What are some of the most bonehead moves made by teams at some point?

[Passchendaele]

Doesn't have to involve players. Could be management stuff.

I seem to recall reading (must've been here) about an NHL GM in the 1930s hiring a random guy he met on the train as a coach. That'd be cringe-worthy today to say the least.

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[Normand Lacombe]

John Bassett not firing and forcing Ballard and Stafford Smythe to sell their shares in the Leafs. The board gave Bassett the approval to remove them. Had Bassett done so, the reign of Ballard maybe never happens.

The NHL not vetting conman John Spanos. A complete embarrassment to the NHL and Islander fans.

John Zeigler nowhere to be found after the Schoenfeld-Kowharski incident and the subsequent walk out of NHL officials.

 

[Kyle McMahon]

Toronto giving Jeff Finger a $4 million per season/4 year contract shortly after the salary cap era had begun still has to be the most baffling free agent contract ever handed out. He was basically an NHL/AHL tweener who played 199 career games. It was so absurd that people just assumed it was an erroneous report until several hours had passed by and it still hadn't been retracted. This would be like a $7 million contract under today's salary cap.

 

[trentmccleary]

Why didn't Calgary have much offensive talent to surround Iginla in the early 2000's? They lost or traded away 1 1/2 offensive lines in a 2 year span.

Martin St. Louis - July 31, 2000: Signed from Calgary as a free agent by Tampa Bay.
Valeri Bure - June 24, 2001: Traded to Florida by Calgary with Jason Wiemer for Rob Niedermayer
Cory Stillman - March 13, 2001: Traded to St. Louis by Calgary for Craig Conroy
Marc Savard - November 15, 2002: Traded to Atlanta by Calgary for Ruslan Zainullin.

 

[streitz]

Everything involving Mikhail Smith as the Jets gm.

Not going to go into it but the funniest/saddest chain of events.

More/less runs Hawerchuk(captain and franchise's best player)
Trades for Housley. Hate for Housley aside the Jets were literally loaded with offensive D men, like 4-5 puck movers. Completely redundant.
Picks a fight with Housley after he gets drunk at the team Christmas party a few years later. Housley then demands a trade at the end of the season(I don't actually remember if he demanded a trade but it was common knowledge he would be gone, Smith's tirade was pretty common knowledge lol). After a few months he trades Housley for nothing.

What takes the cake though. I've tried to find footage but I can't, I wish it was on youtube lol.

Mikhail Smith was obsessed with Russians. Not because he thought they were skilled(maybe that was part of it, no idea) but because they were cheap and would play for league minimum(outside of Zam and the Bulin wall we didn't get any good ones in the Peg lol). Other Euro's too, not that I have anything against Euro's per say as long as they're solid players (ie Steen, Numminen, Selanne ect).
Anyways 1992 draft, I'm watching on TV, whatever same old. Jets first round pick, 17th overall he takes a 25 year old Russian named Sergei Bautin. Bear in mind this is a guy he could have taken in the 11th round, was on no one's radar.
Bautin was a chain smoking, maybe IHL/AHL caliber player. Couldn't skate, couldn't move the puck, was soft, took stupid penalties ect. Nothing good about him, just trash.
When Smith made the pick on TV though, he had this really smug look on his face like he was the smartest GM in the league. 'The Winnipeg Jets will select....(big pause here as he looked around the room smirking) Ssssergei...(another brief pause)....Bautin'.



I don't know if he was worse then Milbury but man I hated Mike Smith.

 

[FerrisRox]

Toronto giving Jeff Finger a $4 million per season/4 year contract shortly after the salary cap era had begun still has to be the most baffling free agent contract ever handed out. He was basically an NHL/AHL tweener who played 199 career games. It was so absurd that people just assumed it was an erroneous report until several hours had passed by and it still hadn't been retracted. This would be like a $7 million contract under today's salary cap.

A strange part of that signing was Ron Wilson, who was the Leafs coach at that the time of the signing and had previously coached the Sharks openly lying to the Toronto media in support of the signing.

Wilson praised the signing of Finger and claimed that when he coached the San Jose Sharks (the club he coached before the Maple Leafs) that he saw "a lot" of Finger because the Avalanche would use Finger to "shutdown" Joe Thornton. The problem with this claim was that it was easy to check (and it was quickly refuted by Avalanche reporters that were baffled by the signing.) Turns out that not only was Finger not used to shutdown Thornton (or anyone) and in reality Finger and Thornton were almost never on the ice at the same time (for obvious reasons.)

 

[sabremike]

March 1991- second darkest day in my entre life as clueless putz and worst executive in the history of pro sports Ed Johnson trades Ron Francis, Ulfie and Grant Jennings to the Pens for John Cullen, Zarley Zalapski and Jeff Parker (who retired a month later). There has never been a more disastrous trade in sports history because it directly led to the darkest day of my entire life: April 13th 1997 and saying goodbye to my beloved team and leaving me with a hole in my heart that will never heal.

 

[WingsFan95]

Bobby Holik signing in 2002 when you consider everything is probably the worst single contract I have ever seen.

