15 WORST NHL TRADES OF ALL TIME

[@owenkrepps4966]

Anson Carter for a top five greatest player of all time

[@ReepsFilms]

the drip was ahead of its time

[@centralhockey12]

ReepsFilms I love this comment, my man Anson Carter had that drip locked in 😂😂

[@DaeLh]

@Ahmad jj I guess he was that low because he didn't play in New York for to long before he went to Russia. Other players on this list have had an impact over a longer period on their new team.

[@rudypericolo]

The Caps were prepping for a rebuild, dumping all of their high salaries. As a long time Caps fan I gotta say this was one of their "best" ever moves just getting rid of the insane contract they game him was a small act of genius. One of their worst* moves as getting Jagr in the first place. He was just a terrible pick up for the tight checking d-first team the caps were back then. He either couldn't or wouldn't buy into and play within the Caps' scheme. He briefly ruined the capitals. The Caps were not a terribly exciting team back then but they were a consistently good team having made the playoffs 18 or 19 times in the previous 20 years. Jagr wouldn't come back on D, was having very (for him) sub par offensive stats and was an invisible man come playoffs. Just terrible but, I still have to thank him because without those awful "Jagr" years.... there'd be no Ovechkin years. *we don't speak of Forsberg trade, too painful

[@frankzepp236]

Jagr is somewhat lucky if he is top-15 of all time, he is down there with guys like Nick Lidstrom and the recently deceased Red Kelly. You have to remember that half of the top-20 all-time consists of pre-1980 players. The gap to number 10 is not great though.

[@trusspike1527]

These are also the 15 best trades of all time...

[@SJM6791]

Great point!!

[@charlesc747]

Trusspike15 haha true

[@citizenkill1965]

Trusspike15 sick

[@jdstibbs4242]

Perspective is everything!

[@sharkoshak7656]

Woah

[@JohnDoe-ly3wx]

The Blackhawks trade Panarin for Saad is becoming a horrible trade to look back on

[@ReepsFilms]

Great pick, forgot about that one

[@NoClient88]

J Goose 😔

[@GrimGod81]

That was a bad trade at the time never mind having to look back.

[@DEaFTONES99]

Some trades is done because of salary cap.

[@boland73]

J Goose sounds like the Hawks were trying to get back the core that won them the cups. Also they had to ship out a lot of people, like Panarin, Hjarlmarsson and others, because of salary cap problems aka not being able to afford to keep everyone

[@Boffin55]

Worse trade all time. Teemu Selanne for Oleg Tverdosky & Chad Kilger

[@skalet66a]

I second that choice!

[@onnitamminen9306]

Yup

[@oggamer3737]

Well now we can add to WPG worstt trade’s PLD for Laine and roslovic. Holy shit that is bad trade for WPG.

[@holoholopainen1627]

Atleast Selanne - Won a Stanley ! If He would have moved to ARIZONA - with The Team - You never know If there would Be More TORONTO - MATTHEWS from ARIZONA ?

[@shrimpflea]

I disagree. Best trade ever. For the Ducks.

[@84montecarlonazi]

Pretty much every trade Peter cherelli made should be on this list

[@weissblitz100]

PC: "Taylor or Tyler"??? - "I choose Neither" lol

[@allsystemsgo8678]

As an Isles fan all I can say is God bless the man. 😊

[@opinionaytedonhockey]

Top 15 worst Contracts. 4th Milan Lucic

[@VortechBand]

@@opinionaytedonhockey #4 = Milan Lucic ELC, #3 = Milan Lucic 2010-13, #2 = Milan Lucic 2013-16, #1 = Milan Lucic 2016-23

[@mikelynch7271]

Pete the Meat was a shit GM

[@fawgy3702]

17:15 don't forget Chiarelli was also behind that Seguin trade

[@CinematicComics]

yep chia pet is a POS.

[@blakeference6646]

Yes I am an Oilers fan and a Jets fan but everyone in Edmonton knows how stupid Peter Chiarelli is

[@Tsamokie]

Tyler needed to be mentored, not traded. Imagine if he was still with the Bruins. Wow.

[@chadbarry2739]

Chirelli say what you want sighned Chara and brought the cup to boston not everyone can say that ...

[@Michael-uv1gk]

Ferg y Gave away Blake Wheeler too

[@danielbeard9567]

In my 45 years watching the Bruins this was by far the best trade they ever made when the Black Hawks traded forwards Phil Esposito, Ken Hodge, and Fred Stanfield to the Bruins for defenseman Gilles Marotte, center Pit Martin, and goalie Jack Norris

[@crbrearley]

Espisito trade was surely the worst (or best i guess) trade in NHL history.

[@bobmclean8595]

Definitely this would be the worst (or best) trade of all time

[@christopherengel7436]

Great, excuse me, GREAT trade for Boston

[@fk101st]

Yes that was the worst trade ever for Chicago. Heard it on morning news before going to school. Esposito was the main man I knew it was a huge mistake for Chicago. I was proved right for many seasons. The Bruins had a great team for years to come. I still haven't gotten over it. Pit Martin did prove to be a good player on the line with Dennis Hull and Jim Pappin.

[@chrispswann6825]

The Gretzky trade obviously. The greatest player of all time traded in his prime for Jimmy Carson, Martin Gelinas, and draft picks which Edmonton used to select Martin Rucinsky and Nick Stajduhar. Well at least Pocklington got 15 million in that trade as well!

