The Most Painful Moment in Each NHL Team's History

I don't consider it a huge secret that I am a fan of the Detroit Red Wings. I'm also a huge fan of the NHL in general. I think I'm pretty fair and objective when I cover Detroit's hockey team, but, make no mistake, when I'm watching the games, on comes the fan hat.

I feel I need to preface this article with that information, because when I write about the most painful moment in each team's history, there is certainly some subjectivity to consider.

How I felt when something happened will certainly make some people feel differently. After all, opinions are like elbows: everyone's got his or her own and isn't afraid to throw them in your face from time to time. Some fans will see things differently than the rest of the world, with judgement clouded and blind faith aplenty.

There was some question in my mind as to where I would go and how far I would reach to find each team's "painful" moment. I decided to stick mainly to on-ice activity and for the most part steer away from tragedy. There's plenty of that out there to find, but I'll keep away from it as much as I can.

I'm not trying to be Debbie Downer today. I'd like to keep things in perspective, and while we all love sports, it is, after all, just a game.

I will attempt to pick the moment in each franchise that was the most unnerving, gut-wrenching or heartbreaking. I'll apologize in advance for bringing up the past and the unpleasant recall that it may summon. At this point I usually exclaim "Enjoy now!"

But, realistically, you may not.

Anaheim Ducks

Despite winning the Conn Smythe Trophy on the losing team, the fifth time in league history that has occurred, Jean Sebastian Giguere was inconsolable after the New Jersey Devils slipped past the Anaheim Ducks in Game 7 of the Stanley Cup Final in 2003.

It was a huge step forward for the young franchise that traded punches with a veteran-filled New Jersey team that took its third title in eight years. The Ducks' unlikely Stanley Cup run started with a first-round upset sweep of the defending champions, the Detroit Red Wings.

The cup final pitted the Niedermayer brothers against one another and featured one of the most brutal checks in history as Scott Stevens knocked Ducks star Paul Kariya out cold with a hit in Game 6. Kariya would amazingly return to the game and inspire a 5-2 win to force a Game 7 back in New Jersey.

The Disney magic dust would run out, though, as Martin Brodeur got the best of the French-Canadian-goalkeeper duel 3-0.

Boston Bruins

With respect to the 2010 3-0 series collapse in the Eastern Conference Semifinals against the Philadelphia Flyers, the most awful Bruins loss would have to be in Game 7 of the 1979 Stanley Cup semifinal against two-time defending Stanley Cup champions (and not-so-friendly rivals) the Montreal Canadiens.

The Bruins had forged ahead, going into the third period 3-1 and looked poised to end the Canadiens' cup run and bring the title back to Beantown.

The Canadiens scored twice to tie the game before Boston regained the lead with about four minutes left.

Fabled coaches Scotty Bowman (Montreal) and Don Cherry (Boston) pulled out all the stops with vital seconds ticking away. At the 2:34 mark, the Bruins screwed up a line change, giving Montreal a power play for all but 30 seconds of the final period.

Bowman assembled his top power-play line featuring five future Hall of Fame players: Guy Lafleur, Jaques Lemaire, Steve Schutt, Larry Robinson and Serge Savard.

Les Habitants tied it up on a goal from Lafleur and won it in overtime.

I can't imagine how the scene would have played out in Boston Garden.

Buffalo Sabres

The Buffalo Sabres fans have felt cursed forever, and Exhibit ZZ would be Brett Hull's overtime Stanley Cup-winning goal with the mysterious and conveniently ignored "skate in the crease" rule.

While it's easy to say that the rule is stupid and honestly didn't affect the integrity of the goal, Sabre-nation and Lindy Ruff would have none of it.

The rule is correctly explained in this clip. Sorry, Buffalo.

Calgary Flames

There could be a valid argument about what is more heartbreaking: getting to the Stanley Cup Final versus never getting that far in the playoffs.

Of course we want our team to advance as far as they can, but can there be a greater sense of defeat than a one-goal loss in Game Seven of the championship in your sport? The Calgary Flames' magical run, and possibly Jarome Iginla's best shot at Stanley Cup glory, was trumped by an equally magic run by the Tampa Bay Lightning in 2004.

Thanks to the NHL lockout the following year, Calgary had an extra season to reflect on the bitter defeat, while Tampa held their crown for an extra 12 months without playing a game.

Carolina Hurricanes

I know I said in the intro that I would try to keep the painful moments limited to on-ice activity, but I would be remiss if I didn't include a sad relocation tale...or two, maybe three. The Hartford Whalers and their brass bonanza headed to NASCAR country in 1997 to become the Carolina Hurricanes.

