Why Cubs fans will miss being the ‘lovable losers’

When the Boston Red Sox snapped an 86-year drought and finally won the World Series in 2004, I didn’t know what to do with myself. I was only 13 years old at the time, but I’d been raised a diehard baseball fan. I knew how things worked.

Everything I’d been taught, both by the team and by fans around me, indicated that I wasn’t supposed to experience the joy of a World Series title. That’s not what being a Red Sox fan was about. It was about being stupid enough to love them unconditionally, even when they were good enough to get your hopes up only to rip that stupid, naïve heart of yours out in the most painful way possible.

Hell, just 12 months earlier I watched Grady Little feed my soul Aaron Boone on a silver platter. It was horrific and gut-wrenching, but it also felt perfect. It was my first true heartbreaking initiation; I finally knew what it meant to be a suffering Sox fan. I was never going to see this team win a championship.

But then I did.

Growing up, I often thought about how I might react the moment I watched the Sox finally break the “Curse of the Bambino.” I figured I’d scream my face off watching it on TV, hug my loved ones, go running through the streets.

None of that even came close to fruition in October 2004.

It turns out, when every part of your brain convinces you that it’s not going to happen — that this team will find some godforsaken way to blow it, even in the most unlikely of circumstances – your body sort of shuts down when you actually see it happen.

When Keith Foulke tossed the baseball to first base and shattered an identity rooted in misery, all I could do was sit on my couch, completely still with a slight smile. I remember just feeling completely numb.

I have to imagine that, in the early hours of Thursday morning, when the Cubs broke their 108-year drought, a lot of Chicago fans felt and reacted the same way I did a dozen years ago.

And I envy them, because that’s a moment that can never be duplicated. For better or for worse, their lives as baseball fans are now changed forever.

As a Sox fan, I’ve always felt somewhat of a connection to the Cubs organization. There’s obviously the history of embraced misery – just as the Sox had the Boone homer to reinforce their doomed existence in ’03, Cubs fans had Steve Bartman – but there also tends to be a mutual appreciation of franchises rooted in history, tradition and fanatical support.

Both teams have been around for over a century. Both play in one of the oldest, most revered and unique ballparks in the country. They rarely change their logo or uniforms much. Their fans show incredible, loud passion for the game.

As somewhat of a baseball purist, the Cubs have always seemed, to me, like the National League version of the Red Sox.

A link also exists in the pure genius that is Theo Epstein, who was the chief engineer behind both the 2004 Red Sox roster and this year’s Cubs team. As an executive, Epstein not only helped both organizations snap the respective “curses” that plagued them, but big-picture roster and front office building meant he also put them in a very strong position to keep getting back to baseball’s summit in the years to come.

But a newly discovered faith in the Sox and the stability of a talented roster core wasn’t the only thing that made me feel differently about the organization in the years following 2004.

The fanbase’s identity shift from “lovable losers” to a proud and confident (and, depending on who you ask, obnoxious) bunch was inevitable, and one that I expect Cubs fans will also experience as soon as the reality of their incredible season starts to actually sink in.

It’s a wonderful and incredibly satisfying moment to watch your team finally capture the glory that seemed virtually unattainable for so long, and that’s something no sports fan would ever want to give back. But there’s also a certain pride and charm in being part of a fan base that shows unbreakable allegiance to a team that continuously finds a way to let you down. 

The inability to win when it matters tattoos a fan base. The self-loathing, the jabs from opposing fans, the constant reminders of ineptitude — it brings an “us against the world” mentality.

As a Red Sox fan, I miss feeling like the underdog – no matter how talented the roster is — and I think Cubs fans will too.

When you finally win one, “us against the world” becomes “the world against us.” The stigma drops and there’s suddenly a target on your back. The burning desire to end the drought turns into an immense pressure to stay on top. It’s a completely different existence as a sports fan.

In Boston, there was less patience, for better or for worse. No more “there’s always next year.” Fans both old and new got that elusive taste of glory and they refused to let it go. They couldn’t get enough, and it didn’t matter the cost.

It meant the Red Sox had to assume a new identity as well. Increased revenue meant the team could afford to consistently gobble up marquee free agents on the market and, thus were expected to be perennial contenders. The same team and fanbase that bashed the Yankees, their arch-rivals, for writing blank checks on their way to titles now followed the same blueprint.

And, yes, it worked, for the most part. The Sox rode the waves and went on to win two more World Series in the next decade. Obviously, as a fan, experiencing those two runs was incredibly enjoyable as well. But the victories taste just a little bit sweeter when the world is expecting you to come up short.

When you win against the odds, it’s incredible bliss. When you win with the odds, it’s almost a relief.

With the Cubs now proven winners and, at this point, in an excellent position to be competitive for years to come, the odds are with them. So while the future is very bright in Chicago — certainly much brighter than it has been for quite some time — it’s also going to feel very different.

That’s not necessarily a bad thing but, speaking from personal experience, I think Cubs fans eventually will yearn for the days in which they felt like baseball and its higher powers were working against them.