Which GM hire was most damaging for their team?

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Chiarelli for Edmonton was a disaster. I don’t know if hes the worst but considering he got a generational talent and sewered the roster, it was pretty bad.
Chiarelli wasn’t even the worst GM recently. Mac T traded Petry when he was willing to re up for 4.5 long term. MacT didn’t want to commit to term when he was still young and hands down our best D man on a shallow D core.

MacT/Tambo/Lowe sewered the roster for one of the worst stretches ever in the history of the game.

Chiarelli also sewered the team but it was after he had built it back up to playoff caliber in just two offseasons. People love to talk about how he inherited the McDavid pick but forget the team at the time 0 top 4 D men and 0 NHL goalies. That’s not even an exaggeration. In two offseasons he had to add 3 top 4 D (Larsson, Sekera, Russell) and brought in Talbot while Klef and Brossoit were able to step up and round things out. That made the D just good enough to be a strong team again if they were all healthy but Klef and Sekera going down with career ending injuries in the coming years collapsed his house of cards and the D never really recovered until Nurse took a couple steps and prospects like Bear stepping up to get us back there.

Chiarelli’s drafting was the best we’ve had since the 80’s too with guys like Jones, Bear, Marino, Skinner, Kesselring, Desharnais, McLeod all outside of the first round.
 
The Oilers hat trick of Chiarelli, Holland, and now Stan Bowman has done immeasurable damage. They would have at least one Cup by now if the team was properly run, but here we are in Year 10 of Connor McDavid wondering if John Klingberg’s bionic hips and a goalie with a .902 save percentage are the solutions on defence and in goal. Just complete idiocy from a group of has beens every season.
Holland did a great job fixing the damage that Chia caused. The Oilers made the playoffs every year including a conference final and Cup final. His biggest mistakes were hiring Wright as head scout and the Campbell contract. People complain about the Nurse contract but it’s really only a 2.5 overpay and he’s invaluable to the team.
 
Ron Hextall spent Pittsburgh’s limited assets making the team worse. He closed their contention window, Dubas just locked it shut with with his trademark poor blueline construction and terrible goalie decisions.
Hextall was a double agent. I couldn’t believe the Pens hired a lifelong Flyer to be GM. It’s like the Oilers hiring Mike Vernon as the GM.

Chiarelli wasn’t even the worst GM recently. Mac T traded Petry when he was willing to re up for 4.5 long term. MacT didn’t want to commit to term when he was still young and hands down our best D man on a shallow D core.

MacT/Tambo/Lowe sewered the roster for one of the worst stretches ever in the history of the game.

Chiarelli also sewered the team but it was after he had built it back up to playoff caliber in just two offseasons. People love to talk about how he inherited the McDavid pick but forget the team at the time 0 top 4 D men and 0 NHL goalies. That’s not even an exaggeration. In two offseasons he had to add 3 top 4 D (Larsson, Sekera, Russell) and brought in Talbot while Klef and Brossoit were able to step up and round things out. That made the D just good enough to be a strong team again if they were all healthy but Klef and Sekera going down with career ending injuries in the coming years collapsed his house of cards and the D never really recovered until Nurse took a couple steps and prospects like Bear stepping up to get us back there.

Chiarelli’s drafting was the best we’ve had since the 80’s too with guys like Jones, Bear, Marino, Skinner, Kesselring, Desharnais, McLeod all outside of the first round.
If you look at the bright side, Mac T’s choices got the Oilers Mcdavid and Draisaitl so maybe he was the best GM…
 
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There is an alternate universe where the Islanders have Luongo, Spezza, Chara, Connolly, Jokinen, and Dany Heatley because they didn't use the pick on DiPietro.

People will counter that his job was to execute the wishes of ownership, but even in the Yashin trade Marshall Johnston has gone on record about how he had no leverage and would have had to take whatever the Islanders offered, and has they come at him with Chara and a 2nd, he would have cut his losses and gone with it because the Senators simply could not afford to keep Yashin.
 
ok so i have to defend milbury a bit here. he made some good trades too, and he did build a pretty fun team in the early 2000s.

mike peca for tim connolly and taylor pyatt was a great trade, he flat out stole aucoin from tampa, and the wendel clark and mathieu schneider for kenny jonsson and the luongo pick was savage.

so as much as he is fun to point to because he made the highest volume of spectacularly one-sided trades, he probably isn’t the worst of all time given that he also had his share of good trades, and he helmed that team through some absolutely bonkers conditions: two of his owners went to jail and he was constantly going between stripping the team down for parts and making it rain like they were the rangers.

that said, fun is fun, so here is the islanders team that could have been in the years before the lockout:
heatley jokinen bertuzzi​
straka peca czerkawski​
blake spezza dumont​
bates lapointe scatchard​
with someone from later in the 2003 first round (kesler, perry, mike richards) on the way​
jonsson chara​
hamrlik aucoin​
kasparaitis mccabe​
luongo​
salo​
 
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Brad trievling flames. We all know why. Panthers fans should have brad statue in front of their arena.

Ehh that's with a major benefit of hindsight. On paper, the consensus was that Calgary made an excellent trade. Weegar has been a very good dman but nobody expected Huberdeau to drop off as significantly as he has. He had just finished with an 116 point season.
 
Brad trievling flames. We all know why. Panthers fans should have brad statue in front of their arena.

