The thought of the Cubs getting to—let alone winning—the World Series, had entered the realm of outlandish fantasy. After all, the team’s current 107-year championship drought is the longest in not only professional baseball but also football, hockey, and basketball. The Cubs taking the pennant seemed like a sure sign of the apocalypse, as when W.P. Kinsella, in his short story collection The Thrill Of The Grass, has the Cubs finally triumphing… right before Armageddon. The team couldn’t even get a break in science fiction: Although the Star Trek novel Articles Of The Federation suggests a fresh start for the franchise as the New Cubs, the perennially losing team comes last in its division in 2380. The 1993 movie Rookie Of The Year proudly ended with a Cubs championship, but had to enlist a 12-year-old pitcher who’d had a miraculous accident to get there. And of course, 1989’s Back To The Future II famously featured the Cubs winning after defeating only-too-appropriate 100-1 odds in 2015 (another year where, in the real world, the Cubbies got tantalizingly close—but not close enough).

Outside of a time machine, the current closest thing we have to a recent Cubs championship arrived in a PlayStation commercial. Some fans have had understandable trouble watching it, as it simply cuts too deeply.

The pain of the Susan Lucci-esque continual losses of “America’s Team” became recognizable comedy fodder for the American culture at large. We’re not sure how many Simpson writers are from the Midwest, but a few isolated jokes show that they know the plight of the Cubs fan well.

Even on Sunday’s “Treehouse Of Horror XXVII,” Lisa comments that a dry Springfield is a “drought of Chicago Cubs-like proportions.” A previous TOH saw Kang and Kodos collapsing the entire universe to get to a Cubs win.

The suffering they cause aside, the Cubs are the type of team that breeds long-lasting loyalty, bolstered by famous fans like Bill Murray and John Cusack. Even people who don’t actually live here anymore, like Northwestern alumnus Stephen Colbert, refuse to believe that we can’t break the goat curse. Still, even Colbert called the Cubs entering the playoffs last year a sign of end times.

As possible replacements for the Steve Goodman-penned “Go Cubs Go” (possibly the lamest team song in all of sports), current rock stars and Cubs fans like Eddie Vedder and The Mountain Goats have penned their own odes to the continually also-ran franchise. The latter also ties the end of the world to a future Cubs championship.

Of course, rather than goats or destiny, those decades of loss could have a simpler explanation: business. The front office knew it could fill the beautiful, yet slightly broken-down Wrigley Field with 100 percent bush-leaguers, and fans would still want to party in the Friendly Confines. Once the Chicago Tribune bought the team from Wrigley, and WGN became a national cable channel, the Cubs were branded as “America’s Team”—and the unwavering devotion they inspired meant its owners didn’t have to worry too much about them being any good. The Cubs, lovable losers that they were, became part of the cult fandom that grew around Chicago sports teams in the ’70s and ’80s, even inspiring a long-running play, Bleacher Bums, that depicted the daily lives of those permanent fixtures behind the outfield.

In the 1990s, sitcoms like Bonnie Hunt’s The Building, the Olsen twins’ Two Of A Kind, and Jason Bateman’s Chicago Sons loved to put their characters in apartments right behind Wrigley Field—even though it was pretty clear that said characters were not, in fact, multimillionaires.

It’s easy to see why “Cubs fan” became a sort of convenient shorthand for “plucky underdog.” It takes a special kind of love-blind hero worship to believe in a team that’s amassed 10,000 franchise losses. That kind of epic failure takes on its own grandeur, one buoyed by the legend of the inimitable Harry Caray, a never-ending flow of Old Style beer, and team-specific traditions like throwing the visiting team’s homers back onto the field. With the Cubs mythology and the inexplicable hometown pride both going strong, regardless of performance, management had no real reason to puff up its dugout with actual stars, and it didn’t really spend a lot of coin doing so. The ones that did emerge—like Ron Santo, Ernie Banks, Andre Dawson, Ryne Sandberg, Sammy Sosa, Kerry Wood, among others—offered the occasional glimmer of hope before retreating into the annals of baseball history. No matter. The stadium was full enough.

That front-office philosophy changed, however, when the Ricketts family took over ownership of the team in 2009, bringing in noted Red Sox curse-breaker Theo Epstein in 2011, who’s concentrated the team on winning for once. And the proof is in the playoffs: The Cubs have made it to the National League Central Series for two years running now. Nate Silver himself has pegged the team to take it all this year. And yet it’s still hard to imagine the Cubs as anything but those underdogs. After all, that “lovable loser” status has worked pretty well for Chicago since its inception, a city whose mottos have included “I Will” and “The City That Works,” even as a second run to New York (and now sliding into third). It’s the kind of indomitable city that could switch the direction of an entire river—quite an engineering feat for the year 1900. Or the kind that would put on a giant world’s fair in 1893, only twenty-some years after a massive fire that would have sunk a lesser burg.


Chicago’s reputation has since swung far away from fairs and fires, which any native who’s ever visited another country and revealed their place of origin knows. (These days, it comes down to two things: Al Capone and Michael Jordan.) And yes, lately the city is getting a new reputation for just about the worst reasons possible. It’s true Mayor Rahm Emanuel recently avoided a Chicago Public School teachers’ strike by pulling the reasonable budget the teachers were asking for from tax increment financing funds: a no-brainer that still didn’t happen until the 11th hour before the midnight deadline. Even worse than that is the mayor’s (and the city’s) bungling over the disturbing rise in crime—particularly shootings, particularly murders—over the past year. The statistics are so startling that other cities, like New York and London, have written extensively about the uptick in Chicago shooting deaths, as the city itself and its residents appear powerless to stop the carnage. More to the point is the recent Onion headline “Rahm Emanuel Concerned Gun Violence Could Spread To Parts Of City He Gives Shit About,” written by people who actually live here, which is only funny because it’s true. Or rather, not funny.

If this does turn out to be the Cubs’ year, it couldn’t have come at a better time. In fact, it might even have been worth the century-long wait. A Cubs win, just like in that hurtful PlayStation commercial, might have the effect of pulling the city together, reminding the world that, instead of being a murder capital, Chicago is still the city with heart. It’s the city that never gave up, even after so much failure. It’s why so many of us stay here to raise our families even with shootings just blocks away, even as we watch our friends and neighbors flee for the suburbs and beyond. We’re still hopeful that this horrible tide can turn. Just like it appears to be doing for the Cubs.


The big question remains, though: If the Cubs actually win, what would that mean for their beloved underdog persona? After all, everyone loves a winner. But as the Cubs have proved for decades now, it turns out they may love losers even more.