Which teams may replace the Cubs and Red Sox in transcendent torture?

For multiple generations, two sports teams were synonymous with Sisyphean struggle: the Chicago Cubs and Boston Red Sox. Curse-riddled and fatally myopic, those flagship baseball franchises endured arduous championship droughts – over a century in the Windy City, and more than eight decades in New England.

With each near-miss, the desperate yearning and fatalistic paranoia of both fanbases transcended sports and captured the mainstream zeitgeist as cultural touchstones – learned, leviathan truisms of daily life.

When the Red Sox finally won the World Series in 2004, then, snapping an 86-year wait, and when the Cubs followed suit in 2016, ending a 108-year odyssey, a vacancy emerged for sports’ next great ‘lovable loser,’ tasked with satisfying the perverse ‘transcendent torture’ fetish of fans around the globe. 

Every great story seemed to have been written, every eternal thirst poetically quenched. No team immediately assumed the mantle of outsized ineptitude, mothballing one of sports’ greatest vectors of meaning: the venerated team that cannot get over the hump.

What made the Cubs and Red Sox so special? Defining ‘transcendent torture’

While both organisations chafed at the ‘lovable losers’ label foisted upon them, that characterisation contained a kernel of truth. However, their crossover appeal – i.e., their ‘transcendent torture’ – was underpinned by more than mere wins and losses. Namely:

1. The romance of baseball
The daily cadence of baseball, from February through October, is akin to a charming soap opera. Hometown ballplayers become extensions of family, while favourite announcers provide comforting ambient background noise to workaday banality. That creates tighter bonds between teams and fans, and more extreme emotions tethered to their travails. Yes, basketball provides huge emotional swings, especially late in games, but a lack of idiosyncrasy leaves it short of baseball’s spiritual hook. Meanwhile, the NFL is undoubtedly the most popular league, but its short season can feel transient. And the NHL struggles to gain and retain attention, toiling a distant fourth in the pecking order.

2. Major market exposure, resources and demands
While difficult for fans of small market teams to admit, franchises in major markets generate more interest – love, hate, support, disdain – than those in less celebrated locales. Bluntly, big market teams matter more, to a wider cross-section of people, than their comparatively provincial foes. Furthermore, with major markets come major resources, as larger fanbases contribute to greater revenues while demanding more frequent success. If a team expects to lose, then loses, there is no story. But if a team expects to win, then loses, intrigue accumulates. Big market expectations are thus intrinsic to the mass appeal of a lovable loser.

3. Intergenerational community reverence 
To leverage true crossover appeal, a team must also be deeply rooted in its community – ideally, for multiple generations. There is poetry in one generation of fans passing down star-crossed passion to another, akin to a bittersweet family heirloom. Shared trauma binds generations in cities where allegiance to a beloved team is pronounced. If a team has only recently moved to a conurbation, however, or recently been fashioned via contrived expansion, there is a challenge for it to gather a local foothold, let alone garner national and international affection.

4. National household recognition
To resonate with a mass audience, a team must first be known to said audience. This is the ‘household name’ litmus test, and it measures the extent to which a team would be identifiable to a casual sports layperson if dropped into inane kitchen table conversation. If someone says, ‘the Yankees,’ for example, 99.9% of Americans know that is a baseball team. The same applies to the Lakers, the Cowboys, the Globetrotters and the Celtics in their respective sports. Oh, and yes, the Cubs and the Red Sox, of course. The Flames, the Kraken, the Blues, the Sharks and the Blue Jackets? Not so much.

5. International interest
Transcendent torture also relies on international exposure, investment and participation. For the Cubs’ victory parade, 5 million people flocked to Chicago – the seventh-largest gathering of humanity, for any reason, in recorded history. (1) People flew in from around the globe because the story – the torturous, uphill trek – captured their interest. Piggybacking off the ‘household name’ litmus test, above, if few in America know who the Blue Jackets are, their exploits are unlikely to register globally.

6. Iconic aesthetics – brands, uniforms, ballparks
A formula to achieve the above – intergenerational relevance that emanates from a city to all corners of the world – is notoriously difficult to quantify. Conventionally, winning helps, as does procuring high-profile superstars. This, of course, is the Yankee doctrine, which has been replicated by other powerhouses, such as Ferrari, Real Madrid and the Lakers.

