The Washington Capitals have made the playoffs 23 times in 29 seasons. That’s the good news. Now here’s the bad news:

The Caps are the most underachieving, unlucky team in the history of North American sports. Name a team that has failed to live up to its seeding in the playoffs more often than the Caps. You can’t.

The Caps are like Sisyphus, who in Greek mythology, according to Wikipedia, was a “king punished by being compelled to roll an immense boulder up a hill, only to watch it roll back down, and to repeat this action forever.”

Caps fans are like Charlie Brown, about to kick the football, when Lucy pulls it away — time and time again. (Will Charlie Brown ever get the little red haired girl)?

If you arrived in town yesterday, you can say that the Caps aren’t the Chicago Cubs (no titles in more than 100 years) or the New York Rangers (no championships for the half century before 1994), but that misses the point. First, the Rangers did win a Stanley Cup before their drought. Second, no sports franchise has failed more often in relation to how long the team has been around. No team has more often lost as the higher seed (at least 10 times), lost more two-game series leads (seven), lost more three or four overtime playoff games (four) or lost more Game 7s (seven) than the Caps.

Now Washington is finding new ways to lose. With 6.6 seconds left in Monday’s Game 5 against the New York Rangers in the second round of the NHL playoffs, the Caps allowed the Rangers to tie the game and send it into overtime. Then just a minute-and-a-half into the extra period, Marc Staal got one past the Caps’ Braden Holtby.

The steady Joel Ward for some reason decided to hit a home run with Carl Hagelin’s head with 21.3 seconds left, earning a high-sticking penalty. Then the normally reliable Holtby did an “I’m rubber, you’re glue, everything bounces off of me, and then you score” routine.

Two games earlier, Washington fell in triple overtime to the Rangers, the fourth time in their history that the Caps have lost a three or four-overtime game.

Looking back at their history, the Caps have won a lot of regular season games, but only twice in 37 seasons have they clearly overachieved during the playoffs, in 1990 when they made it to the conference finals, and in 1998, advancing to the Stanley Cup Finals.

It took the Caps about a decade to find their groove, but even once they started getting to the playoffs in the 1980s, Washington had trouble getting over the hump in the playoffs.

In 1985, the Caps finished with the third-best record in the NHL and won six games more than the New York Islanders, but lost a first round series to them 3-2.

The next year, the Caps again finished with third-best record in the NHL, but lost in the second round to the New York Rangers, 4 to 2. The Rangers were two games under .500 during the regular season. The Caps surrendered a 2 games to 1 lead, and remarkably, outscored the Rangers 25-20 during the series.

In 1987, the Caps lost in the first round to the Islanders despite finishing with a better record than New York during the regular season. The series ended with the “Easter Epic,” the NHL’s first quadruple overtime game since 1951. Pat LaFontaine scored the game-winner for New York. Oh, by the way, Washington led 3-1 in the series.

In 1988, the Caps once again lost to a team they had a better record than during the regular season, the New Jersey Devils, in the second round of the playoffs. The series included a 10-4 loss to Devils in Game 3. Sean Burke was one of many goalies who got hot against the Caps over the years.

In 1992, the Caps finished 11 points better than Pittsburgh during the regular season, but fell to the Penguins in 7 games after blowing a 3-1 series lead. The Caps scored 20 goals in the first four games.  This may have been Caps’ best team ever, with Hall of Famers Dino Ciccarelli and Rod Langway, and Caps stalwarts Peter Bondra, Dale Hunter, and Kevin Hatcher. Even goalie Don Beaupre made the all-star team. Caps fans couldn’t believe the constant failures in the playoffs, and couldn’t take any more. This was 20 years ago.

In 1993, the Caps, who had six points more than the New York Islanders in the regular season, lost to the Islanders in the first round, 4 to 2.

In 1995, the Caps again blew a 3 to 1 first round lead in losing to Pittsburgh in 7 games.

After winning the first two games in 1996, the Caps lost four in a row to the Penguins in the first round.  Game 4 was the fifth-longest in NHL history. Petr Nedved ended the Caps’ misery, scoring in the final minute of the fourth overtime. Olaf Kolzig had 62 saves. Jaromir Jagr had 12 shots for Pittsburgh, while Peter Bondra had 11 for the Caps.

In 2000, Washington, which finished 18 games over .500, lost to — you guessed it –Pittsburgh, 4 to 1 in the first round. The Penguins had a .500 record during the regular campaign.

In 2003, Washington won the opening two games of its first round series against Tampa Bay, but lost the next four to the Lightning, including Game 7 in triple overtime at home.

In 2008, the beginning of the Alex Ovechkin playoff era for the Caps, Washington lost Game 7 of a first round series to Philadelphia, 4-3 in overtime at home.

In 2009, the Caps had the second-best record in the Eastern Conference, but lost in the second round to Pittsburgh (who else?), which finished with five fewer wins than Washington. The Caps jumped out to a 2-0 series lead, but then lost two of three games in overtime. Then in Game 7, the Caps fell behind 5-0 in the second period on the way to a 6-2 loss.  It was the sixth time the Caps had lost in the playoffs to Pittsburgh. Four of those times the Caps had two-game leads in the series.

In 2010, the Caps won the President’s Trophy with 121 points and a record of 54 wins, 15 losses, and 13 overtime losses. Top-seeded Washington gave up a 3 games to 1 lead in losing in 7 games to the 8th-seeded Montreal Canadiens.

In 2011, the Caps were swept by Tampa Bay in the second round despite finishing with the second-best record in the NHL.

In Game 3 of the second round series against the Rangers, the Caps fell to New York in triple overtime, 2-1. Ovechkin went scoreless despite 35 minutes of ice time, and the Caps fell to 0-4 in games that went at least three overtimes.

Then there was the Game 5 fiasco.

Maybe the Caps will rebound to win the final two games of the series to erase the memory of the goal with 6.6 seconds left in Game 5. Some will say it’s simply a hockey series against the Rangers.  But the Caps will not just be playing against the Rangers.

They’ll be fighting against history.

Click here to read this article on Bleacher Report.

Also see Washington Capitals: 25 best players in team history, from Langway to Ovechkin.