[@dontbetonit813]

Gretzky was getting hosed in Edmonton. It was a fluke they got him any way if Nelson Skalbania realized the NHL was not going to give him a franchise he would have kept Gretzky.

[@appletile2887]

Then Pocklington was able to pay off his wife and his lawyer

[@Jonathan2342]

Pocklington is still hated in Edmonton for the Gretzky trade. The only time I saw grown men cry over hockey when not playing

[@nicproctor4818]

I think that Gretzky trade was a well-played, league-directed move to push/grow the NHL brand west...

[@samrosen9954]

He was sold not traded

[@DevilzFan]

I was pissed when the Devils traded Kurvers, but then Niedermayer became my all time favorite player , so it worked out haha

[@michaellee8815]

5:00 I’m sorry, “a kings ransom for the Rangers”?? We traded McD AND had to throw in JT Miller to get LIBOR HAJEK…. That trade was a disaster for the Rangers, and now McD just helps Tampa win cups

[@Peksisarvinen]

Could've made this list with nothing but Chiarelli and Milbury trades.

[@jamesholmes5242]

Peksi Sarvinen so true...it’s mind boggling what was going thru both of their heads when the made those deals. Only possible explanation is they took bribes, or just got straight up finessed...a toddler could make better deals

[@Chakdefatte194]

Chaelli ducked the oilers up for years.

[@cloudsopowera6248]

Marcel Dionne is the most *underrated* lopsided trade

[@timoaksel9320]

He was a free agent. Detroit let him go.

[@Underdogbassist]

While Brett Hull did lead the league in goals three times, the Rocket Richard trophy didn’t exist until after Brett Hull left the blues in 1998.

[@holoholopainen1627]

The 1st Winner was Teemu SELANNE !

[@carlosanaya4149]

What? When did that began?

[@douglasmacleod6247]

Flames still win that trade because they won the Cup in 1989. Their only Cup so it’s definitely worth it.

[@sebastienlandry7868]

My top 3 worst GM 1. Mike Millbury (easy, no contest) 2. Peter Chiarelli (who manage to trade the 2 2010 first pick, but still in love with Lucic) 3. Rejean Houle (just not made for that job)

[@MrMusique1970]

No way , Houle was the WORST EVER !!! When your nickname is " peanuts " ; that mean that YOU ARE NOT AN ALPHA MALE !!!! He destoyed all the 1993 Stanley cup Champions team full of FLYING FRENCH CANADIANS (12) then brrought Koivu who scored an average of 15 goals a season. Wow ! You build a team on a player that scored a 22 goals season high !!!! We never won the cup again...

[@kpowers8489]

Millbury is definitely the worst gm of all time singlehandedly destroyed the islanders franchise, no prospect pool with an underachieved roster

[@tobinlbeach]

@@MrMusique1970Bien dit Le Gaulois. Peanut is one of the best reason I'm proud to call myself a Nordiques fan.

[@joe7346]

Chiarelli won a Cup though don't forget

[@sebastienlandry7868]

@@joe7346 Give you that, put him third then

[@chrisnurnberg9599]

January 2, 1992: Traded to Toronto by Calgary with Doug Gilmore, Jamie Macoun, Ric Nattress, Kent Manderville and Rick Wamsley for Gary Leeman, Alexander Godynyuk, Jeff Reese, Michel Petit, and Craig Berube. Got back some of what they lost in the 1991 trade. This helps them go to the Western Finals twice with this core from the trade.

[@sdgakatbk]

There are some lopsided older trades. Ken Hodge was in two of them. In 1967, Phil Esposito, Ken Hodge, and Fred Stanfield to the Bruins from the Black Hawks for Pit Martin, Gilles Marotte, and Jack Norris. The Black Hawks got a solid center, a physical defenseman, and a borderline goalie. In return the Bruins got a Hall of Fame center, a 2 time all-star on right wing, and a solid forward-and 2 Stanley Cups. According to the book Thunder and Lightning by Phil Esposito and Peter Golenbock, at a team party after the 1966-1967 Black Hawks season, a drunken Phil Esposito told coach Billy Reay and GM Tommy Ivan "We've a great team here, you could almost have a dynasty, but you two are going to screw it up." Owner Jim Norris had wanted Phil to play more physically instead of a finesse game, which didn't help Phil in Chicago. In May 1976, Rick Middleton to the Bruins from the Rangers for Ken Hodge. Phil Esposito had been traded from the Bruins to the Rangers in during in November 1975 after the Bruins got off to a sluggish start. The Rangers had been struggling in the mid-70's after being an elite team in the early 70's. Ken Hodge was in his early 30's, but had clicked well with Espo in Boston and had had a number of very productive years. Rick Middleton had played 2 seasons with the Rangers and had solid numbers. Ken Hodge played a little more than 1 season with the Rangers, producing 68 points before retiring. Rick Middleton played 12 seasons with the Bruins with 898 points including 1 50 goal season, and 4 40 goal seasons.

[@michaelkatz8106]

You are quite correct. But being traded to Boston is what made Phil Esposito's career. At the much smaller ice of the Boston Garden, (hockey rinks were not uniform at the time), size had a greater impact than speed. The area behind the net was incredibly narrow, so even if you could push Espo behind the net half of him was still in front of it.

[@pierretur]

Pierre Turgeon for f***ing Kirk Muller. After 24 years I'm still mad...