For our wonky purposes, however, an absence of winning is essential. Therefore, a heavy reliance on aesthetics – iconic brands, awesome stadiums, classy uniforms – is required to engender aspiration among fans. If you ripped the Cubs from Wrigley, or forced the Sox from Fenway, their penchant for failure would have been ordinary. By contrast, embracing their quaint confines made their torture transcendent. The lyrical backdrop turbocharged the Shakespearian tragedy.

7. Pop culture hyperbole
Speaking of Shakespeare, and furthering baseball’s inimitable romance, a fine literary tradition nurtured the baseball starvation of Boston and Chicago. “All literary men are Red Sox fans,” John Cheever once said. (2) And that maxim speaks to the hyperbolic meditation of many famous writers – Gammons and Shaughnessy, Montville and King – enthralled by irresistible case studies in sporting futility.

Such literary lionisation evolved into wider pop culture, with regular references in films, television shows, music and art. The Cubs’ drought was featured in Back to the Future II, while Ferris Bueller went to Wrigley on his feted day off. Red Sox movies peaked with Fever Pitch, while regular baseball motifs are embraced by Bostonian actors like Matt Damon, Ben Affleck and Mark Wahlberg.

Each melodramatic column and every aspirational scene burnished the legend of both teams, which fed itself in a self-fulfilling jamboree. Life imitated art, and art inspired life, producing a virtuous cycle of enlivening exaggeration.

8. Long championship droughts 
This almost goes without saying, as a prerequisite to our entire discussion. Chronic clumsiness defined the Cubs and Red Sox, who derived meaning and significance from their inability to win a championship across many decades. To me, such droughts become interesting when they span multiple generations – i.e., at least 35 years. Anything less than that can be dismissed as a blip or temporary fad, while a few decades more is required for a drought to become a thing.

9. Regular macabre heartbreak
Mere failure is not enough, though. In fact, recurring predictable defeat yields apathy, not acclaim. To become a lovable loser, a team must regularly come close to winning it all, only to capitulate in heartbreaking fashion. The varied nature of macabre heartache endured by the Cubs and Red Sox – Bartman, Buckner, Durham, Dent – stoked morbid curiosity in their frailty. Seemingly inevitable gut punches humanised those teams, whose propensity to clutch defeat from the jaws of victory generated underdog goodwill.

The net result was an epochal phenomenon – ancestral craving drizzled with ghoulish pain – that penetrated pop culture. And with those criteria as our guide, we can embark on a full-scale search for future lovable losers among the 124 teams in the big four leagues. Without further ado, then, let’s dig in.

Underwhelming candidates

Right now, across the big four leagues, the Arizona Cardinals have the longest championship drought, at 78 years. The Cleveland Guardians are next, at 77 years, followed by the Sacramento Kings, without a title in 74 seasons.

The Cardinals have only been in Arizona since 1988, however, the Kings in Sacramento since 1985. As such, they lack the kind of multi-generational trauma, rooted in one community, that underpins eventual transcendence. The psychological scarring is only now making its way from father to son, from mother to daughter, and that dilutes the overall potency of their narrative. 

Sure, it would be a cool yarn if any of these barren teams eventually win a championship. It would be an occasional, one-off, feel-good tale, though – a Cinderella run that resounds for a month or two – rather than a sustained, all-encompassing complex that colours every waking moment of a marquee organisation trying to decipher the code.

Cleveland Guardians

Admittedly, the Guardians have a more compelling case for common appeal. This, after all, is a franchise that has logged four fruitless pennants since last winning the World Series, in 1948. A franchise that seems plagued by bad juju and ingrained mediocrity. A franchise that even lost to the Cubs in that fateful 2016 Fall Classic. 

Some attribute Cleveland’s baseball incompetence to the Curse of Rocky Colavito – a supposed spell cast against the team when it traded the star outfielder to Detroit. Yet regardless of origin, to explore Tribe misery is to talk of Willie Mays and his trademark catch; Édgar Rentería and his World Series Game 7 walk-off; and an epic ALCS collapse against the Red Sox in 2007. Even Terry Francona, exorcist of Boston’s hex, could not salve Cleveland’s woes, which are generally self-inflicted and born of volitional inferiority.

Without a World Series title this year, Cleveland will tie the 1903-1980 Philadelphia Phillies for the fourth-longest championship drought in baseball history, but its toil lacks magnetism. There are few books and documentaries about it. There is no drought-focused romcom. Nobody is defacing local infrastructure begging for baseball salvation. Cleveland just plods along, coming up short year after year, to little hysterical eulogy. Ownership indifference begats austerity and failure in a predictable cycle of meh, and nothing stops the dreary status quo.

