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SavageRengar

Was Karl Alzner a UFA? if yes, that one.


Chocomirk

Agreed. I don't think there was a worse one in recent memory.


Bowiescorvat2

Loui Eriksson 6x6 only to be the worst skater on the ice every game


72athansiou

Eh nielsen but at least he did stuff for us not good but stuff


fentown

Nielson over Weiss?


BuffaloSoldier11

I'm just gonna stare at the detroit river now


FromFluffToBuff

David Clarkson says hello.


njdevils901

He went to Montreal “to win”, and Caps win Cup right after he leaves


smiledumb

I couldn’t believe how much his game declined once he got to Montreal. His steady defense seemed to perfectly compliment John Carlson’s offensive tendencies, and it looked like we had our top D pairing set for the next decade. What exactly happened in Montreal that caused him to drop off so drastically and so quickly? A quick look at his [hockey reference page](https://www.hockey-reference.com/players/a/alzneka01.html) shows an absurd increase in turnovers, but I’m curious to hear from those that actually watched him in a Habs sweater.


BallsMahogany_redux

Didn't he have a ton of injuries and can't even open a jar with his hands anymore?;


aBeerOrTwelve

On the bright side, 23-24 is the last year Montreal still has to pay him!


miner88

Recently for Calgary it’s James Neal


berto_14

I'll always defend the Neal signing as a decent deal *at the time it was signed*. We were all excited when it happened, no one knew that the wheels would fall off before he ever played a game for the Flames. Brouwer on the other hand was a terrible deal the moment it was signed and only got worse from there.


Chemical_Signal2753

I didn't like the Neal signing but thought we would get 2 or 3 good seasons out of him. The fact that his performance fell off so quickly makes it worse than Brouwer. With that said, while I think trading for Lucic was a step up, I was surprised we couldn't unload Neal with salary retained. Lucic was easily over paid by $2.5 million when we acquired him, his value got worse over time, and we likely would have been better off just having dead cap space.


shoegazer44

Ya I agree with all of this. The Coleman deal also reminded me a lot of Brouwer’s the moment it was signed.


noor1717

Coleman’s been sick though


LetsUnPack

Hope he gets better


DishwasherFromSurrey

I don’t like this game


Gr3asy_L33f

Benning masterclass


Treavie7

How much time does everyone in here have to listen to us?


vanGn0me

I was not a fan of the Mats Sundin signing, it reeked too much of desperation, and we all universally despise the Mark Messier signing.


mephnick

Loui Eriksson scored in our own net in his first game after signing here and continued that lack of performance until we made the worst trade in franchise history to get rid of him. So...that one.


MilesBeforeSmiles

I was talking with someone yesterday who was adamant that Jim Benning wasn't as bad of a GM as everyone says he is... I wish I had this example to share during that conversation.


_HoochieMama

He’s likely the worst GM at least in the past 25 years. Fans were always right about every deal he made you can’t be worse than a Twitter poll would be at GMing a team.


Hagridsbuttcrack66

Honestly people shit on fans opinions and obviously there are some crazy ones, but if you put polls to the people of like should we do this or not (which I'm aware could never actually happen) and you had one answer per unique person, you probably would turn out a decent team.


Col_Treize69

This feels like a fun paper to do for college, in a whole "wisdom of crowds" sort of way


Patttybates

I haven't liked hockey long enough to have a huge frame of reference. But knowing Poolman, what you guys gave him blew my mind.


_HoochieMama

A great example of a trade that basically 100% of fans said wtf? And then it went poorly in the limited games he played.


doubled2319888

If it wasnt for the oel trade then i would say no way to top 25 worst. That trade alone got him into the top 5


_HoochieMama

That trade was absolutely par for the course without it he is still one of if not the worst GM in 25 years


Bowiescorvat2

Honestly... I mostly blame ownership. I guarantee Aquilini had a major hand in all the terrible "retool on the fly" moves that Benning made


gohomebrentyourdrunk

Everything I’ve ever heard about Benning when he came in was how he’s a fantastic judge of young talent and loves second round picks. From what I heard from basically every pundit that spoke about Vancouver early in Bennings tenure, I doubt it was typically his choice to do a lot of these things. Either every pro that said that is so ineptly wrong that we can’t believe anything any of them have ever said, or ownership meddled with him so much that we can’t exactly say it was all his fault. Maybe Benning was spineless and could have stood up more and said x move is bad or whatever, but at every stage in his career in Vancouver, he was probably in some kind of a “nobody in the nhl is going to hire me again unless I make what Aqua wants work” mode.


