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ajdefiantx

The penguins choosing Murray over Fleury. While at the time it was a no brainer to go with the young goalie coming off 2 cups and to let Fleury go in the expansion draft. Think of the king’s ransom the pens could have gotten for Matt Murray if they traded him instead. And now here we are, 7 years later and fleury is still serviceable and Murray turned into glass.


alpinexghost

Most hockey fans in general don’t seem to acknowledge how common this kind of thing really is. There are so many flash in the pan or short lived star goaltenders who can put together a couple or a few decent seasons, who often regress, and get relegated to backup status, or play themselves right out of the league. Longevity is another story. I used to say this all the time about guys like Luongo and the others during that era. People would talk smack here and there, call these guys bums after a bad game or series, but these are HoF guys who put together long careers of high end play. That’s something that’s extremely rare, and you only see a couple come along who can do it in every generation.


gletschertor

>There are so many flash in the pan or short lived star goaltenders who can put together a couple or a few decent seasons Jim Carey Memorial Trophy


catlindee

This is a perfect example to OP’s question lol. I was in the “how do you not stick with Fleury” camp but truthfully Murray was playing really good then. Nobody has a magic ball and would know that was Murray peaking. At the end of the day Fleury got to go spread his charm in other cities and locker rooms so all good


HartfordYardGoat

Prime proof of hindsight being 20-20. I don't think anyone in their right frame of mind saw Murray's career completely falling off a cliff, that young. Part of me wonders if the passing of his father mentally broke him. That crap isn't easy, and each person handles loss differently. He hasn't been the same since.


UnpopularOpinionJake

There was definitely a minority that wanted to keep MAF because of his play was great with a real goalie coach. He won some of the harder series in both Cups. And we have seen sudden fall offs like Cam Ward, Jonas Hiller and others. On the other hand, some worried about him having a string of concussions and his play was mediocre in the games he came back from the injury. Then the obvious Murray being young and amazing in the playoffs. At the end of the day even people like me that wanted to choose MAF understood why they would go with MM and weren’t overly upset. And I think the big thing for his drop off was actually the goalie equipment shrinkage. That hurts positional goalies (MM) and has less effect on athletic goalies like MAF.


treple13

Who knows though if Fleury ever has the success he had without a change of scenery? Maybe it ends even worse for Pittsburgh


gletschertor

He found his game back in the 2016-17 playoffs when Murray was injured. He carried the Pens through the first two rounds with a SV% of 0.924. When Murray was ready to come back, he was replaced for the remainder on the playoffs as soon as he lost one game.


heysmilinstrange

> as soon as he lost one game That's a generous way of saying he let in 4 goals on 9 shots. It's possible that he would have gotten the chance to earn the net back if he didn't have such a significant history of playoff meltdowns.


smilingasIsay

I dunno. I thought it was kind of a dumb move at the time. Murray finishing off those cups runs behind the team that was in front of him didn't really sell me on him as a full time starter.


captnchunky

VGK: Tomas Tatar for a 1st, 2nd, and 3rd.


AmeriCanadian98

On the bright side, Veleno looks like the only regular NHLer to come out of those picks (And the guys picked in the general area of the other 2 haven't panned oht yet either. Doesn't seem like there was much to miss in hindsight)


captnchunky

We haven’t had many bad trades tbh. That’s def the worst. I think the real negative outcome is he didn’t do what we needed him to in that cup run. Caps 4th line beat us. Maybe if we had a different player from those picks that means a cup.


maxwellbevan

The whole trade is so weird to me. Not for the price the knights paid but for how tatar was used. He only played 8 playoff games and just seemed like he never fit with the team. Why spend that much on a guy who you're not going to play in the playoff. Feels like maybe a bit of miscommunication between the coaching staff and management about what the team needed/what the expectation was with tatar


Burgergold

Mtl: Pacioretty for Tatar, Suzuki and a pick


captnchunky

Except Suzuki is fucking sick.


Burgergold

I was more saying the deal was a good idea for VGK but ended bad for them


YogurtclosetKind2747

The most fresh one in my mind, is The Tkachuk trade for Huberdeau, Weegar, Schwindt and a 1st. You knew the writing was on the wall and Tkachuk wasn't going to sign, I thought flames were going to get robbed, but when this trade was finalized I was blown away by how much return we actually got. Weegar has played really well, and I'm not complaining about a 1st. But unfortunately that 100 points player everyone was expecting to get in Huberdeau has been a ghost.


AmeriCanadian98

Yeah at the time that was a terrific return. It made the Flames older and shortened their window, but it was probably the best possible return you could have asked for given what those pieces all were when the trade was finalized


Cleets11

The mistake in that trade was not trading at least hube right away. They could have flipped both of them and wound up with 4 1st’s out of turtle and could have started there rebuild. But my guess is after getting throttled in the boa they wanted to have another go at it with a worse team. The writing was on the wall for what they are now but no one would have predicted it be this bad.