Besides, the whole name change and identity shift messed with the consistency of Cleveland’s baseball hunger. I do not have a strong view either way on the politics or morality of ditching the Indians moniker, but that 2021 rebrand created a line of demarcation that distances the Guardians from their heritage. The Indians failed to win a World Series between 1948 and 2021. The Guardians, by comparison, have only just commenced a similar journey.

Cleveland Browns

Across town, the Browns have long been characterised by bumbling incoherence and cartoonish disorder. One of just four NFL teams never to reach the Super Bowl, much less win it, the Browns have fashioned a distinctive identity as inept self-saboteurs.

Nevertheless, that through line – and any residual public sentiment – was upended when the Browns ‘suspended operations’ between 1996 and 1998 as controversial owner Art Modell sought to move his franchise to Baltimore. The NFL placed Browns intellectual property into trust; a compromise created the Baltimore Ravens, an expansion team owned by Modell; and a new franchise was conjured in Cleveland, gifted the Browns’ iconography.

As such, while not officially considered an expansion team, the regen Cleveland Browns lack seamless continuity with their long-suffering forebears. Many 1995 Browns became 1996 Ravens, while a new stadium, owner, and head coach affirmed the divergence. 

Yes, the current Browns have been just as hapless as their spiritual namesake, and that may develop into a more gripping parable with time. But right now, there’s a little something missing from the Browns’ ceaseless flailing. It just doesn’t quite reverberate.

Buffalo Bills

The Buffalo Bills can make a good claim to trendy torture, with 60 desolate years punctuated by four consecutive Super Bowl losses between 1991 and 1994. Scott Norwood’s ‘wide right’ missed field goal to potentially win Super Bowl XXV is particularly haunting, and the recent uptick catalysed by quarterback Josh Allen has authored fresh agony – six straight playoff eliminations, including two conference championship game defeats. But with the exception of deep-fried chicken wings and the cardiac pacemaker, has anything of universal allure ever come out of Buffalo, New York? Not really. And portraying the hometown football team as a magnet of enchantment is a hard sell.

Minnesota Vikings

The same applies to the Minnesota Vikings, 56 years dry and also possessing four Super Bowl losses without a redeeming win. Alas, and though nobody in the Twin Cities wants to hear it, the Vikings are not a pre-eminent NFL brand. In fact, you would have to wade through at least a half-dozen teams of wider appeal before arriving at the Vikes. I have nothing against Minnesota, which undoubtedly has a loyal and passionate fanbase. I’m just stating the obvious: that the Vikings’ travails are of little concern to a global audience at scale. And that stunts their claim to wider significance.

Philadelphia Flyers

A similar problem afflicts the Philadelphia Flyers, who have lost their last six trips to the Stanley Cup Finals. In fairness, such a harrowing record of profligacy is pretty special – at least in our masochistic mission – but the Flyers are probably the fourth most popular team in their own city, so any delusions of grandeur are exactly that. Delusions.

Brooklyn Nets

Though difficult for contemporary readers to fathom, Brooklyn harboured the original lovable losers: the hard-luck Dodgers, who infamously lost seven World Series – including five to the crosstown Yankees – before finally winning it all in 1955. In fact, the phrase ‘Wait ‘til next year’ was coined in reference to the Lords of Flatbush, who preceded the Cubs and Red Sox in glorious inadequacy. (3)

Such a wry inferiority complex served as a neat microcosm of Brooklyn, an autonomous city before annexation by New York in 1898. A sardonic streak of rebellion inflected the Brooklyn psyche, and a sense of repressed independence characterised the borough, often ridiculed as a glorified suburb.

Of course, in 1958, the Dodgers moved to Los Angeles, leaving Brooklyn without a professional sports team and accentuating the patina of a downtrodden underdog. It was not until 2012 that big time sports returned to Brooklyn, when the NBA Nets were lured to a sparkling new arena.

Fittingly, the Nets have endured a nomadic existence that speaks to their status as a civic afterthought. Since forming in 1967, the Nets have played in eight different home arenas – settling in Brooklyn via Teaneck, Commack, West Hempstead, Uniondale, Piscataway, East Rutherford and Newark.

As such, despite a 49-year NBA title drought, and the natural out-of-town predisposition, the Nets lack deep emotional ties to a steady community. Sure, they have loyal fans, including many who have followed them on a dizzying trek around the wider metropolitan area, but vagabonds are rarely adored by the general public. And besides, New York has another fatally flawed basketball team that commands more attention, as we will soon discover.