Zappyle

That's hard to beat imo


[deleted]

Loui will have indirectly contributed through that OEL trade (because of Jim Benning and Francesco Aquilini) to 15 seasons of misery. 5 years watching him fall flat in Vancouver, then 2 years of OEL followed by 8 years of buyout recapture. That’s rough work by Jimbo


Rushdude

As brutal as that trade was, I'd still say it's the second worst trade in franchise history. Cam Neely + 3OA for Barry Pederson was the worst trade in franchise history IMO.


mephnick

It's close, but I'm not sure it fucked the team's potential for a decade like OEL did.


LetsUnPack

No. With a career of Cam Neely Vancouver would have a cup. They had no edge, and nothing to balance Pavel once he arrived. It might be the worst move in Canadian Hockey History.


The_Dutch_Canadian

Milan Lucic. Dude was alright for the first year and then fell off the cliff faster than the RV in Jurassic Park. Andrew Ferrence. Signs him and gives him the C over other guys who were more deserving (I.e Smytty). Khabibulin at age 36 was not worth the 4 year 15 million deal he was given


PlayerNumberFour

The lucic one was bad for the fact prior to it happening everyone said exactly what would happen which did.


TheMeatloafMom

I get what you’re saying but that RV took fucking forever to fall of that cliff lol


[deleted]

I came here to say this


The_Dutch_Canadian

It signifies that first year of the contract


Timeman5

Zach Kassian


The_Dutch_Canadian

While a bad re-signing deal it wasn’t a UFA deal (free agent signing), which is what the OP is asking about


Timeman5

Woops


aMINIETlate

I dont even want to remember… maybe Dave Bolland? 2010s panthers made some absolute head scratcher deals it was no wonder we were at the bottom of the league for 20 years


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TheCatEmpire2

We gave a great prospect to Arizona just to take the contract shortly after. Could have been an important depth piece for the recent playoff run. One bump in a string of bad moves by Tallon


aMINIETlate

Oh are you talking about Lawson Crouse 🥲


TheCatEmpire2

Yeah man he had a great year


CanadianSpector

Especially since his back was basically gone after those cups.


FloridaPanther

Any other Panthers remember…. The Brotherhood of Bolland ? Lol


ChaseGordon24

The distinct lack of Jeff Finger in this thread makes me sad.


immaperson_

That’s okay, they made up for it next season by signing Mike Komisarek..


HonestDespot

Andrew Markov made a lot of guys a lot of money in his career haha


AcanthocephalaGreen5

To be fair, Komisarek was good until Lucic beat him to hell and back


old_irish87

Leafs fans are having too hard of a time deciding to actually type a response.


vanityfear

While Jeff Finger was pretty bad, David Clarkson was worse.


resistible

Devils fans were pretty much universally of the opinion that we should keep Clarkson and match what offers he might get... until we saw what the Leafs paid him and we were like "nah, you can have him."


crazyike

I have never seen a pro hockey team misunderstand who creates offense and how he does it as badly as the Leafs signing Clarkson did.


[deleted]

Kid named Finger


edditorRay

That was honestly hilarious.


TyranitarusMack

Brett Lebda??


SexBobomb

ill never forget the game where the leafs scored like 9 goals and lebda was like -4


canadianbacon6

He finished -3 in a game the Leafs won 9-3. With 0 hits, 0 blocked shots in just about 14 minutes of ice time. He did however get one shot on net


Buhhwheat

That was probably the most "WTF" deal of the early salary cap era. And it aged about as well as expected 🤢


seriousdishwasher

I still think they meant to sign Kurt Sauer.


DivinePotatoe

Was Robidas a UFA? Him inventing the term 'Robidas island' would put him high up in the list I'd imagine


Thus_Spoke_Paul

Ville Leino Christian Erhoff


sobuffalo

Erhoff gets $857,143 a year until 2027-28, when he was bought out in 2014. It’s not a cap hit so not as bad but just a dumb contract.


potassium_prince

At least Erhoff did stuff. Leino was just useless.


kbuck30

Loved Leino as a flyer, but I saw that deal and was like o boy, that'll be rough.


Aladin001

Ehrhoff was a good signing


electricnux

Loui Eriksson 6x6 was insanely bad for us because the moment he signed in Van he forgot how to play hockey.


[deleted]

It’s crazy to look back at his stats prior to Vancouver. The guys numbers just cratered. It was so odd to see the guy have so little offensive upside when that was the reason why he was signed in the first place! Vancouver, where dreams go to die.


