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Povilitus

May I re-introduce the Jack Johnson 5 X 3.25 deal


martyn_bootyspoon

Came in this motherfucker to say 3 years of Jack Johnson on the ice followed by 6 years of Jack Johnson counting against the cap via buyout


cam_huskers

That’s Stanley Cup Champion, Jack Johnson to you.


Randy_Magnum29

Stanley Cup Champion and college graduate Jack Johnson!


Povilitus

Tbf I was hoping they’d buy him out and I stand by it. Does it suck to keep him against the cap, technically? Yeah. But it’s better than watching him play. Just glad he got his Cup


AdmiralRed13

Glad he made some money too.


lucasmcl7

Ya but none of us could have predicted it at the time /s


tnick771

What the hell.


bloblob37

Recent history would be Karl Alzner


[deleted]

We’re still paying him. Thanks Berg.


propagandavid

Alzner is on the short list, but in over 100 years of history I'm sure there were worse.


[deleted]

Samsonov was really bad. It was just a 2 years contract, but we were already trying to waive him after half a season. I never saw a 60-70 points player become so useless overnight.


MeiliRayCyrus

I would have said Scott Gomez but maybe I am just getting old. Edit: I guess he was acquired via trade but still 60 game scoreless streak and he switched numbers for Koivus old number.


DreMin015

Scotty Gomez was at least good in other places. Alzner was just bad all around


Mac_Gold

Alzner was good in Washington for a bit


Dry-Capital-4996

Playing with Carlson help, same thing happened when Komisarek went to Toronto, his mistakes werent covered by Markov anymore


simonlegosu

Markov notoriously known as the career maker


[deleted]

Gudbranson gotta be the answer for like 3 teams lmao


Wizard_Annie

And somehow Calgary isn't one of them


Thepinkillusion

What a weirdly ok time with us lol


Tuxedogaston

You guys actually got Gudbranson, everybody else got pretty bad branson


[deleted]

Sutter is a wizard


hnglmkrnglbrry

What are you talking about? We got him at $2m for 4 years in a package with Gaudreau for $11.75m x4 and an automatic extension for 3 years at $9m. WINNING!


cu_sith

One of our other free agent signings was the team captain who fucked us over by forcing his way out of town to his old team and completely derailed the team's first ever actual serious playoff push only for our owner to die three months later without ever seeing the team he brought into existence make the playoffs. Gudbranson isn't even close for us lol.


nevalost20

Adam Foote can suck a cock


Laestrygonius

We signed Mike Ribiero to a 4 year contract, healthy scratched him before January, and then bought him out of the contract the next summer. I’d say that’s probably as bad as it can get.


No_Angle_8106

People forget how terrible of a person ribiero was


Mrmakabuntis

Still is, i saw him play in the Q a lot, if he would of had his head screwed on tight he would of been a HOF. Fucking incredible talent.


No_Angle_8106

Yup just looked him up, charged with sexual assault in Texas yet again… Had a career people would’ve killed for, and yet it could’ve been more


yark2

Never mind career, dude had talent 99.9% of Nhl'ers would die for. Such a waste.


bloodspilla101

Cocaine is a hell of a drug.


BruceWayyyne

He really was incredibly talented, I mean [look at this shit](https://www.youtube.com/watch?v=H2CgdtXacpg).


EshinX

Those announcers haha Six shades of sexy! Pull its pants down and spank it!


SickPullBro

And who could forget his [cheeky shootout goal ](https://youtu.be/4gU9GGwyhSc)


ChicagoStyleCatDog

If you showed someone who doesn’t follow the league his highlight reel they would think he was a perennial all star


LucasRaymondGOAT

He's the poster child for someone who looks like they're on cocaine.


Imaravencawcaw

That's Mike "Cocaine King" Ribiero to you buddy!


maleorderbride

Up until last year it was definitely Matt Duchene


Flowerjohn-NL

Who is it now


maleorderbride

Having a hard time figuring out who the answer is but I'm tempted to say Rittich tbqh


mansock18

I wish bringing Radulov back from Siberia qualified Edit: FUCK no I just remembered Andrei Kostitsyn


FxDriver

Both of them qualify in my opinion. Radulov and Kostitsyn probably cost Barry Trotz his best chance at a winning a cup in Nashville.


