Now what? How winning the World Series changed Cubs fans forever

“Be careful what you wish for, lest it come true.” – Aesop’s Fables.


For 108 years, from the rambunctious youth of Al Capone through the political retirement of Barack Obama, fans of the Chicago Cubs were defined by one mutual wish: to see their beloved baseball team win a World Series championship. Subsumed into the psyche and identity of every Cubs fan on earth, that wish took on astounding significance, eliciting talk of fate and karma, philosophy and kismet, faith and cosmic probability.

With each fruitless season, the Cubs inspired more fascination. Sure, it was morbid fascination, sports schadenfreude mixed with mild self-masochism, but it was fascination nevertheless. Defeat became the Cubs’ elixir – the more they lost, the more people were engrossed – and analysis of their supposed curse occupied psychologists and historians, psychists and statisticians, ballplayers and bleacher creatures.

Some diehards were convinced it would never happen, that the hapless Cubs would never win it all. There would always be a black cat or billy goat in the way, so there was no use getting worked up about the team’s chances. However, when the Cubs finally scaled the mountain in 2016, banishing every skeleton in the Wrigley closet, an existential crisis lay beyond the champagne and tickertape. A century unmoved, the spiritual coordinates of Cubs fandom changed overnight.

When Kris Bryant whirled a throw across the diamond to Anthony Rizzo, recording the final out of a championship season long deemed improbable, everything it meant to root for the Cubs swivelled on a dime. “Now what?,” fans asked each other, suddenly unmoored from their life’s firmest anchor. “How do we live in a world where the Cubs are champions?”

Theories are still trickling in, and consensus is yet to be found.

Losing, and the billy coat curse, defined Cubs fans’ identity

For over a century, Cubs fans were so defined by their infamous title drought that some loyal boosters worried about the complicated aftermath of a hypothetical championship win. “There’s less suicide among Cubs fans because we have something to live for,” comedian Tom Dreesen once joked. “I fear the day the Cubs win the World Series. The following morning, 20,000 people will jump off the Tribune Tower, because what’s the use?" 

Echoing that sentiment, musician Steve Goodman once penned an improvised ditty, entitled When the Cubs Go Marching In, which captured the emotional dichotomy at the heart of Cubs fandom: “Here’s to all those Cubs fans, who have had to hold their breath. And sometimes you think they might win, and it scares you half to death.”

Then there was Cubs diehard Dennis Flavin, who conflated baseball yearning with human immortality. “I smoke, I drink, and I stay out late,” said Flavin, quoted in Cubs Pride. “Because god has made me a promise. He will not allow me to die before the Cubs win the World Series. He has assured me that, whatever happens in my life, I will not pass away before the Cubs win it all. The day it happens, I’ll have to decide whether I even want to live anymore anyhow.”

Accordingly, Cubs fans dealt with a complex soup of emotions during the 2016 World Series against the Cleveland Indians, another team synonymous with untimely defeat. Many Cubs fans were paranoid. Most were hopeful. All were nervous beyond words. In the tensest corners of Wrigleyville, though, a silent sliver of Cubs fans approached the Fall Classic with trepidation. For the first time in many lifetimes, a Cubs world championship seemed likely, not merely possible, and such an outcome promised to shake North Side baseball fandom to its core. Some dreaded the inevitable tumult, fearing it would erase core tenets of Cubs ideology.

Indeed, on the morning of Game 3, with the World Series tied at one game apiece, Yahoo Sports tapped into that contradictory axiom by publishing a YouGov poll that found ‘one in four diehard Cubs fans’ would actually miss the championship drought if it was eventually snapped. Additionally, 86% of poll respondents said they found camaraderie in losing. “Addicted to losing,” roared the headline. “Some Cubs fans want their team to lose the World Series.”

This is the classic gambler’s torment, of course. The anticipation of winning has a similar effect on the human brain as winning itself. As a roulette ball spins around the wheel, gamblers receive intermittent hits of dopamine – regardless of the outcome. These rushes of dopamine become addictive, then gamblers impulsively try to attain them. The outcome of any individual spin is relatively academic, because the gambling brain lights up in orgasmic-like bliss – win, lose or draw.

