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NHL’s 21st Century Misery Rankings: #31-#21

These clubs hardly know what misery is.

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NHL: Stanley Cup Final-Washington Capitals at Vegas Golden Knights
Jun 7, 2018; Las Vegas, NV, USA; NHL commissioner Gary Bettman presents Washington Capitals left wing Alex Ovechkin (8) with the Stanley Cup after game five of the 2018 Stanley Cup Final against the Vegas Golden Knights at T-Mobile Arena.
Gary A. Vasquez-USA TODAY Sports

Sports are often a channel for entertainment, but droves of fans are overwhelmed with misery instead.

No matter what sport you follow, there are an abundance of unhappy fans wherever you go. That definitely applies to the NHL, where the Stanley Cup is often toted as the hardest trophy to attain in sports.

Since the turn of the century, 11 different teams have lifted the Stanley Cup in eighteen different seasons. That means fans of 19 other teams (and the Vegas Golden Knights) have cheered for their teams year after year only to watch them fall short of acquiring hockey’s greatest prize.

A lack of success among two-thirds of the league brings about a plethora of misery. Already feeling the sadness overwhelm you? Well, this list will try and justify your misery against the rest of the league.

The game has evolved so much since it’s inception in the early 1900’s, so for the purpose of this exercise I will be looking at NHL teams and their playoff success since the turn of the millennium.

Dallas Stars
The Dallas Stars were the last team to win the Stanley Cup before the turn of the century. Where will they end up on the 21st century misery rankings?
Getty Images

One of the biggest challenges I had here was determining what’s more miserable: coming so close to the grand prize without winning, or suffering through an utter lack of torment within a fan base. After drinking digging deep down, I believe that you need to take the glass half full approach. This is entertainment after all. Although suffering a crushing loss is demoralizing, it’s better than watching your team stink for a decade (or two, in some cases). As someone who follows the Canucks, the 2011 Stanley Cup Finals loss was a gut punch. Still, that result was better than being in an alternate 2011 universe where the Canucks lose in Game Seven overtime to the Chicago Blackhawks instead. If you disagree with that, feel free to take this list and make it your own.

Although this exercise solely looks at playoff series since 2000, there is a small bias for Stanley Cup victories previous to that. Hey, championships fix everything. If a fan of the Dallas Stars want to complain about their franchise floundering through the 2010’s, they can at least reminisce on winning it all back in 1999.

However, none of the teams on part one of this list know what sadness really is, at least since the turn of the millennium. While most of these fan bases suffered through some periods of sadness, they can plug their ears with Stanley Cup rings now.

The stats below are reflective of the 2000 playoffs onwards.

#31: Pittsburgh Penguins

Since 2000: 198 GP, 112-86 with a .565 winning percentage.
Series Wins: 23 (1st) Made playoffs 14 out of 18 seasons.
Four Stanley Cup Final appearances (2008, 2009, 2016, 2017). Three Stanley Cup wins (2009, 2016, 2017).

The turn of the century was a tough time for the Pittsburgh Penguins. Their streak of 11 straight playoff appearances came to a crashing halt during the 2001-02 season. Mario Lemieux played in only a minority of their games, and Jaromir Jagr was traded following the conclusion of the 2000-01 season.

2016 NHL Stanley Cup Final - Game Six
These guys don’t look too miserable.
Photo by Dave Sandford - Pool/Getty Images

However, a couple years of misery brought the team Marc-Andre Fleury, Evgeni Malkin, and Sidney Crosby in three straight drafts. They’ve basically been a Cup contender ever since Crosby’s sophomore season, and became the first team to win back-to-back Cups in this millennium.

They have more Cups and more playoff wins than any other team this millennium. Sadness? Misery? These things should be long forgotten for Penguins fans.

#30: Vegas Golden Knights

20 GP, 13-7 with a .650 winning percentage.
Series Wins: 3. Made playoffs once out of one season.
One Stanley Cup Final Appearance (2018).

Uhhh, I still have trouble comprehending this team’s accomplishments from last season.

