Capitals, Blues, Jets can stake convincing claims to having the most tortured NHL fan base

The Washington Capitals entered the NHL in 1974. In their 43 years of existence, they have made only one Stanley Cup Final appearance -- in 1998, when they were swept by the Red Wings -- and they have given their fans plenty of heartache. Mitchell Layton/NHLI via Getty Images

Which long-suffering fan base is most deserving of a Stanley Cup this spring?

Greg Wyshynski, senior writer: With due respect to the Toronto Maple Leafs, who will be treated like the Chicago Cubs of hockey when Great American Auston Matthews delivers a Stanley Cup to that fine Canadian city, the answer here is the Washington Capitals.

For decades, the Capitals have had underwhelming teams that were loaded with talent. The 1988-89 team that won the Patrick Division and lost in the first round featured Dale Hunter, Mike Gartner, Dino Ciccarelli, Scott Stevens, Rod Langway, Kevin Hatcher and Larry Murphy. Washington squandered stellar careers from Olaf Kolzig and Peter Bondra through the 1990s into the early 2000s, too.

That was all before the Capitals drafted Alex Ovechkin and the Rock The Red era began, which ushered in a unique kind of pain for this franchise and its fans: championship-caliber teams that were constantly finding new and inventive ways to fall short of them. The Capitals have made the playoffs in nine of the past 10 seasons. They've been eliminated in a seven-game series in seven of those postseasons. Three times by the New York Rangers. Three times by the Pittsburgh Penguins. Once by a No. 8-seeded Montreal Canadiens team that finished 33 points behind them in the standings.

Since the Capitals entered the NHL in 1974, they've played in a championship round three times: the conference final in 1990, when they were swept by the Boston Bruins, and in winning the conference in 1998 against the Buffalo Sabres before being swept in the Stanley Cup Final by the Detroit Red Wings. In the process, they've seen every conference and geographic rival lap them -- heck, even the Philadelphia Flyers at least have two Cups to their name, although they were won during the Ford Administration.

If the Capitals won the Stanley Cup this season, it would come after many of us assumed their window to win had closed. Even their general manager admitted that 2017 was their "all-in" campaign. It would finally give championship ease to the Washington fans, both the long-suffering ones and the ones who jumped on the bandwagon and landed on a pitchfork in the past decade. Best of all, it would give Ovechkin a ring, and put to rest most of the counterarguments against his hockey god status that rely on the shortcomings of his teams.

Emily Kaplan, national NHL reporter: OK, Leafs and Capitals aside, I'm tempted to pick the Flyers considering the hysteria we saw in Philadelphia after the Eagles' Super Bowl win on Sunday. Philly's a fervent sports city that can get behind its teams, in good times and bad, but especially when they win that jawn. Philadelphia won the Stanley Cup in 1974 and then again in 1975. Despite making the Stanley Cup final six more times -- most recently in 2009-10 -- they haven't been able to seal the deal since. It's been a tantalizing stretch for a franchise that ranks second all time in points percentage (.575)* behind only the Montreal Canadiens.

(*As an aside, the Vegas Golden Knights actually are above both the Canadiens and Flyers in this category, but let's give them a few seasons before we rank them as an all-time great.)

All of this said about the Flyers, I have to give my nod to the St. Louis Blues, who haven't won a Stanley Cup since the inception of the franchise in 1967-68 -- which ranks as the second-longest Cup drought in the NHL. Only Toronto has suffered for longer. What especially stings for St. Louis, just like the it does for Washington, is that its teams have been competitive, year in and year out. Heck, the Blues made the Cup Final in their first three years of existence. They've won a Presidents' Trophy (in 2000) and have sustained remarkable success (a 25-year playoff streak from 1979-80 to 2003-04, an NHL record). They've never lacked for superstars, from Bernie Federko to Brian Sutter to Brett Hull to Al MacInnis to Keith Tkachuk ... but none were able to bring the Cup home. Meanwhile, they've seen the rival Chicago Blackhawks win three Cups -- despite long stretches of futility when the Blues were actually winning. Well, this season Chicago is last in the Central Division and St. Louis had a terrific first half. Maybe it's the year karma catches up.

Chris Peters, NHL Insider: There's no question that Capitals fans have been teased the most in recent years. I think that level of heartache puts them right up there with Maple Leafs fans, who get bonus points for longevity and that 2013 series against the Boston Bruins. (I know, Toronto ... I'm sorry for even bringing it up.) But since Greg detailed the Capitals fans' lament as well as he did, I'm going to go in a different direction and say the good people of Winnipeg are at least on the list of most deserving.

Here are fans who actually had their team taken away in 1996 and probably thought a Stanley Cup was to be nothing more than imagined for their city. Even though the Jets came back in a different form -- when the Atlanta Thrashers relocated to Winnipeg in 2011 -- those scars from the team moving to Phoenix are still pretty fresh. Things are looking up, though.

The Winnipeg Jets 2.0 are now leading the Central Division and look like a team ready to make some noise. I don't know if they have enough yet to truly challenge some of the other more experienced teams they'd face in the Western Conference in the postseason, but they'd be a tough out at least.

But let's talk about long-suffering. Winnipeg is actually home to a three-time Stanley Cup champion. That would be the Winnipeg Victorias, which became the first team outside of Quebec to win the famous trophy in 1896. They won again in 1901 and successfully defended the title into 1902 (Source: hhof.com). The Stanley Cup hasn't been back since. The Jets did win three titles between 1976 and 1979 in the World Hockey Association, the NHL's short-lived competitor, but that's not the same, of course.

Since the Jets returned to Winnipeg, they have made the playoffs just once and got swept right out of them by the Anaheim Ducks. Now, however, the pieces are in place to do some damage. For teams like the Jets, the championship window may be smaller because it's harder to attract free agents to Winnipeg, which is often on no-trade lists. That's why you have to give credit to Jets GM Kevin Cheveldayoff for what he's built since the move. He hasn't been perfect, but the team's draft record is very strong, and they've built a legit contender because of that. The window is at least cracked open right now and will probably open a little wider in the next few years.

It's been a crazy roller coaster for this market historically, but it at least seems to be trending in a very positive direction.