The Most HEARTBREAKING Moment For All 32 NHL Teams!

No matter what NHL team you cheer for, at some point you’ve had to endure utter heartbreak as a fan. It could’ve been a crushing playoff loss, or perhaps the departure of one of your team’s top stars.
Today we’re taking a look at The Most Heartbreaking Moment for all 32 NHL Teams!
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All of our videos are edited following the "Free Use" Guideline of KZbin as well as the Canadian and United States copyright acts.

[@operatorcobalt2700]

Henrik Lundqvist DID NOT fail his team his team failed him I don't care ik it's click bait but you don't do that. Most disrespectful thing I've ever seen about Hank

[@miikamessi]

Everyone can have their opinion. What u gonna do?

[@briansantarossa2331]

Team game. He failed them, they failed him

[@operatorcobalt2700]

@@miikamessi it's literally not his fault Hank saved 13 gsax (goals above expected) in that whole playoff run the rangers score -12 xgf (expected goals for) literally his team scored 12 less times than they should have.

[@operatorcobalt2700]

@@briansantarossa2331 it's literally not his fault Hank saved 13 gsax (goals above expected) in that whole playoff run the rangers score -12 xgf (expected goals for) literally his team scored 12 less times than they should have.

[@Rorschachqp]

As a Kings fan, I believe that 2014 team had no business to be in the 2nd round, let alone be conference champs. It was all Henrik.

[@notNajimi]

the arizona coyotes situation deteriorated so fast that this video basically went out of date last night when they played their last game in AZ…

[@criminalrappergreasygod8886]

King Henrik is such a legend. He’s a big reason why I’m a goalie fan. Sure wish he was able to hoist the cup.

[@dw1784]

As a Pens fan, I have mad respect for Henrik. I know Fleury and him dueled it out for career victories for many years and clearly Fleury won that battle. But, as much as I love Fleury, even to this day, I would have traded him for Henrik if given the chance. Fleury just had a better team around him to win more games (and Cups) during the same time period.

[@ethanparker7900]

at least he got to go to a cup final

[@ImDembe]

@@ethanparker7900 Making the finals is not even in the same universe as winning it.

[@ethanparker7900]

​@@ImDembe but at least he got to experience going that far cause some people don't get to go that far and if they do some dont get to even play a single game in it

[@GeofftheTurkey]

As a wings fan I’d have to disagree on the most heartbreaking moment. I would say it has to be the car crash that took out Vladimir Konstintinov (sorry if I spelled that wrong).

[@HandlethisYT]

That is for sure the most off ice heartbreaker the wings. Like Pelle Lindbergh for the flyers.

[@tvelis513]

Was going to post the same and saw you beat me to it! It’s Vlad for sure and not to forget the trainer Sergei Mnatsikonov

[@neilplace8522]

Yep that was stunning and brutal. I remember my whole family just sitting around crying. Probie dying hit us hard too.

[@uprebel5150]

Yeah, that was painful.

[@lesevesel2898]

That was a trigger moment for the Wings that put them over the edge against the Avs. But yeah, Vladdie getting injured because of a sleep-deprived limo driver was devastation.

[@higgy04]

As a Penguins fan, it was heartbreaking to see Dave Volek score for the Islanders in OT in Game 7 of the 1993 Wales Conference Semi-Final to eliminate a Penguins team looking to three-peat. What was worse was seeing Tom Barrasso's career fall apart. After that goal, he couldn't stop a beach ball in most games.

[@brendenstuder6119]

Let's not forget the non-call hook by Jagr of all people on Malkin in the 2013 conference finals that lead to the gaming winning goal in that sweep. I remember being really choked about that, and it is honestly part of why I hate Boston so much.