In fact, some research points to near-misses being even more persuasive than winning in terms of factors that keep people gambling. Gamblers become easily addicted to the great what-if. There is a surge of adrenaline, fearful euphoria and edgy giddiness contained within the anticipation. Serial gamblers live in suspended states of potentiality, away from actuality, and their ceaseless escapism baffles the mind. The same was perhaps true of Cubs fans who yearned for that elusive title – its arrival would close the casino, leaving high rollers without their fix.

When the lovable losers won, an identity crisis consumed Cubs fans

The Cubs did not lose the 2016 World Series, though. For all the frightful talk of hexes and witches, dropped flyballs and bobbled grounders, the Cubs won. It took seven games, a biblical rainstorm and an impromptu team meeting on the cusp of elimination, but the Cubs won. They actually won. Delirium flooded Wrigleyville as the lovable losers conquered the world.                                             

“That year was as exciting as any I've had, and the Cubs were an enormous part of that,” says Cubs blogger Michael Cerami of Bleacher Nation. “In terms of my favourite memories, there are probably too many to recount. Miguel Montero's grand slam against the Dodgers and Javy Baez's straight steal of home in the NLCS always stand out. But I think my actual favourite memory was the walk home after Game 7 of the World Series. The city was absolutely buzzing. There were people everywhere. And I specifically recall seeing grandmas dancing on the tops of their garages in the alleys of Wrigleyville, with horns blaring and people singing and smiling. It was the best version of the city.”  

As a new day broke over said city on 3 November 2016, though, a gradual realisation seeped into the collective consciousness: everything had changed, and it would never be reversed. For the first morning in 39,467, Cubs fans woke up as world champions. Every frame of reference was skewed, every reliable truism scotched. Sure, there were manic celebrations – graves to visit and a parade to enjoy – but when the tears dried and the cleanup commenced, how would life go on? Many struggled to find an answer.

The Boston Red Sox were offered as a symmetrical case study – Cubs fans gifted guardrails from their once-cursed cousins to the east. The Red Sox infamously went 86 years between World Series titles before vanquishing their jinx in 2004. Curse, Inc. swept the world in the aftermath of that hallowed championship, Boston steering the most overcrowded bandwagon in sports history, but some Red Sox diehards missed a simpler age. An element of authenticity was lost in the transition from perpetual losers to serial winners, and some questioned the price of that transaction. Others flat out rued it, mourning the loss of their philosophical bedrock.  

“What would it be like tomorrow?,” wrote Dave Bry in the Guardian, advising Cubs fans on an impending identity crisis. “In a world where the Red Sox can be champions? What kind of person would I be? Would I find myself feeling cheerful and happy all winter? With nothing to complain about? Next baseball season, next April, I was supposed to suddenly become optimistic? Repeat that sentence to yourself in a heavy Boston accent to learn how unnatural it sounds to a Red Sox fan over the age of 15.

“I lay in bed, staring at the ceiling this time, discombobulated. In a sense, once the Red Sox had finally won, I didn’t know who I was any more. Losing was the Red Sox’s most definitive, most distinctive feature – and by extension, in baseball fan terms, my own. Suddenly, I was just like everybody else. One of the stranger pangs of sadness I have ever felt swelled in my chest. I knew that watching baseball would never be quite the same again. And I realized that true happiness – at least this kind, this kind that I’d been dreaming of for 26 years – is beyond my capacity to feel.”

The Cubs became just another team after winning the 2016 World Series 

Others chimed in with similar observations, though their concerns were submerged by 5 million people showing up for the Cubs’ title rally – reportedly the seventh-largest gathering in human history. “Curses have power,” wrote Jeva Lange for The Week. “The power to bring entire cities of people together, to give fans something to live for, to draw an audience of 40 million fans and onlookers who just want to witness a sliver of the magic that comes with breaking free of something 108 years in the making. But shattering curses has consequences, too. And some of them are bad.