For fans, feelings of pure joy and elation must have been the overarching emotions when watching this team complete the impossible.. They were consistently fast, exciting and dynamic. The Golden Knights started off red hot and never really cooled down. Even in the playoffs, they ripped through the Los Angeles Kings, San Jose Sharks and Winnipeg Jets with ease, going 12-3 through the first three rounds of the playoffs. They gave a scare to the Washington Capitals early on before the magic ran out.

2018 NHL Stanley Cup Final - Game Five
Vegas’s incredible season ended in misery, but that’s a drop in the water compared to most franchises around the NHL.
Photo by Ethan Miller/Getty Images

This wasn’t just one of the best expansion seasons in NHL history, but really in the history of North American sports. Their loss at the hands of the Capitals was their first real taste of misery, but as a franchise they’ve yet to experience real pain. Disagree? They’ve already won more playoff series than a number of franchises since 2000.

#29: Detroit Red Wings

Since 2000: 182 GP, 97-85 with a .532 winning percentage.
Series Wins: 18 (2nd). Made playoffs 16 out of 18 seasons.
Three Stanley Cup Final appearances (2002, 2008, 2009). Two Stanley Cup wins (2002, 2008).

When you make the playoffs for 25 straight seasons, it’s really hard to be too upset about your franchise.

Sure, current Wings fans are probably fed up with the team’s salary issues, and missing the playoffs for two straight seasons after making it for 25 straight can be tough. Right?

Detroit Red Wings v Pittsburgh Penguins - Game Six
Nick Lidstrom casually chillin’ with his fourth Stanley Cup in 2008.
Photo by Bruce Bennett/Getty Images

You know what a Toronto Maple Leafs fan might say? Boo freakin’ hoo. The Red Wings rode into the new millennium with two Cup wins, right after winning two straight before the turn of the century. Detroit did what many teams struggle to do: they transitioned from an aging core right into one that could continue competing for the Cup. It certainly helped that defenceman Nick Lidstrom was playing like a number one defenceman with both cores.

#28: Chicago Blackhawks

Since 2000: 134 GP, 77-57 with a .574 winning percentage.
Series Wins: 18 (T-3rd). Made playoffs 10 out of 18 seasons.
Three Stanley Cup Final appearances (2010, 2013, 2015). Three Stanley Cup wins (2010, 2013, 2015).

If we’re talking 2010 and beyond, you’re looking at the most successful franchise in the NHL. People still argue about what a modern day dynasty looks like, and you won’t get much closer than the Chicago Blackhawks.

With three Stanley Cups in six seasons, the Blackhawks won with a formidable core supported by an ever-changing yet effective ensemble. Corey Crawford has also risen from an underrated keeper to one of the league’s best. His value to the Blackhawks was on display this season after the team cratered without him.

We do have to consider the tire fire in which the Blackhawks were before they entered this decade. They missed the playoffs in six of the first seven seasons of the millennium before drafting their franchise cornerstones.

While it might be a stretch to say that Jonathan Toews is one of the 100 best players of all time, there’s no doubt that Blackhawks fans can revel for years in this team’s recent success.

#27: New Jersey Devils

Since 2000: 149 GP, 80-69 with a .536 winning percentage.
Series Wins: 16 (T-3rd). Made playoffs 12 out of 18 seasons.
Four Stanley Cup Final appearances (2000, 2001, 2003, 2012). Two Stanley Cup wins (2000, 2003).

New Jersey had certainly been itching to get back to playoff hockey after a tough stretch in the 2000’s. However, it wasn’t long ago that the defensively dynamite Devils were regularly bringing home Cups to the Meadowlands.

Gomez holds Stanley Cup
Remember when Scott Gomez was lifting Cups on the regular?
Photo by Dave Sandford/Getty Images/NHLI

Before missing the playoffs for five straight seasons, the Devils were a regular member of the postseason party. If you look at the Devils from the late-1980’s all the way until 2010, they’ve been an incredibly consistent organization. From 1987-88 season up until 2011-12, the Devils only missed the playoffs three times.