[@michaelzilkowsky2936]

As an Islander fan, it was exhilerating to see Volek score not only the winning goal but that beautiful snap shot to the short side on the drop pass by Ferarro; as Dick Irvin said in his color commentary, 'you see them practice that [ 2 on 2 crossover drop pass drills], often they don't work']. Having said that, I can understand Barrasso's trouble in and after that game. He got hosed on the Thomas goal, the bright boards leading to the puck darting out quickly to Thomas on the edge of the crease, Barrasso had no chance [that awful clearing pass by Samuellson was the same as Snepts' clearing pass intercepted by Bossy in the 82 Final]. Then the goal by Hogue.... how many times did Don Cherry say on Coaches Corner, 'keep your stick out of the way!'.... If the defenseman hadn't deflected the slapper from 60', Barrasso would have made the easy save.....but the knuckleball action put on the puck totally handcuffed Tom and he ended up flopping and laying on his back as the puck dribbled in..... I think that goal shook him up more than either of Volek's goals.

[@john-ic9vj]

​@@brendenstuder6119the high scoring penguins scored 2 goals THE ENTIRE SERIES. Maybe not the most hearrbreaking moment, but definitely the most embarrassing

[@jross859]

Also game 7 1996 east final vs Florida ranks up there

[@blackace5744]

The 2010 finals loss wasn’t the most heartbreaking moment in Flyers history. The most heartbreaking moment has to be the tragic death of Pelle Lindbergh. He was their next Bernie Parent and only months after helping the Flyers get to the 1985 finals and winning the Vezina he died in a car accident. I’m pretty sure his number is still unofficially retired and even 30+ years later people discuss him as a what if. If it has to be an on ice thing I would argue the Scott Stevens hit on Eric Lindros effectively ending his Flyers career and changing him for good was more heartbreaking. I think that 2000 Flyers team was actually more talented and had a better shot at the cup than the 2010 finals team.

[@stevencooke6451]

Those are true heart-breaks. Many of these aren't even sports heart breaks. You could add Barry Ashbee to that list.

[@bentompkins927]

Let’s be honest this video could be just as long and only list flyers heartbreaks

[@AnimalClans]

Sharks fans are way more bitter about how they lost in 2014 than losing the Final in 2016. Also, Seattle wasn't making their return to the NHL. They never had an NHL team. They did win the Stanley Cup in 1917, but they were with the Pacific Coast Hockey Association. The NHL was founded the next year.

[@neilplace8522]

Surely the Pens biggest heartbreaker was when Mario announced he was ill. Im a Wings fan but that moment transcended hockey & can still choke me up.

[@uprebel5150]

But when he came back he was a force to be reckoned with. Wings fan here too.

[@tomplum5644]

pens 2018 loss has NOTHING on 93 or 75 losses to the islanders

[@randytroy9727]

As a pens fan it was pretty heartbreaking to see them miss the playoffs in 17 years.

[@tamueid2488]

Arizona is about to have their new most heartbreaking/heartwarming moment on their final game

[@waynehough13]

poor click bait with the thumbnail, Lundqvist never let the Rangers down.. will go down as one of the greatest goalies ever not to win the cup

[@jayvashisht684]

*the greatest

[@MarkLewis-qe4pj]

100 percent

[@stevenmcnabb9185]

The most heartbreaking moment for the Philadelphia Flyers was Pelle Lindbergh's fatal car crash in 1985. No loss on the ice can ever compare.

[@misterwhythewhat1416]

I would of thought detroit's worst moment would be the vladimir konstantinov limo accident.

[@GarretMartinn]

I mean, what do you expect from somebody who can’t be bothered to look up pronunciations of players. Actual in-depth research? Come on now.

[@deadshotdaquiri6383]

I was rooting for the Kings to take their second cup in 2014 but man, Lundqvists reaction broke me.

[@ghostdog5441]

Lemeuix getting cancer. Brutal.

[@Rashman101]

When the JETS left Winnipeg after the 1996 season. That was the most painful sports loss by far.

[@neilplace8522]

I’ll buy that. Losing your team has to be the ultimate heartbreak.