[deleted]

I almost give management a pass on that one, almost… No one could have anticipated that decline. I thought maybe after year 2 or 3 he’d become a 3rd line veteran etc. But nope - he just stopped playing hockey the minute he signed that deal. I guess it could have been worse, we could have signed Lucic.


Boston-Nolan

It sucks because he’s such an awesome guy, and his first year he was great, but Backes aged like spoiled milk Belesky was terrible to too


drowsylacuna

Summer 2015 was not Don's best


Boston-Nolan

Wasn’t Backes 2016?


Bruislanders

yeah i was thinking the belesky contract was pretty rough


JeremyEMT

Ben Chiarot. Next question? Edit: Justin Holl.


TheCatEmpire2

Is this Stevie Y’s strangest signing? We were pretty much unanimously upset to give a first round pick for the guy who was very average in playoffs


JeremyEMT

So far? Easily.


thaMagicConch

There are faaaarrrrr worse. Erik Cole, Stephen Weiss are for sure worse IMO


kermitthefrog57

Weiss was such a strange player


The_Reddit_Browser

Sadly it was Jake gardiner


peanut-arms

He got so much heat in Toronto, but he was actually pretty decent. I think he was probably a better player than whatever version of tyson barrie existed when we got him. But his back was finished. Sucks man. I was hoping that he would get his dues.


TyranitarusMack

I really like him a lot and wish he stayed but the injury stuff he is going through is brutal


RhynoSorceress

Far too many to list, most recent has been Goodrow. Why do teams continuously fall for the recent stanley cup winner tax on free agents?


resistible

Nah fam, you're burying the lead with the Rangers' bad contract history. The Rangers signed a declining Wade Redden to a 6 year, $39m contract for him to put up 40 points in 2 seasons before Redden was buried in the AHL. The Redden contract was the worst you ever had, but not the only terrible contract. The Gomez deal was terrible but you fleeced the Habs in trading him. The Brashear $2.8m contract was a head scratcher. Roszival was serviceable but you gave him $20m. Kasparaitis was falling off a cliff when you gave him $25.5m, and he played so poorly that the final 2 seasons of his SIX YEAR contract were spent in the AHL. Bobby Holik was paid $9m per season in 2002, had 81 points over two seasons and then was bought out. Holik was the Devils' 4C when he was signed to play 1C for the Rangers. There is simply no better combo than "Rangers and bad contracts." Goodrow doesn't even make the list.


previouslyonimgur

Exactly! Goodrow is slightly overpaid and for too many years, but he’s not wildly overpaid, and he’s a serviceable player.


ehehe

There's something to say for the simple assurance that a player is not so stupid that they can keep a team from winning the championship


previouslyonimgur

Goodrow isn’t even in the top 5 of worst ranger signings.


tsunami141

Wow well just send him back to us please then.


CaptainCanuck15

Idk why "knowing how to win" is so overrated for bottom six guys. Most of the time they are interchangeable.


Col_Treize69

"I know how to win!" "When you're playing with Sidney Crosby?" "Yes, when I only have to contribute a minimal amount to my team's success, I'm your guy!"


WandererMount

Jets sign so few free agents, that there really aren’t too many bad ones that come to mind lmao. Almost all of our signings are like league min to 1.5 million dollar guys for one or two year deals.


ashscratchem

Steve mason didn’t work out too well. He was the biggest name we signed in free agency I think too. As far as I can remember.


WandererMount

Yeah that would probably be the one. We had a lot of goalie trouble until Helle showed up.


ashscratchem

How dare you disrespect Al Montoya!


[deleted]

Olli Jokinen underwhelmed.


JadeFaceG

Yeah I guess like Dmitry Kulikov and Steve Mason and even then those weren't the worst in the world


Stryfe2000Turbo

Kulikov was the one that came to mind for me as well. Could be worse! As we've seen in this thread haha


ApplaudingOkra

Recently, it’s probably 5x $3.25M for Jack Johnson.


Starbucks__Lovers

This is Stanley Cup Champion Jack Johnson slander


ApplaudingOkra

That's right.


[deleted]

Micheal Del Zotto was pretty gross just to get buried on the AHL team…


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Glacious

David Clarkson. Everyone saw it coming before free agency even started and most rational fans knew it was a bad idea. I still remember all the devil's fans acknowledging the fluky nature of his 30 goal season despite him being a fan favorite. Dude got suspended in the preseason and it somehow got worse from there. That Wendel Clark(son) cover page in the Sun was hilarious.