While Hartford provided the smallest market in the NHL at the time and one of the smallest arenas, its fans were extremely loyal, even through the leaner times in franchise history.

Chicago Blackhawks

As I mentioned earlier, the only thing worse than a Game 7 loss would probably be a Game 7 home loss.

The Chicago Blackhawks did just that in 1971 against the Montreal Canadiens.

After taking a 2-0 series lead, the Blackhawks lost four of the next five games in what would be one of the most painful playoff exits in Chicago's 49-year Stanley Cup drought.

Colorado Avalanche

In the relatively short existence of the Colorado Avalanche, the most painful moments have probably been the retirements of franchise icons Joe Sakic and Patrick Roy.

However, it can't be forgotten that these Avalanche hail from the province of Quebec and were known as the Nordiques.The team had struggled financially and was sold to investors from Denver, Colorado.

What makes the relocation particularly sad was that the team that headed to Denver had been the top seed in the Eastern Conference the previous year, and would win the Stanley Cup their first season as the Avalanche in 1996.

Columbus Blue Jackets

In such a short and unsuccessful existence, the only real painful moment in the Columbus Blue Jackets' history would be the departure of their captain and franchise leader in every meaningful statistical category: Rick Nash.

While everyone knew that Nash wanted out and that the franchise was shopping him, it marked the end of an era for the young club.

Nash had helped get Columbus into the playoffs for the first and only time in franchise history in 2009. The team barely had time to grow any playoff stubble as the Jackets were sent home in four games by Detroit.

Dallas Stars

Dallas Stars fans can look at Brian Marchment as the creator of some of Dallas' most painful moments, but hockey fans should remember that there wasn't always hockey in Texas.

The self-proclaimed "State of Hockey," Minnesota, let their team leave for the Lone Star state in 1993 after several years of poor attendance and bad management.

The promise from the NHL of a new franchise was brought to fruition in 2000, but for the next seven years, NHL hockey ceased to exist in Minnesota.

Detroit Red Wings

I think there is a fair argument that could be made that while this incident snapped the Detroit Red Wings to life and helped galvanize the team, it was still painful, both literally and figuratively.

The Avalanche would add insult to injury, quite literally, by eliminating the Red Wings from the playoffs in 1996.

Detroit had cruised through the regular season with flash and style, setting an NHL record for regular season wins with 62. They had just defeated the St. Louis Blues in seven games with one of the most memorable goals in franchise history.

Then, in came the Avalanche, who defeated Detroit twice at home, where the Wings had lost only three regular season games. In Game 6 at Colorado, Claude Lemieux hit Kris Draper from behind, essentially breaking his face.

The Avalanche went on to win the game, the series and eventually the Stanley Cup. The hit from Lemieux began a blood-feud between the two clubs, producing some of the most intense and memorable hockey in NHL history.

Edmonton Oilers

The Edmonton Oilers had an all-star team in the mid-1980's and won four Stanley Cups in five seasons. The interruption in their ongoing Stanley Cup parade rests infamously on the shoulders (unfairly) on Oiler rookie defenseman Steve Smith.

In a tie game with the Flames in a hotly contested seven-game series, Smith ricocheted a pass off the leg of goalie Grant Fuhr for what would be the game- and series-winning goal for Calgary. The Oilers probably shouldn't even have allowed themselves to be in that position, with all the talent they had on their roster.

The rivalry matchup with Alberta neighbor and some inspired play by Mike Vernon, Lanny MacDonald and Hakan Loob kept Calgary in the series. Smith's costly error made the difference in the series and in NHL history.

Florida Panthers

It's rare that a single game can represent the most disappointing moment in a franchise's history. It could be said that the Florida Panthers should have been happy just to be there in the 1996 Stanley Cup Final against such a powerful Colorado team.

The Panthers delayed the inevitable as long as they could in Game 4. John Vanbiesbrouck used some sorcery and incredible play to keep the Avalanche at bay as long as he could. The third overtime was too much for the outgunned Panthers, however, as Colorado took home their first Stanley Cup.

Los Angeles Kings

Of course we all know that the center of the hockey universe is Los Angeles.

Stop laughing.

It may surprise some of you to know that the City of Angels wasn't always bubbling over with hockey fever.

Seriously, stop laughing.

All jokes aside, the last time the Kings' bandwagon was this full was in the 1993 playoffs when Wayne Gretzky came within a Marty McSorley stick blade of bringing the Stanley Cup to Los Angeles.

OK, so it was more than an illegal stick that cost the Kings. We could hang the loss on Barry Melrose's hair, Kelly Hrudey's headband or just general apathy from the Los Angeles team.