[@anthonypastore7518]

Another devastating moment for Habs fans was the death of Howie Morenz

[@dw1784]

For me it was Pittsburgh losing to Detroit in '08. I have been a Pens fan since I was 6 and saw all 5 Cup wins. Losing to Detroit was the first (and only) time I've ever witnessed a Cup Finals loss as a fan. Hossa was inches from tying it at the buzzer and sending Game 6 to OT. It was so close, yet so painful!

[@brendenstuder6119]

But we got our win back the next year so it is ok.

[@tythegolfer6279]

Pens Suck. Caps Rule.

[@clippedwings0]

That whole series I kept thinking, "Hossa is the only guy who really wants this", he was playing his heart out. When he left for Detroit after that I couldn't really blame him, and I was glad he did eventually win with Chicago (and not with the Wings against the Pens).

[@dw1784]

@clippedwings0 It was bad karma when Hossa lost to Pittsburgh. However, most people forget that the Pens backup in '08 was Ty Conklin. Who was the Wings backup in '09? Ty Conklin lol He suffered the same fate as Hossa. At least they could cry together. I was mad at Hossa for leaving and laughed when it bit him hard. But like you, when he won in Chicago and eventually won 3, I was happy for him. I don't believe he ever won a Selke trophy (I could be wrong), but he was that good without the puck as well. One of the best 2-way forwards to play the game. He was overshadowed in Chicago, because he wasn't one of the young guys, but he was equally as important, and I respect him for that.

[@john-ic9vj]

Absolutely not. The penguins had the revenge the next year

[@danielficarra2557]

That call in 03 still gives me chills. I went to his retirement ceremony best moment of my life

[@blakeallen2721]

As a Caps fan, 2017 kinda broke me, but 2010 (along with other years in the 2010s) really laid the ground work. To this day I cant even hear the name "Halak" without feeling a rock in the pit of my stomach.

[@AHFAN11]

a kid I went to school in grade 7 with was a canucks fan and was rooting for them to win and basically refused to accept any opinions of them possibly losing. I was convinced they would choke and choke they did. he was pretty grumpy that week.

[@vanillaflounder376]

2021 is the most heartbreaking for isles fans and no one will ever say otherwise. Nothing compares to that team😢

[@Damphouse]

As an Avs fan, the 02 WCF is even worse for me. I've legit wiped that memory out of my brain completely

[@justin_whitewolf2538]

yeeep, poor Patrick Roy getting smoked that last game made 13 y/o me have a crisis lol

[@claudelemire2451]

Another turning point in the 1993 Stanley Cup finals Los Angeles bad memories: Montreal was trailing in the last moments of game 2 and the Canadiens coach Jacques Demers made a bold and desperate move to ask to measure the curve on a stick. In Game 2 with the Kings up 2-1, Marty McSorley was caught with an illegal stick, which led to the Canadiens tying the game on the powerplay and winning it in overtime. Canadiens player Eric Desjardins was the first defense man to score a hat trick in Stanley Cup finals. That was the year Montreal won 11 overtime games out of 20 games. Still a record.... what a rush.

[@collinquinlivan9713]

As a Blues fan I would say the 1999 season when Roman Turek let up 3 goals in less then 2 minute in game 7. They were the best team in the league that year and possible the best blues team period. They were absolutely stacked with household names. I thought for sure that was gonna be of first cup. Instead we were left waiting another 18 seasons

[@jarrodhen8063]

WOW!!! You thinkfor Detroit the Draper hit was more heartbreaking then a player getting paralyzed a few days after winning the cup?🤔

[@dominicscarangelli-zc2mc]

As a penguins fan it was the 2023 season where we did not make the playoffs for the first time in the Crosby era

[@SigmaRho2922]

The conference final loss for the Islanders in 2021 was marred by an 8-0 loss to Tampa in game 5 on the road. They later became the second team in nhl history to force game 7 after losing a game by 8 goals or more in a playoff series. But like the other team they would lose game 7 on the road with the final score in that circumstance being 1-0.