The man was a good two-way forward in the Devils system that contributed to Cup runs for sure, but it's not like he was even the 5th most important player on the last title team of 2000. So 2 years removed he's 32 and is coming off a contract paying him 3.5 mill a year. Glen Sather gives him 5 years at 9 million a year. That's 2002 money. I forget where that salary ranked at the time but I do know it was pretty damn high and up there with the big boys. Furthermore this was a 5 year contract for a 32 year old two-way forward of limited offensive output. What in the hell? Pre-cap for sure, but here's what the Rangers roster turned out to be for the 2002-03 season:

Lindros, Messier, Leetch, Nedved, Barnaby, Bure. Kovalev was traded during the season.

Bure was the highest paid player that year and next at 10 million. And although I'm not sure what Holik's payroll was those first two seasons I can't imagine it would have been far removed from the 9 million average.

It is absolutely insane how Sather gave him the contract and I'll be forever convinced there were other reasons, off-ice reasons why. There simply can't be any other answer outside Sather suffering a mild stroke.

Now I know there have been bigger busts in terms of Free Agent signings but this was a ludicrous contract for a team in absolutely no need for top player talent for a 32 year old with limited output. Like.....no it's the worst.

After that I think it's probably the Messier for Nichols trade in 91. I mean yeah, I know Pocklington was still losing money and couldn't afford to end the holdout but Messier was a year removed from a Hart winning season and Nichols was only a year younger than Moose and clearly nowhere near the same level. I know there were other pieces in there but basically it boils down to that, add in the fact Nichols really didn't want to be in Edmonton I really doubt the Oil couldn't get a better deal.

Lastly, Sean Avery getting a 4 year 15.5 mill contract in 2008 with the Dallas Stars. Now this decision can be definitively put on Brett Hull being co-manager of the team with ties to Avery in Detroit. Paying a player like Avery near 4 mill a year on that team was simply stupid. He was making half that previously and at age 28 it's not like he showed himself worth more with a career high 18 goal, 48 point season. He was traded 23 games into his contract which again the Rangers took on but I think Avery was cheaper to them, I forget what the score was but this was the last contract Avery had and retired after completion.

 

[The Panther]

I seem to recall reading (must've been here) about an NHL GM in the 1930s hiring a random guy he met on the train as a coach. That'd be cringe-worthy today to say the least.

That actually might not be a bad idea for Edmonton right now.... new coach on a train, new GM on a plane.

 

[The Panther]

Why didn't Calgary have much offensive talent to surround Iginla in the early 2000's? They lost or traded away 1 1/2 offensive lines in a 2 year span.

Martin St. Louis - July 31, 2000: Signed from Calgary as a free agent by Tampa Bay.
Valeri Bure - June 24, 2001: Traded to Florida by Calgary with Jason Wiemer for Rob Niedermayer
Cory Stillman - March 13, 2001: Traded to St. Louis by Calgary for Craig Conroy
Marc Savard - November 15, 2002: Traded to Atlanta by Calgary for Ruslan Zainullin.

I think the Flames could live without Stillman (since they got Iggy's buddy Conroy). But those others ones... Good grief, those are awful.

The Flames FOR SURE win the 2004 Stanley Cup if not for sending away St.Louis and Savard for basically nothing.

 

[The Panther]

Bobby Holik signing in 2002 when you consider everything is probably the worst single contract I have ever seen.

I started a thread about that a while back. I still can't get my head around that contract. Worst contract in history. Absolutely ridiculous.

 

[The Panther]

It doesn't get mentioned as often as it should, but how about Detroit's (read: Jacques Demers bending Jimmy Devellano's ear) bonehead trade in June, 1989? Do you know the one I'm talking about...?

In 1988-89, the Wings had a moderate setback, sagging to a .500 record, but still finishing 1st in the crappy Norris. Apparently, Demers and Devellano thought they knew what the team needed. So, they send Adam Oates and Paul MacLean to St.Louis. In return, they got veteran Bernie Federko, who was 33 and wanted no part of the Wings.

So, how'd this one shake down?

Federko scored 57 points (-8) and retired. Done.

MacLean immediately had a strong, 36-goal season for St.Louis before retiring prematurely the next year after a rib injury (which, presumably, wouldn't have happened if he'd been in Detroit). Oh, and how about Oates? Oh yeah, he scored another 1221 points, finishing top-10 in scoring seven times and 1st in assists three times. Had a 142-point season for Boston. As late as 2002, he was still scoring at a point-per-game.


I know people can say, "Well, Oates wasn't Oates yet." But actually he was. He'd just scored 78 points in 69 games (90 point pace), with limited PP-time behind 155-point Yzerman.

 

[NyQuil]

It is absolutely insane how Sather gave him the contract and I'll be forever convinced there were other reasons, off-ice reasons why. There simply can't be any other answer outside Sather suffering a mild stroke.

I was a Ranger fan in those days.

There was a bidding war for Holik's services and Sather was adamant that he win. He wanted to make a big splash that off-season.

Incidentally, he also went and signed Kasparitis that same off-season IIRC at 4.25 million over 6 seasons. He was 30 at the time.