“A sports curse is a special anointment, the mark that separates a truly damned franchise from the rest of the teams that are just regularly bad. Curses allow you to believe that there is something divine, or perhaps diabolical, behind your year-after-year disappointment and misery. You and yours alone have been singled out to endure this suffering; you can map your family history by the close calls of the home team and the utterances of ‘there's always next year.’

“Naturally, when that (finally!) ends, there is excitement, pyrotechnics, screaming, crying (there is so much crying in baseball), smashed cars and smashed champagne bottles. But after the broken glass has been swept up the next day, in the early morning afterglow of the celebrations and the drinking and the fireworks, after even the presses have whirred out At Last! in big, bold letters across the top of the local paper, then you, suddenly, are indistinguishable from the rest. Occasional winners. Occasional losers. Curse-less.”

Though steeped in taboo, I have always agreed with this unpopular notion. Championship droughts hold a strange allure. In a world of ephemeral emotion, teams of unquenched yearning have a gravity and purpose that distinguishes them from more conventional competitors. It can be difficult to discern meaning in modern sports franchises, which operate as vacuous vehicles of corporate growth. When greedy owners can uproot and transplant teams at the drop of a hat, crisscrossing the country in search of profit, mission statements seem hollow, roadmaps transient. On the contrary, traditional teams defined by the mutual hunger of a community take on a deeper level of importance. They matter, in a sea of sports that do not. And in this regard, the terminal pursuit of promised glory made the Cubs the most purposeful sports team on earth. Until they won, that is. Until the curse was reversed. Then, the Cubs became just another team trying to win just another championship. Their unique selling point was gone.

“Let me put it this way,” says Cerami. “There’s really no chance the next World Series win, whenever it comes, will be as sweet as the last one. That was unique to us and it definitely takes at least a little bit of the magic away.”

How the Cubs, and their fans, have changed since 2016

Baseball may have lost something when the Cubs won, too. One of the game’s founding creation myths – one of its ineffable fables, passed down from one generation to the next – suddenly had a rational, mystery-agnostic conclusion. In some ways, the Cubs losing freakishly would have been more compelling than the Cubs winning unexpectedly. There is a reason why Stephen King is a multi-millionaire, after all. We have an inexplicable taste for the macabre. King would never have let the Cubs win, but they did, and one of sports’ most unfathomable yarns died with the billy goat curse. 

Of course, King is a passionate Red Sox fan (which perhaps explains his penchant for horrifying tales), and comparisons between Boston and Chicago survived the Cubs’ 2016 peak. Theo Epstein was the architect of both curse-busting seasons, but similarities in ownership ethos ran even deeper. Just as Epstein was forced to ‘feed the monster’ in Boston – to appease a swelling fanbase with blockbuster moves rather than build organically for sustainable success – he was asked to front muddled gentrification efforts on the North Side. The Ricketts family, owners of the Cubs since 2009, seemed to lose sight of their winning formula – intentionally or otherwise – and fans were left feeling short-changed when a promised dynasty did not materialise at Wrigley Field.

“The Rickettses are perfectly happy to indulge Chicago’s strong devotion to its civic religion until the point that it begins to interfere with profits,” wrote Ryan Smith of the Chicago Reader. “A little more than a week after the World Series victory, crews power-washed the chalk-drawn memorials off Wrigley’s walls in order to continue the 1060 Project, the five-year, $750 million plan to remake both the stadium and surrounding neighbourhood. Soon after the messages were scrubbed, chain-link fencing, concrete barriers, green tarps, and cranes appeared. Men in hard hats were hauling, drilling, hollowing out history. Another section on the Sheffield side had been levelled to allow construction vehicles inside. Through the gap, one could glimpse the sullied guts of the place. Where grass once lay, only concrete and rubble remained. A hulking bulldozer, a white ‘W’ flag attached to its cab, sat in shallow centre field next to a vacant area that was once bleacher seats. The lot where a McDonald’s once stood was a hole in the ground, the site of what will eventually be the Ricketts-owned Hotel Zachary. From the vantage point of the intersection of Clark and Addison, it was construction as far as the eye could see—a skeleton of a building here, a foundation for another there. It was a strange feeling: this baseball stadium turned shrine had become a dissected corpse.”