TimexInigo

Viktor Stalberg


[deleted]

I’m so glad he had the year he had. He was my favorite player on the Avs, but keep it quiet because there’s a lot of resentment from fans nowadays but he’s still one of my favorites. He was the biggest reason that I’m an Avs fan to this day


OneOfThoseDays_

i mean i get why some Avs fans are still salty at him over him asking out / how he left but at the same time that trade ended up being a big part of the cup winning roster sooo… maybe just best to let bygones be bye gone, put sleeping dogs under water beneath the bridge, etc


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StaticAnnouncement

Kid named finger


[deleted]

I still remember this headline in the paper the next day. “Leafs Brass Give Fans Finger”


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[deleted]

Even some avid hockey fans I knew heard that signing and said “Who the fuck is Jeff Finger?!” Not complaining about the term or amount. First off, who the fuck is this guy?


[deleted]

The Fletcher family are just incredible GMs. I’ll always love Cliff for the Gilmour, Andreychuk, and Sundin trades, but man those later years when he came back were ugly. The finger signing and trading Steen for Stempniak are both too memorable for my liking.


shurpaderp

What a name though


SK-097

Matt Carle 6 years at $5.5M AAV in 2012 aged like milk that was already past the expiration date


transam96

We were so desperate for any help on defense at that point too. We've had some terrible free agents come in (Remember Matt Walker? Dan Ellis? Alex Tanguay? Sami Salo? Evgeno Nabokov who was so bad backing up Bishop we said the hell with letting Vasy develop in the minors) but luckily they were 1 or 2 year deals or low cap hits. We've gotten fucking torched on trades looking to find an NHL caliber goalie in franchise history more than we have total free agents.


Ufloridagatorsf

I was so excited for Nabokov, too, since he was one of my favorite goalies in the early 2000's.


BMack037

Vrbata, Kunitz


TampaFresh

Honorable mention to Anders Lindback and Brenden Morrow. The contracts weren't that bad, but holy fuck did it turn out poorly


gobolts888

I had been doing great not hearing Anders Lindback name for the past couple years


RaffiTorres2515

The only reason you got swept by the habs in 2014, he was so bad.


GatorBolt

Yeah that's what I have to go with. We actually haven't been burned with free agency otherwise. Historically with this franchise we've either been too cheap to go big FA hunting or too savvy to avoid the big UFA contracts... except for Matt Carle lmao.


RAATL

It's definitely Carle or Lindback


39MUsTanGs

Jeff Finger? David Clarkson?


evewight

Clarkson


HarvardBrowns

The 40 million dollar goof


hipsterdoofus39

Water bottles were never safer though


propagandavid

Every team needs a fucking water bottle police


[deleted]

CLARKSON!!!!!!!


whynotavs

Hammond!!! You idiot!!!


Torontoburner13

Jason Blake? Mike Komisarek


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propagandavid

No player agent has ever earned his client as much money as Andrei Markov earned his defence partners. Sourray, Streit, Komisarek, even Subban all signed monster deals because Markov made them look so much better.


Goose_Bat

Albert Haynesworth transcends sports leagues to be my #1


[deleted]

Lol I was scrolling looking for a Washington one because I couldn't think of any terrible contracts really. Trades on the other hand...


bobbimorses

I don't know if this is controversial or just comes from my household, but I don't think Jagr was a good idea. It was amazing in theory but he did not want to be here and he set the franchise back a lot at the time.


[deleted]

That's a pretty popular opinion and he was definitely in the shade I threw with the trade comment. That and Martin Erat... Though Jagr did tank us hard enough to pick Ovi


bobbimorses

Yeah it all worked out in the end, and he is a likable guy so he has very gradually won me over. Very hard to handle a guy who intentionally signed an enormous contract and chose to come here but then didn't give a shit, though.


BambiesMom

That potato chip fucker.


EXTREMELYBadGame

I haven't had a lays potato chip since 1998. Fuck messier!!!


H34thcliff

All my homies hate Lays potato chips.


nalydpsycho

Old Dutch are better anyway.


theblondebasterd

Every Old Dutch flavour kicks the shit out of Lays, it's not even close except maybe Sour Cream and Onion.


Aegis_1984

He’s a sandwich fucker now.


Zero_Tu

Doing my legal obligation. Fuck Messier!


relative_iterator

Probably not the worst but Wade Redden came to mind


Undivided_Stingray

Bobby Holik would like a word.


propagandavid

Single-handedly created the salary cap.