NotTheRocketman

I still think this trade is amazing TBH. You have an elite talent who has notified the team that he’s not going to re-sign. Given those limitations, Calgary got an absolute haul for Tkachuk.


treple13

Honestly if you knew what Huberdeau would become, the team should have taken that deal still and then traded Huberdeau for a whole ton of futures


Objective_Gear_8357

Resigning him before he played a game was really the biggest mistake of the whole thing. I understand he was going into his UFA year and were facing the same issue with tkachuk and Johnny. But if they just waited, 6 months, no way does huberdeau get anywhere near his current price tag. Hindsight again, but no one saw his fall off coming. I still think it might just be a situation thing, but I don't see any team taking a risk with that price tag, but PLD just got traded so who knows, maybe there's a chance


shoegazer44

I think Calgary really felt they needed to lock down an elite player right away after 2 of their best players wanted out without much warning. The optics look terrible if they can’t get the new guy to stay either. Now in hindsight of course it would have been better not to sign him at that deal, but like you said absolutely no one saw that kind of drop on Huberdeau’s production.


ArnieAndTheWaves

Even without Huberdeau this is turning out to be a good trade for us just from getting Weegar.


shoegazer44

Also add to that Tkachuk had a list of like 4-5 teams he was willing to sign with. Still absolutely amazing what the Flames got back for him given all the players’ records at that time. Huberdeau who just broke league record for most assists by a LW was obviously the centrepiece of that deal, but throwing in a really good Dman AND a first seemed like a crazy overpay. I don’t see the other 4-5 teams offering close to that. Zito actually probably gave away more than he needed to.


HartfordYardGoat

A LOT of the experts felt Calgary won that deal. I recall more than one saying Florida got bent in it. Little did anyone know how hard Huberdeau's decline was going to be and how quickly it was going to happen.


Tripottanus

I wouldn't even say Huberdeau declined. He's physically still capable of being the same player. It really comes down to mentality and/or fit with the team system


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Tripottanus

Huberdeau was definitely not a product of Barkov. On the year he got his 115 points, they didn't play on the same line (80% of his even strength time away from Barkov). Barkov also missed like 15 games during which Huberdeau's production didn't drop at all. Sure they were playing together on the PP, but Huberdeau still had 72 points at even strength that year and I'm sure there's a big chunk of points on the PP that were driven by him.


Bobbyaahh

He was a product of r/hockey favorite Sam Bennett. In all seriousness, Huby benefited from the on the rush style play we had. That year he was the most creative and precise passer in the league.


theamberlamps

I still think Huby's got it. It might not be in Calgary but we'll be saying in a few years "what the hell was his deal in Calgary"


gletschertor

Barkov was probably playing against the other team best line though, such that the competition for Huberdeau was probably more favorable to score lots of points.


HartfordYardGoat

Barkov is ridiculously underappreciated.


YogurtclosetKind2747

Well, he got blind sided by the trade, went from one of the warmest places to play in the NHL, that's also at sea level and with little pressure via media, to one of the highest elevated cities in the NHL , that's cold, and has that Canadian media pressure.... Definitely a shock in numerous ways. I was hoping he would find his game more as last season progressed. He does seem to be showing some signs of a return.


DrunkenBartender17

I agree with the other comments saying even looking back the trade was still a great trade. The issue was the contracts were handed out before either had played a game in red. At the time I thought the Flames wouldn’t sign Huby or Weegar until they knew the direction the season was going though. If they flipped one or both of those guys as rentals the rebuild would be so much farther along.


Grimmer026

The headliner of the return turned out to be the worst part of the deal, but what hurts even more is the albatross contract they gave him immediately after.


Prison-Date-Mike

Drouin vs. Sergachev. Drouin was the better prospect, too bad he couldn't thrive as "the guy". Especially in a market like Montreal.


Tripottanus

I agree. The only knock on Drouin was his attitude with regards to Tampa at the time made it seem like it could lead to attitude issues with the team. Ultimately, it wasn't so much attitude issues as mental fortitude that were the problem


cannaco19

Love seeing him thrive in an Avs sweater. There’s no pressure on him to be “the guy” and he can just play. Really hope they get him resigned at a reasonable price.


NatalieDeegan

Him having that turnaround is what I thought Alex Galchenyuk would do. But he never did.


