Peter Chiarelli and the NHL's All Time Poor GM Reigns

[Hobnobs]

I can't remember but when that trade was made where the Leafs playing where chances are they knew they would be giving up a top 5 pick or not? Plus was Luongo thought to have been a top 5 pick that the Leafs knew what they might be missing out on? The recent example that I know of is when Brian Burke made the Phil Kessel trade and trading those two 1st round picks that turned out to be Tyler Seguin and Dougie Hamilton, with the difference being that trade was made prior to the 2009-2010 season.

Yea, there was no way anyone would think leafs would have finished bottom-5 the next year. There were strong signs of decline obviously but Leafs traded the pick at the deadline of 96 to get stronger for the playoffs by aquiring Clark and Schneider ...

 

[LeafsNation75]

Yea, there was no way anyone would think leafs would have finished bottom-5 the next year. There were strong signs of decline obviously but Leafs traded the pick at the deadline of 96 to get stronger for the playoffs by aquiring Clark and Schneider ...

Even if they had their 1st round pick in 1997 would they even selected Luongo, considering they still had Felix Potvin. I know he was replaced 2 years later when they signed Curtis Joseph, however it goes to the saying just because a specific player was available at this pick it doesn't mean the team who originally had that pick would have selected them.

 

[Hobnobs]

Even if they had their 1st round pick in 1997 would they even selected Luongo, considering they still had Felix Potvin. I know he was replaced 2 years later when they signed Curtis Joseph, however it goes to the saying just because a specific player was available at this pick it doesn't mean the team who originally had that pick would have selected them.

What I meant was that nobody expected the pick to be in the top-5 that season. So they didnt originally trade a top-5 pick even though it became one. As for not picking Luongo, its possible but he was BPA iirc and back then they wouldnt be in any rush to get him into the NHL. They coulve picked him, he wouldve dominated the AHL, got some call ups, Potvin loses his starter job and gets traded.

If they dont pick Luongo then at best Leafs lost Tkaczuk and at worst Brewer. Still not that great tbh.

 

[Bexlyspeed]

Not to defend Milbury, he was a bad GM, however, when he traded Palffy he was commanded to do so by ownership who wanted to spend as little money as possible and basically only bought the team to try to develop the land around Nassau coliseum.
they quickly found out that with Nassau politics it would now be possible and put the team back on the market.

 

[ManofSteel55]

The Isles were only going to make the trade if he was available..... and he was the best player available when the trade happened (when the Oilers were OTC).... so yes they did.....

No they didn't. The Oilers didn't have him next on their list, apparently they wanted Joel Eriksson-Ek. Still an awful trade, but it wasn't Barzal+ for Reinhart, it was picks for Reinhart.

 

[ManofSteel55]

I agree with your points. This will be a failed season in retrospect because the team is going to miss the playoffs, BUT they're 14-9-1 since Nov.21 and were 47-26-9 last year with an exciting playoff run that would have seen them in the final-four but for a blown 3-0 lead with three minutes left in a game. The only problem is that in between 8 great months last season and 2 good months this season to date are six bad weeks in October/early-November 2017. Unfortunately, those six bad weeks cost them the season.

I didn't like the Eberle trade because they certainly could have got more for him. I'm fine with the Hall trade, which I think is going to be good from a future perspective.


The only move Chiarelli has made that I think was clearly poor was the Eberle for Strome trade. (Having said that, I quite like Strome, and Eberle essentially played himself off the team with his zero-effort performance in last spring's playoffs). But he's not one of the worst G.M.s ever because his team had a bad six weeks.


No, this is all about Milbury. Could coach. Could not manage a team.

The thing is, that they couldn't have gotten more for Eberle. He played his value down so low that only a couple of teams had interest because of his salary, and those teams apparently weren't offering anything good. Cody Eakin from Dallas was one rumor. Strome obviously happened. Either way, we were getting a project player who had slumped for a couple of years either way.

 

[ManofSteel55]

I disagree with this. Why exactly did he have them by the balls as opposed to Pastrnak, Gaudreau, Monahan etc? Look at JG for example, he held out until the reg season yet settled for the Flames offer of 6.75 million.