[@williammartin2349]

Pittsburgh winning in San Jose was the first of the back to back not the second

[@walkingcorpse2704]

Habs fans might agree with you but they fail to realize that it was a massive oversight by the GM and Owner of the team to ignore the OBVIOUS bad chemistry between Tremblay and Roy.

[@johnsimpson3927]

Yes exactly. It's never talked about how much they did not like eachother. Or how we at morning skate Roy threw a pick and Mario after some comments

[@walkingcorpse2704]

@@johnsimpson3927 Tremblay would always make fun of how Roy spoke, that's why they never got along.

[@QuackAttack]

This happened before my time but even now, it really does make one wonder what the people at the top were thinking 😵‍💫

[@walkingcorpse2704]

@@QuackAttack not only that but he originally wanted to play for the Nordiques (now Avalanche) kinda like how Eric Lindros never wanted to play for the Nordiques but the GM drafted him anyways

[@skithunter8990]

That Vancouver game was painful to watch. I shut it off after the first period , then watched the smoke rising from downtown a couple hours later.

[@jaredslootweg6777]

Man those Vancouver riots were brutal. As someone who has lived in BC all my life, the fact that the city with our own park and the trophy that was named after lord stanley should've been an easy win. I don't condone the riots by any means, but I definitely can understand why so many people were heartbroken and dissapointed. If the Vancouver Canucks win the Stanley Cup playoffs for the first time, you can imagine the dedication it would take to have Lord Stanley be a jovial cheering and showboating.

[@chinaclause914]

As a Blackhawk fan 2017 should have been Ottawa that team will forever have my heart for being so close because if they would beat the pens they’d definitely beat the predators

[@U_Jelly]

As a Hurricanes fan, i felt like most of us knew we couldn’t beat the Panthers last year

[@mr.turdlybird4387]

Rangers in 2014 were never supposed to win but in 2017 they had the lead over Ottawa most of the series

[@A-man-Capitals301]

Jackets won series in 19 not 18...

[@LordBitememan]

Wings, the hit on Draper???? Dude! The Limo crash that ended Konstantinov's career!

[@Streetkillz13]

I don't know what's worse this or the Flyers. Most heartbreaking Patrick Kanes goal, not Pelle Lindbergh's death in his mid 20's.

[@darrencole97]

Anything that caused the Islanders to go to Brooklyn is bad. Sadly I only have gotten to see them live despite being an Islanders fan since the mid 70’s.

[@WarioSaysSo]

17:38 - Pittsburgh Penguins = There most Hearthbreaking is a tie with two other events: 1st it was Mario Lemieux original premature retirement in 1997 due to all his pain and injuries. Lemieux would have broken so many record otherwise.... 2nd is the 1992/1993 season Play-Off Exit. The Penguins was a natural big favourite to win again the Stanley Cup for a 3rd straight time = 3-Peat after having had a franchise greatest season crowned with the President Trophy and Lemieux despite having missed 30+ games still won the scoring league, MVP and more + Jagr & Francis & Stevens having super season as well. And in 2nd round they dropped the ball and all of a sudden lost to the NY Islanders, who was not a great team in the 90's. This was a Pens year!!! This hit was much-much heavier then the 2018 Play-Off exit as not only had the Pens not been that dominant during the season (5th in East) but more so there play was stretched from being a Cup favourite among there rivals. They had looked worn out and even if Sidney Crosby & Malkin was on fire, same can't be said of the whole team. Also no Pens playe rmade any of the All-Team All-Stars.

[@higgy04]

Dave Volek ruined Tom Barrasso's career as well as his own in 1993. Barrasso couldn't stop a beach ball in the seasons following that disastrous moment and Volek retired dealing with back issues during the 1993-94 season.