They were the two best positional players available on the free agent market that year. It was a bad year for the talent level of free agents and bad timing for Sather's spending spree.

 

[Tarantula]

Ottawa, I could not believe they went with Redden and not Chara. Redden gets a huge deal, and eventually gets buried in the A, and Chara gets a cup with Boston.

 

[NyQuil]

Ottawa, I could not believe they went with Redden and not Chara. Redden gets a huge deal, and eventually gets buried in the A, and Chara gets a cup with Boston.

Redden actually got a small deal (termwise), which is why they picked him.

Chara wanted five years (the maximum at the time) for 7.5 million a year (the maximum at the time) while Redden was willing to take 6.5 million for 2 years, allowing the Sens some cap flexibility with Jason Spezza and Dany Heatley's re-signings on the horizon.

Redden was also willing to take 6 million if Chara were also signed.

A million here or there doesn't sound like much today, but at the time, the cap was 37 million (IIRC), and the Sens were right up against it, to the point where they traded for Tom Preissing and had him in the line-up simply because his salary fit at $600K.

Looking back, it looks like a pretty easy decision to make, but Chara had just come off a disappointing and injury-plagued playoffs in 2006 where some questioned his ability in the "post-lockout era" where obstruction was heavily penalized.

Finally, it's come out since then that Chara was bitterly disappointed in how Ottawa treated his friend and countryman Marian Hossa (signed him and then traded him right away for Heatley) and that he wanted an opportunity to be a Captain of his own team. It's been argued that he would rather have left anyway, and that his salary demands were part of that.

Meanwhile, Redden played out his two years at 6.5 million, was the one who was actually most affected by the "new" NHL (he had learned his trade in the dead puck era and injuries had slowed him as well), and then was rewarded for his lackluster play by the Rangers who signed him for 6 years at 6.5 million for some reason. The Senators had actually attempted to trade Wade but he employed his NMC on a couple of occasions to stay.

A lot of things conspired for this decision, and yes, ultimately it was the wrong one.

I'm just providing a little context as to why it was such a complex problem and not as obvious as it seems today.

 

[BigBadBruins7708]

Sinden and Jacobs completely misreading what the post 05 lockout FA market would be and making sure they only carried a few contracts past 2004.

went from 104 points in 2003-04 to 74 points in 2005-06

players lost:

Nylander
Gonchar
Rolston
Knuble
Lapointe

players signed:

Zhamnov
Isbister
McEachern
Reasoner
Jurcina

 

[K Fleur]

Sergei Zubov for Kevin Hatcher.

A guy who ended up borderline HOF defenseman traded for a big, slow, dumb player that didn’t even use his size to be physically imposing.

The rumor behind the trade being that Mario Lemieux didn’t like how Zubov played on the power play. One of the most effective power plays(95-96 Pens) of all time...

The Pens actually have made a couple of terrible “skill for size/toughness/grit” trades in their history.

 

[FerrisRox]

March 1991- second darkest day in my entre life as clueless putz and worst executive in the history of pro sports Ed Johnson trades Ron Francis, Ulfie and Grant Jennings to the Pens for John Cullen, Zarley Zalapski and Jeff Parker (who retired a month later).

Parker's concussion in, I think, his first game as a Whaler was terrifying. He was unconscious for five minutes after the hit and when he died a few years back it was not at all surprising to see that he suffered from CTE.

 

[sabremike]

Parker's concussion in, I think, his first game as a Whaler was terrifying. He was unconscious for five minutes after the hit and when he died a few years back it was not at all surprising to see that he suffered from CTE.

Wow I wasn't aware he had passed away. So 2 of the 3 guys in that trade are no longer with us and Cully almost died from cancer. I didn't think it was possible for that trade to be more depressing but yeah.

 

[District 5]

Wild: Doug Risebrough Trading Nick Leddy for Cam Barker... ick

North Stars had some BAD 1st round picks in the 80s...
83: Brian Lawton 1st overall
84: David Quinn 13th overall (No GP in NHL)
86: Warren Babe 12th overall (21 gp, 7 pts)

They finally figured it out in 88 with Modano.

 

[FerrisRox]

Wow I wasn't aware he had passed away. So 2 of the 3 guys in that trade are no longer with us and Cully almost died from cancer. I didn't think it was possible for that trade to be more depressing but yeah.

It was discovered after his death that Zalapski, just like Parker, suffered from CTE.

 

[tony d]

Ottawa drafting Brian Lee in 2005 instead of Anze Kopitar.

 

[Peter Tosh]

Islanders made some really horrible moves in the 90’s early 00’s.

Mike Milbury's Top 15 Worst Moves As A GM

 

[Normand Lacombe]

Bobby Clarke giving away Brad McCrimmon to Calgary for a draft pick in 1987. Clarke and McCrimmon were embroiled in bitter contract dispute that was personal to Clarke. Clarke would years later call McCrimmon a "drunk" and a bad presence in the room, an assessment that McCrimmon's teammates disagreed with. This trade was a major reason why the Flyers swiftly fell from Stanley Cup contenders to a non-playoff team.

 

[The Panther]

Really, we could just list the Maple Leafs' total transactions and management moves from 1979 to about 1990.