Draisaitl was a huge offer sheet risk. There were tons of rumors that multiple teams were looking at offer sheeting him. For all we know, Montreal might have had one in agreement with his agent, basically forcing Chiarelli to cave. Gaudreau doesn't belong on this list, he couldn't have been offer sheeted at all and it was sign or sit home for him.

 

[Chief Nine]

Harry wasn't great at the end by any means, and the economics of the game passed him by in the early 80s, but he was far from a bad GM, even then.

His teams won divisions through the early 90s, made a couple conference finals, would've won one of them and probably a cup if not for one of the dirtiest cheapshots in NHL history taking out Neely's knee and hip.

His stubbornness to negotiate on contracts cost him some good players like Oates and Kristich, he never really padded out the roster with top level talent on the 2nd and 3rd lines, relying too much on Oates/Neely to carry the whole offense, and he never had a decent goalie after he drove Moog out of town, but when I think of bad GMs, I think of those who put their team into the toilet for years, who liquidated all the talent they had, who put them in financial hell. You have to think of Lowe, Bergevin, Chiarelli to an extent, or guys like Waddell and Maloney who could just never get out of the basement no matter what they did.

Harry Sinden was a good GM, just not a great one after 1987 or so.

How much of the penny pinching was his stubbornness and how much of it was Jacobs' orders is another question

Harry Sinden did exactly what he was tasked to do: Put. Fannies. In. Seats. Don't. Spend. Money.

 

[LeafsNation75]

No they didn't. The Oilers didn't have him next on their list, apparently they wanted Joel Eriksson-Ek. Still an awful trade, but it wasn't Barzal+ for Reinhart, it was picks for Reinhart.

I wish others said that about the Phil Kessel trade to Toronto. Yes it was obvious that the Bruins would select Tyler Seguin at #2 in 2010 with the Leafs pick and let's be honest, no one would have thought Dougie Hamilton would be available for them at #9 in 2011. Although I think some Bruins fans overhyped him because of the trade. Anyway the point is just like the Oilers did, the Leafs traded picks for Kessel.

 

[Voight]

Draisaitl was a huge offer sheet risk. There were tons of rumors that multiple teams were looking at offer sheeting him. For all we know, Montreal might have had one in agreement with his agent, basically forcing Chiarelli to cave. Gaudreau doesn't belong on this list, he couldn't have been offer sheeted at all and it was sign or sit home for him.

Huge offer sheet risk yet he didn't sign until mid August. Interesting.

 

[ManofSteel55]

Huge offer sheet risk yet he didn't sign until mid August. Interesting.

There's no timelines on offer sheets and negotiations take time, even in an offer sheet scenario. But if you followed this past summer, you should remember all of the rumors swirling about offer sheets for Draisaitl. You are also including guys who hadn't just come off of a top 10 season in points, so they aren't exactly the best comparables, as good as they are. Gaudreau has had a top 10 finish, but Calgary really played hard ball with him because he actually held no leverage, unlike the other players discussed.

 

[Dennis Bonvie]

Harry wasn't great at the end by any means, and the economics of the game passed him by in the early 80s, but he was far from a bad GM, even then.

His teams won divisions through the early 90s, made a couple conference finals, would've won one of them and probably a cup if not for one of the dirtiest cheapshots in NHL history taking out Neely's knee and hip.

His stubbornness to negotiate on contracts cost him some good players like Oates and Kristich, he never really padded out the roster with top level talent on the 2nd and 3rd lines, relying too much on Oates/Neely to carry the whole offense, and he never had a decent goalie after he drove Moog out of town, but when I think of bad GMs, I think of those who put their team into the toilet for years, who liquidated all the talent they had, who put them in financial hell. You have to think of Lowe, Bergevin, Chiarelli to an extent, or guys like Waddell and Maloney who could just never get out of the basement no matter what they did.

Harry Sinden was a good GM, just not a great one after 1987 or so.

How much of the penny pinching was his stubbornness and how much of it was Jacobs' orders is another question

"Harry Sinden was a good GM, just not a great one after 1987 or so."

Yet his teams went to the finals in 1988 and 1990.