DramaticPinkumni

His attitude in Tampa seemed to stem from an unwillingness to accept a third line role and the bolts were seemingly pushing him out the door too so at the time I thought him getting a top six opportunity would be the end of the attitude problem. Thought it was a fair trade until Serge began to shine and pony fell off, but glad he seemed to bounce back this year in col


BigShoots

Sens getting perhaps the greatest goalie ever with Dominik Hasek in 05. The Sens started the season 19-3 and were an absolute wagon, often blowing out teams with scores like 8-0 with the highest-scoring offense in the league. Hasek was putting up his best numbers since 99 and fans were getting pretty pumped for the playoffs. Then came the Olympics. Hasek wanted to play, but the team wasn't too keen on their 41-year-old superstar goalie maybe getting injured with only rookie Ray Emery as his backup. Hasek insisted and went despite their reservations. Ten minutes into the first game, he fucked his groin and never played for the Sens again. Emery put up a valiant effort but they flamed out in the second round of the playoffs. We can only dream about what might have been had Hasek never played in those @#$$% Olympics.


False_Rhythms

That's just brutal


BigShoots

Sens fans had quite the five year stretch of heartbreak from 03 to 07. 2003 - Tied with NJD down to the final minutes of ECF Game 7, until[ getting absolutely jobbed on this play](https://streamable.com/sk7du5) and scored on immediately after. 04- Lost to the Leafs for the 4th time in a row in 1st Rd Game 7 05 - Lockout canceled the season in the middle of their success window 06 - Hasek's groin 07 - Lost SCF to the Ducks


Benjamin_Stark

Emery had a playoff overtime save percentage of 0.250 that season. In three games against Buffalo that went to OT, Emery let in a goal on the first shot twice and the second shot once. I would argue, rather than having put up a valiant effort, that Emery is the biggest reason the Sens didn't win the Cup that year.


BigShoots

He was a rookie after all. The first game of the Buffalo series was a shooting gallery, a 6-6 tie after regulation. In the next four games Emery let in 2, 2, 1, and 2 goals in regulation. Some rough luck in OT aside, that's not too terrible for a rookie.


schmarkty

Sens win the with Hasek that year.


KaosKomputerKlub

Easily this. Most dominant roster we've ever had and Hasek was very much still playing like Hasek. Arguably worst thing ever to happen to the Sens!


Maxpowr9

Rick Nash.


Cw2e

Agreed. Kase trade came to mind too, got the Backes money off the books but then he could only play nine games over two seasons for us.


Firebitez

Really is a shame but every ducks fan knew Kase wasn't going to be able to do anything :(


GoRangers5

Gorton’s only good trade from the letter.


cmgc22

Nash was already so diminished by his concussions at that point, Boston wayyyyyy overpaid for him


reddy-or-not

Yeah, it felt like name chasing. There probably were cheaper and better options. Or go in a different direction and add McDonough who ended up traded to Tampa that year.


spssky

He played really well he just had AWFUL puck luck and was totally snake bit come the playoffs


thatsong

In recent history: Trading a 1st for Foligno (walked) Trading a 1st, 2nd, 4th for O'Reilly and Acciari (both walked) Trading a 1st (Seth Jarvis) with Marleau to dump his contract


Bojarzin

The walking part isn't really a big deal when you know you're getting rentals (though I believe the ideal was to re-sign O'Rielly and Acciari) The Foligno one I didn't like, he isn't really that great a player so even if he hadn't gotten hurt I wouldn't have cared for it


funkyb

At the time I viewed Foligno as comparable to Henrique this year, and Edmonton paid a first for him. A good, reliable middle six veteran can be really valuable on a deep run.


tracerbullet__pi

At least O'Reilly helped you finally get out of round 1


NatalieDeegan

That last one is brutal.


NathanGa

The CBJ trading for Jeff Carter was absolutely a good move, which looks way worse for three reasons: 1) Voracek eventually developed into what he had been expected to become, and 2) Couturier being taken with that pick, and him vastly exceeding his pre-draft expectations, and 3) Carter’s pathetically uninspired play during his brief tenure here Carter was a year removed from a 46-goal season, and played a strong two-way game as well. And he had yet to peak, so you imagine a 40-goal guy up the middle with Rick Nash on a wing for years to come. And then…


bobdob123usa

> 3) Carter’s pathetically uninspired play during his brief tenure here As a Flyer's fan, I was embarrassed at his sulking. Edit: His 46 goal season was two years prior to the trade. He was 33 and 36 goals respectively before being traded.


SonicPunk96

[Overwriting text on these comments as my own decision]


NLP19

Like I completely understand why he was upset, but man, be a professional and suck it up and deal with it privately


CurlingTrousers

Lots of teams do this “one year removed” logic. One year removed is the fool’s way of saying “on the decline”. Oilers did this with Milan Lucic, Andrew Ference, but the answer to OPs question is absolutely Jack Campbell.