[@bigtimetimmyjim6486]

Well, you got Mathieu Schneider in the deal too, so it would not have been too bad if you were able to re-sign him.

[@pierretur]

@@bigtimetimmyjim6486 Schneider/Malakhov...

[@MrMusique1970]

I remember, that's a very RARE trade that Montreal had an advantage. Captain Kirk was finish ; first he was very intense and average skater then he had beton in his skates and was intense no more....

[@davidtuttle7556]

@Spork Spatula in his defense he got sucker punched by the rat from my team. Dont be too hard on him. As Caps fans we abhor what happened to Turgeon, and our guy did it.

[@jaredabbate2402]

pierretur i feel ya...

[@jefffuller9918]

A great trade. In 1980 the Islanders traded Billy Harris and Dave Lewis to the Kings for Butch Goring. That missing piece led to 4 straight cups and 5 straight finals for the Islanders.

[@alyssinwilliams4570]

I'd like to submit the following trade: Flames swapping their 1990 1st round pick (20th overall) to New Jersey, trading up so that they could draft Trevor Kidd. New Jersey, meanwhile, used that 20th overall pick to take.. Martin Brodeur. So.. yeah, essentially trading Brodeur for Kidd. Speaking of the Flames, 91-92 season, they sent Doug Gilmour to Toronto, along with 4 other players, for Gary Leeman (and 4 other players). Gilmour had great success in TO, while *none* of the players the Flames got did anything of note. On the flip-side, in 2004 the Flames sent a 2nd round pick to San Jose for Miikka Kiprusoff, arguably the Flames best goalie of all time. This one probably wouldnt be top-15, but probably top-25 or top-30

[@conspiraciesarejustgreatst2059]

Why are there 200 dislikes? There's literally no reason to dislike this video. It's got great info and every player is given a full rundown

[@iprey4surf]

The dislikes are from the players that got traded and turned out crappy. Nobody likes to hear how lame they were.

[@kkst3552]

Leaving the Esposito trade out makes me wonder what else he left out. I guess the Esposito trade is too far back in time for him.

[@Radeo]

"Top 10 Times Teams Traded Away a Goalie That Became a Reliable Starter for Another Team" (no draft picks)

[@bramstedt8997]

Radeo blues trade Bishop for basically nothing. We’re stuck with Jake Allen for years (until Binnington road in on a white stallion) while Bishop is constantly in the vezina conversation. Oh, and Big Ben was a STL native too

[@TheAngryCanadian1109]

Radeo belfour

[@paulmorphy6638]

The Rick Middleton for Ken Hodge, straight up trade, became a stain on the Rangers history especially for the fans every time Middleton and Boston came into the Garden. Middleton scored 898 points to Hodge's 68.

[@ntibbs100]

Jean Ratelle and Brad Park for Phil Esposito and Carol Vadnais wasn't to shabby neither

[@Rometiklan]

Adam Oates, Paul MacLean to St. Louis for Bernie Federko and Tony McKegney to Detroit. Russ Courtnall for John Kordic Phil Esposito, Ken Hodge, Fred Stanfield to Boston for Gilles Morotte, Pit Martin, and Jack Norris to Chicago. Doug Gilmour to Toronto for Gary Leeman to Calgary.

[@DrunkenGuitarGuy]

agree on courtnall for kordic, i loved kordics fights but even as a kid i new that one was stupid, leeman for gilmour was a 10 player deal so not that simple

[@Leafsdude]

@@DrunkenGuitarGuy "leeman for gilmour was a 10 player deal so not that simple" Actually, part of why it was such a bad trade for Calgary was that all 5 players they got in the deal were gone within 3 seasons, while Gilmour and Macoun would remain in Toronto for most of the decade. The trade occurred on January 2nd 1992. Leeman was on waivers and off to Montreal on January 28th. Godynyuk was picked by Florida at the June 1993 expansion draft. Berube was traded to Washington on draft day 1993. Reese was traded to Hartford in November 1993. Only Petit was still in Calgary at the end of the 1993-94 season, and he left as a free agent that summer. Gilmour wasn't traded until the 1996-97 season (and he got the Leafs pretty decent return, too) while Macoun was traded at the 1998 trade deadline. Add in that Gilmour was undoubtedly the best player in the trade numbers-wise, and it's quite massively one-sided.

[@jimbuccellato5442]

@@Leafsdude Detroit getting rid of Oates was a horrible call by Demers, getting his buddies McKegney and Federko to Detroit. Oates stopped setting up Yzerman and started setting up Hull....rest is history

[@DrunkenGuitarGuy]

@@Leafsdude well said, gotta admit the details were foggy for me, gilmour was great obviously, was sad to see berube go as a leaf fan though, at the time left leafs without a tough guy, baumgartner came not long after though

[@treerat7631]

That was a bad trade when the red wings got rid of Adam Oates

[@SombraPiloto]

Not sure how you can not include Francis, Samuelsson, and Jennings to Pittsburgh for Cullen, Zalapski, and Parker to Hartford. Was the beginning of the end of my beloved Whalers and one of the most lopsided trades in league history.

[@francischabot1412]

Forgot about that trade but yeah it was pretty bad. I guess many trades could be included. I mean you could make a case for Ribeiro - Niiiiiniiimaaaa too. Ribeiro was a head case but had a couple of good seasons in Dallas while the other guy simply was not a NHLer anymore.

[@arthurpasseri8874]

I was thinking the same... The Whalers died that day...

[@rdspam]

Penguins fans appreciate that one.

