Just⁢ hours prior to the Chicago Cubs‘ inaugural World Series game in over seventy years, I found myself in a dimly​ lit bar⁣ a few blocks south of Wrigley Field, seated next to a man who had been drinking there for twenty-five years and whose heart had been repeatedly crushed by the team ⁤he cherished for even longer.

He reminisced about attending ‌day games at Wrigley with ‍his father. ‍His childhood was filled with tales of pennants won and World Series lost. His dad had been present ‍when the Cubs fell to the Detroit Tigers in 1945, the last time the “lovable losers” made it to⁤ the Fall Classic⁢ until that fateful ⁣day in October 2016.

Throughout more than a century without a‌ World Series title, the Chicago Cubs became symbols of defeat. In his⁢ nearly sixty years of life, he had experienced enough⁢ hope to understand its fragility — the collapse in ‘69, the⁢ downfall in ⁤‘84, ⁣and Bartman’s moment ‍in ‘03.

“Talk about the sins of the father coming back to haunt the son,” he remarked⁤ with a‍ sigh.

He resolved not to revisit ‍those ​feelings. So, as Cubs fans around him buzzed with new hope before the⁢ first pitch, the man perched at the bar remained untouched by the excitement enveloping the north side. He gently sipped​ his beer while watching a rerun of Jeopardy on a dusty television ⁢in the corner.

What is ‍the limit of a fan’s loyalty?

This scene resurfaced in my mind recently while contemplating⁢ the sentiments surrounding another legendary franchise notorious for ⁤its championship drought.

Long ago, the Stanley Cup was paraded down Bay Street in‍ downtown Toronto with such regularity that it instilled a pride that has somehow managed to endure through fifty ‌years of mediocrity.

The Toronto Maple Leafs‍ captured five championships in the 1940s and claimed another in 1951, just before a floatplane carrying Bill Barilko met a tragic fate in a northern Ontario forest.⁢ A decade would pass before Barilko’s remains were discovered, and the Leafs won another Cup in 1962, marking the ⁤beginning of a four-Cup run that decade — the last great era for the ​NHL’s wealthiest ​and most supported team.

This is part of the⁢ narrative. Once an immensely dominant franchise, the ‍Maple Leafs have become the⁤ hockey equivalent of the Cubs. An astonishing six decades have passed since they last hoisted the Stanley Cup.

Toronto’s current roster ‍is an offensive juggernaut, spearheaded by Auston Matthews ⁢— ⁢arguably the best goal scorer to have ever donned a Leafs jersey. The team also features exceptionally ⁤skilled playmakers like Mitch Marner and William Nylander. Although veteran John​ Tavares is past his peak, he has been one of the most impactful players ⁤throughout his career. The comment section below will certainly provide varied opinions regarding the​ worth of ​the Core Four, as well as issues ⁤of ⁤defense, goaltending, ​“grit,” coaching, and management, spanning both past and present, young and old.

The reality remains that even with regular-season achievements, the team has succeeded in winning merely one‌ playoff round since 2004.

Following a harsh decade where the team made the playoffs only once between 2005 and 2015, the current generation rejuvenated the hope among fans.‌ However, that hope has been shattered⁤ time ‌and again, ‍often‍ in dramatic fashion. Since Matthews joined the team in ​2016, Toronto has endured five first-round Game 7 defeats, including last spring against the Bruins.

Most of ‌the⁤ team’s supporters have never‌ witnessed the Leafs reach a Stanley Cup Final, let alone claim victory. This perennial disappointment has become a‍ hallmark of the experience. The annual springtime fall of ‌the ⁢Leafs has become part ​of the lore. Yet, each autumn, the fans return with renewed ⁤optimism.

Anthony Bellissimo, who was just 7 years old when‌ the Leafs last secured the Stanley Cup, has spent his life yearning to experience the glory that lingers in a distant corner of his boyhood memories.

“We’re like Charlie ⁤Brown,” Anthony expressed. “We think this year will ​be the year‍ we kick‍ that football, and every time ​it gets yanked away from us.”

Mario Bellissimo, who was born⁢ a decade after his elder brother Anthony, experienced the Harold Ballard era of the Leafs during the 1970s and ‘80s. This ‍period was characterized by the notorious cheapness​ and contentious nature of the owner, who dismantled the beloved franchise‍ and squandered ​the talents of iconic players like Darryl Sittler,⁣ Lanny McDonald, and Börje Salming. Although there were moments of excitement—such as defeating the Islanders in ⁣’78 and Rick Vaive’s 50-goal seasons—the era was overshadowed by Ballard’s relentless ownership and disheartening outcomes.

“It feels like you’re caught in a relationship with⁢ so much potential, yet ​it’s unfulfilled,” Mario remarked. “And you become a ⁣laughing stock.”

Still, the brothers concur⁣ that their investment in the team’s future is too significant to ​abandon. While the emotional weight is substantial,⁢ it’s something ⁤they must shoulder together. There’s ⁢no option to cast it aside and walk away.

The perpetual intrigue among Leafs supporters ‌persists: “What if they finally break through? What if they actually emerge victorious?”

Christine Dimoff found herself sitting alone in her backyard on a warm, sunny day, shedding tears after the Leafs lost Game 7 of the​ Conference​ Final to the Los⁤ Angeles Kings⁣ in 1993. She reminisced about skipping classes to watch practices at Maple Leaf Gardens​ with ‌her friends. When Vaive scored his 50th ⁤goal, she leapt in delight, throwing orange slices around ⁤her basement. But after this defeat, it was ​the first time she felt genuine hope for the team she ‌cherished, only for that⁣ hope to be‍ violently dashed.

“I​ completely broke down,” Dimoff ‌shared. ‍“I just couldn’t hold it back.”

