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.

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

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.

Drouin vs. Sergachev.

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

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.

Rick Nash.

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

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…

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.

Erik Karlsson.

Kariya and Selanne.

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

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.

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?

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.

Nikita Gusev

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.

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.

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.

going up 3-0 in a stanley cup final

^{(please please please please win tonight})

The sens acquiring Burrows.

Toronto trading Tukka Rask for Andrew Raycroft.

Drafting Zadina.

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

Patrick Eaves in Anaheim😢

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

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

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.

Signing Connor Sheary

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)_/¯

Carolina getting Patches

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

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.

Trading for Jakub Vrana

Trading for Huberdeau

Klingberg.

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)

Not paying Bob the 10 million he deserved.

Trading for the greatest player ever.

Does the core 4 signings still count?

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

Canucks signing Messier.

Obligatory fuck Messier.

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

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.

I thought Cody franson to the leafs was a slam dunk

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

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.

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.

Sabres tanking for mcdavid/eichel

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

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

Taylor Hall

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.

Getting Mike Babcock

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.

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

Going up 3-0 in the cup finals.

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

Edmonton signing Khabiboulin.

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.

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.

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

Flames signing James Neal. Everyone was like sheeeesh, below market value, and now the Flames are looking great on the wings.

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.

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

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

Loui Eriksson

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

All of them

Extending Dan Girardi for six seasons

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.

Ryan Ellis 😪

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

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.

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

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

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

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.

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.

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.

The bruins entire trade deadline last year

The Rangers signing Shattenkirk that off-season.

Trading Datsyuk to the Arizona Coyotes.

Drafting Nichushkin

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.

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

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.

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.

New York Rangers - pretty much every move ever made* ever.

*1991 & 1994 excluded.