A hungrier, more determined Montreal team added another banner to the fabled Canadien rafters, while an arguably more talented Los Angeles roster held on to excuses and missed opportunities.

Minnesota Wild

In their 12-year existence, the Minnesota Wild haven't really had the opportunity to know too much heartbreak. Now that the team has opened up their checkbook, expectations will follow.

In 2002-03, the Wild made an impressive run to the Western Conference Finals before being swept by the Ducks.

It's hard to feel the pain of loss when you have the "Cinderella" name tag, but the Wild-Ducks series featured two improbable clubs on an unbelievable run. J.S.Giguere stopping 122 of 123 shots in the four-game series would have been more frustrating and absurd to me than painful.

Montreal Canadiens

The Montreal Canadiens are typically the providers of the heartache for other teams, but they have gone through their share of painful losses. Possibly the most painful, at least recently, was the only time an opponent has won the Stanley Cup on Montreal home ice.

In 1989, the Canadiens had the second best record in the NHL behind the Calgary Flames,  whom Montreal defeated in the 1986 Stanley Cup Final. The two teams would meet in the Final again, with the outcome being reversed. Calgary and Lanny MacDonald's mustache would lift the cup on the Montreal home ice with a 4-2 victory in Game 6.

Nashville Predators

Another franchise with a relatively short and un-storied history would be the Nashville Predators. Only two seasons ago, Nashville was advancing to the second round of the playoffs for the first time in franchise history. The Predators eliminated the Red Wings in 2011 to reach the second round again but lost to the Phoenix Coyotes for the second year in a row.

Ryan Suter left for Minnesota, but that wasn't a real surprise.

The biggest Predator heartache occurred when the rumors of the franchise relocation began in 2007. Shady ownership dealings, including the Del Baggio fraud in 2008, had the Predators headed everywhere from Hamilton to Kansas City. The ownership group has since been stabilized to allow the team to stay in Music City.

New Jersey Devils

Wayne Gretzky calling the franchise a "Mickey Mouse" organization and the Christmas tree uniforms were both painful in the early days of the New Jersey Devils.

The instability of the early franchise years saw the team, which originated as the Kansas City Scouts and then the Colorado Rockies, struggle with attendance (Kansas City) and ownership (Colorado).

The 2000-01 season had the defending cup champions reaching the Stanley Cup Final for the third time in six seasons to face the Colorado Avalanche. The series featured two of the best goaltenders in NHL history, with Patrick Roy getting the better of Martin Brodeur in seven games.

New York Islanders

The New York Islanders franchise history reads like a tale of two teams. Founded in 1972, the Islanders had success within their first three seasons. It would take them until the 1979-80 season to sip from Lord Stanley's Cup in the first of four consecutive titles.

The emergence of the Edmonton Oilers during that time saw an overlap from the Islanders, who won their final Stanley Cup in 1983 over Edmonton. The Oilers would return the favor the following season by winning the first of their four cups in the next five years.

It's hard to consider the loss to Edmonton painful, especially coming out of an era of excellence, but it seemed to mark the beginning of doom for the franchise.

New York Rangers

Until 1994, the New York Rangers were waiting to lift the Stanley Cup for 54 years. That time was filled with plenty of missed opportunities and heartache.

As an Original Six franchise that plays in one of the most famous arenas in the world, the Rangers were all style and no substance for the better part of five decades.

The Rangers managed to reach the Stanley Cup Final three times in that span, with the most crushing defeat coming at the hands of the Montreal Canadiens in 1979. The Habs led the Rangers two games to one in Game 4, which went to overtime at Madison Square Garden. A win would even the series headed back to Montreal.

It was not to be, however, as Serge Savard backhanded the winner and broke New York's heart. Montreal would go on to win the series four games to one.

Ottawa Senators

While I'm sure that the original Ottawa Senators founded in 1883 had plenty of disappointment, I'll be focusing more on some modern Senator heartbreak.

Insert Alexandre Daigle or Radek Bonk joke here.

In 2007, the Senators reached the Stanley Cup Final for the first time in 80 years, which is less impressive when you realize that for many of those eight decades, there wasn't a team in Ottawa.

While the 2007 edition of Ottawa featured the "CASH" line of Captain Alfredsson, (Jason) Spezza and (effing superstar Dany) Heatley, the Sens were unable to overcome Anaheim and J.S. Giguere, who again channeled his inner ninja to lead the Ducks to their first Stanley Cup.

Philadelphia Flyers

The Philadelphia Flyers have certainly known a storied history. On a personal note, the most painful moment in Flyers history was when they abandoned the Cooperalls, but I think I stand alone there.