[@SombraPiloto]

@@rdspam I was a Pens fan too so I was happy to see Mario (the GOAT imo) and Ronnie Franchise lift the Cup but that was heavily tempered by the damage the trade did to my Whalers.

[@SombraPiloto]

@@TheMercyTrials I was working at the airport FBO when the Red Wings plane flew in to pick up Shanahan and he was quite happy to be leaving. I wasn't a fan because he didn't want to be in Hartford but unlike that whiny little bitch Paul Coffey he at least played hard while he was with the Whalers. Karmanos can suck a giant bag of dicks.

[@stuartmcnair2783]

In 1978 LA Kings trade their 1rst round pick to Boston for goalie Ron Grahame. Boston uses that pick on Ray Bourque who would Win 5 Norris trophies and score over 1500 points and become the highest scoring defenseman in NHL history.

[@bobzani]

1967, Blackhawks traded Phil Esposito for ??? does it matter? He scored 700+ goals.

[@tobinlbeach]

It was a multi player trade. Only guy I remember going to the Hawks is Pit Martin.

[@mikeprevost8650]

Gilles Marotte and the immortal Jack Norris, who was with the Hawks for proverbial cup of coffee. Bobby Hull was livid at Hawks management for pulling that disaster.

[@bobzani]

@@mikeprevost8650 Hawks also gave up Fred Stanfield and Ken Hodge. Hodge was a really good player too.

[@mikeprevost8650]

bobzani so was Stanfield. He was their second line centre between Johnny Bucyk and Pie McKenzie, and played the point on the power play opposite Orr. Took very few penalties, and scored 20 or more goals in every season with the Bruins.

[@ChrisBrown-pz2gu]

Worst trade in Hawks history. Can you imagine what could have happened if they don't make the trade? I'd like to think that they would have steamrolled Montreal in 71 and 73...

[@kevinstull8552]

You could have also included the Joe Thornton trade as well too.

[@phantomstratocaster]

you are thinking it was a bad trade for sj?

[@tweakbunny]

@@phantomstratocaster It was a terrible trade for Boston. They got a couple decent years out of Marco Sturm, Brad Stuart almost immediately went to Detroit, and Wayne Primeau went to Pittsburgh. Thornton won the Hart his first year with San Jose and now sits top 10 in assists all time.

[@phantomstratocaster]

@@tweakbunny just taken joe out of the lockerroom got them a cup

[@chrispswann6825]

Not really. After trading Thornton the Bruins signed Zdeno Chara as a free agent which they probably couldn't have done if Thornton's salary was still on the books. Then Chara led Boston to a Stanley Cup. So it couldn't have been that bad.

[@RRaquello]

​@@chrispswann6825 That was the point of the Thornton trade that most people miss. They traded Thornton with the specific aim of using the money to sign Chara. Of course it was taking a chance, because Chara could have signed with another team, but they must have known they had him in the bag. Maybe tampering involved? So the trade ended up being Thornton-for-Chara, which worked out for both teams. The losers in the deal was the Ottawa Senators.

[@DJDoorGuy]

As a Flyers fan I loved Lindros, however when you look at “what could have been” and some of the other moves and events that took place as a result of the Quebec/Philadelphia deal, it was one of the worst deals ever made, at least for Philadelphia fans....

[@MegaB28]

that trade to me was the worst trade of all time, or the best in my case cause I was a Quebec Nordiques fan, lol

[@Jackthgun]

When Lindos For Forsberg would have been and OK deal and Quebec got him $15 million and 6 other players

[@kokanee2010a]

HE ALSO MISSED THE CLIFF FLETCHER FLEECING OF HIS FORMER TEAM GETTING THE BEST OF RISEBROUGH .

[@garnotte12]

California Golden Seals trade Francois Lacombe and 1st overall pick to the Montreal Canadiens for Ernie Hicke and their 1st round (Cris Oddleifson)...which was the last pick of the 1st round because the Canadiens had won the Stanley cup in 70-71. The Canadiens picked Hall of Famer Guy Lafleur and his 560 goals. This is certainly in the top 5 worst trade of all time!!!

[@heatherdeane8218]

Top 5 best trades of all time

[@slipperynodd578]

@@heatherdeane8218 well all worst trades are best trades depending on your perspective.

[@RoyalMela]

It was good DRAFTING, not good trade. If they drafted someone who was a bust, this would not be a good trade, eh?

[@wphb66]

The one trade that sticks out for me as one of the worst was Irving Grundman's 1982 trade between the Habs and the Caps. The Habs sent Rod Langway, Doug Jarvis, Brian Engblom and Craig Laughlin to the Caps in exchange for Ryan Walter and Rick Green. Ryan Walter was a star for the Caps and DC loved him but his impact in Montreal was negligible. Rick Green was decently solid but the Habs reeled from the gutting of their defensive core and the league's best face-off man. Laughlin went on to be a beloved commentator for the Caps, Langway almost singlehandedly made the Caps into a playoff contender and earned the nickname "The Secretary of Defense". This was one very lopsided trade.

[@bishopthefool]

That trade was horrible. Irving Grundman has been the worst GM in the history of the club... even Réjean Houle was better in the end.

[@thenachofan7677]

This trade disillusioned my dad so much he then became a Nordiques fan

[@donaldcornchowder9112]

Daniel Briere for Chris Gratton, 2nd best trade in Sabres history.

