Down Goes Brown: Can any team trump Maple Leafs’ 50 years of misery?

Kevin Shattenkirk scored the winning goal in overtime and the Washington Capitals defeated the Pittsburgh Penguins in Game 3.

Today is an important anniversary for Toronto Maple Leafs fans.

You’ll notice I didn’t say “happy anniversary,” since this isn’t exactly a day that Leafs fans will want to celebrate. Oh, it marks the anniversary of a happy moment in franchise history; it was 50 years ago tonight that George Armstrong’s iconic empty-net goal sealed a 3–1 win over the Canadiens, securing the franchise’s 13th Stanley Cup.

The not-so-happy part is what’s happened in the 50 years since. Or, more accurately, what hasn’t happened. A full five decades later, the Maple Leafs are still stuck on 13 Cups, as the team’s championship drought has officially reached the half-century mark.

We’ve known this milestone was coming for a while now; it’s been clear for just about the entire salary-cap era that the Maple Leafs weren’t going to win a Cup any time soon. But there’s hope in Toronto these days, as the best collection of young talent the team has had in a generation seems to be on its way towards contending again, maybe as early as the next year or two. For the first time in ages, there’s some genuine optimism that the drought could end someday soon.


Still… 50 years. Man, that’s a long time. I wasn’t alive back then. You probably weren’t either. We knew this day was coming, but it still feels like a big number. From Harold Ballard to Kerry Fraser to JFJ to 4–1, it’s been a rough stretch for long-suffering Leafs fans.

But all that said, have the Maple Leafs really been the NHL’s most miserable team over the last half-century? After all, it’s not like they’re the only team that hasn’t won a Cup since 1967. That list is actually a reasonably long one, meaning even if we rule out one-off teams like the Rangers and Flames, we’re still left with a dozen Cup-less candidates.

So today, as we celebrate Toronto’s dubious anniversary, let’s compare them to the other teams that haven’t won a championship since 1967, and try to figure out how they stack up against the Maple Leafs track record of misery.

St. Louis Blues

The history: Of all the teams who haven’t won a Cup in the post-1967 era, the Blues join the Leafs as the only one that actually existed back in 1967. And only barely; they took the ice for the first time as an expansion team that fall. That’s led to an ongoing argument over whether the Blues and Leafs are tied for the NHL’s longest Cup drought or whether the Leafs technically own the claim outright, which has to be just about the saddest sports debate there can be.

Closest call: The Blues went to the Stanley Cup Final in each of their first three seasons, which sounds impressive until you remember that the NHL stuck all its terrible expansion teams in the same division, guaranteeing one of them a spot in the final. The Blues were the best of the worst all three years, but got swept each time and haven’t been back since.

Low point: The 1999–2000 Blues won 51 games and the Presidents’ Trophy, heading into the playoffs as Cup favourites. Seven games later, they were out in the first round, thanks largely to this long-distance goal:

They might be even worse than the Leafs at: Drafting. Like Toronto, the Blues have been better lately (the Vladimir Tarasenko pick was genius). But this is still the team that took Erik Johnson over Jonathan Toews in 2006, which not only set them back but also helped a division rival build a dynasty. And as bad as the Leafs have been, at least they never no-showed a draft entirely.

But at least: From 1980 through 2004, the Blues made the playoffs in 25 straight seasons. These days, the Leafs are hoping to just get there in back-to-back years.

Are they worse?: This one is closer than you think, especially since the Blues’ three trips to the final don’t really count. But their general consistency and lack of truly rock-bottom moments leaves them a notch behind Toronto on the misery scale.

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Washington Capitals

The history: While they give the Leafs a decent head start by not existing until 1974, the Capitals gain that ground back quickly by immediately posting the worst season in modern NHL history. The 1974–75 Caps team managed just 21 points, and the team didn’t make the playoffs until 1983. And then things got bad.

Closest call: The Caps at least made it to the 1998 Cup final, although they didn’t win any games once they were there.

Low point: At the rate things are going, check back in a few days.