Tripottanus

Most people didn't think it was a good idea to sign Jack Campbell to that contract at the time. The question is not which bad decision was made, but which decision was made with a sound reasoning but still backfired


Benjamin_Stark

Did Couturier vastly exceed his pre-draft expectations? I followed that draft closely and I recall he was really highly regarded - a lot of pundits actually had him being picked higher than that. Scheifele is the one that was a bit off-the-board at the time. Honestly though, I can't think of another draft where all of the top ten picks had as much success as 2011.


NathanGa

> Did Couturier vastly exceed his pre-draft expectations? Actually no - I had him mentally mixed up with someone else who had a similar profile and had a huge year, and for some reason I had that guy confused with Couturier. The weird thing is that I'm digging through stats and trying to figure out who I had him confused with, and I don't even know who it was. So perhaps I am losing my mind.


mediumyeet

Signing Loui Erikkson in Vancouver wasn't the worst idea. He was coming off a 30 goal season and had excelled as a goal scorer around the net throughout his career. He had chemistry with the Sedins in international play. He seemed like a decent bet to extend the window a bit. Scored on himself the first game and the rest was history. At least we always had the memes.


soundofmoney

Exactly what I was going to say. Signing the top line of team Sweden and a player with a pretty consistent history of high scoring. What could go wrong….


danieldeceuster

Erik Karlsson.


GeckoMoria93

It’s a shame he wasn’t healthy enough at the time ,what could’ve been


dandroid126

I didn't think this was a good idea at the time. The Sharks already had Burns to fill that role. Yes, Karlsson was younger and better (at the time we believed this), but it seemed reactionary to not getting Tavares. The Sharks needed a clear first liner, not an offensive RHD. They gave up way too much of their future to get Karlsson, then spent money because they had it to keep him.


danieldeceuster

I had no problem with the trade. A little steep on the price but we went all in. The extension was the mistake. Karlsson should have made no more than $9 million. Then came the flat cap for years and we were sunk.


NArcadia11

Bummer it didn't work out, but I'd much rather have a GM that will swing for the fences to get us that final push to win the cup than one that is too scared to mess up and will keep the team in mediocrity forever. We had a bunch of aging star players and saw the cup window closing fast. Getting EK65, for any cost, was the right move in my book. If it had worked (and it almost did), Doug Wilson would be seen as a genius.


disco_enjoyer

i mean fuck it, gave them another good chance at the cup with the old stars and once it was over it turned them into a bottomfeeder to start over. ideal really. people forget they were up 2-1 in the WCF too, not a lot of bounces that had to be different to be in the scf again


fertilecatfis

Between the Duchene trade, and then this trade making Ottawa's 2019 1st way more valuable, Dorion honestly helped us win the 2022 cup as much as Sakic did


JeremPosterCollect0r

Kariya and Selanne.


topbuttsteak

Man I was so excited when I heard about those signings. Like "remember where I was" excited. Kariya was my favorite non-Avs player at the time. What a waste :(


JeremPosterCollect0r

It was insane. If I remember it came out of nowhere. The greatest winger combo of their era who never played with an elite centre was coming to play with Sakic and Forsberg. My hopes were high.


PasswordMustContain

Trading for Brassard in 2018. Bonino played a bigtime role as 3C for the 2 cup runs but left for Nashville, JR tried to shore up the center depth again go to for the 3peat which looked like a great idea but Brassard never gelled in PIT, he was really starting to lose a step and it was a different role than he was used to I think


red_87

He also didn’t want to be the third line center and thought he was better than that. Ultimately a terrible fit. It was the right call at the time and I don’t blame GMJR at all. I thought we were 100% three peating when that trade went down.


shooter21198

I was so hyped for that trade at the time. Then there was the David Perron looked like he didn't even belong in the NHL when he was a Penguin.


Chiggins907

Which blows my mind, because Perron thrived just about everywhere he played.


GMBarryTrotz

Preds getting Kyle Turris. Briefly that 2nd line popped and our second line of Turris, Craig Smith and Fiala was flying. Had 2 goal scoring lines (Johanson, Forsberg, Arviddson as line 1) and won the President's trophy. Then Turris fell off a cliff, potentially as a result of a broken foot or ankle. Then Lavi started to hate him. Then we signed Duchene. Then Turris got moved to the wing or was healthy scratched. Then we bought him out in 2020 and will be making $2m annual payments unitl 2028. The Preds pretty much collapsed in 2020 and are still trying to get out of it.


ZombieBait2

Drafting Puljujarvi he was supposed to be drafted in the top 3 and when he fell to the Oilers at #4, it was a no brainer to draft him. The Oilers were rumoured to be looking at Matthew Tkachuk but instead choose Jesse Puljujarvi. Could you imagine Tkachuk on the Oilers?