 

[Dennis Bonvie]

Well said. When he fired Pat Burns and hired Mike Keenan that was more or less it for me. They kept trying to bamboozle the fans by putting, as my dad used call them "gate openers" behind the bench. He hired a bunch of former players like Terry O'Reilly and Butch Goring to make the fans happy and sprinkled guys like Rick Bowness and Brian Sutter in there. Then he put Steve Kasper behind the bench who was about as qualified as a blind hippopotamus. We all know how that worked out. He finally got a bonafide NHL coach in Pat Burns and then canned him. Then he hired Mike Keenan. That was the end for me.

Former players O'Reilly and Milbury each took the Bruins to the finals as coaches.

 

[Chief Nine]

Former players O'Reilly and Milbury each took the Bruins to the finals as coaches.

With teams that needed just that extra guy that could put them over the top. This is the theme for the Bruins recipe back then: ice a good enough but not great roster; keep the fans coming through the turnstiles; don't pay top end talent top pay; don't get goal scorers they cost money.

Wash, rinse repeat.

Getting this yet???

 

[Dennis Bonvie]

With teams that needed just that extra guy that could put them over the top. This is the theme for the Bruins recipe back then: ice a good enough but not great roster; keep the fans coming through the turnstiles; don't pay top end talent top pay; don't get goal scorers they cost money.

Wash, rinse repeat.

Getting this yet???

So your view is one extra guy would have made the Bruins champions but Sinden and Jacobs were too cheap to do it?

That's idiotic.

Jacobs is a billionaire. He knows how to maximize profits. Winning the Stanley Cup absolutely maximizes profits.

 

[Chief Nine]

So your view is one extra guy would have made the Bruins champions but Sinden and Jacobs were too cheap to do it?

That's idiotic.

Jacobs is a billionaire. He knows how to maximize profits. Winning the Stanley Cup absolutely maximizes profits.

Hahaha, OK. Let's take Sidney Crosby or Evgeny Malkin off the Penguins. Would that have mattered? There is no way in hell that Jeremy Jacobs would have the caliber of those two players on one of his teams and pay them both market value when there was no salary cap.

Let me try to make this real simple for you (since you infer that I'm an idiot)

1) The Bruins were in the playoffs every year
2) You win the Stanley Cup, sure you make more gate and concession revenue. But's that not what makes an owner more money.

You still with me?

Good, because here comes point #3 if you win it all:

3) The players who are now Stanley Cup champions want more money. That second liner who may have scored 9 goals in the playoffs who's contract is up now wants 2 million more than he was worth before the playoffs started. That RFA second year defenseman who was a +22 in the playoffs is now worth a lot more, etc. etc. etc.

See how this works?

A billionaire like Jeremy Jacobs understands all this. Going for the brass ring doesn't make you the most money. Being in the hunt every year does though. He's in the long game, fans aren't.

I sincerely hope this helps you understand all this.

 

[Dennis Bonvie]

Hahaha, OK. Let's take Sidney Crosby or Evgeny Malkin off the Penguins. Would that have mattered? There is no way in hell that Jeremy Jacobs would have the caliber of those two players on one of his teams and pay them both market value when there was no salary cap.

Let me try to make this real simple for you (since you infer that I'm an idiot)

1) The Bruins were in the playoffs every year
2) You win the Stanley Cup, sure you make more gate and concession revenue. But's that not what makes an owner more money.

You still with me?

Good, because here comes point #3 if you win it all:

3) The players who are now Stanley Cup champions want more money. That second liner who may have scored 9 goals in the playoffs who's contract is up now wants 2 million more than he was worth before the playoffs started. That RFA second year defenseman who was a +22 in the playoffs is now worth a lot more, etc. etc. etc.

See how this works?

A billionaire like Jeremy Jacobs understands all this. Going for the brass ring doesn't make you the most money. Being in the hunt every year does though. He's in the long game, fans aren't.

I sincerely hope this helps you understand all this.

So, players are only going to want more money (and get it) if they win a Cup?

 

[Brodeur]

Growing up in Southern California, I always get asked how I ended up a Devils fan. I tell folks how hockey got on the radar when Gretzky arrived, but then I really got into it with the Kings making the SCF in 1993. But when the missed the playoffs in 1994, I jumped on the bandwagon for this Brodeur rookie who was doing pretty well. When the Kings missed again in 1995, I went back to the Devils...