If a tree falls in a forest…

There are other teams with long losing histories that do not really move the cultural needle, either. In Atlanta, for example, the Hawks last won an NBA title in 1958, and have come up short in their last 45 playoff visit, while the championship-less Falcons have lost two Super Bowls, including that infamous 25-point collapse to New England, the largest in Big Game history. Again, though, there is very little glamour attached to those predicaments. Outside Georgia, few seem to care.

Similarly, the Chargers cradle a 62-year title drought, but they have hopscotched back and forth between Los Angeles and San Diego repeatedly, and the denizens of neither city seem especially bothered. 

Likewise, the Tennessee Titans are perennially turgid, and Kevin Dyson coming one yard short of tying Super Bowl XXXIV for them is arguably the most devastating singular moment in football history, but there is a reason the Titans have zero nationally televised primetime games in 2025. There is no romance there. Just monotonous suckitude. (4)

The Phoenix Suns and their 57-year drought – including three NBA Finals losses – warrant mention, though idyllic sporting odes rarely grow in the desert. 

Then, we come to a phalanx of teams – Brewers, Sabres, Canucks, Clippers, Jazz – defined more by apathetic inadequacy than poignant mutilation. The less said about them, the better.

‘Droughty’ teams that may one day strike a chord

There are several teams that may, further down the line, strike a chord with curse connoisseurs. Generally, these are ‘droughty’ teams with intriguing brands and loyal fanbases that have not won a title in a couple decades. With a little more seasoning, a little more exposure, and – yes – a little more heartbreak, these teams may well carve a more pronounced place in our collective subconscious.

Detroit Lions

Anchored in the blue-collar fulcrum of Detroit since 1934, and without a championship since 1957, the Lions have developed a rabid fanbase of dedicated diehards who pack an atmospheric stadium in hope of glory. Intense coach Dan Campbell has led a recent revival, restoring Detroit to relevance, but there is just something – a certain ineffable magic – missing from their fire. Maybe that will come with increased hyperbolic narration, but I just do not feel it yet. There’s a lack of aura that weakens their case.

Detroit Tigers

The Detroit Tigers may have a greater chance of one day gaining traction as a lovable loser. They have the Old English D mythologised by Ty Cobb. They have a long and heartrending history, stretching back to 1894 and featuring seven World Series defeats. They have won the Fall Classic four times, but not since 1984. And they lost their last two trips to the big dance, despite formidable teams led by Justin Verlander, Miguel Cabrera and Max Scherzer. Comerica Park could be a little quainter, and years of underinvestment have blunted expectations, but a Tigers renaissance is afoot in the Motor City, and it bears all the hallmarks of a public interest tale. Give it another decade or two, and the Tigers’ craving could prevail.

Chicago Bears

A large swathe of Cubs fans also root for the Bears, lending a touch of fatalistic paranoia to the psyche of a fanbase that has not witnessed a Super Bowl success in 40 years. Cubs grow into Bears, of course, while the teams have similarly recognisable brands and historic home fields – albeit, with a new NFL stadium planned for the near future. The Bears last made the playoffs in 2020, and have not won a postseason game in 14 years, so their mystique would benefit from a little more relevance, but they are definitely one to watch. They share some of the Cubs’ DNA, after all. Perhaps doom and gloom is hereditary.

Seattle Mariners

The only active MLB team to never reach the World Series, the Seattle Mariners captivate me. The whole coffee-and-rain milieu is ripe for moody meditation on human futility, while a reasonable argument can be made that no sports team has ever had more Hall of Fame-type players without winning a single championship. Ken Griffey Jr., Álex Rodríguez, David Ortiz, Edgar Martínez and Tino Martinez were all Mariners. So, too, were Randy Johnson, Ichiro Suzuki, Félix Hernández, Robinson Canó and Adrián Beltré. And yet, Seattle has logged just five postseason berths in its 49-year history, with just one of those coming since 2001. In 2001, the Mariners won 116 games, setting the all-time record, only to be blown away by the Yankees in October. 

“No team in baseball history has received more 9+ WAR seasons from individual players than Seattle without winning the World Series,” I wrote in 2023. “The same is true of 8+ WAR seasons and 7+ WAR seasons. Quite frankly, there is no match in the baseball annals for the Mariners’ mix of elite talent and chronic futility. The Mariners are the Achilles of professional sports – immensely talented, yet fatally flawed – and that makes them appealing to me. That makes them charming.”