Early in 2017, this tone deaf lust for profit was laid bare when superfan Ronnie ‘Woo Woo’ Wickers was ejected from a home game because he could not produce a ticket when asked. Wickers had attended Cubs games since the 1940s, becoming a fixture around Wrigleyville, whooping and hollering in full replica uniform. Woo Woo was present through innumerable Cubs nadirs, rattling around the old ballpark on days when only a few thousand showed up. His sudden ejection, once the Cubs were world champions, smacked of misplaced arrogance. The machine was taking over, and tradition fell by the wayside.

“We tried to tell you, Chicago Cubs fans,” wrote Bob Collins of MPR News. “The minute you won a World Series, you ceased to matter. You're just another sports fan of a big money, winning team. You're no big deal if you don't suffer. The curse is gone and so is your identity. You're no longer losers. You're no longer lovable.”

To that end, the Cubs won another division title in 2017 and returned to the NLCS for a third straight year. The Dodgers beat Chicago in five games, however, ending any hopes of a successful world title defence. The Cubs subsequently lost the 2018 wildcard game before falling to a third-place finish in 2019. Manager Joe Maddon was forced out following that campaign, while Epstein resigned a year later following another wildcard exit. It was left to Jed Hoyer, Theo’s trusty lieutenant, to blow up the Cubs’ vaunted core, and he traded Rizzo, Bryant, Javy Baez and Craig Kimbrel at the 2021 trade deadline en route to a 91-loss season. The Cubs were back where they began. Some would say back where they belong.

Admittedly, there is something patently Cub-like about the way they completely capitulated within five years of attaining their holy grail. On top of the aforementioned exits, other prominent pieces of the Cubs’ renaissance disappeared into thin air. Player personnel guru Jason McLeod left, while key on-field contributors like Jon Lester, Jake Arrieta, Kyle Schwarber and Dexter Fowler were all dumped. Supposedly built for repeatable success, the Cubs’ foundation lay in tatters a few short seasons after its pomp. Sure, the Cubs eventually won it all, but in the 21st century, they have still missed the playoffs more often than they have made them. They have still found new, ever more creative ways to kick their fans in the gut, and that is strangely reassuring in some ways.

“At first, we thought we were about to be a dynasty,” says Cerami. “The heir to the Chicago Blackhawks of the 2010s and the Chicago Bulls of the 1990s. Coming to terms with how it wasn't working was tough. It was frustrating. Any by 2018, being a Cubs fan became almost laborious. The freedom of being an underdog is not something we felt again until, frankly, this season.”

Declining attendance and increasing scandal amid Cubs' demise

That laborious fandom was made tougher by frequent scandals that encouraged cognitive dissonance among some enclaves while requiring ethical gymnastics from others. The Cubs acquired infielder Daniel Murphy despite his track record of spouting homophobic rhetoric and continued to employ shortstop Addison Russell despite his 40-game suspension for violating MLB’s domestic violence policy. In 2016, the Cubs’ added Aroldis Chapman, another player suspended under the league’s domestic violence rules, and an apparent tolerance of controversial characters made the organisation look bereft of moral conscience. Cubs fans were asked to perform delicate highwire acts just to root for their team, and some refused to do so out of mere principle.

Growing ire was eventually directed toward ownership, where the Ricketts family reduced team payroll as franchise revenues grew. The Rickettses also became overtly political and alienated some Cubs fans by donating to Donald Trump’s presidential campaigns, needlessly entering the polarised culture wars. When horrid Islamophobic emails sent by Joe Ricketts, father of Cubs chairman Tom, were leaked in 2019, many Cubs fans stopped apologising for the team’s owners – World Series title be damned. Some things are beyond the pale, and certain swathes of Cubs Nation drew a line in the sand.