[@francischabot1412]

I think you definitely forgot Pierre Turgeon for an aging Shane Corson and Murray Barron. Turgeon is in the talk for the HoF this year. Baron sucked and Corson was injured half the time and did not have much success after being traded back to Montréal. Turgeon played an important offensive role for 5 years in St-Louis.

[@mikeappleyard1898]

Doug Gilmour to Toronto. How is this not the #1 worst trade of all time in all sports?

[@niall441]

The joey Mullen trade, St Louise to Calgary. Total steal + Stanley cup.

[@georgeanthony7282]

Maybe I'm old school... but what about the trade of Rangers Jean Ratelle and Brad Park for Bruins Carol Vadnais and Phil Esposito??

[@TheTopheel]

Where is Calgary’s horrendous “blockbuster” deal that sent Gilmour to the leafs in return for the terrible Gary Leeman?

[@thewerd1982]

gilmore didnt do anything for the leafs so it never mattered.

[@Roller11111]

@@thewerd1982 you don't watch hockey do you?

[@thewerd1982]

@@Roller11111 Gilmore won a cup with Calgary then got traded and never did again. Do you watch hockey brah? Fuck the Leafs

[@jimkrueger2369]

Flames had an asshole of a general manager at the time

[@PrattBN16]

@@thewerd1982 That's even the point but ok. It's that Calgary traded Gilmour away for scraps when they should've got more out of it

[@martimaltby6078]

Calgary trading Doug Gilmour, Jamie Macoun, Ric Nattress, Kent Manderville and Rick Wamsley to Toronto for Gary Leeman, Craig Berube, Michel Petit, Alexander Godynyuk and Jeff Reese. Gilmour by himself played more games for Toronto than the five players Calgary received played for the Flames in total.

[@madpatski]

One of the Worst trades: fighter Jon Kordic and Montreal's 6th round draft pick for Russ Courtnall.

[@istazar6781]

John Kordic is legend!!! Russ Courtnall not.

[@faszody]

I was going to bring that one up.

[@thomaspsanzi8947]

"Love The Documentary on Tony Espiisito!" "I Agree, Before a Game You Always Get a Little Nervous, But Then it Turns Into Pure Adrenaline & The Game Is On & The Agression Kicks in!"

[@je7055]

Really surprised the Thornton trade wasn't mentioned, unless I just missed it? Given that he just wrapped up his career and we nearly had a Jumbo Joe vs. Bruins final. Thornton (then in his mid-20s and putting up 100+ point seasons) for Marco Sturm, Brad Stuart and Wayne Primeau - a 2nd-line winger, a 2nd-pairing D-man and a grinder, respectively, all in their late 20s with their most productive years behind them. If Boston valued players in that value range, they could've gotten similar players easily without giving up one of the best players of his generation.

[@kellyconroy786]

The only thing jumbo about Jo was his ego, you missed half of the key components the Bruins obtained in trades which led to the cup in 2011... Bruins easily won this trade

[@je7055]

@@kellyconroy786 ...no, I didn't. That was the trade. They didn't get other assets in that deal. None of the three players were on the 2011 Bruins roster, nor did Boston ever receive any meaningful assets in return for any of them with the exception of Ference, who wasn't a particularly meaningful upgrade from Stuart. Even if you believe he was, surely you aren't claiming that the Bruins "easily" won the trade because they traded two of the three pluggers they got in exchange for the league MVP for an off-puck second-pair D-man. Because that would be the most insane take ever. Even if you want to talk about the cap space that the deal freed up, you'd have a valid point if not for the fact that they could've gotten a much better haul than three pluggers for, again, the league MVP. They didn't win the Cup _because_ they traded a first-ballot HoFer for three bums, they won the Cup _despite_ it.

[@kellyconroy786]

@@je7055 Jo was a bum in the OHL with a terrible disrespect for officials,fans and many hockey towns...he was a complete asshole to teammates in Boston Andrew Ference for those who are "into"hockey was one of the fastest skaters year after year in the NHL in the play off run he was one of the leading hitmen every night had a very good+/- scored a point every two games on average including an overtime winner all while killing penalties . Even with his accomplishments he was not the only player involved as the Bruins acquired future considerations which certainly paid dividends. According to Bruins management and players Jo was not a good fit in Boston

[@je7055]

