If you consider yourself a fan of the Washington Capitals—I mean a true fan—then you are very familiar with the heartbreak that goes along with this distinction.
With the exception of the Cleveland Browns, one can make a very strong argument that the Washington Capitals are the most snake-bitten franchise in all of sports.
The Caps were the first team to blow a 2-0 series lead in the old best-of-five format, falling to the New York Islanders in the 1985 playoffs.
Two years later, the Caps would blow a 3-1 series lead for the first—but not the last—time and would fall to the Islanders yet again in one of the most gut-wrenching Game 7 defeats ever.
In 1992, they blew the first of multiple 3-1 series leads against the Pittsburgh Penguins. The Pens have actually made a habit of rallying from two-game series deficits against the Caps in the playoffs.
The team has lost in four overtimes twice. That is hard to do even if you are trying.
The team has routinely squandered home-ice advantage and failed to live up to expectations time after time after time.
There have been so many heartbreaking failures and defeats in Caps history that picking the worst of the worst is a daunting task.
Brace yourselves, Caps fans, because these will not be pleasant memories at all.
Here then are the five most heartbreaking losses in the history of the Washington Capitals.
I know many people consider last season's collapse against the New York Rangers to have been particularly heartbreaking, and I won't dispute that.
But, in my opinion, the Caps' loss to the Rangers in Game 7 of the 2012 Eastern Conference Final was far more excruciating.
The 2011-12 Washington Capitals were so very different from the teams that had dominated the Eastern Conference the previous four seasons or so.
They were not the Presidents' Trophy winners. They were not the No. 1 overall seed in the Eastern Conference. They were clearly not the best team in the conference—at least they were not as the playoffs began.
On paper, the experts seemed to be right—the Bruins were the much deeper team and just seemed as though they would be far too much for the Caps.
But the Caps discovered how to play playoff hockey, and they shocked the Bruins in the only seven-game series in NHL playoff history in which each game was decided by just one goal.
Joel Ward's overtime winner in Game 7 gave Caps fans everywhere hope that maybe—just maybe—this could be the year.
In the conference semifinals, the Caps would tangle with a very familiar foe, the New York Rangers. It was the third time in four years that the two teams had met. This time, the Blueshirts were the No. 1 seed in the East. What transpired was a tremendous playoff series that only cemented the teams' growing dislike for each other.
The two teams would alternate wins and losses through the first six games, but that hardly tells the story. The 2011-12 version of the Caps was one of the more resilient teams in franchise history, and never was that on display more than it was in this series.
The Caps lost a triple-overtime classic in Game 3 but bounced back to even the series again in Game 4.
With the series tied at 2-2, Game 5 was played at Madison Square Garden. Like pretty much every game in that series, it was a war of attrition. Goals were hard to come by, and in the closing moments, the Caps were clinging to a 2-1 advantage.
But Ward, the hero of Game 7 against the Bruins, would be the goat of Game 5, as he drew a double-minor penalty. With Ward in the penalty box, the Rangers' Brad Richards would score the game-tying goal with just 6.6 seconds remaining in regulation.
To make matters worse, the Rangers would score the game-winner on the second part of Ward's double-minor, just a minute-and-a-half into overtime. Marc Staal's blast gave the Rangers the 3-2 win and a 3-2 lead in the series.
But the Caps would come back to win Game 6 in Washington two nights later, proving yet again that this team was different. There was something intangible about this team that made many believe it had what it would take to get back to the Eastern Conference Final for the first time since 1998.
But the Caps would come up just short against the Rangers. They gave up an early goal and then a second one midway through the third period when they got caught in the middle of a line change. A goal by Roman Hamrlik got the Caps back to within one, but they could not get the equalizer.
Despite the heroics of Braden Holtby and despite the team adopting the type of playoff hockey that had been so successful for other teams in the past, the Caps could still not take the next step. It was a bitterly disappointing end to an unlikely playoff run that, in many ways, seemed reminiscent of the 1998 run to the Stanley Cup Final.
Instead, Game 7 of the 2012 Eastern Conference Semifinals was just another heartbreak for the Caps and their fans.
The Washington Capitals have been to the Stanley Cup Final just once—back in 1998.
In the final, the Caps tangled with the defending Stanley Cup champions, the Detroit Red Wings.
The Caps would lose a hard-fought Game 1 in Detroit, 2-1. It was Game 2, however, that would be the defining game of the series—and also one of the most soul-crushing defeats in the history of the franchise.
Goals by Peter Bondra, Chris Simon and now-head coach Adam Oates had given the Caps a 3-1 lead in the second period.
That lead would hold up into the third period, and when the Caps got a power play with just over 13 minutes remaining, victory seemed assured.
Instead, Steve Yzerman scored a short-handed goal to trim the Caps' lead to 3-2.
Joe Juneau—the man whose overtime winner against the Buffalo Sabres had catapulted the Caps to the Stanley Cup Final—scored on the same power play to give the Caps a 4-2 lead, and everything seemed to be well at hand.
Martin Lapointe would re-ignite the Red Wings' rally with a goal with 11:52 remaining. That would set the stage for one of the truly gut-wrenching moments in the history of the Washington Capitals.