Many fans – mainly bandwagoners, but also some jaded diehards – voted with their feet, skipping games with increased regularity. During the magic carpet ride of 2016, for example, Wrigley achieved a 97% occupancy rate, according to ESPN, but that number shrank to 77% by 2022. Sure, an 88-loss season does not help, nor does a lack of serious investment in elite talent, but apathy has also spread through Wrigleyville, and that may be the Cubs’ biggest problem. Maybe people are just less interested in the Cubs these days, shorn of something historically significant to cheer for. Maybe fans are confused by all the sudden change. Maybe the ultimate story has been told.

“I do think we lost a big chunk of the flyby fans,” says Cerami. “In a pre-2016 world, any moderately impressive Cubs team started getting attention. But after winning the World Series, and going to three straight NLCSs, the edges of the fandom have definitely waned. But truly, the only thing we yearn for now is a fresh start. A good team detached from the history and baggage of the past. A team that makes us care again. That tries. That has their own quirks and narratives and inside jokes. And at this point, I think we're all seeking some semblance of sustainability.”

The pathway to intense baseball fandom is also far more obscured than it once was. Gone are the days of WGN hooking rapt viewers from across the country, Harry Caray converting lifelong fans on a daily basis. We live in a different age, and the Cubs must now compete with other forms of entertainment – TikTok and Netflix, Disney+ and the NBA – for eyeballs that were once singularly trained on their product. That product has also experienced a noticeable loss of intensity since the Cubs won it all, putting the team at a considerable disadvantage. Late-summer battles against St Louis will always generate buzz, but what about those cold and rainy games before the ivy blooms at Wrigley? It is increasingly difficult to sell those tickets beyond a devout core of maniacal fans. 

In one sense, the Cubs have not changed much since 2016. The ivy is still there. The hand-operated scoreboard is still majestic. The rooftop seats are still a draw. Ballhawks still jostle for balls on Sheffield and Waveland. Independent bars still exist, if you know where to find them. They are still the Cubs. However, to a more discerning eye, the ivy has cutouts for sponsored logos; the scoreboard is aped by a digital monstrosity above the bleachers; the rooftops are largely in team control and are rarely full; commercialisation has gripped Wrigleyville; and the ballhawks barely have any balls to field due to a heavily reconstructed stadium. Even the bullpens have been moved off the field, out of sight, to make room for more seats. More eyeballs. More dollars. At some point, you have to wonder whether the Cubs traded part of their soul for that feted title. And, if they did, was it really worth it?

Do Cubs fans miss losing?

Deep down, in the heart of some Cubs fans, is there a part of them that wishes their team never won the World Series? When truly probed, would some Cubs fans declare nostalgia for the good old days, back when their team sucked but at least they knew what to expect? “Yes, absolutely,” says Cerami. “This is the part a lot of fans refuse to admit. But there’s a reason Ross and Rachel don’t get together until the last episode of Friends. That unrelenting chase was everything. We are no longer the thing we were, to borrow a thought from my co-writer, Brett Taylor.”

On some karmic level, indeed, the Cubs were never meant to win, just as Ross was never meant to marry Rachel. Rather, the Cubs – and Ross – were supposed to stay in that suspended state of blind hope mixed with fatalistic realism derived from almost winning – or almost finding the love of your life. Winning the World Series brought a finality to Cubs fandom – of an era, but also possibly of an ethos, and the Cubs are currently searching for a new identity with little clue where to find it.

Some argue that, deep down, Cubs fans never wanted to win the World Series – that the constant fight for, rather than the attainment of, said championship gave structure and meaning to a life devoid of both. I never bought that flawed logic, and it did a huge disservice to so many devotees who strove for the elusive grail. Nobody could look at the unbridled joy of Cubs fans after the final out of the 2016 World Series and seriously suggest it was not the greatest sporting cataclysm of our age. Nobody could eye the forlorn blue caps placed on gravestones across the Midwest and accuse these fans of wanting to lose. However, deep uncertainty has filled the void once reserved for endless pining, and it is fair to question what it means to be a Cubs fan today, now the championship memorabilia is stuffed in a drawer.