Devils fans have certainly been spoiled, which explains why attendance dropped during the recent non-playoff stretch. If the Devils are back to being a playoff contender once again, you could say that the pain was short-lived in New Jersey.

#26: Los Angeles Kings

Since 2000: 106 GP, 56-50 with a .528 winning percentage.
Series Wins: 11 (T-9th). Made playoffs 10 out of 18 seasons.
Two Stanley Cup Final appearances (2012, 2014). Two Stanley Cup wins (2012, 2014).

The Los Angeles Kings wrap up the number of teams with more than one Stanley Cup win this century. We’re starting to reach those fan bases that have endured some pain, but can still wash out the bad memories with a recent Stanley Cup win.

That is, until we bring those forgettable years back to light.

The Kings had a dreary stretch in the early 2000’s where they were nothing but irrelevant. There were eight years (including the lockout) between their playoff appearance in 2002, and their next one against the Vancouver Canucks in 2010. However, that 2012-14 run in the playoffs saw them take home two Cups, while narrowly missing out three straight Cup appearances thanks to the Blackhawks.

Watching the Kings become relevant is another reminder to make astute draft picks, no matter where you’re making selections. Sure, the Kings landed Drew Doughty at second overall in 2008, but Anze Kopitar (11th overall in 2005) and Jonathan Quick (72nd overall in 2005) have also become pillars of the franchise.

#25: Anaheim Ducks

Since 2000: 147 GP, 85-62 with a .578 winning percentage.
Series Wins: 13 (7th). Made playoffs 12 out of 18 seasons.
Two Stanley Cup Final appearances (2003, 2007). One Stanley Cup win (2007).

Fun fact: other than the Vegas Golden Knights, the Anaheim Ducks have the best playoff winning percentage of any other team.

So why haven’t they won more Stanley Cups?

That high winning percentage is largely attributed to the number of Game Seven collapses that this franchise endured in the Bruce Boudreau era. It paints an interesting picture for the Ducks throughout this millennium.

Game 5 - Ottawa Senators v Anaheim Ducks
The Ducks can thank Rob Niedermayer for convincing his brother Scott to propel the Ducks to glory in 2007.
Photo by Jeff Gross/Getty Images

They started out as a Cinderella story with their unlikely run to the Stanley Cup Finals in 2003. Backed by first year head coach Mike Babcock, with Jean-Sebastian Giguere in net and Paul Kariya as the unlikely superstar, the franchise pushed the favoured-Devils to seven games.

They got their redemption after a convincing Cup win in 2007. With some smart drafting, along with pickups Scott Niedermayer, Chris Pronger and Teemu Selanne, the Ducks rolled to a Stanley Cup victory. They hardly lost during that run, posting a 16-5 record in the postseason.

Since then, it’s been choke city in the playoffs, although the Ducks have remained a top seed in the Western Conference for years.

#24: Boston Bruins

Since 2000: 121 GP, 65-56 with a .537 winning percentage.
Series Wins: 11 (T-9th). Made playoffs 12 out of 18 seasons.
Two Stanley Cup Final appearances (2011, 2013). One Stanley Cup win (2011).

Unlike some teams on this list, the Boston Bruins haven’t gone through a prolonged period of pain in quite some time.

They’ve missed the playoffs in three two-season chunks this century. Before that, they have never missed for more than two seasons in a row since they missed the playoffs for eight years between 1960 and 1967.

Boston did go 39 years before bringing the Cup back home in 2011. They had a decent chance of winning it all again in 2013, if it wasn’t for an epic Game Six collapse to the Blackhawks.

2013 NHL Stanley Cup Final - Game Six
You thought you were going to see Zdeno Chara lifting the Cup on a Canucks-based blog? You’re dreaming! Enjoy the Bruins watching the Blackhawks lift the Cup after an epic collapse.
Photo by Gail Oskin/Getty Images

The Bruins looked destined for a rebuild after missing the playoffs for two straight years. However, some astute drafting, along with solid goaltending and defence, has them creeping back into the Cup conversation. Not much to cry about here.