[@dw1784]

I'm also a Pens fan. I was only 8 when Pitt lost to the Islanders that year so I remember watching but the emotions have faded a bit. Big Lemieux fan. I always looked back and wondered how many points he could have had if he had played 1500ish games. He was better than Gretzky in the 90's when I watched him. He might have even made Ovechkin's chase take longer as he might have passed Gretz in goals. I definitely agree with your points, but you forgot about the only Finals loss in their history in '08.

[@WarioSaysSo]

@@dw1784 I fully agree!

[@WarioSaysSo]

@@higgy04 That had gone under my radar! About Dave Volek

[@dw1784]

@@higgy04 Barrasso always made me nervous. I never saw him as a great goalie, just good enough (sometimes), yet he just got inducted into the HOF, so I guess many experts disagree with me lol I did not know that about Volek. I almost corrected you on his career, until I looked it up to confirm what I was about to say, only to find out I got him mixed up with another player, and you were definitely correct lol

[@CODEWHITESPAGHETTI]

The Toronto one should be different. It should be when Gretzky high sticked someone in there is no call which led to Toronto, losing the series and missing the finals against Montreal. The dream matchup.

[@grousetheghoul2754]

EXACTLY !!!! The NHL wanted the Kings to win the Cup and an all Canadian final would've been a financial disaster.

[@CODEWHITESPAGHETTI]

No Canadian team will win any time soon

[@chief3619]

As a MN fan, I’d say it was more heartbreaking to see our franchise leave and see them win a cup in that Dallas clip you had earlier. As a close second, since we’re talking about the wild and not the north stars, I’d say the Brent Burns trade. Every piece of that trade is no longer on this team and Burns is still, while slowing down, questing. He may never get it but, I’d assure you we never will either.

[@jakeswick1843]

For Pittsburgh, What about the year where they blew a 3-0 playoff lead to the New York Islanders in the playoffs

[@rdspam]

When your most heartbreaking moment is falling short of a third straight cup, you’re doing pretty well (though it wasn’t).

[@hectic105]

As far as that moment from the Flames/Lightning game goes, it was the right call. I’m a Flames fan who was heartbroken at that series loss, and I remember how angry people were about that, but the camera angle showing the puck potentially being over the line was misleading a bit. Given the angle of the camera, it’s impossible to deduce where exactly that puck was when we see the gap between the goal line and the puck. It’s POSSIBLE it was over, but by no means was that clip definitive, which is what it would have needed to be. If the camera was directly over the goal line and we had a clear shot of the puck being past the line (which we didn’t in the actual overhead camera) then I’d say the complaints are legitimate. But the only camera that had a clear view of a puck was the one from that angle shown and it’s just not enough. Besides, the Flames were burnt out at that point. Iginla was being covered so much that he was a non presence for those last couple games and the rest of the team just couldn’t muster the energy anymore. There’s a lot to blame the series loss on, that one moment just isn’t actually one of them I think.

[@Frankingatoryt]

Update: Arizona losing the Coyotes

[@walkingcorpse2704]

Here's the thing, Krys Draper and Claude Lemieux BOTH stated that it was actually Kozlov's hit on Adam Foote that started the rivalry between the wings and the Avs

[@neilplace8522]

I remember it well. Kozie slammed his face into the glass. What a time to be a hockey fan!

[@walkingcorpse2704]

@@neilplace8522 I hope y'all make it to the finals so we can have our first rematch since 2008

[@ByzCathGAA]

UPDATE: Arizona Coyotes most heartbreaking moment. They are no more…they leave for Utah. However, they had a hell of a final home game against the Oilers. *Also I find it fitting the worst for the Avs involved the Wings, and the worst for the Wings involved the Avs.*

[@leehumphries4325]

Disagree about Dallas. They were a total underdog that season and just lucky to be there. To me the most heartbreaking thing was letting Modano walk and wear another sweater.

[@mrmoose7500]

as an isles fan, its game seven in tampa, losing 1-0 on the only shorthanded goal in both regular and post season.