@@kellyconroy786 Future Considerations paid dividends? How many goals did Future Considerations score in their Cup run? Future Considerations is a professional courtesy between GMs that exists only because teams can't technically trade a player for nothing. 99% of the time it's a conditional 7th rounder with conditions so unrealistic the pick never gets traded. The only thing BOS got from shipping Sturm to LA for FC was an open roster spot for a less crappy player. I can't speak to Thornton's character, so I'll take your word for it. I certainly didn't find him particularly likeable, but again, he was one of the most valuable assets in the league whether he was an asshole or not, and they could've gotten more for him. Look at Lindros-he was a baby who refused to play for the team that drafted him, so QC/COL got a haul in exchange for him that helped them win the Cup four years later. That was before he'd even played a game in the NHL and proven he was elite. The Nordiques still got Peter Forsberg, a point-a-game D-man in Steve Duchesne, Ron Hextall, a premier two-way pivot in Mike Ricci, a couple of other roster fillers inc. Chris Simon, and both of Philly's 1st-rounders for the next two seasons. Thornton was an established young player at that point and they got three pluggers for him. Totally agree that Ference was a solid second-pair guy, but c'mon, he wasn't as irreplaceable as someone like Chara. There are dozens of solid second-pair D-men in the league. But *even if* you're the biggest Ference fan in the world, and you believe there's no way they ever win the Cup without him, they could've just traded Thornton to CGY for him and much more. The Flames were desperate for a playmaking C to play with Iggy. They'd picked up Langkow but he would've been a much better fit at 2C behind Thornton, and CGY would've actually had depth at the C position. BOS could've gotten Ference, a 1st-AND, say, a 22-year-old Mark Giordano (Phaneuf was two years younger than Gio and had already become CGY's star D-man; CGY would probably take that deal thinking they were fleecing BOS). And probably another decent middle-six forward like Huselius, or a grinder/PKer like Yelle, or another pick/prospect. CGY would've finally had their all-star center to complement Iggy, and the cap space to lock him up. Meanwhile, BOS would've had Ference and Giordano on their 450k deals. Someone like Huselius or Yelle would've been making 1.5mil. So in addition to getting Ference in a package like that, whom you judge as a key cog in their Cup win, they would've gotten a future Norris winner in Gio, a forward just as good as or better than Sturm, and picks/prospects, while only taking on ~2.4mil in salary. Sturm, Stuart & Primeau combined for ~5mil at the time. They could've still signed Chara in the offseason with cap space left over. I absolutely agree that trading Thornton was the right move given Savard still being healthy and Bergeron establishing himself, but they could've gotten enough in return to win 2 or 3 Cups instead of just one.

[@toddhawkins6322]

Hall is on his third team now. After 16 games on Arizona he has the 4th worst plus/minus already. He was traded twice now for a reason. And forget the Hart; he never should have won that year.

[@Narnia61]

Fifth team now and and traded 3 times.

[@wlfgngpck3102]

In all fairness on the Hasek trade, Chicago already had Ed Belfour who was himself a Vezina winner and at that time more established than Hasek. I understand the analysis here is quality of the players post trade, but I think Chicago probably felt they already had a star goaltender and didn’t need Hasek. And until the late 90s they were right.

[@williamcorreia4220]

How could you not have the Phil Esposito Deal in '67 from Chicago to the Bruins. Ken Hodge AND Fred Stanfield also became contributing members of the two time Cup winning Big Bad Bruins. Bobby Hull's comment on the trade," I just lost my right arm". Espo HOF career and greatest score of his time.

[@Actionronnie]

If you take a player for a straight up draft pick type trade. Robert Picard to Winnipeg for a 3rd rounder to Montreal. Habs select Roy.

[@owensig3783]

Actionronnie big oof Winnipeg - from a Winnipeger

[@n176ae]

Newer one: Playoffs MVP Ryan O’Reilly (77pts) For the 31st pick and 3 guys that combined for 29 total points. Absolute steal

[@ericmetz9097]

As a Sabres fan I can attest to this. One of those players also quit on us :(

[@redmoko9837]

That one was absolute highway robbery. Doug Armstrong in particular has done a good job of this lately, though the trade for O'Reilly is certainly the king. Also worth mentioning though are Ryan Reaves for Oskar Sundqvist and a 1st round pick (Klim Kostin), and Jori Lehtera for Brayden Schenn. Neither one of those two deals belongs on this list, but they're both building block deals that helped bring home the Cup.

[@christopherengel7436]

Tage Thompson is playing pretty well now though. Just took the young guy some time to get his skates under him.

[@handsomemcwonderful]

Why did Markus Naslund drive you to practice?

[@PerfectCell9]

Cause he’s a nice guy

[@northernsurferboy]

Naslund was a bad trade but at the time Pittsburgh has stacked with forwards and there was no playing time for Naslund

[@ReepsFilms]

friend of a friend

[@arikashtontube]

1. Chicago trading Phil Esposito to Boston; 2. California Golden Seals trade 1st overall pick (Guy Lafleur) to Montreal for Ernie Hicke and the 10th pick in the draft 3. Edmonton trading Wayne Gretzky to LA

[@raywateredge6444]

You missed the worst 1 of all time The Chicago Boston deal that sent Espo to Boston.

[@sixclocks]

espo ken hodge and fred stanfield for gilles marotte pit martin and a goalie named jack Norris. it was basically espo for marotte as he was an up and comer. boston did not want to trade marotte but they did. espo made himself hated by Chicago management because after finishing 1st and breaking the Muldoon curse the hawks went out in 6 games to the leafs in the 1st round. leafs won the cup espo told management they were fools. they traded espo then and proved they were fools. hodge and stanfield were I believe rookies when traded. definitely the worst trade in hawks history and maybe the worst of all time.

[@ChillydontCap]

@@sixclocks You traded the greatest goalie ever.

[@sixclocks]

which goalie? jack Norris? he may have played a couple of nhl games but that was it.

[@ChillydontCap]

@@sixclocks Dominic The Dominator Hasek

[@joshuamattern2072]

@@ChillydontCap 'Greatest goalie ever'? If you're from Buffalo, maybe. He is great, but not the greatest ever. And the vid left out the fact that when they traded Hasek, they had Ed Belfour starting, and he had been for years. They also had Jimmy Waite, who was more highly regarded than Hasek, waiting in the wings as the next goalie prospect. Yes, Hasek turned out to be better than Waite, but this was a case of having a logjam at one position.