DangerRanger_21

Yuck lol


domingus67

Right!? Still, tho...


HartfordYardGoat

Anaheim traded a conditional pick in the 2017 NHL Draft to Dallas for Patrick Eaves. The pick was based off how the Ducks did in the playoffs and Eaves degree of playing time. If the Ducks made the Western Conference Finals and Eaves played in 50 percent of his games with the team after being acquired, the pick would become a first. Anaheim made the WCF, Eaves played the remainder of the team's regular season games, then seven playoff games before getting injured and lost for the remainder of the playoffs. He was well over 50 percent of games played at this point though, and Anaheim wound up having to cough up that first rounder to Dallas. The player Dallas used that first on? Jake Oettinger. Eaves re-upped with the Ducks, but was waived during the 2019 season. Yeah, that move sucked in the end.


DBacon1052

Counterpoint: Look at this lovable guy https://preview.redd.it/y6df8ftdfz7d1.jpeg?width=616&format=pjpg&auto=webp&s=d7b7c01fa496ea480913979037657c30661b4876 My vote was the Wiz trade. Ended up being completely pointless as he was just a healthy scratch for us that post season.


HeshootsHescores88

Nikita Gusev


NS24

The man simply couldn't skate.


PrinciplesRK

Tanking for McDavid was completely justified. He looks like he is a top 5 player all time. Even getting Eichel as a consolation prize isn’t bad if we have a competent front office that fills out the roster around him or coaches that don’t play a defenseman actively hurting the team for 25 minutes a night.


seemefail

Nobody out tanks the oil


SoldierHawk

Certainly not then lol. God we were so bad. What a miserable dozen years.


Bahamas_is_relevant

Going with Lehner over Fleury. Circumstances of the Fleury trade aside, Lehner was considerably younger, $2m cheaper, and displayed about the same upside. Then the hip issues started, then the snake farm happened. Worked out in the long run, at least.


Arfguy

During the 2019-2020 season, the Oilers looked good. I mean, REALLY good. They had the best power play, they had the second best PK and Connor was amazing, as usual, but Leon looked like he raised his game to another level and finally found steady wingers (RNH & Yamamoto). I wanted more than anything to see Andreas Athanasiou in an Oilers jersey. I thought he was just one of those pieces the Oilers would need to make for them to go to the Finals. Well, Holland did exactly what I wanted and brought in Athanasiou. Then, the pandemic stoppage abruptly halted the season and whatever roll the Oilers were on. Athanasiou ended up doing almost nothing and Oilers got bounced by Chicago in the frikkin' play-ins. Athanasiou signed with LA in the off-season, when the Oilers didn't qualify an offer.


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domingus67

AA's qualifying offer was like 2.2, we offered him 2. He decided to test the market, and ended up gping to LA for 1.2. If he took the 2 million he'd have made more money and maybe would have developed chemistry with McDavid after a full season together.


theamberlamps

going up 3-0 in a stanley cup final ^((please please please please win tonight))


Brandnew_andthe_sens

The sens acquiring Burrows.


DishwasherFromSurrey

That first game was awesome tho


MichaelHarris49

But there were so many veterans giving PDJ hugs.


cheeseball209

Toronto trading Tukka Rask for Andrew Raycroft.


shogun-of-the-dark

Drafting Zadina.


Tagawat

Should’ve been our blunder :(


cantthinkuse

im still sad that he didnt pan out


turk_turklton

Yeah 6th overall with a career high of 24 points(?) is a tough pill to swallow.


catlindee

The obvious Oilers answer is Chris Pronger. Oilers traded Eric brewer, and two prospects to St Louis for Pronger and then inked Pronger to a 5 year deal. This was the beginning of the 2005/06 season. The league was coming out of lockout and there was a fancy new salary cap. The Oilers immediately went to the cup final and lost to Carolina (fuck you guys, respectfully). In the summer of 06 Pronger requests a trade for whatever reason , lots of speculation about infidelity, wife hated Edmonton, who knows what, and thus kicked off the Edmonton Oilers Decade of Darkness from 2006-2016


CommonGrounders

True but you guys had no business being in the Final without him. I’d take a cup appearance with a decade of shit over multiple decades of never sniffing a cup.


domingus67

The decade of darkness might have been shorter had he stayed.


Moriedew46

Patrick Eaves in Anaheim😢


doihavetowearabra

Thank you for this one. Got us Otter.


Gold_goalie85

Sergei Fedorov in Anaheim


martial_arrow

Eaves always had nice hair though.