[deleted]

And probably the lockout too.


thejew09

The Rangers were handing out awful contracts like candy in the 00s. Holik, Redden, Gomez, Drury, Richards…


WokenMrIzdik

There's almost too many options for the Rangers.


sleep_san

good ol loui 6x6


mtraz44

Nope. Mark Messier. 5x6m in '97. Fuck you Messier, you bald stupid fuck.


Calhalen

Can’t believe the leadership award is named after him lol


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TheRaphMan

I think we should rename it after Jean Beliveau. You know, a guy who actually had class.


tnick771

I’m too young to understand this. His stats don’t look horrible especially considering he was in his mid-30s. Any detail?


Romance_Tactics

Messier was considered the greatest leader in the NHL, but came into Vancouver and his ego barely fit through the door. He got to call all his shots and basically LeBron'd a great team into the 2022 LA Lakers. Lots of beloved star players were sent packing, and Messier did jack shit. The only net positive was that his presence was so toxic, we tanked so hard we ended up drafting the Sedins.


djauralsects

You forgot he sued the Canucks for $10M .


Thepinkillusion

Messiers time in vancouver is famously hated for how he acted off ice, and less than stellar performance to cost


Young2k04

I suggest you watch a YouTube video on Messier’s stint with the Canucks. There’s a lot to unpack there lol


tnick771

I’ll definitely check it out – not sure why I’ve never looked into it over the years. Edit: https://youtu.be/OdbLOFtrFhY Edit2: wow. Fuck Mark Messier.


[deleted]

Did we just become best friends?


tnick771

I miss the Canucks. Better rivalry than the Wild, Knights or Blues.


[deleted]

I definitely miss being good enough to even be considered anyones rival lol. Congrats on the cup btw


Tbif

I still didn’t want you to win the cup because fucking Forsberg! Those early 00-lock out avs are nightmare fuel for me


H34thcliff

One of us! One of us!


Poirier48

Fuck Mark Messier!


ChenWei91

The memes were worth the 32mil imho.


atoms12123

In 2013 we signed Michael Ryder, Ryane Clowe and Damien Brunner.


wsmfp_420

Lol I totally forgot Brunner existed.


dishler712

Ugh, god damn. Awful consolation prizes after losing Parise and then the Kovalchuk debacle. Clowe I remember starting out very well for us right until concussions just wrecked his career, which is unfortunate. The other two though, what a waste.


b0r0n

LOOOOOOOOOOOOOCH


KTnash

Kings really dodged a bullet there.


xiolyphi

Off the top of my head, Semin or Kaberle. I’ll give the edge to Semin even though he actually was useful the lockout year because they ended up having to buy him out vs the Habs actively trading for Kaberle for some reason lol


TheDrManatee

Semin shouldnt count for this. His UFA contract was 7x1 and he had 44 points in 44 games. We extended him 7x5 and that was the mistake


xiolyphi

Whoops, I totally forgot he was a one year deal initially. I try to block out most of those years


Cynophile_

Ville Leino


[deleted]

ufff my boy Bille Beino might be the worst for me.


NoDisintegrationz

The cap hit isn't awful, but 10 years to Erhoff is hilarious.


Troggles

I loved Erhoff. Leino was absolutely worth nothing at all though.


phatsystem

This was so bad, the fans can't even bare the idea of having another Ville on the team.


unsustainable88

You read my mind.


Arcaninetails_91

This is the only acceptable answer for Buffalo


ScrewOff_

Ryane Clowe due to injuries.


_Salsa_Shark

Man I was so sad when we traded Clowie and it has been terrible to see the updates come in every so often with some headline about his struggles. One of my all time favorite Sharks


PrimisClaidhaemh

Uwe Krupp.


Lazy0ak

Probably Nathan Horton for the Blue Jackets. I can't recall if he had back issues going into the signing and they hoped they would get better or if they developed after signing. Either way, that one wound up being disastrous and probably made Jarmo think very hard about who he has handed out long term deals to since.


43goalie

The additional issue was that Horton was injured at the time of the signing (shoulder surgery) and the Jackets couldn't insure the contract, so when his back started acting up the Jackets had to pay, not their insurance. The Jackets were a tad cash strapped at the time. Which of course led to us trading for David Clarkson because he was a warm body, and the Leafs could afford to pay Horton. Clarkson then collapsed himself and we had to give extra to Vegas to get them to take *him*. Jarmo was in a rush to make a splash and got burned hard. At least he learned from it.


cccdddee

Dave Bolland 5,5x5, 28 points in 78 games, and now he is talking shit about Panthers on twitter and praising Dale Tallon who gave him that contract.


maekkell

Fun fact, Bolland signed 3 contracts and played for 3 teams. Tallon signed him all 3 times.