“Unlike what many believed, Cubs fans never wanted to lose, nor were we all that lovable about it,” wrote Josh Timmers of Bleed Cubbie Blue in 2019. “Certainly, we loved the Cubs unconditionally, and we always found a place for them in our hearts, no matter how bad they were. But we never found happiness in losing. We found happiness despite losing.”

The future of Cubs fandom in a post-curse world 

Maybe this is the singular point of the entire debate. The ‘lovable losers’ tag was always a media construct despised by hardcore Cubs fans – not because they felt entitled to success, like the baseball folk of Los Angeles and New York, but because results (good or bad) were immaterial to the quintessence of Cubs fandom. These fans have always loved their team unconditionally, and they will continue to do so. Hyperbolic conjecture will be left to the commentariat.

“Some people have said the Cubs are famous for losing,” baseball historian Donald Honig once wrote, as quoted in Cubs Pride. “It is fairer to say the team has become famous because it is beloved, that the loyalty and enthusiasm of Cub fans have created a unique aura. Losing teams have been known to be abandoned by their followers. Cub fans have kept it all in perspective.”

Indeed, to Honig’s point, bad baseball teams are plentiful, but most of them play in sparsely populated mausoleums dripping with indifference. Just look at the Oakland A’s, currently drawing around 2,000 fans for some games as a move to Las Vegas beckons. The Cubs, by contrast, draw millions to Wrigley each season regardless of their results. Though perhaps diluted in a post-curse environment, that attraction will always be worth something. People enjoy the Cubs experience, and in a world of endless stress and recurring disappointment, that is good enough for me. Let people enjoy things for the sake of enjoying them.

Why, ultimately, do we root for sports teams? To see them win? No. Commissioner Rob Manfred was correct in some respects when he called the World Series trophy a ‘piece of metal.’ Sure, it is cool to hoist that trophy as the last team standing in October, but the memories created in the process are infinitely more valuable. Rather than wins and losses, trophies and championships, sports fandom is about kinship and solidarity, nostalgia and magic, family bonding and pure escapism. Sports fandom is about community and belonging and fun – all of which the Cubs still possess, making them intrinsically meaningful to those who believe. Even the aforementioned A’s have meaning in that context, and we should cherish the pleasant distractions all sports teams provide. These are the most important of the unimportant institutions in our lives.

We should also try not to generalise the contours of collective fandom. Cubs fans are not an amorphous group, and there is a whole spectrum of emotional investment in the team. When talking about Cubs fandom, it is easy to become esoteric and draw grand, meta conclusions. I mean, what other team inspires references to Aesop and Job, Sisyphus and Camus? What other team inspires such romantic projection? What other team, but the Cubs?

Perhaps it is all a lot simpler than we realise. Perhaps it is about the ballpark and beer, the ivy and seagulls, the scoreboard and marquee. Perhaps it is flying the ‘W’ flag after a pleasing, relatively nondescript April win. Perhaps it is singing Go Cubs Go with your brother or your buddy. Perhaps it is watching with a smile instead of a scowl. This is supposed to be fun, people. It is not supposed to be root canal for the mind.

As recently explained, I subscribe to the fluid fan concept, meaning that individuals should have the freedom to choose what role sports play in their lives. We often take sports far too seriously, to a point where the daily machinations of our chosen teams carry a life-or-death hue. That is not healthy, and it is also incompatible with the evolving entertainment landscape. Ultimately, sports are a form of entertainment, right there with podcasts, music and true crime documentaries. On the whole, we do not tolerate bad shows or awful songs, playing them on repeat, so why do we tolerate bad baseball? If team owners are intent on driving the sport towards homogenised commercialisation, let them. Beat them at their own game by becoming a more conscious – and less emotional – consumer. Enjoy the Cubs, but do not let them consume your life. Lord knows they have already done that for too long.

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1 comment

  • As a Cubs fan I always wanted them to win a WS it’s up there with my favourite sports moments , I didn’t think it was ever going to happen and I am so glad I got to see it . I would love to see them win another although it couldn’t top the last one , for now I just want them to be a competitive play off team . Great article though .

    Mike Head

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