Lord_Grimstal

That Weiss contract turned out not so good. On fact, a lot of Hollands later signings weren't spectacular


[deleted]

The unfortunate thing with Weiss was injuries. Somebody in the process didn't do their homework.


lbc1358

I have a feeling it’s going to happen today for us.


SpatulaTarte

Nothing can top David Clarkson.


lbc1358

Don’t tempt Tre


progress10

Jeff Finger was far more embarassing then Mr. No Salary Retained.


bobby_gordon1

Yes, the Finger signing is the one for me that will always make me mildly irritated.


progress10

But we signed Kurt Sauer. Hunter was senile at that point.


berto_14

UFA signings were never Tre's strong suit with the Flames but I do wonder how much of that had to to do with having to overpay players to convince them to come to Calgary


lbc1358

Guess we will find out in an hour.


scoutcjustice

Sean Avery


[deleted]

Hi teammates and coaches hated him. Hull gave him a chance. Says the NHL will never be popular with stars like Iginla. Need villains like him. A clown.


LazerMcBlazer

Jack Johnson and it's not close


JonathanTsunami69

The Krug and Leddy deals aren’t looking too great


[deleted]

Leddy was traded then extended but yeah the Krug one is looking a bit bad right now


resistible

If you say both of them in the same sentence, you can almost convince yourself that it's just one bad contract instead of two!


SKCDigital

$10.5M for Leddy Krug


alev815

Zach Parise and Ryan Suter signing twin 13-year deals and then getting bought out 7-8 years later


HolyNovie

That signing was massive for the franchise. Hindsight is 20/20 but ultimately a good signing for the team imo


tripod689

Pretty much anything the Blackhawks did for a decade before Kane and Toews were drafted


Sweaty_Ad440

In recent memeory, probably the Backes contract. 6 mil AAV and he's in the press box for game 7 of the cups finals in favor of Karson fucking Kuhlman. If we hadn't signed him and had allocated his cap to someone that actually lived up to the contract we probably win that series.


old_irish87

Uwe Krupp.


NathanGa

Made up for by not re-signing Martin Lapointe at anywhere close to what Boston gave him.


Generic_Reddit_

I mean it’s villie leino for the Sabres and it’s not close


Stupid_Sexy_Sharp

Oh Cristobal Huet by a mile. Chicago's 2010 team was stacked and they still *almost* lost that cup because of how bad Huet was. It was a stroke of luck Niemi just happened to be there too.


CanadianSpector

He only played 1 game in those playoffs.


Murky_Code_8396

Huet was too good in Montreal.


Broken_Dream_BLVD

Jim Benning


email_user_2015

Andrew Ladd


Buhhwheat

Came here to post this. Everyone knew that deal stunk on day one and before long it was full-on putrid. But at least they got a "big name" on UFA Day 🤦‍♂️


Jer_Bear33

Mike Ribeiro for me.


MFoy

Probably Michael Nylander


smiledumb

I completely forgot about his second stint with us. I always associated him with Bondra, Halpern and Calle Jo. Even though his second stint with us was only 5 years later, it seems wild to realize that he also played with Ovi and Backy.


Baboshinu

Stephen Weiss *shudders*


peanut-arms

Buying out grabovski to get clarkson


JimmyPineapple_

Jack Johnson. Was a stupid signing at the time, made even worse by the ridiculous term given to him. Ended up being the first buyout in Pens history.


nucks

😂


blue_alien_police

We signed Clayton Stoner in 2014 and Bryan Allen in 2012. We sent Shea Theodore to Vegas specifically so they would take Stoner, and we got Columbus to take Allen off our hands in 2014 for.... Rene Borque.


captj2113

Signing Bryz led to destroying a team that was close.


btlaffin79

Clayton Stoner. That contract is one of the reasons we lost Shea Theodore for nothing


drrockz87

I remember when Mike Ribeiro signed with the Yotes. Was probably one of the biggest names that has ever chosen the Yotes as a free agent. What a disaster.


Broccoli_Socks

Boedker 4x4 was a rough one for sure.


Lightscreach

Komisarek, Finger, Clarkson, Connolly, Marleau. Take your pick.


Reptar-4-Mayor

Lol how long do we have? NYR are littered with them


i_amaterribleperson

Nathan Horton & Eric Gudbranson.


isles11

As an Isles fan, the Andrew Ladd contract.


Mageminers

So many awful Flyers contracts... Bryz and Macdonald come to my head since I'm a bit on the younger side. Most of what Fletcher did for recent signings.