With just about 10 minutes remaining in regulation, Esa Tikkanen came into the Detroit zone and faked a slap shot. Chris Osgood went to the ice to block the shot, and Tikkanen, still in control of the puck, maneuvered around Osgood.
Tikkanen had as wide-open a net as anyone could possibly hope for. Inexplicably, he missed the net. As the puck trickled just wide, the Caps' hope for a Stanley Cup went awry right along with it.
Doug Brown would tie the game with 4:14 left in regulation, scoring from a very difficult angle. From there, the Red Wings were dominant and Kris Draper's goal with 4:46 left in overtime completed the comeback and gave Detroit a 2-0 series lead.
The Wings would win the next two games in Washington and would repeat as champions. No team has won back-to-back Stanley Cup championships since the 1997-98 Red Wings.
The Caps, meanwhile, have never even made it back to the Eastern Conference Final since that magical run in 1998.
Now, sure, the Wings were the better team. It is very likely that, even if Tikkanen scored and the Caps won Game 2, Detroit still would have won the series.
Then again, maybe not. If the Caps had won Game 2 and gone home with a split, what would that have done to the psyche of the Red Wings? How much confidence would the Caps have drawn from that win, knowing they were heading home in control of the series?
Instead of a crushing defeat, the Caps would have had a huge win, a ton of confidence and all the momentum.
Alas, it was never meant to be. Tikkanen's miss was one of the biggest blown opportunities in the history of the franchise, perhaps even the biggest ever.
The fact that the team simply could not hold on to a two-goal lead in the third period—twice no less—combined with Tikkanen's blown opportunity, makes Game 2 of the 1998 Stanley Cup Final one of the most heartbreaking defeats in the history of the franchise.
The third most heartbreaking defeat in the history of the Washington Capitals was so bad, it actually has a name.
The 1986-87 version of the Washington Capitals was not the best team in the history of the franchise. Far from it actually. The 1986-87 Caps finished with a record of 38-32-10, good for 86 points.
In the playoffs, the Caps would meet the New York Islanders for the fifth consecutive season. The Isles had won three of the previous four meetings between the clubs, but the Caps had won the most recent series.
Along the way, the Islanders had become the first team in NHL playoff history to rally from a 2-0 series deficit to win a best-of-five series when they beat the Caps in the 1985 division semifinals.
Thus, the stage was set for more drama. The teams would split the first two games of the series. The Caps then went to Long Island and won the next two games to take a 3-1 series lead.
But the Caps would lose Game 5 on home ice, and would then drop Game 6 back on Long Island.
Game 7 would turn into one of those rare games that was so epic it actually has a name—"The Easter Epic."
The Caps would hold a 2-1 lead until late in the third period, when Bryan Trottier tied the game at 2-2.
From there, though, things took a turn for the surreal.
For the next three overtimes, Caps goaltender Bob Mason and Islanders goaltender Kelly Hrudey made amazing save after amazing save.
The two goalies were just in a different zone, and for the longest time, it seemed that there was just no way either team would be able to score.
Finally, at the 8:47 mark of the fourth overtime, Pat LaFontaine ended the drama in excruciating fashion for Caps fans.
LaFaontaine took a puck that was standing on end and fired a slap shot from just inside the blue line. It is hard to tell whether the puck was deflected, or even if it might have been deflected more than once.
Regardless, Mason never saw the puck, and as the red light came on, it ended the 10th-longest game in NHL history and the longest Game 7 in NHL playoff history.
It also remains embedded in the consciousness of Caps fans everywhere as one of the all-time low points in franchise history.
For the Washington Capitals and their fans, the Pittsburgh Penguins represent a house of horrors.
The teams have met in the playoffs a stunning eight times over the years. Even more surprising is the fact that the Penguins have won the series seven of eight times. Twice, they have overcome a 3-1 series deficit, and twice more they were able to climb out of a 2-0 series hole.
Included in this was the four-overtime defeat in Game 4 of the 1996 playoffs. Yes, for those keeping track, that makes two four-overtime games that the Caps have lost in their tortured history.
More than a decade later, though, the teams would match up again. Unfortunately for the Caps, time did not make the Penguins any less devastating to their plans for success.
The 2009 Eastern Conference Semifinals between the Penguins and Capitals remains one of the greatest playoff series in NHL history. But just as in years past, the Caps dominated early in the series but could not close the deal.
Ever since they were drafted No. 1 overall in consecutive seasons, Alex Ovechkin and Sidney Crosby were on a collision course. They were the faces of the NHL, the present NHL in the wake of the recovery from the 2004-2005 lockout and the future of the league.
With the NHL surging in popularity, all it was going to take was a matchup between the league's marquee players to allow the NHL to reach all new heights.
In the 2009 playoffs, the Caps rallied from a 3-1 series deficit to upend the New York Rangers, and when the Carolina Hurricanes scored two goals in the final 90 seconds to beat the New Jersey Devils in Game 7, one of the most anticipated playoff series in NHL history was finally a done deal. The two teams would not disappoint.