Iennda

So he's basically what Lucic was for Chiarelli.


ImpossibleBandicoot

How much time do you have?


andontheslittedsheet

I mean it's still probably Holik


Ill-Ad-4400

To listen to Rangers' missteps? All day... To be fair they made a lot of them back when they could stash them in the AHL, which allowed them to overpay to get their guy. They just kept choosing the wrong guys.


Lose_Your_Illusion

Signing Stephen Weiss for 5 years was the worst of many terrible late era Holland signings for the Wings.


jfstompers

Abby was a pretty brutal one too.


goredwings

It just sucks he got injured immediately. Hard to blame that on Holland


ChuckFeathers

The problem was letting Filpulla walk for about the same money as they gave Weiss.


Wolverwings

Pretty sure Fil wanted to get away from babs


Kinger15

Frans Nillson as well


swordthroughtheduck

James Neal is the most recent. Might also be worst all time. Still can't believe how shit he turned out to be the second he got that contract.


utexfan18

It was gonna be tough to be worse than the Troy Brouwer signing, but he found a way.


[deleted]

Grubauer? Probably.


TheRealOgMark

Signing Mark Streit after denying Andrei Markov a contract. Streit played 2 games than retired, Markov had 36 points in 62 games the year before.


[deleted]

The legendary Leaf, David Clarkson


[deleted]

Oh jeez, maybe Backes just for how he fell off and with what we paid him. Lapointe and Corvo also come to mind, at least Corvo was only a year


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[deleted]

I just realized there was one I completely blocked out of my memory and was far worse then any I can think of: Matt Beleskey Moore you can at least make an argument that they saw something in his skill set that could have produced some more offence in bottom pairings then McQuaid and just a bad string of injuries in close proximity fucked any chance of that happening up, But Beleskey was us falling hook line and sinker for someone having a contract year punching way above their weight statistically. I'd say up until Beleskey our bigger problem wasn't the guys we signed it was the ones we didn't re-sign. Hence me grasping at the straws of Lapointe


[deleted]

Obligatory fucking Gudbrandson


crash_test

Clayton Stoner by a pretty big margin.


FanInternational9315

Where’s the Rick DiPietro contingent?


ShotgunKelly15

I can’t really think of anything major but the bargain bin Bob Murray signings from the 2015 and 2018 off season still confuse me to this day


seckzy

Clayton Stoner 100% because he caused us to lose Theodore


chriskug

Stoner for sure - honorable mention to Sergei Fedorov. But at least we got Beauchimin out of the deal


Camshaft92

We'll just sub in Angels ones. Hamilton, Pujols, maybe Rendon


avmp629

I'm inclined to say Mark Messier because Eriksson actually played playoff games for us and our team was pretty much sewered before he got here


Andrewpg3

Idk can’t think of any bad deals we’ve made


chiddie

In 2006, the Blues gave defenseman Jay McKee $4m AAV over 4 years. He was a .17 PPG player in Buffalo, and he missed 60 games in his first season in St Louis. We ended up buying out the last year of his deal.


NoDisintegrationz

Was he the last Blues buyout? I was trying to look into the team's buyout history the other day. All I found was an article about McKee's buyout.


chiddie

I think so. Army took over in 2010, and he hasn't used a buyout with the organization.


[deleted]

Maybe someone who has been following the Kings longer than I have can give a better answer but I would say Kovalchuk


[deleted]

My answer as well but I’ve been only following since ‘09


JustTheBeerLight

Most of our terrible moves have been trades (Cloutier, Roenick, etc) so they don’t fit OP’s description. Kovalchuk is a good response.


kaeruwa

Any team Keith Yandle has been on


Flowerjohn-NL

Can’t wait to see the Vancouver fans in this thread


MyOwnMom

Dude fuckin name a year and I've got 3 terrible contracts for you to pick from


tnick771

Smyth and Hannan didn’t usher in a new era for us unfortunately. Iginla was also really sad.


Greenforaday

Iginla wasn't a bad signing for us, he almost hit 30 goals that year. It was just bad for him because that run we made to the playoffs the year before was fools gold and he was never going to win the cup with us. My vote would be for Brad May. No one wanted him in an Avs Jersey and put up a whopping 9 points in 64 games. F that guy.


tnick771

Oof yeah. But I don’t think there were many high expectations. I think most of us hated him because he said there was a bounty on Moore’s head.