Give the Mariners a little more time, and a little more attention, and that charm could echo beyond the Pacific Northwest. After all, according to Greek mythology, an upside-down trident is symbolic of bad luck, and the Mariners had that as their logo for decades. So yeah, the potential for a curse is there. I’m watching with bated breath. (5)

Pittsburgh Pirates

The Pirates have a classic brand, hewn by Honus Wagner, Roberto Clemente and Barry Bonds. They have a beautiful ballpark, with arguably the most picturesque city skyline backdrop in sports. They have enough winning (five World Series titles) in their 134-year history to author baseline expectations. They have the blue collar fanbase and a 46-year championship drought in need of breaking. They even have the best pitcher in the world, Paul Skenes, who resembles a young Roger Clemens. But, alas, they also have a parsimonious owner, Bob Nutting, who has very little interest in fielding a winning team, and whose brazen malpractice has wounded a generation.

Remarkably, the Pirates last won a postseason series – not counting the one-game wildcard era – in 1979. They last won their division in 1992, and have failed to finish above fourth in 79% of the seasons under Nutting’s ownership, dating to 2007. Those are prime credentials for a lovable loser – except, well, the complete insouciance of management towards even trying to look competitive drains any joy from a sorry situation.

With new ownership, and a refreshed commitment to winning, the Pirates could be an incredibly fun and infectious team to admire. Instead, they meander along, wasting the prime of a generational phenom while adding zeroes to the bottom line. Nutting should be ashamed of his negligence.

San Diego Padres

Without a world championship in their 56-year existence, and bearing two failed pennants, the Padres have under-the-radar potential to become lovable losers. An energised fanbase has flocked to Petco Park in recent seasons, inspired by a fresh sense of urgency from ownership, and a slew of superstars now call San Diego home. A brewing rivalry with the big, bad Dodgers is redolent of the Yankees-Red Sox feud around the new millennium, but it may take a few more October showcases to introduce the Padres to more casual viewers. One to keep an eye on.

Cincinnati Bengals

Joe Burrow may be the coolest sportsman on earth right now, and his quest to win a Super Bowl ring will become a central NFL storyline in the decade ahead. However, whether Burrow can elevate the Bengals – a moribund franchise with an all-time 0-3 Super Bowl record – to trendy appeal remains to be seen. Despite a 58-year championship drought, the odds seem stacked against him. There is just a lack of pizzazz there, and even Burrow may be unable to change that.

Noteworthy anomalies

Before moving on, I want to mention two teams that do not qualify for lovable loser consideration yet – by virtue of comparatively short title droughts – but who have potential further down the line: the Colorado Rockies, a case study in disaster, and the New York Rangers, who never seem to get things right.

The Rockies have never won their own division, let alone the World Series. Colorado has finished below .500 for seven straight years and is on track to lose more than 100 games for a third consecutive season. The reasons for such recurring disappointment are myriad. Altitude. Humidity. Perennially atrocious pitching. Indifferent ownership. Dated philosophies. Anachronistic processes. Woeful drafting and development. Cronyism. Myopia. Aversion to analytics. And yet, the Rockies continue to draw fans to Coors Field, Denver’s largest outdoor bar, in a bittersweet tale of self-sabotaging loyalty. That is noteworthy to me. It hints at a lovable loser, and that may be the case one day – if new management can first restore dignity.

As for the Rangers? Well, they are an Original Six team with baroque iconography, engaged fans and a storied arena. They last won the Stanley Cup in 1994 and have gone deep in the playoffs enough since to regularly break fans’ hearts. In Henrik Lundqvist, they had one of the greatest goaltenders of all-time for 15 years and still failed to win a championship. So look out for them moving forward. Their inability to seal the deal may eventually resonate.

Prime contenders for transcendent torture

Finally, we arrive at my prime contenders for transcendent torture – teams of genuine consequence with a proclivity for gruesome catastrophe, whose vexed efforts to win it all have the best chance of animating the ordinary.

New York Jets

Without a Super Bowl triumph in 57 years, and having last reached the playoffs in 2010, the Jets have become a byword for comical calamity. Under the outmoded aegis of owner Woody Johnson, this franchise has developed a reliable tendency to shoot itself in the foot – cycles of hope, attached to a slew of saviours, ending in predictable disappointment.

Take, for instance, the rise and fall of Aaron Rodgers, who ruptured his Achilles four plays into a much-hyped Jets debut then never rekindling his Hall of Fame production. There may be no finer example of the Jets’ patented blend of high hopes and crushing disappointment – just the kind of alchemy that enthrals sadistic onlookers.