Anyways, the Kings GM in the mid-90s was Sam McMaster. He pretty much traded away my childhood favorites, albeit now I can look back and understand that there were some other circumstances involved. But it's funny to read an article from when McMaster was hired and how it notes that the Kings had the 3rd oldest roster. And his first few big trades made the team older.

May 1994: Luc Robitaille for Rick Tocchet and a 2nd rounder

Years later I would understand that Gretzky and Robitaille were combative. So they swapped out Robitaille for one of Gretzky's friends. But Tocchet didn't fit and they swapped him for Kevin Stevens a year later. Then things came full circle when Stevens was swapped for Robitaille after McMaster was fired in 1997.

February 1995: Alexei Zhitnik, Charlie Huddy, Robb Stauber for Grant Fuhr, Philippe Boucher, Denis Tsygurov

Was a bummer to trade a 22 year old defenseman in Zhitnik who already had 48/52 point seasons on his resume for a 32 year old Grant Fuhr. Allegedly Zhitnik had some run-ins with the Russian mob in LA, so perhaps it was best for him to get out of town. Meanwhile Fuhr was brought in since Kelly Hrudey was struggling. Fuhr had a rough time and wasn't an upgrade. He'd leave via free agency and had a renaissance in St. Louis. Boucher ended up being a late bloomer, but the Kings only got one good season before he left.

February 1996: Darryl Sydor for Shane Churla, Doug Zmolek

Sydor was struggling, but this is probably a prime example to be patient with a 23 year old D.

February 1996: Wayne Gretzky for Roman Vopat, Craig Johnson, Patrice Tardif, 1997 1st rounder

Gretzky was an impending UFA, so it was going to be tough to get a good return. Vopat was supposed to be a Michal Handzus type center, but didn't pan out. 1997 was supposed to be a deep draft, but the Kings used the pick on somebody who they didn't even sign.

Although one of McMaster's parting gifts was moving Marty McSorley and Jari Kurri in a package to get Ian Laperriere and Mattias Norstrom. I had incorrectly pegged the disastrous Sandstrom/McEachern for McSorley/Paek trade on McMaster, but that one was made by his predecessor. McMaster has been with Columbus since their inception. He was an amateur scout for awhile, but it looks like he was switched to pro scout under the current management.

 

[sharkhawk]

No love (or hate) for Bob Pulford? He basically ran the hawks into the ground in the late 90s. Best move rocky did when he got the Hawks was kicking Pulford to the liquor business.

 

[Hobnobs]

No love (or hate) for Bob Pulford? He basically ran the hawks into the ground in the late 90s. Best move rocky did when he got the Hawks was kicking Pulford to the liquor business.

The Pulford/Wirtz combo was a deadly one for sure.

 

[Killion]

The Pulford/Wirtz combo was a deadly one for sure.

Indeed. And quite the trio when you add R. Alan Eagleson to the mix.... who was a childhood friend of Bob's & his older Brother, playing Lacrosse with both.... forming the "Blue & White Investment Club" in Toronto in the early 60's, looking at business opportunities, acquiring car, clothing & jewellery sponsors for the players & advising Pulford, Carl Brewer & a few other Leafs on their contracts.... eventually forming the NHL Players Association in 1967 with Bob Pulford as the first Player President (Pierre Pilote Asst VP) & so on..... Pulford eventually going on to be the long tenured GM in Chicago..... "the ultimate company man who sold us out" according to Carl Brewer who had quite the falling out with his former teammate.

 

[Chili]

A review of the work of some of the post 1967 expansion teams GM`s would be interesting.

Alot of questionable deals in hindsight, including by the original six teams.

The Pens seemed to trade their first rounder often, which ended when Eddie Johnston took over. EJ`s first draft he would have had the first overall but it had been flipped with Minnesota. EJ was a sharp talent evaluator though and came out with the better player (Bob Errey over Brian Lawton).

Similiar to the old saying, a coach is only as good as his goaltender, I believe a gm is only as good as his scouts (which for some gms includes themself).