[@AMan_629]

I disagree with the islanders one. The game 7 shutout vs Tampa in 21 was my saddest day as an isles fan. With that beat up, not good habs team waiting for us in the cup finals, it truly felt like that was our year. Not only that but it was the islanders’ true last chance to bring glory to the old barn. It was the only season since 83 that the isles had an actual chance to get it done. To lose on a short handed goal in a 1-0 game was the most heartbreaking experience I’ve had as a sports fan. Especially with the context added after the fact. Since then, missed playoffs in 21-22, made playoffs by 1 game, first round exit in 6 last year, made playoffs by 3 points w/ a losing record and will most likely suffer another 1st round exit. With no prospects to look forward to, bad contracts all over and a gm w/ the best job security in the world who doesn’t know when cut his losses. It seems like this franchise is on the path to another 20 years of misery and has nothing to show for it. At the height of this core they’ll be remembered as “the team that was 1 power play mistake from winning a cup”.

[@ryfiore]

The Pens one was pretty heartbreaking. For me personally, the most heartbreaking moment was watching Vegas take Fleury.

[@LOLMAN9538]

Honorable mention for the Bruins: The Collapse (2023 Stanley Cup Playoffs R1 vs Panthers)

[@larrykinnard]

You could say that the sweep of the Bolts against the BJ's was a godsend. Look what happened two years after, two Back-to-Back Stanley Cups!

[@brendenstuder6119]

The 2010 reverse sweep that Philly pulled on Boston I think is more of an eye sore to Bruins fans than losing to one of the best teams that ever hit the ice (even if they were up in the 3rd period) in 1971. The Columbus Blue Jackets, their entire existence is just heartbreaking. The Leafs I think the first round losses to the Bruins get a bit of a recency bias, because that non-call high stick by Gretzky in the Conference finals in 1993 left Leafs fans irate for years, and they haven't been back to the Conference Finals since. Otherwise I'd say these are pretty good picks.

[@grousetheghoul2754]

Exactly, Fraser stole from the Canadian people when he stole an all Canadian final by making sure LA won that series. And it was indeed the worst call in NHL history.

[@monicamason3414]

I agree with the Flames loss. Though to this day I can say I know where I was when the Flames DID win and my husband not only say he can't; he has the riots in his history of Canuck love.

[@type4647]

You're wrong about a few things likely do to your age. Without a doubt, the most heartbreaking moment for the NY Islanders happened in game 3 of the 84 finals--2nd period ...Messier scores "the goal". The Oilers were unleashed after that for good. Its the moment the Isles dynasty died. kzbin.info/www/bejne/lXKTq6GFedZmqsk

[@rossb18isles]

Nah the islanders has to be game 7 2021. I cried so much after that game

[@TheManTheMythD]

Not a Coyotes fan, but for me the most heartbreaking moment for them was that time Shane Doan almost scored on a delayed penalty against the Coyotes. Somehow the puck got shot way up into the air, and he tipped it down the ice toward the empty net. Since it was above everyone's head, technically it didn't count as possessing the puck, so it didn't trigger the whistle. The puck slid down the ice and missed the net by a few inches. Would've been amazing. Probably the only time someone almost scored with a shot on net when they weren't even allowed to have the puck

[@kevinmorrissey2105]

Isles fan is definitely 2021 game 7 conference finals vs Tampa. Lost 1-0 on the only shorthanded goal we allowed all season. We would’ve killed Montreal

[@islesfan186]

For the Islanders - Game 7 in 2015 was in Washington, not at the Nassau Coliseum, and that was HARDLY the biggest heartbreak. I’d put Tavares leaving for Toronto way ahead of losing a game 7 in the first round in an opponents home rink

[@stevencooke6451]

Many of these hardly count as heartbreaking. For instance, the remarkable run of the Panther in 1996 leading to a sweep by the Avs was disappointing, but hardly shocking. Florida's biggest disappointment would have been swept by their cross-state rivals after compiling one of the best seasons in NHL history. But even that is not really heart-breaking. To be heart-breaking either an apparent victory has to be taken from you, or a beloved player is traded or leaves the team. Or, truly heart-breaking: a player actually passes away. This feels like click bait in many cases.