Lurking in East Rutherford, New Jersey, adrift of true New York, diminishes the Jets’ appeal somewhat. And ownership’s oxymoronic hybrid of aloof micromanagement can feel repellent. But one day, calcified with a few more false dawns, the Jets’ saga may cross the Rubicon. Their drought is certainly one to follow.

Miami Dolphins

While Miami is often lampooned as a small market, thanks primarily to the Marlins’ elective impotence, I’m always bullish on the city’s sporting potential. It is a diverse, vibrant, happening metropolis that is often misunderstood. It is all too easy to write off Vice City teams as soft, laconic, nonchalant and fair weather. But the potential is enormous – especially with the befuddling football team.

For a significant stretch, indeed, the Dolphins were a legitimate powerhouse. Between 1972 and 1973, under legendary coach Don Shula, Miami went 32-2, including playoff games, en route to consecutive Super Bowl wins. Famously, the ‘72 team went undefeated – the only time that has ever happened in NFL history. Then, in the 1980s, the world fell in love with Dan Marino, the Dolphins’ matinee idol quarterback who embodied football’s quantum leap into technicolour modernity.

However, despite carving a place on the Mount Rushmore of all-time quarterbacks with many records and the eternal goodwill of besotted fans, Marino never won The Big Game. Through 17 seasons, he played in one Super Bowl and lost – heavily. And in that regard, he is the fitting face of a franchise that never fulfils its glittering potential.

Marino is remembered as the greatest player without a ring, while the Dolphins are the sleeping giant nobody can seem to wake. In fact, 52 years have now passed since the last Dolphins title, and annual inquests typically fail to articulate why. Some blame culture. Others decry softness. Many even point to a curse, with the Dolphins’ stadium sitting on the site of an ancient Tequesta burial ground. (6) Whatever the cause, Miami has not won a playoff game since 2000, and its last two trips to the Super Bowl ended in dejection.

Here in Britain, the Dolphins are held in near-mystical esteem due to their apotheosis coinciding with the advent of NFL on terrestrial television. It is impossible to tell the story of Britain’s love affair with American sports without deferring to Marino, who inspired a generation while blessing as sacred the cool aqua and orange. And it is that potential – that image, mystique and power – which keeps people hooked on the Dolphins, even as reality upends the illusion. It is difficult to resist the fantasy.

New York Mets

Mets fandom is a peculiar form of torture. Formed in 1962 from the orange and blue ashes of the departed Dodgers and Giants, New York’s National League team became known as – yes, you guessed it – the ‘lovable losers’ in its infancy. (7) The first Mets iteration lost 120 games, while a .348 winning percentage carried through their first seven seasons. Then, inexplicably, they won 100 games, and the World Series, in 1969, before settling into underwhelming normality.

A further world championship came in 1986, but they have been paying a karmic price ever since. Those ‘86 Mets, after all, benefited from the Red Sox’ epochal implosion – Bill Buckner’s eternal gaffe leading New York to a World Series title, but transplanting a smidge of Boston’s cursed kismet in the process. The Mets have never won another championship, and their last two trips to the Fall Classic ended in defeat. Misfortune seems to regularly befall the Mets, who have a habit of riding the magic carpet into an oncoming 7-train.

Just last year, for instance, the Mets parlayed a wildcard berth into a thrilling playoff run, knocking off Milwaukee and Philadelphia before succumbing to the Dodgers. Similar feel-good vibes characterised 2015, when a young team upset the odds to win the National League pennant, then lost to the Royals. And going even further back, a 97-win team lost the 2006 NLCS, while the crosstown Yankees ended the 2000 mirage in an anticlimactic Subway Series.

All told, the Mets specialise in building likeable teams that embark on giddy, often unexpected runs to the cusp of ultimate victory, only to crash and burn at the optimal moment. And that is the exact blend of personable exhilaration and abrupt agony we are trying to find.

When Steve Cohen spent a little of his $21.3 billion to buy the Mets, his favourite team, in 2020, the stakes increased dramatically. And when Cohen dropped another $765 million, potentially rising to $805 million, to lure Juan Soto away from the Yankees, those stakes were pushed into the middle of the table. The Mets went all-in, sparing no expense in pursuit of elusive glory, while piercing a new stratosphere of pertinence.

Some find it hard to root for such an exorbitant spender, but with a hip brand, clean uniforms, and a shadow of countercultural insurgence, the Mets have all the resources to go global. Indeed, their current kinetic energy is reminiscent of the late-1990s Red Sox, who built a critical mass of talent amid a furnace of mounting enthusiasm.