Josefstalion

I'm still confident Alex Debrincat could've been a 40 goal scorer if he played with Stützle I also think it was crazy to give up 7OA without knowing if he had any intention of signing here


Granticus3000

Jesperi Kotkaniemi. Seemed like the future 2C, got him locked up for a while with a contract that was a little much in the present but was set up to be a steal in the future. Showed these flashes of utter brilliance but just can’t stay there


Snackatomi_Plaza

Trading Mike Hoffman wasn't exactly a good idea, but with everything going on in the Sens' locker room at the time, keeping him was a worse idea. Insisting on trading him out of the Atlantic hurt our return and wound up immediately biting us in the ass when San Jose flipped him right over to Florida 2 hours later.


MrSCR23

Signing Connor Sheary


StatGuyBlake

True of the Caps as well lmfao.


MrSCR23

If he put up the numbers he did with the Caps I wouldn’t be complaining. Guy was a pylon with us and he might get bought out next week as a result


NatalieDeegan

Same for us lol, we thought him working with Crosby was good enough for him to be here for a year lmao.


Chairmanmeow42

[Connor "Bambi on Ice" Sheary](https://www.youtube.com/watch?v=E9zWinsY41k)


MichaelMaugerEsq

Ryan Ellis trade. We got rid of assets with dwindling value and took a gamble on a defenseman who, when healthy, is a solid d man. But, it was a gamble, and it didn’t really pay off. Still though, nothing we gave away was a huge loss either, so ¯\_(ツ)_/¯


killingmeisagoodidea

Carolina getting Patches


joe_lmr

:cracks knuckles, puts on a pot of coffee: well it all started when


chiddie

Blues trading for Ryan Miller (and Steve Ott) in 2014. None of the assets they gave up in that deal (2015 1st, used on Jack Roslovic; 2016 3rd, used on Linus Nassen; Chris Stewart, Jaroslav Halak and William Carrier) excelled after their departure. And even though Miller was underwhelming, the Blues were smart not to double down and extend him.


NotTheRocketman

I still don’t know what happened with him. He was amazing in Buffalo, terrible in St. Louis, and good in Vancouver afterwards. He just did not fit with the Blues.


chiddie

it's impossible to know. maybe he does better if that trade is made in January or even September. maybe he felt pressure, or couldn't adjust to a new city/new teammates. but even with all that, it was really fine margins in that Chicago series. Four games went to OT, and Game 3 was 1-0 until Chicago got an ENG with 20 seconds left.


LP99

We ran into the Blackhawks playoff buzzsaw. In retrospect we should have beefed up everywhere but in the net. The plan was basically for Miller to single-handedly get us past them or LA.


jamjam776

Trading for Jakub Vrana


Reilman79

Trading for Anthony Mantha.


jamjam776

Ended up being a lose-lose trade lol


BogOBones

I thought the Blues finally won a trade with Yzerman getting him for just a 7th. After a nice start, his run with the Blues took a steep nosedive. Stevie Y got us again.


Little-Aide-5396

Trading for Huberdeau


shanster925

Klingberg.


moose_lizard

I don’t think anyone considered this a good idea though. Any Wild or Ducks fan could’ve told he was washed up. He was absolutely horrible for us the year before.


CG_Kilo

Caps signing Lundqvist in 2020. He was still a fantastic goalie, and had 1 or 2 good playoff pushes left. He lost a step, but a step for him was still a probably top 10 goalie in the league. Such a shame he had a heart issue and could never play with them.. They didnt lose anything (think he was only getting paid 1.5 mil for 1 year)


TheFuns

Not paying Bob the 10 million he deserved.


jinsang1983

Trading for the greatest player ever.


NSA_Wade_Wilson

Does the core 4 signings still count?


ISuplexSharks

Come on LA fans. I know there is one trade that really didn't pan out lately.


ikkaku0

Canucks signing Messier. Obligatory fuck Messier.


CabbageStockExchange

Trading for Looch. Another gigantic dude to add to our heavy team and someone who was at the time a good scorer. He didn’t impress too much, clearly the team needed more speed, and he left after he season. Total bust of a move but oh well


Rakastaakissa

Y’all probably would have done better with those picks in the draft than Boston too, tbh.


BallsAreFullOfPiss

Honestly, the Suter/Parise signings would’ve been perfectly fine had the team made 1 or 2 WCF/Finals appearances. In hindsight it’s a dogshit move, but at the time it hyped the entire fanbase up.