[@tythegolfer6279]

Rangers beating Caps or Pens beating Caps were more heartbreaking. Holtby i felt so bad for.

[@Whirlpool730]

18:45 nah, it's gotta be getting reverse swept by the Kings in the first round in 2014. Watching your rivals not only do to you what has only been done 4 times in nhl history, but to then watch them win it all was absolutely that franchises lowest point.

[@darthmid_gaming7875]

As a wings fan, im pretty sure we would all agree vlady was the most tragic thing to happen.

[@olmrgosh1128]

My Vancouver Canucks team in 2011 was a dark day in British Columbia

[@edwardofgreene]

As a Blues fan the most heartbreaking moment was not the Yzerman goal, though that one does rank high on the list. For me it was 1983 when I read the front page headline in the paper saying that Raulston Purina was selling the Blues to a Saskatoon group!! Maybe it doesn't count because in the end it didn't happen. None the less, at that moment, I was never more heart broken as a fan!! Nothing compares to loosing your team, or even the fear of it!!!!

[@johnhaley9706]

Ralston Purina then refused to show up for next year's draft causing St Louis to forfeit their high 1st round pick and the NHL to sue them. You could also pick as worst, the fiasco w Brendan Shanahan and losing Scott Stevens by court order. I was so pissed at Ron Caron.

[@thomaskeane5723]

Wrong for the Penguins. The 1993 Game 7 loss to the Islanders, when Kevin Stevens fell to the ice fully face-first after being knocked out, was worse. This was after the Pens won the President's Trophy that season.

[@bavier6355]

the colorado cup coming up so much is so funny how did they manage to hurt so many teams in one run 😭

[@ziggy9114]

Man, getting swept by Columbus is tough

[@JH-jw7pu]

Seems like the Avs first cup win devastated a lot of teams on the way lol

[@toph_toff974]

As a habs fan. I am enduring af rn XD

[@Mck499]

As a predators fan, the 2017 early was completely bs. However the linesmen did follow the rules he was supposed to even though the rules were bs

[@grahamdamberger7130]

We keep saying it. Gretzky was NOT traded. He was SOLD to LA by Pocklington for $15M, but he only agreed to it if McSorley and Krushelniski joined him. So the trade was those 2 for Jimmy Carson, Martin Gelinas, prospects and draft picks. It does not directly involve Gretzky. Other mistakes I would like to point out: 1971 was Montreal's 17th Cup of 24 in its franchise history, with #18 coming just 2 years later in 1973. Also, Toronto was eliminated by Washington in 6 games in 2017 (though the Leafs were a WC team that year). 2018 and 2019 were the years they fell in 7 games to Boston after, and it wasn't just Game 7 that was their Achilles heel. Game 6 in some series were where they also struggled, setting up Game 7 (also Game 5 in the play-in series against Columbus during the bubble playoffs).

[@thunderwolfgaming7961]

As a Avs fan I would disagree that loss was though but the saddest moment was the career ending hit on Steve Moore god it was Brutal

[@Dannnyc]

As an Islanders fan it’s game 7 of the ecf in 2021

[@christopherkopke7593]

7:41 I disagree completely as bad as the hit was it’s not it’s heartbreaking is the 2013 Stanley cup semifinals vs Blackhawks blowing a 3-1 lead and losing in overtime in game seven just killed me especially since I knew the winner that series was going to win the Stanley Cup also 2009 failing to repeat and Crosby hoisting the cup at Joe Louis arena is a sacrilege

[@Ickabodxx]

Yes, that is the Kings most heartbreaking moment, but you missed the key detail. The Kings were up 1-0 in the series and by a goal with only a couple minutes left in game two in Montreal. They were very close to coming back to LA with a 2-0 series lead when Marty McSorley was given a 2 minute minor for an illegal stick blade. Montreal tied the game on the penalty, winning in overtime. The Kings never recovered in the series. To Kings fans, that stick was a curse until the cup win in 2012. Ask any Kings fan, they know.