#23: Tampa Bay Lightning

Since 2000: 127 GP, 71-56 with a .559 winning percentage.
Series Wins: 14 (6th). Made playoffs 9 out of 18 seasons.
Two Stanley Cup Final appearances (2004, 2015). One Stanley Cup win (2004).

Ahhh, the mid-2000’s, the years where Gary Bettman might have partied even harder than Alex Ovechkin.

Not only did Bettman manage to ruin hockey for a season, two southern U.S. teams brought home Cups in consecutive seasons. That started in 2004 with the Tampa Bay Lightning, who started to rise to prominence two years earlier, before capping things off with a Cup win.

Stanley Cup Finals: Lightning v Flames
The three pillars of the Lightning’s 2004 Stanley Cup win: ‘Nasty Boy’ Knobbs, Andre Roy, and Hulk Hogan.
Photo by Dave Sandford/Getty Images

The inevitable decline happened in the following years, highlighted by three playoff misses from 2008 to 2010. Now, the Lightning are considered one of the premiere franchises in hockey, led by Steven Stamkos, Nikita Kucherov, Victor Hedman, and cunning general manager Steve Yzerman.

There have been some odd playoff misses since they made it back to the playoffs in 2011. They missed some years due to terrible goaltending, and injuries did them in during the 2016-17 season. As long as the Lightning stay healthy, they should remain a contender in the years ahead.

#22: Colorado Avalanche

Since 2000: 117 GP, 62-55 with a .529 winning percentage.
Series Wins: 11 (T-9th). Made playoffs 10 out of 18 seasons.
One Stanley Cup Final appearance (2001). One Stanley Cup win (2001).

It’s hard to believe that a team that finished with 48 points a year ago is only the league’s 22nd most miserable franchise in the 21st century. Avs fans might disagree and if they do, it’s all recency bias.

On the one hand, Colorado has never come close to reliving their glory days through the 1990’s and early 2000’s. They haven’t won a game in the second round of the playoffs since before the lockout, and they’ve missed the playoffs in six of the last eight seasons.

Sakic walks in
Joe Sakic lifts his last Cup in 2001 during the Avs’ reign of dominance.
Photo By: Brian Bahr/Getty Images/NHLI

On the other hand, they were arguably the league’s most dominant franchise for nearly a decade. Joe Sakic, Patrick Roy, Peter Forsberg, Rob Blake and Adam Foote anchored a team that continuously made it to at least the Conference Finals. From 2000-2002, the Avalanche made it to at least the Conference Finals, and they brought home the Cup in 2001 as well.

There are teams who are perennially disappointing, then there are teams who have only disappointed for a handful of years. Unless you’re a teenage Avs fan, you can still reminisce on the not-so-distant glory days during tough times.

#21: Washington Capitals

Since 2000: 117 GP, 66-70 with a .485 winning percentage.
Series Wins: 10 (13th). Made playoffs 13 out of 18 seasons.
One Stanley Cup Final appearance (2018). One Stanley Cup win (2018).

If it weren’t for the Capitals finally bringing home the Cup, Washington would certainly rank much higher on the misery rankings. Instead, they currently have the happiest fan base in hockey.

2018 NHL Stanley Cup Final - Game Five
Alex Ovechkin and the Washington Capitals finally ended years of misery in D.C.
Photo by Bruce Bennett/Getty Images

Winning cures everything, and the Capitals were finally able to bring home the Cup after a number of playoff flops. For more than a decade however, the Capitals couldn’t get past the second round despite three President’s Trophy’s and one of the best rosters in hockey.

Of all the Stanley Cup winners this century, the Capitals are the only team to win it all despite having a playoff record below .500 over the last 18 seasons. Only four teams have made the playoffs more often than the Capitals since 2000, which further exacerbates their struggles.

None of that matters for them anymore, even if this fan base has suffered through a lot before winning it all. They rank dead-last right now in misery, but it took 42 years for their fans to finally tasting glory.

Fans of these teams haven’t shed too many tears lately, but the waterworks should start flowing when parts two and three of this list come out. Stay tuned.