[@grumpyguy2877]

Sabres traded Hasek because they had to either pickup his 9 million option trade him or lose him not that they were trading him so he could win a Stanley Cup. Sabres were owned by John Rigas who owned Adelphia cable were rocked by business scandal. Sabres were very effected by this and would file for bankruptcy.

[@chrisod22]

Rick Middleton for Ken Hodge. Maybe the biggest steal ever.

[@sixclocks]

because the rangers traded ratelle and park for espo and Vadnais. it did not work out for the rangers as espo was playing hurt [according to him.] so the rangers thought the reason was he did not have ken hodge. the rangers got fleeced twice.

[@bbb462cid]

@@sixclocks Espo hated the Rangers from his time in Boston and he also said that when the got there, the room had such a bad attitude about not winning being OK it made him sick. Espo had some odd ailments from his time in Boston, and he did play hurt often so I wouldn't say he was lying, but I'm saying he had other factors in NY as well.

[@arumforyou]

@@sixclocks and Joe Zanussi

[@sixclocks]

@@arumforyou I forgot him.

[@SheepOnDrugz]

How about Cam Neely and Vancouver's first round pick in the 87 draft (3rd overall, Glen Wesley) for Barry Pederson? Pretty lopsided trade.

[@theperfectending1398]

wow

[@petelamoureux9656]

These are 15 of the worst trades of the last 30 years. The three worst trades of ALL TIME SHOULD BE: 1. Boston fleecing Chicago for Phil Esposito IN 1968. That deal sent the Bruins to two Stanley Cup titles while the Hawks suffered through a 49 year Cup drought. 2. The Penguins fleeced the Whalers in 1991 when they sent John Cullen and Zarley Zalapski to Hartford for Ronnie Francis, Ulf Samuelsson, and Grant Jennings. After the trade, the Pens won the next two Stanley Cups while the Whalers continued to languish in mediocrity until they moved to North Carolina. 3. The Flyers stole Hall of Fame defenseman, Mark Howe from the Whalers in 1982 in a three way deal with Edmonton that landed Hartford ONLY Risto Siltanen. Howe led the Flyers to multiple appearances in the Stanley Cup finals while the Whalers continued on the road to nowhere. ***Incidentally, the Hockey News ranked these as the first, second and seventh worst trades in history as of their publication in 1995.

[@Chiefsfansince-qb1kt]

Thank you for your list of trades. Very interesting. But, I think there are 3 trades you overlooked, (possibly because of your age, you sound young, like in your early 20's, which, I wish I still was). However, you didn't mention the trade by Philadelphia of Patrick Sharp to Chicago for Matt Ellison. Though Matt was a tough, tenacious, grinding type of forward with a willingness to go hard to the net and score tough goals, his career (unfortunately) didn't pan out as the Flyers had hoped. Sharp meanwhlie went to Chicago in 2006 and flourished, as he became a key piece in 3-Stanley Cup Winners (2010, 2013 & 2015). Sharp is now flourishing in his next career, that as a Network TV analyst during the playoffs with NBCSN. The other trade also involved the Chicago Blackawks. In the summer of 1967 the Blackhawks traded Phil Esposito and Ken Hodge and Fred Stanfield to the Boston Bruins in exchange for Pit Martin, Jack Norris and Gilles Marotte. Esposito, along with Bobby Orr were the lynchpins of the Bruins team that went on to win 2-Stanley Cups (1970 & 72), Hodge was a key 2nd line player for the B's during that era and Stanfield was an excellent special teams player. Of the 3 traded to Chicago, Pit Martin was the only player who made a significant contribution, playing alongside Dennis Hull and Jim Pappin for several seasons on the "Scooter line." Esposito also was the key player for Team Canada in the 1972 Summit Series where Team Canada prevailed over the Soviet Union hockey team in an unforgettable series that saved Canadian dignity. Finally, the 1988 trade that sent Wayne Gretzky to the LA Kings from the Edmonton Oilers in exchange for Jimmy Carson, Martin Gelinas, 3-1st round draft picks and cash. This was a complete cash-out by Peter Pocklington, Oilers owner at that time. He was in debt, couldn't pay Gretzky what he wanted and found a partner in LA owner Bruce McNall who seemed to have deep pockets at the time. Though the Oilers went on to win the Stanley Cup in 1990 with Mark Messier as Captain, they declined shortly afterward (Messier was traded to the NY Rangers) and have never returned to the level they achieved during the 1980's with Gretzky. However, the LA Kings fortunes turned around quickly with Gretzky on their roster. In the 1988-89 season, Gretzky and the Kings began a climb that brought them into the realm of the NHL's elite teams. In 1993 they played Montreal in the Stanley Cup Final, losing in 5-games. But until that time they were a 1st or 2nd round playoff elimination team if they made the playoffs at all. Just my thoughts.

[@ReepsFilms]

Yes 3 extremely lopsided trades that I definitely overlooked. Thank you for the input !!

[@appletile2887]

Montreal traded Tony Esposito who was Chicago's equal to Glenn Hall

[@holoholopainen1627]

Even Esa Tikkanen Been to More Stanley Cup - Finals than Wayne #99 GRETZKY ! With Capitals and RANGERS !

[@scottodell4371]

How about the Rangers trading Brad Park, Jean Ratelle, and Joe Zanussi to the Bruins for Phil Esposito and Carol Vadnais?

[@gerryzaccaria3838]

Park and Ratelle went on to run the Boston offense an defense with the CAT's system and went to the finals twice (should have gone and won the cup in 79) Ratty had almost 500 pts with the bruins.