The early 1990s, marked by beloved players such as Doug Gilmour and Wendel Clark, remains one‍ of the brightest memories for many Leafs fans today. The late 1990s ⁢and early 2000s also sparked optimism ​with ⁢Mats Sundin and a roster ‌filled with all-stars.‌ However, the Leafs met elimination‌ twice in the Conference Finals, in ‘99 and⁣ ‘02. For devoted fans, those near-miss seasons are regarded as the golden days ⁣against which the current team’s talent is continuously measured.

These days, following Toronto’s customary springtime elimination, Dimoff‌ retreats to her cottage, inhaling deeply ⁢by the lakeside to escape the disappointment.

“I suppose⁢ it’s all part of being a fan,” Dimoff reflects. “It encompasses the highs and ‍lows—and it’s nice to experience ⁢a wide range of emotions.”

Leaf fans basically doing that with you.”

Several years ago, Dimoff and her friend ⁣Sylvia Hargittay — who she’s held season tickets with for nearly three decades — started a podcast called Ladies Talkin’ Leafs, as a cathartic outlet for their passion. Through the podcast, they connected with other ⁤fans across Canada and ⁣around‍ the world. They‌ met a woman in Winnipeg who runs a​ Facebook group dedicated to female fans of the Maple Leafs. They have regular listeners ​in places like France and Japan.

“They’re everywhere,” Hargittay said. “In any small ⁢town there ⁢is going to‍ be somebody who is a Leafs fan — and that’s not just here, that’s around the world.”

That’s a big ⁣part of the reason the misery of‌ Leafs fans is so ‌widely ⁣celebrated by fans of opposing teams.

“That’s part of what pulls us together,” Hargittay said. “Everybody wants to⁤ pull us down, but they’ll never break us.”

But what is it that draws these fans out ‌year after ‍year, to face such disappointment and mockery? How does a team that hasn’t won a⁣ championship​ since 1967 still ‍have fans fill the seats in opponents’ rinks?

Like fans of the Cubs and the Boston Red Sox — 86 years — before them, lovers of hockey’s most famous losers teeter on nostalgic fatalism.

For some older‌ fans, the last Stanley Cup parade is a distant ‌memory. But for most, it’s a story passed​ on through the generations, accompanied by grainy footage of George Armstrong riding ‌in a convertible next the Cup down Bay Street. There is a sentimental longing — an echoing joy‍ that fades the further a ‌victorious era recedes with the past. And as the decades ​go, unfulfilled expectation becomes as central‌ to a team’s identity as all the winning ever had been. The shared disappointment ⁣becomes an inexplicable​ part of the passion.

The Gilmour era, the Sundin era — each brings bittersweet​ memories of what ‍almost was. The pain of those ⁣losses is still⁣ palpable for fans like Dimoff and Hargittay, but accepted like an old regret — a broken-heart that, eventually, you’re⁤ all the better for.

But the past decade has ‌been particularly⁤ painful. The romance turned toxic for fans like Mario Bellissimo, ⁣who has seen what ‍appeared to be the ⁤team’s ⁣most ⁢promising⁤ years squandered, while the next generation of ⁣fans⁢ are set aside by ‍exorbitant ticket prices and lack of personal connection to the team.

“There’s no curse,” he said.⁣ “There’s just ⁣been poor management, ‌poor leadership.”

His biggest⁢ fear⁢ is what it will mean for future generations. For years, the Bellisimo family has ⁤sponsored a ‌bursary for students at the middle school‌ he and his brothers attended. They always give a night at a Leafs game away as‍ part of the presentation. But in the last few years, none of the students have raised their hands when asked if they wanted the tickets. ​Teachers have suggested that ⁤he bring tickets to a Raptors or TFC game instead.

“I⁣ think we’re starting to age out,”‍ Mario said. “To ​see ⁤that there’s not⁤ enough of the next ⁢generation that ‌want to step in anymore, that’s really sad for me.”

Even the devoted have ‌dabbled in apostasy. Anthony Bellissimo is ​only in his mid-60s, but ‍he knows the stories of fans who lived entire lives ⁤without seeing their team win a championship.

“That’s the real fear ‍now. Maybe it’s just not going to happen,” he said. ​“Maybe I’m going to be like one of those Cub fans or Red Sox fans …”

After the Leafs fell in another ⁣Game 7 last season, Anthony broke up with the Leafs for a month, refusing to listen ​to or read anything about the team. They just needed ⁢some time apart.

“We should have broken ​up long ago,” he said.

But no⁣ matter how ⁣many times they say they‌ won’t return, they do. A new season, a new promise, a familiar hope that,​ maybe, this time it ‍will be different. A new coach, tougher defense, better goaltending — is it enough this time?⁤ The feeling amongst many Leaf fans seems more hopeful than the recent past.

“Cautious optimism,” Hargittay called it.

“There’s a bit of excitement,” said Dimoff. “A little bit less ​negativity.”

After‍ all, a drought has to end sometime, right?⁣ It did for ‍the Red Sox in 2004, for the Cubs in 2016. Surely it won’t take​ so long for the Leafs to finally do the same?

One day, ⁢this might ⁢all be trivia. Maybe they’ll live to see it.

Outside of Scotiabank Arena, a⁢ row of life-size bronze statues of Maple Leaf greats stand ready⁤ at the home bench of an imaginary game. The ⁣likeness of Bower, Keon, Horton, Mahovlich stand among them, all frozen in past glory, while thousands of fans ⁤fill the space beyond them, ready to do it all again.

(Illustration:​ Meech Robinson / The‌ Athletic. Photos: Vaughn Ridley and Claus ⁤Andersen / Getty Images; Rick Madonik / Toronto Star via Getty Images)