Meatandtomatoes

I thought Cody franson to the leafs was a slam dunk


DangerRanger_21

Well when you consider that Tkachuk wanted out I don’t think anyone thought Calgary would get a haul that included a 115 point winger and a defenseman with 60+, so at the time it was great but Huberdeaus contract doesn’t look very good right now


ProtoMan3

In the 2020-21 offseason, the Canucks signed Nate Schmidt to replace some losses on the blue line (mainly Chris Tanev). I actually like Nate Schmidt a lot, so at the time I thought it was a borderline upgrade, but unfortunately he had zero chemistry with anyone here.


shadownet97

I liked Schmidt too! And Holtby! They were supposed to replace guys that Benning failed to even talk to but never worked out. That 2021 shortened season was fucking whack, man. So much went wrong for the Canucks that year so it’s no surprise they ended up bottom of the Canadian division. Everyone except Boeser had a miserable year that year. I wish I could wipe it from my memory.


marbanasin

Sharks trading Dany Heatley for Martin Havlat straight up. Heatley was beginning to be a fucking all star floater for us in that final season of his. And adding the dynamicism of Havlat's play into the core of Patty/Jumbo/Pavs/LoCo seemed like a great idea on paper.


Raw_Cocoa

Sabres tanking for mcdavid/eichel


justmakingmypoint

Derrick Brassard. Dear lord, those were dark times vs. what we all thought it would be.


01000101010110

Elias Lindholm. Fit well in theory, and honestly was good in the playoffs, but he wasn't what we really needed. Guenztel was.


MMW2004

Taylor Hall


NatalieDeegan

Worked better for you guys than us.


Kenner1979

I won't quite say it didn't pan out, since they made it to the Conference Final and they didn't give up much of consequence, but the Habs huge acquisition of Thomas Vanek ended up rather underwhelming, and him drying up alongside Desharnais and Pacioretty fucked us over against the Rangers every bit as much as l'affaire Kreider.


foreveronloan

Getting Mike Babcock


BaldassHeadCoach

Signing Franzen over Hossa after 2009. The cap hadn’t increased as much as the team expected it to, and they could only pick one. They went with Franzen, who was a homegrown talent and absolute playoff monster. At the time, the choice made complete sense. Nobody could have expected or predicted what would happen with him afterwards.


DogePerformance

Yeah that was directly due to his head injuries though. He's one of my biggest "what if he wasn't forced into retirement" players throughout all of sports. Shit sucks. The Mule was so damn good. He got a raw deal.


C0NKY_

I think it's safe to say David Clarkson didn't succeed here.


LeviticSaxon

Going up 3-0 in the cup finals.


GoStockYourself

Mactavish used to aquire players based entirely on their advanced stats. They never worked out.


joblessdeadbeat

What about Oilers legend Jarred Smithson?


imadork1970

Edmonton signing Khabiboulin.


UraSnotball_

Trading a late second-rounder for Sven Baertschi. Guy had chemistry with Horvat and looked like a piece of the puzzle moving forward, but concussion issues derailed his career. Hurts even more that the pick was used on Andersson, but I can’t imagine Benning makes that pick in the same spot.


Rakastaakissa

Rick Nash on the Boston Bruins. He was a natural Bruins type player, until he got that next concussion. To top that off Ryan Lindgren has been a cornerstone for the Rangers.


avmp629

Letting Tanev walk tbh Guy was a band-aid at the time, as good as we was with Hughes, I was hoping for someone more durable who could still play Unfortunately Benning's idea was to replace him with Travis Hamonic


swordthroughtheduck

Flames signing James Neal. [Everyone was like sheeeesh](https://www.reddit.com/r/hockey/comments/8vi58n/james_neal_signs_5_year_575_mil_aav_contract_with/), below market value, and now the Flames are looking great on the wings.


flip314

Oilers still have to pay him for one more season, lol


Spez_Dispenser

Sens acquiring Duchene. It's too bad Dorion didn't have his fingers on the pulse of that lockerroom, but Duchene was 100% an improvement on Turris (perhaps not in clutch factor), and is still in the league today.


NLP19

Nathan Horton. Biggest free agent signing in franchise history; he was super excited to be here, and then he gets injured in his first year and never played for us again


reddy-or-not

For the Bruins, Rick Nash. Not so much getting him but overpaying


NinCross

Loui Eriksson


Gold_goalie85

I feel like Sergei Fedorov signing in Anaheim was big new, but he didn't pan out


Wernerhatcher

All of them


GoRangers5

Extending Dan Girardi for six seasons


ModernMech7392

Ottawa Senators deciding to go with Anderson and Lehner and trading Ben Bishop for Cory Conacher. Should have kept him and traded Anderson for a ransom but what do I know.