[@Zytharros]

My most heartbreaking loss was the Canucks falling to the Rangers in ‘94.

[@cnjdev]

I disagree with the thumbnail. The Rangers failed Henrik; he didn't fail them. That 2014 Cup final was 3 OT losses in LA and the 2 games in NY split.

[@Brainfogmusic-66]

nah the most heartbreaking moment for philadelphia was when we lost lindros. i wasnt even born yet and i know that

[@edschramm6757]

Say what you will about the call on pavelski's injury, but vegas still imploded. I maintain the biggest single mistake made was Vegas's coach not calling timeout after the first goal. When Couture immediately turned to the bench and went "thats 1", TO should have been called to slow up the resurgence. Which was likely happening in some fashion with or without the penalty - their captain went down, and Thornton commanded "lets make sure he has something to come back to". If that doesnt light a team on fire, nothing will

[@ManMythLegend123]

The worst from mtl was not giving carrey price a cup.

[@GarretMartinn]

1:23 that team was in Glendale, not Phoenix. The fans really did show up in the early 2010s.

[@mood-top328]

Why Mario Tremblay why

[@Mandalor10]

One recent example for Chicago is them getting embarrassed by Nashville in 2017. Chicago won the president's trophy and were the favorites to win the cup. They would get swept by the 8th seed Nashville Predators. This officially ended the Hawks dynasty. The team would collapse and they still haven't made it back to the playoffs.

[@AnimalClans]

That Flames goal is officially inconclusive. That camera angle that shows the puck across the line only proves the puck was ABOVE the line. No angle on the goal line shows that it actually was across it.

[@Dxnger_jax]

23:43 as a Canucks fan our saddest moment is signing mark messier

[@Hockeydoge25]

He never played for you know one wants to remember so it didn't happen

[@cletusanne]

It was the Gretzky trade for me. I never went to another NHL game again.

[@joshuaneal7552]

If a player from the losing team wins the Conn Smythe, they really shouldn't present it right then and there on the ice immediately upon completion of the series, literally two seconds before presenting the Cup. When Giguere won it in '03, he wanted no part of that.

[@ChadDanforth1426]

The Patrick W trade is hilarious

[@driedpaprika_60]

Patrick R

[@nathancjarrett]

The last goaltender to raise a Cup for the Habs is Patrick Roy. They will not have another.

[@pontusbackman1863]

Islanders biggest heartbreak-The Mike Milbury era 😅

[@stevencooke6451]

Yes, hiring was a moment of heartbreak for the franchise.

[@zachsattack_2020]

im suprised he didnt use the 2007 cup final for ottawa

[@Ratel3000]

I disagree with the worst moment in San Jose's history. Kings eliminate the San Jose Sharks after going down 3 games to none in a reverse sweep. That team also goes on to win the cup.

[@beezy22]

Watched hockey since late 80s and the one thing that still unforgivable is when Montreal traded Patrick Roy to the Avalanche midway during the 1995/1996 NHL season …..that wasn’t a smart move but a steal for the Colorado Avalanche……

[@jacobsteel130]

fuck that clickbait. i get you want clicks but don’t say anything about Lundqvist. he is the only reason the rangers had success for the past decade

[@clee666]

Patrick Roy and Wayne Gretzky trade both shocked me as a kid. Also the Dallas cup-winning goal against the Sabres in was non-sense to me.

[@patrickhamos2987]

bro no xD for the Isles it's losing the Drive For Five in 85 vs edmonton. believe me.

[@markjones2854]

Islanders most heartbreaking loss is easily the 2021 loss to Tampa. They would’ve beaten Montreal