These Mets are the first in team history for whom winning is a demand rather than a dream. A $325 million payroll assures that, as do average crowds of 38,000 filling Citi Field. Expectations have never been higher in Queens, and if the Mets fail to win during Soto’s 15-year contract, pushing their title drought beyond the half-century mark, theirs could really be the torture that transcends. The pressure is on, then. As is the scrutiny.

Toronto Maple Leafs

At the outset of this study, the Toronto Maple Leafs were the first team that popped into my mind. For nine straight seasons, you see, a fancied Maple Leafs team has been eliminated from the playoffs prematurely, running Toronto’s Stanley Cup drought to 58 years.

The apoplectic meltdown of a maniacally invested fanbase following another meek playoff exit has become annual tradition. At this very moment, indeed, Maple Leafs fans are mourning a second-round loss to the Florida Panthers – another exasperating letdown that ended the complicated tenure of esteemed president Brendan Shanahan. 

An elite exec with a big reputation and a bold vision, Shanahan seized control in April 2014 and devised a comprehensive plan – the Shanaplan, indeed – that, in theory, would all but guarantee a Cup. A long-term, ‘scorched earth,’ root and branch rebuild produced great excitement and a tantalising core, headlined by Auston Matthews, Mitch Marner, William Nylander and John Tavares. Alas, that much ballyhooed core delivered just two playoff series victories, including the Leafs’ first since 2004, offset by six Game 7 losses, becoming just another sad, cautionary tale in a demoralising paean.

Once upon a time, the Maple Leafs commanded a dynastic empire – much like the Cubs and Red Sox before their respective downturns. An Original Six bulwark, the Maple Leafs have won 13 Stanley Cups in their rich history, but the last came in 1967 – an eternity for a city almost singularly devoted to its cherished team.

There are myriad theories pertaining to Toronto’s playoff voodoo. Many trace the demise to the scandalous ownership of Harold Ballard, a divisive enigma who was sentenced to nine years in prison for fraud. Others refer to various curses, while pragmatists point to NHL expansion, the fluctuating Canadian dollar, sheer misfortune, and an engrained habit of freezing in the limelight.

Whatever the rationale, the Maple Leafs’ Cup drought has developed a life of its own. And while the passion of dedicated fans can often veer to extremes, resulting in vitriol that outsiders find off-putting, there is something deeply evocative about the Maple Leafs. Critics luxuriate in the Leafs’ demise, but their brand is crisp, their lore considerable. Despite a steady dose of external ridicule, the Leafs’ exploits preoccupy a city year-round, and that gusto outweighs common hatred.

Indeed, if any story has the power to catapult ice hockey back into mainstream pop culture, away from the doldrums of sporting neglect, it is the Toronto Maple Leafs winning the Stanley Cup. Such a story would pique dramatic interest – certainly in Canada, and likely around the world. I would love to see it happen, though a few more decades of suspense would ripen the joyous fruit.

New York Knicks

It is tricky to envisage a Manhattan powerhouse ever becoming a lovable loser. To the wider populace, there are just too many snarky, elitist connotations there to cast a Big Apple team as some kind of plucky underdog. However, there is more to the Knicks’ constitution than immediately meets the eye, and a peek under the hood reveals a nuanced, riveting culture surrounding a latent juggernaut.

The Yankees’ consistent success – and, some would say, their trademark arrogance – clouds outward perceptions of New York sports. Gotham has celebrated 18 world championships since 1973. None, though, have been won by the Knicks, whose title drought stands at 52 years. And far from lazy stereotypes of easy opulence, the gritty New York sports fan knows immense frustration, personified by the city’s worshipped basketball team.

The Knicks unite New York like no other team. While baseball, football and ice hockey provide representative splits in terms of fan interest, even conservative estimates suggest 75% of New York basketball fans root for the vaunted Knickerbockers. (8) The concrete jungle is a fertile breeding ground for basketball talent and fervour, and since 1946, the Knicks have served as a centralising vector of that passion. Seeing them finally win it all is a dream shared by generations.

The Knicks’ brand is universal, driving a franchise value of $7.5 billion. (9) Their home, Madison Square Garden, is The Most Famous Arena in the World. ™ And their staunch fanbase is sprinkled with stardust, from Spike Lee and Jerry Seinfeld to Ben Stiller and Timothée Chalamet. Knicks games are an event, and though it has often been decried as a distracting sideshow, such glitterati attention sustains the team’s relevance.