They might be even worse than the Leafs at: Protecting series leads. The Capitals have a stunning history of repeatedly blowing two-game leads in the playoffs; it’s kind of their thing. Granted, it’s not like Leaf fans can get all high and mighty about protecting playoff leads, but the Caps have dedicated decades to their craft.

But at least: The Capitals have won three Presidents’ Trophies in the last eight years; the Maple Leafs have only topped 100 points once in their history.

Are they worse?: This one may be too close to call. The Caps have had lower lows, both in the regular season and playoffs. But they’ve also had higher highs, including that one trip to the final. Let’s see just how heart-breakingly this season ends before we make any final decisions.

Florida Panthers

The history: They joined the league in 1993 and were in the Stanley Cup final three years later. But since then, they haven’t won a playoff round.

Closest call: That trip to the final ended in a sweep at the hands of the Avalanche. The fourth game was a triple overtime 1-0 final, because mid-90s NHL hockey was super exciting.

Low point: They’ve had an up-and-down ride in the market, often struggling with attendance and finding themselves the subject of countless relocation rumors. But the low point may have been the time the glass broke during a home game and they replaced it with plywood.

They might be even worse than the Leafs at: Front office/coaching dysfunction. And when you’re talking about a team that once tried to make their coach wear a paper bag over his head, that is really saying something.

But at least: They’ve finished first in their division twice in their history, which is one more than the post-1967 Maple Leafs have managed.

Are they worse?: They’re certainly more forgettable, I guess, seeing as I originally left them out of this post entirely and had to be reminded to go back and add them.

Ottawa Senators

The history: The modern Senators have existed since 1992, when they arrived as a laughably mismanaged expansion team. Their early years were embarrassing, including a botched expansion draft and accusations of intentional losing that indirectly led to the creation of the draft lottery. But since first making the playoffs in 1997, the Senators have been one of the league’s most frequent post-season participants.

Closest call: Unlike the post-1967 Maple Leafs, the Senators can lay claim to an appearance in the Cup final. That came in 2007, when they faced the Anaheim Ducks.

Low point: That final appearance lasted just five games, their beloved captain shot the puck at the other team’s star player, and the Senators scored the Cup-winning goal into their own net while the Ducks were changing lines. Other than that, it went well.

They might be even worse than the Leafs at: Winning playoff series involving the Leafs. Is it bad to be on the losing end of a rivalry against the least-successful team in the league? It seems bad.

But at least: The Sens are still alive in this year’s playoffs, and looking good in the process. In fact, they’re 10 wins away from leaving this list altogether.

Are they worse?: Can you really compare the two teams? Well, the Senators didn’t exist before the early ’90s. The Maple Leafs did, but had Harold Ballard as their owner. I’d call it pretty even.

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Nashville Predators, Columbus Blue Jackets, Minnesota Wild

The history: Let’s combine all three relatively recent expansion teams into one entry. It’s like a Voltron of playoff failure.

Closest call: None yet, although the Predators might change that this year.

Low point: Between them, these three teams have made just one trip to the conference finals. That was by Minnesota back in 2003, and when they got there they set an NHL record by scoring one goal in an entire playoff series.

They might be even worse than the Leafs at: Um… retiring numbers? I got nothing.

But at least: The Predators have P.K. Subban, and if you can’t have a Cup, that’s pretty much the next best thing.

Are they worse?: Sorry, newbies. We’re just including you here for the sake of completeness.

Arizona Coyotes

The history: They were born in 1996 when the original Winnipeg Jets relocated.

Closest call: None, really. Even if you don’t count the Jets years, the Coyotes are the oldest team to have never even made it to the finals.

Low point: Every time over the last 20 years that they’ve been rumoured to be on the verge of moving. So, the entirety of the last 20 years.

They might be even worse than the Leafs at: Winning playoff rounds. They’ve only managed to win two series, and those both came in 2012. Say what you will about the Leafs’ Cup drought, but at least they worked in a stretch where they made four conference finals in a decade. That’s not much, but it’s a lot more than the Coyotes can claim.

But at least: Their existence inspired a little kid named Auston Matthews to take up hockey, and I hear he turned out to be pretty good.

