I sometimes can’t see straight. And if it feels like that for me, I can’t imagine how full the hearts are of Cubs loyalists all over the country.

Tonight

For generations, we have held strong along with so many other families.  Depending on our generation, we’re exhausted, pessimistic, or cautiously hopeful. But either way, we all just freaking love this team. We want it so bad. No Boston fan, Cleveland fan, or anyone else has ever wanted anything the way Cubs fans want this Series.

I’ve had my dog in Cubs gear. I’m wearing blue and red underwear, in addition to my lucky playoff shoes. I’m convinced this curse might actually be real, unless I wear/say/do the same things I have done this entire playoff run.

I will watch every last pitch of this series in hope that all of my ancestors before me finally see one of the greatest moments in sports history.

So share your stories of sports pain with me below. Fly the W. And please cross your fingers for my grandpa.