 

[Damisoph]

John Ferguson Jr. had a pretty tough run for the Leafs. Whether his moves were at the behest of ownership, pathetically holding on to the "glory years" of the late 90s and early 2000s.

Trades Tuukka Rask for Andrew Raycroft. (apparently the thought at the time was Justin Pogge was the superior goalie)

Traded our 1st with other assets to SJ for Vesa Toskala. After the blunder that was the Raycroft trade, JFJ needed another starting goalie. Doug Wilson took that pick, moved up and turned it into Logan Couture.

Signed Jason Blake to a 5 year deal. Didn't really hamstring the team in terms of cap, but Blake was a peripheral player, and became a whipping boy for Leaf fans with his style which was skate around the zone and take an ineffectual shot from the high slot.

Then we had the really bad version of Cliff Fletcher, and motherf***ing Burkie.

 

[Killion]

John Ferguson Jr. had a pretty tough run for the Leafs. Whether his moves were at the behest of ownership, pathetically holding on to the "glory years" of the late 90s and early 2000s.

Trades Tuukka Rask for Andrew Raycroft. (apparently the thought at the time was Justin Pogge was the superior goalie)

Traded our 1st with other assets to SJ for Vesa Toskala. After the blunder that was the Raycroft trade, JFJ needed another starting goalie. Doug Wilson took that pick, moved up and turned it into Logan Couture.

Signed Jason Blake to a 5 year deal. Didn't really hamstring the team in terms of cap, but Blake was a peripheral player, and became a whipping boy for Leaf fans with his style which was skate around the zone and take an ineffectual shot from the high slot.

Then we had the really bad version of Cliff Fletcher, and mother****ing Burkie.

.... Indeed though I tend to cut some of the Leafs GM's slack as theyve all faced running interference from Ballard, Stavro's, MLSE & Rogers/Bell & Uncle Larry. Ive seen lists "Worst GM All Time" & on some, the 3 most prominent names making the Top 10 are MacNamara, Imlach of the late 70's & Gord Stellick.

You can pretty much alibi those guys, give them a pass with the exception of Imlach given who & what they were dealing with. Punch not so much, who during his very short tenure went on a Holy Tear (and important to remember he was following orders to a large extent), a culture of rebellion & "me first" that had been brewing in the dressing room for some time coming to a head & which lingered like a bad smell well into the 2000's.

Dysfunction that began in the early 60's when Stafford Smythe & Harold Ballard began selling the Farms', off-loading contracts, selling talent, demanding trades & receiving little or nothing in return. Then you had the Keon Affair followed by Sittler.... Fletcher with Stavros... JFJ & Burke victims themselves of the Boardroom & Executive power struggles that followed to a large degree. Panic'd into action. Stupidity. What had been instilled in the organization all those years ago, then the revolt late 70's early 80's permeated every aspect of the organization under Ballard, under Stavros, MLSE & I'm sorry to say to this day.

 

[Hobnobs]

.... Indeed though I tend to cut some of the Leafs GM's slack as theyve all faced running interference from Ballard, Stavro's, MLSE & Rogers/Bell & Uncle Larry. Ive seen lists "Worst GM All Time" & on some, the 3 most prominent names making the Top 10 are MacNamara, Imlach of the late 70's & Gord Stellick.

You can pretty much alibi those guys, give them a pass with the exception of Imlach given who & what they were dealing with. Punch not so much, who during his very short tenure went on a Holy Tear (and important to remember he was following orders to a large extent), a culture of rebellion & "me first" that had been brewing in the dressing room for some time coming to a head & which lingered like a bad smell well into the 2000's.

Dysfunction that began in the early 60's when Stafford Smythe & Harold Ballard began selling the Farms', off-loading contracts, selling talent, demanding trades & receiving little or nothing in return. Then you had the Keon Affair followed by Sittler.... Fletcher with Stavros... JFJ & Burke victims themselves of the Boardroom & Executive power struggles that followed to a large degree. Panic'd into action. Stupidity. What had been instilled in the organization all those years ago, then the revolt late 70's early 80's permeated every aspect of the organization under Ballard, under Stavros, MLSE & I'm sorry to say to this day.

Cliff Fletcher was just bad though.... Constantly trying to make the team as old as he was