Knicks fans demand success, and despite a poor track record of scandal and interference, owner James Dolan consistently spends towards that goal, stoking recurring hope. That pining often meets an agonising fate, leaving a tapestry of heartbreaking vignettes.

For the Red Sox, it was Pesky holding the ball; Dent skying the pop fly homer; Buckner botching the routine grounder; Boone winning the pennant.

For the Cubs, it was Santo and the black cat; Durham and the slow roller; Bartman and the foul ball.

For the Knicks, it is Larry Bird saving the Celtics. It is Michael Jordan thwarting Patrick Ewing. It is Hakeem Olajuwon blocking John Starks’ last-second three-point attempt, which would have clinched a 1994 title that ultimately slipped away. 

It is Reggie Miller’s eight points in nine seconds. It is Ewing’s last-second layup miss. It is Pat Riley returning with the Heat to win an explosive semifinal.

It is Reggie Miller (again) with the three-point dagger in ‘98. It is becoming the first eighth seed to ever reach the NBA Finals, then losing to Tim Duncan and the Spurs. It is being swept in the playoffs by the Nets.

It is LeBron choosing Miami over New York. It is Kyrie Irving and Kevin Durant choosing Brooklyn over Manhattan. It is Riley, Phil Jackson and Steve Kerr combining to win 20 titles as NBA coaches yet none of them coming in blue and orange.

At times, the Knicks have veered from sheer incompetence to egregious mismanagement. Between 2013 and 2020, they failed to make the postseason, with the latest reshuffle landing Leon Rose as president and Tom Thibodeau as head coach.

Spearheaded by Rose, and orchestrated by Thibodeau, the Knicks commenced on a gradual build to contention, logging 47- and 50-win seasons that both ended in conference semifinals heartache. This year, they improved to 51 wins and went one better in the playoffs, beating the Celtics in thrilling fashion to reach their first conference finals since 2000.

Amid a cadre of cardiac comebacks, the Knicks of Jalen Brunson and Karl-Anthony Towns rekindled New York’s zest for basketball. Fans flooded the streets in celebration when the Knicks downed Boston, and the team’s never-say-die attitude created enthusiastic momentum redolent of Ewing’s peak.

Indeed, there’s a wistful nostalgia to the Knicks and their renaissance. The ‘90s Knicks struck a chord with millions and were lionised in pop culture – from Steve Brady, the quintessential Knicks fan, in Sex and the City, to Joey Tribbiani wearing Knicks garb in Friends. Right now, as we hurtle through a rich vein of ‘90s reboots, hankering for innocent distraction, rooting for the Knicks is a way to honour our fond curiosity for that time and place. It is akin to drinking from a Central Perk mug or grabbing a cinnamon swirl from Magnolia Bakery. All that is old becomes new again, and the Knicks ride that sentimental wave.

Alas, just when the 2025 fairytale began to seem real, the Knicks fell apart – in unprecedented fashion. In Game 1 of the conference finals to Indiana, the Knicks led by 14 points with 2:50 to play. In the previous 28 years of NBA basketball, teams leading by that margin, with that amount of time left, were 977-0. Yet somehow, the Knicks lost – their stunning fall immortalised by the Pacers’ Tyrese Haliburton parodying Miller with an emphatic ‘choke’ gesture to the crowd. (10)

Prone to emotional overcorrections devoid of logical long-term consistency, the Knicks promptly fired Thibodeau after losing in six games to Indiana. With no obvious succession plan in place, the team is currently flailing around, attempting to find a replacement, after ousting the guy who delivered its greatest success in a quarter-century. The debacle is so eminently Knick-like as to inspire this entire article. There can be few more storied franchises with a greater flair for self-sabotage. Few more powerful teams whose torture transcends.

Final thoughts

Ultimately, no team wants to be known as a lovable loser, nor does it want to be associated with frequent failure. It just sort of happens over time, congeals into the ethos, the miasma, the identity, the lore.  

A lot of Cubs fans hated the patronising moniker, just as many Red Sox rooters loathed prerequisite references to the trade of Babe Ruth. Nevertheless, those strands were woven into sports’ wider tapestry, and they became centres of abundant intrigue. 

None of the teams analysed in this piece want to assume that mantle, and most probably will not. But all it takes is one or two, whose hunt goes viral, and a whole new chapter unfurls before us. 

I, for one, cannot wait to see what becomes of these damsels in distress. Because their thirst is our fascination, and that will always be true.