Are they worse?: They’re on their way, but check back in another few decades and we’ll talk.

Winnipeg Jets

The history: This gets a little tricky, since we’re combining the old Jets (1979–1996) with the current version (2011–today). The NHL doesn’t technically do that, viewing the two teams as separate entities, which is why Patrik Laine was chasing Ilya Kovalchuk’s rookie records instead of Teemu Selanne’s. But as a wise man once said, when you’re a Jet you’re a Jet all the way. For misery-measurement purposes, it’s the same team.

Closest call: Do you count WHA titles? Because if so, the Jets won three and shouldn’t even be on this list. (Nobody counts WHA titles.)

Low point: Moving to Phoenix has to rank right up there.

They might be even worse than the Leafs at: Existing.

But at least: They perfected The White Out, which is much cooler than the Maple Leafs’ version — The Empty Seats While Guys In Suits Eat Caviar And Drink Imported Beer Out.

Are they worse?: The combined Jets are one of the few teams that can say that they’ve had far less playoff success than the Maple Leafs, so they’ve at least got a case to make. But 50 years of failure still trumps 23.

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San Jose Sharks

The history: They arrived in 1991 as an expansion team, kind of, although not really. It was complicated. But after a rocky start, they finally hit their stride for good in the late ’90s and have only missed the playoffs twice in the last 20 years.

Closest call: They came within two wins of a Cup last year before losing in six to the Penguins.

Low point: Take your pick. The Sharks have earned a reputation for regular-season excellence followed by post-season heartbreak, so there’s been plenty to choose from. But for pure misery, it’s hard to beat 2014.

They might be even worse than the Leafs at: Not blowing a 3-0 series lead. The Sharks’ collapse against the Kings made them one of four teams in NHL history to blow a three-game series lead. Amazingly, the Maple Leafs aren’t one of those teams. Yet. Wait, hockey gods, forget I mentioned this.

But at least: The Sharks have been a good team for a long time. This gets into one of those existential sports fan debates – is it worse to be a contender every year only to have your heart broken again and again, or to be so consistently bad that you never bother having any hopes to dash?

Are they worse?: If you’re young and/or new to hockey fandom, the Sharks at least give the Leafs a run for their money.

Vancouver Canucks

The history: They arrived on the scene in the 1970 expansion, and immediately lost out on a Hall of Famer after the NHL couldn’t read a roulette wheel. That kind of set the tone.

Closest call: The Canucks have come as close as you can, making it to game seven of the Cup final twice, in 1994 and 2011.

Low point: That 2011 series ended with a bad loss on home ice, followed by a riot, followed by zero playoff series wins in the years since.

They might be even worse than the Leafs at: Designing uniforms. Say what you will about the Leafs’ decade of failure on the ice, they’ve always looked reasonably sharp while they were doing it. The Canucks, um, not so much.

But at least: They’ve been to the final, and unlike the Capitals and Blues, they even won a few games while they were there.

Are they worse?: I don’t feel like having my house burned down, so let’s say they’re just slightly behind Toronto.

Buffalo Sabres

The history: The Sabres arrived with the Canucks in 1970 and quickly established themselves, even making the final in 1975, and rarely missed the playoffs until the last decade or so. They took a back seat to teams like the Canadiens and Bruins for much of that time, and at one point didn’t win a playoff round for a decade (until this happened), but eventually made it back to the final in 1999.

Closest call: That trip to the 1999 final ended in controversy when the Stars’ winning goal sure seemed like it shouldn’t have counted.

Low point: See above.

They might be even worse than the Leafs at: Winning the draft lottery. Seriously, you finish dead last and then you get handed a shiny new franchise player. Is that so hard, Buffalo?

But at least: In Dominik Hasek, the Sabres can lay claim to one of the best goalies ever — maybe the best, period. Hasek won back-to-back Hart Trophies as league MVP, an honour no Maple Leaf has claimed since Teeder Kennedy in 1955.

Are they worse?: They’re awfully close, and if they can’t get their stalled rebuild into gear soon, they may even fall behind the Maple Leafs within another few years.

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