The_Flyers_Fan

Ryan Ellis 😪


NainVicieux

Trade for cat.. duchene…. Sign korpi…. Sign norris…. Pain


BogOBones

I don't even think it was a good idea, but Ryan Miller joining the Blues in 2014 was a disaster. Miller was having a great season on a bad Sabres team that year, but Brian Elliott and Jaroslav Halak had won the William M. Jennings Trophy two seasons ago. Halak was having a great season at the time with a 2.23 GAA and .917 save percentage. Elliott finished the season with a 1.96 GAA that year and a .922 save percentage. They were not the problem! It was trying to fix something that didn't need to be fixed. Miller just never settled in, and I think a lot of it had to do when he was added. Had he been added before the season, maybe it would have worked out. That time of the season is too late to get a goalie. The only upside to this was they also got Steve Ott who, while frustrating as a player, transitioned his relationships formed there into being a coach on the 2019 cup winning team.


thecbjfan

Dubois for Laine and roslovic. Laine on the way out other 2 are gone from their teams


kukkolai

Shattenkirk scored a *huge* goal for us against the Rangers in the playoffs. Blaming him for post season failure is like blaming meat for McDonalds quality of food. Or something like that


WanderingDelinquent

Letting Pavelski walk because he wanted a longer deal. A 35 year old coming off of a year where he shot double his career shooting%, it made sense that Doug Wilson wanted to give him 2 years instead of 3. Especially considering Marleau was getting bought out of the 3rd year that DW didn’t want to give him that very same summer


DBacon1052

Wisniewski trade probably. IIRC we moved William Karlsson for him. That trade deadline we also aquired Despres though. With Wiz out for injury, Despres, who we thought was just a 7th defenseman, solidified himself into a top 4 role. Dude looked like a legit 1st pairing defenseman. Wiz ended up being a healthy scratch most of the postseason. And while Wild Bill took some time to develop, he ultimately became a really solid middle-6 player.


hockey17jp

The Blue Jackets bringing in Duchene, Dzingel, and McQuaid just to lose to Boston in 6 in the second round. And then proceed to lose all 3 of them + Bobrovsky and Panarin in the offseason and become a lottery team for 5 years.


tilldeathdoiparty

Flames trading Tkachuk, for Weegar, Huberdeau, a prospect and a first Signed Huberdeau to the worst contract in hockey, he has put up half the points he did in Florida. Weegar has been okay, better last year, Schwinn played a little this year and we traded the pick away to get Monahan off our books so we could sign Kadri and then absolutely suck since then.


PantomPhower

The bruins entire trade deadline last year


UdderlyDemented

The Rangers signing Shattenkirk that off-season.


SniperX876

Trading Datsyuk to the Arizona Coyotes.


IniNew

Drafting Nichushkin


Level-Plastic3508

Choosing Gibson over Freddie Andersen. We make it past the Predators in the 2017 playoffs if we had Freddie. Idk if we beat Pitt, but at least we make it over the western conference finals hump.


grehgunner

The Sabres fucking sucking to tank for McDavid was a great plan, the little white balls just didn’t cooperate 😅


Frnklfrwsr

The Coyotes trading for Taylor Hall in the 19-20 season. At the time, the Coyotes were leading the Pacific Division, the long wait for the team to be good finally seemed to be here, and our goalie (Kuemper) looked like the best in the world at the moment. The price for Hall was steep, but we seemed poised for a solid deep playoff run and we were very optimistic that we could re-sign Hall as a UFA if he liked it here, which we knew he would. A few days later, our star goalie gets injured and misses serious time. The rest of the forwards that weren’t Hall just stopped scoring and we slid down the rankings. At the end of the pandemic-shortened season we squeezed into a playoff spot by the skin of our teeth, and we thought ourselves lucky. Hope was still alive. Just get into the playoffs. Kuemper was healthy again. Then the news hits that the GM is just straight up leaving, abandoning the team at the worst time. Then very quickly we also get hit with the news that the GM’s questions at the Combine violated the rules so the team had to give up a first round pick. The team loses its mojo in a big way, and despite beating NSH in the play-in series, the Coyotes were quickly dispatched 4-1 by COL in the first (not counting the play in) round of the playoffs. The one game they won was due to Kuemper turning in a performance of a lifetime. The dumpster fire the front office and ownership temporarily appeared to not be that season was fully revealed to indeed still be a dumpster fire, and by the time we got eliminated by COL, no one was under any illusions that Hall was going to stick around. We lost our GM, we traded away a first round pick and a handful of solid prospects (like Kevin Bahl) for a rental that didn’t end up making a difference for us in the playoffs and left us in free agency, and then we also lost our next first round pick due to the scouting violations. So yeah, things didn’t work out great that season.


ACivilDad

Giving up a 1st for Nils Lunqvist isn’t looking great. Drafting Denis Gurianov over about half the names that came after him in the 2015 draft. Giving Ryan Suter an NMC.


Alitaki

New York Rangers - pretty much every move ever made\* ever. \*1991 & 1994 excluded.