Five of the first six games were decided by just one goal. Three of the games went into overtime. The highlight of all of this was Game 2, when Ovechkin and Crosby each scored hat tricks. The Caps would prevail, 4-3, to take a 2-0 series lead, and, in an unsettling way, things felt like the '90s all over again.
When the Pens won Game 3 in overtime, and then won Game 4 by the score of 5-3, fans everywhere had to feel like they had just jumped into a flying Delorean and had gone back to 1995. The Pens would win Game 5 in overtime and head home to, presumably, put the series away.
But Dave Steckel would score in overtime of Game 6, and, suddenly, the Caps had the momentum heading home for what promised to be one of the all-time great Game 7s in NHL history.
It never worked out that way, though. What was supposed to be an instant classic turned into an epic blowout. Marc-Andre Fleury stoned Ovechkin on a breakaway attempt early in Game 7, and goals by Crosby and Craig Adams—just eight seconds apart in the first period—gave the Pens a lead they would not relinquish.
The Caps wilted under the pressure of a game of this magnitude. With a trip to the Eastern Conference Final within their grasp, the Caps simply did not even show up.
The Penguins would win Game 7 by the final count of 6-2 and, yet again, would get the best of the Caps in a playoff series. Pittsburgh would go on to win its first Stanley Cup since 1992. The Caps have never quite been the same.
The teams have not met in the playoffs again since the epic 2009 Eastern Conference Semifinals, but they are both divisional rivals now in the new Metropolitan Division.
On November 20, the two teams met as divisional rivals for the first time since 1993 and the Pens blanked the Caps 4-0. It was the fifth straight time the Penguins have beaten the Caps.
Whether the Caps can exorcise any of these lingering demons in the months and years to come remains to be seen. They certainly did not get off to a good start the other night.
What makes one heartbreaking moment worse than the other? It is hard to say. But what happened to the Washington Capitals in the spring of 2010 remains, in my opinion, the most devastating defeat in the history of the franchise.
The 2009-10 Washington Capitals were not just good—they were great. They won the Presidents' Trophy with a record of 54-15-13, amassing 121 points along the way and becoming the first non-Original Six team to crack the 120-point barrier.
The team was absolutely loaded with talent, and it had weapons up and down the lineup. Alex Ovechkin was playing better than ever, as were Nicklas Backstrom, Alexander Semin and Mike Green. If ever a Caps team seemed destined for greatness, it was this one.
When the playoffs began, the Caps drew the No. 8 seed, the Montreal Canadiens. The Caps had finished the regular season 33 points better than the Habs. Nevertheless, the Caps and Canadiens had split their four regular-season battles.Still, on paper anyway, the Canadiens seemed to be no match at all for the high-powered Caps.
Problems began in Game 1 when the Caps lost in overtime, 3-2.
In Game 2, the Caps had to rally from a three-goal deficit to win in overtime, 6-5.
After the Caps won Games 3 and 4 in Montreal to take a 3-1 series lead, it was all over except the shouting.
But, as Caps fans know, nothing is ever that easy.
In Game 5, the Caps came out flat, never found their rhythm and lost, 2-1.
In Game 6, the Caps threw everything they possibly could at Canadiens goaltender Jaroslav Halak. Halak had other ideas, though, as he stopped 53 of 54 shots fired on him and Montreal tied the series at 3-3 with a 4-1 win.
That set the stage for Game 7—and the most heartbreaking defeat in the history of the franchise.
Just over halfway through the first period, Semin had a glorious opportunity to score. But, as was often the case with Semin in the playoffs, he came up small, striking the post.
Then there was the Caps' power play. The Caps had the best power play in the NHL during the regular season. Against the Habs, though, the power play went a pathetic 1-of-33. In Game 7, the Caps had four more power-play opportunities, and they failed each and every time.
Meanwhile, the Canadiens capitalized on one of their power-play chances and held a 1-0 lead into the third period.
In the opening moments of the third period, it looked like the Caps had tied the game at 1-1, but a very controversial goalie-interference call nullified the score. The frustration and missed opportunities continued to mount.
As the third period rolled on, the Caps had chance after chance after chance. Halak stopped them at every turn.
The Habs took a 2-0 lead with just under four minutes to go. Brooks Laich finally got one past Halak to make it 2-1, and the Caps would get a glorious power-play chance in the closing moments with a chance to tie the game and extend the season.
It never happened, and the Canadiens became the first No. 8 seed to rally from a 3-1 series deficit to defeat a No. 1 seed.
Halak ended up stopping 131 of 134 shots over the final three games. The Caps simply did not know how to excel in a playoff game when their offense was taken away from them.
The reason the 2010 Eastern Conference Quarterfinals defeat was so devastating was multi-tiered. That version of the Caps was as good a team as has ever donned Caps uniforms. Yet it could not put away an inferior opponent, could not hold onto a 3-1 series lead and simply could not capitalize on the numerous opportunities that were handed to it throughout the series.
Many, many Caps fans felt, and still feel, that the 2009-10 Caps offered the franchise its best opportunity to win a Stanley Cup.
What it got instead was the most heartbreaking defeat in the history of the Capitals.