The Monahan with a 1st for capspace to sign a 32 year old Kadri is 100x if not 1000x worse than the Tkachuk trade. The Tkachuck trade itself is actually a decent trade all things considered, it's everything before and afterwards that's awful.
 
All these other GMs doing not hold a candle to Mike Milbury. It’s almost as if he was intentionally sabotaging the franchise. If you even halved the amount of horrendous decisions he made, NYI would’ve been at least a competitive team.

It says something that so many of his peers trash talk his trades, and don't even try to hide how badly they fleeced him.

 
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Which GM in NHL history did the most damage collectively through trades, bad draft picks and overpaid free agent signings?

Chiarelli with his disastrous Oilers tenure including the Koskinen contract, Yakupov pick and infamous Hall trade?

Milbury trading Luongo and Chara? His overpayment of Yashin?

Those are 2 of the obvious ones. Any under the radar picks? Curious to hear who has done the most damage in your opinions.
Did Chiarelli tell the Oilers to draft Yakupov while he was still the gm in Boston? If so why would they listen to scouting advice from a random GM in the opposite conference.
 
I was his advocate, but for Flyers it’s Ron Hextall. Slogan “Building through the draft” in reality turns to most terrible drafts in Flyers modern history. Except 2015, where it was really hard to make the error (Hello Bruins). Rubtsov, Patrick, Frost, Farabee and O’Brien combined 416 pts, of which 339 scored 2 of them (Farabee and Frost).
Big part of Giroux prime years (from his 26 to 31) was literally wasted. No big trades, only one big signing (JVR). And after firing Ron explained his passivity just like “Team is not ready for contending yet”.
So when your best players are 29-30 years old and you think the team is not ready, so why they were in roster? Why you didn’t trade core and didn’t made true rebuild?
 
I’m going to preemptively say that it was not Jim Benning.

As terrible as he was for the Canucks—I think a lot of his decision making was influenced by owner Francesco Aquilini interfering with hockey operations.

Either trying to rush the rebuild (Eriksson, Beagle, Sutter, OEL, etc) or not allowing the team to spend when they needed to (the disastrous post-bubble off-season, or the general lack in investment in hockey ops that led to them running out of time a lot).

That’s not to say that Benning wasn’t out of his element—but it is to say that things were made so much worse by ownership.

Generally for any other GM listed in this thread, I think ownership is an important consideration to evaluate their performance by.

I'll counter with....... Jim Benning. (weird how Allvin n co don't have the issues ur describing) Aquilini stepped in after he shit the bed repeatedly
 
Chiarelli wasn’t even the worst GM recently. Mac T traded Petry when he was willing to re up for 4.5 long term. MacT didn’t want to commit to term when he was still young and hands down our best D man on a shallow D core.

MacT/Tambo/Lowe sewered the roster for one of the worst stretches ever in the history of the game.

Chiarelli also sewered the team but it was after he had built it back up to playoff caliber in just two offseasons. People love to talk about how he inherited the McDavid pick but forget the team at the time 0 top 4 D men and 0 NHL goalies. That’s not even an exaggeration. In two offseasons he had to add 3 top 4 D (Larsson, Sekera, Russell) and brought in Talbot while Klef and Brossoit were able to step up and round things out. That made the D just good enough to be a strong team again if they were all healthy but Klef and Sekera going down with career ending injuries in the coming years collapsed his house of cards and the D never really recovered until Nurse took a couple steps and prospects like Bear stepping up to get us back there.

Chiarelli’s drafting was the best we’ve had since the 80’s too with guys like Jones, Bear, Marino, Skinner, Kesselring, Desharnais, McLeod all outside of the first round.
Imagine if he had traded 16th overall for Talbot and Kevin Klein instead of Reinhart...
 
Surprised there's no mention of John Chayka yet. Threw away assets to try to speed up the rebuild, which I guess did result in a playoff series win (in the play-in round though), then he was pretty bad other than that, quit on the team, got some draft picks for the Coyotes forfeited, and we failed to recover so badly that we relocated. Now we're Utah instead of Arizona.
 
Mike Millbury is a Bingo free space. You can make an entire team of four lines, three D pairs, and two goalies that were involved in trades away from the Islanders.

After that, I’d go Jim Benning. He was a supposed scouting mind but he picked Juolevi over Tkachuk, and picked Jake Virtanen because he was a local boy. And he placed zero value on first round picks, as they were common fodder for some incredibly stupid trades.

Don’t sleep on John Chayka either. He was a con artist GM for a Coyotes, fitting for a team exclusively owned by con artists. He was an alleged analytics genius but nothing he did showed any analytic savvy (read: signing empty calorie scorer Phil Kessel as a push to be competitive). The trade for Taylor Hall is still bearing fruit… for New Jersey, who ended up drafting Dawson Mercer with one traded pick, traded for Jonas Siegenthaler with the other pick, and got Kevin Bahl as a prospect piece that they traded for Jakob Markstrom. Don’t forget his private combines that cost them two draft picks either.
 
The one thing I will say in order to be fair to Milbury is that I do give him a SLIGHT pass on the Yashin trade. Both Spezza and Chara were unproven at the time. Yashin was a legit star, and was still quite productive with NY.

It wasn't just the trade but also the contract.

10 years for $87.5M? That's nuts.
 

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