Roundtable: Which NHL team will break it's Stanley Cup drought first?

Inspired by the Cubs ending their 108-year Stanley Cup drought, our staffers figure out with NHL team will raise Lord Stanley’s Cup again, first.

The Chicago Cubs ended their 108-year World Series drought with an exciting, drama-filled Game 7 win over the Cleveland Indians on Wednesday. The title marked the longest time between championships for a professional team, leaving the NFL’s Arizona Cardinals franchise as the current active leaders at 69 years.

There’s no absence of similar streaks in the NHL, most notably the Toronto Maple Leafs’ 48 seasons since their last dance with Lord Stanley. The Philadelphia Flyers are next at 40 years, with the New York Islanders at 32 and the Calgary Flames clocking in at 26 seasons. 

Not taking into account franchises that have yet to win the Cup (Blues (48), Sabres (45), Canucks (45), Capitals (41) and Coyotes (36) lead in that department), which of the NHL’s four longest championship droughts if most likely to end first?

Our resident staff of NHL watchers gives their take:

Jeremy Fuchs

The most “ready” team of this group is the Flyers. They have the veteran scoring—Claude Giroux, Jakub Voracek, Wayne Simmonds. They have the youngsters—Shayne Gostisbehere, Sean Couturier, Travis Konecny, Ivan Provorov. They have depth—Dale Weise, Pierre-Edouard Bellemare, Boyd Gordon, Michael Raffl, Matt Read. 

They don’t have goaltending, at least the type of goaltending that can transcend a team and take them on a deeper run. They’re not as stacked as a team like Pittsburgh, which could get by with passable goaltending because the rest of their team was so good.

After AHL demotion, Andrew MacDonald focused on sticking with the Flyers

But compared to the other teams on the list, the Flyers are the most complete. The Maple Leafs are young and talented, but they, just like the Cubs, will need a few years of gestation before they’re ready. The Islanders have one of the best players in John Tavares, but they’ve dismantled the rest of the team around him and have a somewhat unstable goaltending situation. The Flames have a ton of talent up front, but not a ton of talent in the back. 

None of these teams are immediate favorites, although Philly will be if they can get a goalie upgrade. But if this the year that curses end, perhaps fortune will favor the Flyers. 

Daniel Friedman

The Maple Leafs may not be as close to competing for a playoff spot as the other three aforementioned teams, but this is a marathon, not a sprint, and I think they'll ultimately be the one that comes away with a Stanley Cup first. Why? Three reasons: Braintrust, resources, foundations. They've hired the smartest minds in hockey to run things, with a front office that boasts Brendan Shanahan, Lou Lamoriello and Kyle Dubas, and Mike Babcock behind the bench. One might say they've brought a bazooka to a thumb wrestling match, but when you haven't won a Cup in nearly 50 years, you can't possibly be accused of overcompensating. Team ownership has deep pockets and, lately, has spared no expense in rebuilding the franchise. There's little reason to believe that will change when the Leafs are ready to turn a corner and contend. And, most importantly, there are strong roots in the ground. Auston Matthews is the centerpiece, but Toronto has also plucked William Nylander, Mitch Marner, Morgan Rielly, Carl Grundstrom and Nikita Zaitsev through the draft and other transactions. There's a foundation to build off of here. They'll have depth down the middle, something all winning teams have, and they'll have the cash and flexibility to surround those players with the right pieces. Toronto is a far cry from the contender it aspires to be, but I think it gets there in the (relatively) near future.

Islanders forward Brock Nelson is adding to his family's decorated hockey lineage

Michael Blinn

The Islanders appeared to be on the right track, but through a reduction of talent, the team has taken a big step back. I can’t say the same for the Flyers, who are reaping the benefits of GM Ron Hextall’s slow rebuild. There’s a whole lot of young, burgeoning talent at both ends of the ice (Koceny, Gostisbehere and Provorov), have a sizable window remaining with their core veteran talent (Giroux, Voracek, Couturier and Simmonds), and while goalies Steve Mason and Michal Neuvirth aren’t elite-level talents, they’re stable enough to backstop a team to the Cup. Hey, if Antti Niemi can do it...

Don’t get me wrong, I don’t see this year’s team being world-beaters, but the pieces are there and I wouldn’t be surprised if Philly jumped into the top tier of a wide-open Metropolitan Division sometime soon.

Joshua Kloke

​The Maple Leafs. While I think the Flames will turn it around and contend this season, it's become largely clear that in order to win a Stanley Cup, your team needs to follow a clear trajectory: lose consistently, stockpile draft picks, develop said players properly into a core to build around and then allow to develop slowly in the NHL. The Maple Leafs are somewhere between the third and final step. Sure, it won't happen in the next few years but they're on the upward swing. For years the Maple Leafs did the exact opposite: icing a marginally talented roster and then just continually tinkering. Somewhere around 2013 the Flyers should've stopped doing that and gone full rebuild. But here we are.