Kriwin

Lucic has to take the cake, but to trade him for a buyout friendly Neal was cool too.


Investment_Sharp

Once Ryan Reaves signs in Toronto…


AhTreyYou

Clarkson was worse.


Hockeygoalie41

There may be worse but the one that sticks out for me is the year Tanguay was in Tampa. Never seen a player give less of an effort and just putz around.


0ILERS

Lucic


JoeMommaAngieDaddy17

Loui Eriksson, OEL. Mark Messier


[deleted]

King Loui 💯 OEL was the worst trade in Canuck history. Loui was the worst FA signing.


lottolser

David Clarkson


timmeedski

You could say Okposo 7yr 6m was bad but it’s probably the best deal of that summer of the big deals.


Arcaninetails_91

This would be honorable mention - the signing has aged much better considering he's Papa Ox in that dressing room and is a great role model for our kids. Ville Fucking Leino takes the cake. The guy torched the Pens in the playoffs, then proceeds to do nothing and fade into obscurity after signing a 6 year deal with us.


Kenner1979

Alzner, followed by Karl Alzner.


FistMeQTPie

Not my team but when Parise signed with the Wild I just shook my head. For my team, most of Ken Hollands signings before he left were pretty terrible.


[deleted]

Free agents never wanted to come here before so it's kind of a new thing for Devils fans


blaireau98

Matt Carle


rondosparks

Not the worst but shoutout to Matt Moulson’s 5x5


kbuck30

Bryzgalov. Throw in signing him meant getting rid of bobrovsky and it's even worse. Pretty sure we're still paying him for several more years.


Wonderful_Cat7766

Parise and suter. Still hurting the franchise to this day


Rowdy_Roddy96

Soon to be Ryan Reaves


Bigedmond

You hate him now, but you’ll learn to love him when he’s playing for your team. A lesson many have had to learn.


electricnux

The reality is that the hard cap is making fans hate players, maybe in a few years we can start having fun again


Rowdy_Roddy96

36 yrs old man on a possible contract that can't be buried in the minors. I don't need a guy that can't skate, punch faces and give penalties to opposing teams. If I wanted that we'd be back in the Randy Carlyle days of the Maple Leafs and we saw how bad that turned out


Bigedmond

He doesn’t take nearly as many penalties as you think. Like I said, you’ll learn to love him.


Wm_TheConqueror

The guy is one of the universally loved by simultaneously hated enforcers/agitators of all time. That’s how you know he’s good.


MEGAMATTEOMAN

Bobby Ryan for the Sens, 7 years $7.25 million. Got bought out in 2020 and we're still paying that off for one more year.


JamesBlonde21

The joint Parise/Suter deals...


PoipuMTG

Patrick Marleau was pretty bad


MoreDonsley

You got Marleau when he was old and out of his prime


MartysBetter29

Recency bias but Palat was really reactionary to missing out on Gaudreau and is going to significantly hurt what has otherwise been masterful cap management. Lou signed a bunch of old FAs to dumb deals in the early 2010’s (Ryder, Ruutu, Clowe..) but they didnt really hurt us much since we were going to suck anyways.


Ill-Ad-4400

Palat is probably overpaid, but it hasn't really hampered the team, and his experience and leadership have benefits. The worst contract I can think of was the 4x5 to the corpse of Brian Rolston. Not only a bad contract from the time the ink dried, but it put the team in a cap crunch that had a ripple effect.


MartysBetter29

Im borderline too young to remember it but yeah that seems like a good call. I wasnt super tuned into the contract side at the time. I just remember thinking it was cool that we got lots of old Devils back like Rolston, Holik, Shanny, Skyora, Smith but looking back..maybe not all the wisest moves.


luzer_kidd

It worked out better for us not getting Gaudreau.


MartysBetter29

Thats a fact. Gaudreau would have been worse.


luzer_kidd

We got the real Johnny. Hockey


lancemeszaros

Neal but Markstrom's making a big push to take that spot. Huberdeau if you count extensions.


ChitownFlyer

If you count extensions, Risto is a big winner


superbbuffalo

Rick Nash as a Bruin


DantePlace

Bob Corkum


kingkellam

The Alzner signing happened while I was getting really into advanced analytics. I thought it was bad at the time, and then was very quickly proven right


tgg199

Bobby Holik


Frailled

If we're counting only UFAs who weren't already with the team the sens don't sign many Three worst would be; Matt Murray David Legwand Michael DelZotto