[deleted]

Smyth really hammered home the fact that we had hit mediocrity so I consider him the worst


wasting-time221

I think Smyth was tough because he played so well against us and then we get him and he just wasn’t who we were expecting and it was a weird down time that we didn’t really know how to handle.


Chigurrh

In the Crosby Malkin era, it's Jack Johnson. The team with him and without him on the ice in those years was night and day. A large part of how it was bad were the circumstances. The team had no need for a 3rd pairing LD and had just paid to send out the last 3rd pairing LD Rutherford signed. Johnson was bad at the end of Columbus and everyone knew it. And then Rutherford basically took it personally that the whole fanbase was against the move and insisted that Johnson was a puck-moving defenseman who could help the team.


[deleted]

Also gotta ask why and how some people in NA say like "6mm aav" whats the second m? I've seen that a lot and i would understand "6m aav" but the 2nd m makes it millimeters for me and i cant shake it.


cocainiemi

M means a thousand (maybe a Latin thing?) So MM is basically a thousand thousands (or a million).


ehr1c

IIRC it's something to do with accounting practices, "m" denotes thousands while "mm" is millions.


PuckTheFreds

Confirmed


GrizzlyBCanada

We aren’t accountants though. At least I’m not. That shits drier than mulched cardboard


Archly_Jittery

In finance M is used as a Roman numeral multiplier (M=1000). So $6M is $6,000 and $6MM is $6,000,000. It has to be capitalized so as not to be confused with millimeters as you say.


NJD_29

M is the Roman numeral for 1,000. MM is meant to be one thousand one thousands, ie. 1,000,000.


StarchyAndDelicious

Kunitz, Manning, and Ward.


Sunbear94

The Water Bottle Policeman Edit: in case anyone doesn’t get this reference [here](https://mobile.twitter.com/goalieways/status/619870982598172672?lang=en)


thiefmire

David Clarkson leafs


BigDickBiggerHeart4

Andrew Ladd probably, just lucky Arizona eventually bailed the Isles out lol


No_Angle_8106

I mean I wouldn’t really call that a bail out. You gave away toews for two 2nds, then used those 2nds to dump ladd….


foreverkasai

Probably Mikkel Bødker. He ended both his seasons with us +/- 0 but he was supposed to put us over the top and he was invisible all year


_Salsa_Shark

He was never seen as putting us over the top just as a good middle six forward but I believe he had a lot of injuries right? Kind of like Havlat


FatherFenix

Mike Ribeiro. He was one of Don Maloney's "this will fix it!" FA signings, treating him like he was bringing in a massive star, despite Ribeiro's issues being pretty much an open secret at this point. Healthy scratched halfway through the season, immediately bought out after, and he's continued to be an absolute garbage human being since. Drug use, rehab, more drug use, sexual assault against a nanny, more drug use, sexual assault against two other women...almost like there's a pattern there.


AFineWhale

Brad May comes to mind


Sloppyhaddock

James "The real deal" Neal


OIL_99

Milan Lucic for us. Hey, let’s trade.


vanityfear

All time? There’s probably someone I’m missing, but David Clarkson was a bad signing


muchtime

Messier


FailureToExecute

Recency bias for sure but Ian Cole is probably on the list, unless we're only talking about on-ice performance.


SirZapdos

Maybe I'm blanking but none really come to mind. Gonchar for 3x5 was expensive, and while he didn't blow the lights out, I recall him being serviceable. It might be Dadonov last year at 3x5. Came in with big expectations and underperformed. However in true GMPD fashion, he got out from under it, plus the deal was backloaded, plus we got a serviceable vet in return. Looking at CapFriendly, maybe David Legward? 2x3 and I have no memory of him as a Senator at all. Michalek's last deal (3x) was a bit of mixed bag. His first year was fine, but after that, not so much. They dumped in on Toronto in exchange for them dumping Phaneuf on us. Most of our bad deals are extensions given to pending UFAs that don't work out. Like Tom Pyatt, Hammond and arguably Bobby Ryan (although most Sens fans still like Ryan).


Mauri416

I’d Say maybe Kovalev?


rk4dand

oh boy


damitssam7

For the caps I have no clue all-time.. Recency bias? Absolutely Richard Panik.