I'll reach back to two years ago for my most painful Flyers loss. The 2010 Stanley Cup Final between Chicago and Philadelphia featured two hungry franchises that were both thirsty for success.

Patrick Kane's anti-climatic mystery goal to end it in sudden death prolonged the agony for the orange and black faithful.

Phoenix Coyotes

The Phoenix Coyotes history is filled more with controversy and instability than anything else. Last year's team took an improbable run through the playoffs, falling just short of a Stanley Cup berth. While the Conference Finals were unfamiliar territory to the Coyotes, also unfamiliar have been the sellout crowds.

Hockey returned to Winnipeg in the form of an ill-conceived expansion franchise from Atlanta, and many are wondering and waiting for the same fate for Phoenix. While Winnipeg is one of the smaller markets in the NHL even today, its fans were incredibly loyal. With a small arena, and rising salaries and expenses, the team was sold to an investment group in Arizona for the 1996-97 season. When the NHL returned to Winnipeg, the Manitoba masses rejoiced and never (seriously) considered calling their team anything else.

Pittsburgh Penguins

Without question, the most painful moment in Penguins franchise history was when Mario Lemieux announced his retirement from hockey. While his career was filled with plenty of spectacular moments that took our breath away, "Super" Mario's body let him down.

He probably could have topped almost every record that Gretzky broke or set.

Instead, we are left to cherish the highlight reels and memories that Lemieux left behind.

San Jose Sharks

The San Jose Sharks have been a model of what an expansion franchise can become. It took them only a couple of years to make not only the playoffs but also an impact in the playoffs, with a monumental upset of the Detroit Red Wings in 1994.

Since then, the Sharks have flirted with, and owned, on occasion, the league's best record.

Such was the case in 2008-09, when the top-seeded Sharks faced the 8th-seeded Anaheim Ducks. The Sharks had set a franchise record for wins (53) and points (117) but fell flat in six games to their division and interstate rival with the decidedly less menacing name.

St. Louis Blues

While pessimistic readers might think that I'm throwing this in here as an opportunity to enjoy one of my all-time favorite Red Wing moments, this might be one of the most crushing moments in St. Louis playoff history.

The St. Louis Blues had played the top-seeded Red Wings even through seven games, matching them punch for punch before Steve Yzerman's goal in the second overtime.

Honorable mention for St. Louis would be losing in the 1986 Conference Finals to Calgary after winning Game 6 in the "Monday Night Miracle" game on Doug Wickenheiser's overtime goal.

Tampa Bay Lightning

After making an improbable but impressive run through the Eastern Conference, Tampa Bay ran out of goals in the final game of the 2011 Conference Finals. In an amazing goaltending display from Tim Thomas and Dwayne Roloson, the Boston Bruins' Nathan Horton broke Tampa's hearts with the only goal of the game.

Toronto Maple Leafs

This time, Kelly Hrudey's headband was on the winning side of heartache, as the Los Angeles Kings, led by Wayne Gretzky's hat-trick, slipped past the Toronto Maple Leafs. Doug Gilmour had the season of his life in 1992-93 and had an incredible effort through the playoffs.

A non-call of a high stick to Gilmour from Gretzky in Game 6 preceded a Gretzky winner to stay alive and force the seventh game.

Vancouver Canucks

I'll steer clear of the 2011 Stanley Cup Final for those Vancouver Canucks fans who are still a little raw and sensitive and rewind to the 1994 Final against Mark Messier and the New York Rangers team of destiny.

All right, no I won't.

They both sting, but the 2011 scab is a little more fresh.

Washington Capitals

The Washington Capitals are no stranger to an early-round playoff loss or to falling short of expectations.

An especially bitter season was the 2009-10 campaign, when the Caps became the first non-Original Six team to top the 120-point total. They also led the league in scoring with 313 goals.

Led by high-scoring Alex Ovechkin and his 109 points, the Capitals headed into the postseason against the Montreal Canadiens and took a 3-1 series lead.

The Canadiens roared back, summoning the ghosts of Les Habitants and rode the hot net-minding of Jaroslav Halak to steal Game 7 in Washington despite being out-shot 42-16.

Winnipeg Jets

I'll spare anyone the disappointment that might exist in Atlanta over the Thrashers leaving for Winnipeg. There might be some residual pain that the Jets elected to go with a new and improved "Jets" logo and decided to not wear red pants anymore.

The reality is, almost all of the angst from the Jets leaving town in 1995 is gone, leaving nothing but plenty of frequent flyer miles as the Jets await realignment.