[@BeerBaron23]

What about the Habs sending Eric Desjardins, John LeClaire and Dionne to Philly for Recchi, the Habs pretty much gave Philly a mini dynasty right there....

[@GdF420]

A mini dynasty allright, with zero Stanley Cups

[@marcelleclair4452]

Terrible trade for Montreal. Awesome for Philadelphia. They got a top D and a 50 goal man.

[@cloudsopowera6248]

What about Chicago trading *Phil Esposito* to Boston? Golden Seals giving their 1st rd pick turned *Guy Lafleur* to Montreal? Boston trading *Ken Dryden* to Montreal? Mats Sundin trade? Whalers shipping *Ron Francis* to Pittsburgh? Brad Park and Jean Ratelle shipped to Boston for aging Phil Esposito? Montreal trading Chris Chelios?

[@estellegrignon]

You really did the Habs dirty by including Roy and McDonagh, but forgetting when they fleeced the Golden Seals off their first overall pick in 1971 to get Guy Lafleur, or when Boston traded Ken Dryden and Alex Campbell for Paul Reid and Guy Allen.

[@CharlesABelair]

Or Bob Gainey fleecing the Sharks hard with the Craig Rivet for Josh Gorges + 1st round pick of 2007, which became Max Pacioretty. A trade that keeps on giving today for the Canadiens. Or when the Canadiens got Alexei Kovalev for some rando named Joseph Balej.

[@estellegrignon]

@@CharlesABelair the Rivet deal! They made a trade tree for it, and it somehow lead to Jake Allen!

[@CharlesABelair]

@@estellegrignon Yep as well as Nick Suzuki of course !

[@tedvdw1975]

Cliff Ronning, Sergio Momesso, Geoff Courtnall, Robert Dirk to Vancouver for Dan Quinn and Garth Butcher to St. Louis. Perhaps not horrible, Quinn had some solid seasons and Butcher was steady enough, but that pretty much solidified Vancouver for the next fiver years.

[@jeffdickson125]

i was just going to mention this one. Great memory! Life long blues fan here, and that one killed a possible Cup run in my opinion. Story goes that then GM Ron Caron panicked when a possible trade for Ron Francis and Ulf Samuellson fell thru at the last minute

[@dirtybaystrangler]

I remember when Seguin was sent to Dallas due to his hard partying in Boston. I worried about him being sent to a place like Dallas to overcome his partying ways, but he has done very well.

[@artvandelay1967]

this happens more than we know. Vancouver traded Vaive and Derlago -two top picks to Toronto for Tiger Williams and Jerry Butler....Vancouver won the trade the first year...but lost it every year after. Derlago never got straight, Vaive did- and had a great career.

[@heatherdeane8218]

was more than just his hard partying

[@RRaquello]

I wouldn't have that trade in here because Seguin never really turned out that good. He had a couple of good years, but never turned out to be any all-time great. I'd say the same with the Taylor Hall trade. Really, what did the Devils get out of that? One good year from Hall, then they had to get rid of him because he wouldn't sign a long term deal, which was actually doing them a favor.

[@dirtybaystrangler]

@@RRaquello Maybe not an all time great. However, how many guys come to the NHL and become Oveckins or McDavids? Only a fraction of a percent do, hence why they're "once in a generation" talents. It was pretty obvious after his short tenure in Boston that he wouldn't live up to the hype. Since coming to Dallas Seguin has been at least consistent, and that is really what is most important to a team.

[@RRaquello]

@@dirtybaystrangler That's true, but after all these years it's interesting to look at the original Seguin trade. Brian Burke was roasted for the trade that sent the Seguin draft pick to Boston for Phil Kessel. As I remember, Toronto sent two #1's to Boston for Kessel. The #1's turned out to be Seguin and Dougie Hamilton, now with the Devils. But who has ended up having the better career? Kessel or Seguin & Hamilton? I'd say Kessel has done more than both those players put together. Seguin has been good, but Kessel has been better. Hamilton has bounced around through 4 different teams, leaving the first three unsatisfied with his performance, and I suspect that's how the Devils will end up. Neither player did Boston much good, nor did any of the players or picks they acquired when they traded them, and I think if they kept Kessel, they might have won at least one more Stanley Cup, as Kessel could have played the same role for them he played for Pittsburgh in helping the Penguins win two cups..

[@BrotherAlpha]

A couple of these weren't bad trades, they were bad luck. When a player gets traded and then injured nearly right away, it's hard to argue it wasn't a bad deal.

[@christopherharper8009]

All those ads made it hard to watch the whole thing but I did it.

[@leeharcus7001]

I remember when Hull was traded to St.Louis. At the time of the trade, everyone thought St.Louis got the short end of the stick and that Calgary should have added for to the trade.

[@AD-df5tm]

Because Hull was a 6th round pick that nobody cared about. It only became a bad trade because he inexplicably became a hall of fame player. You can't really blame Calgary for not anticipating that their 6th round pick would become one of the 100 greatest players ever.

[@jeremyhawley8512]

Hull never won the Rocket Richard Trophy... Led the league in goals but that trophy didn't exist then.

[@shylo_moxii]

it was made in 98-99

[@jeremyhawley8512]

@@shylo_moxii yeah i know... Salanne won it first

[@mdvr4125]

Gretzky to the Kings completely changed the trajectory of 2 franchises

[@OilFan702]

How are you going to miss the Gretzky trade lol?

[@ericdouglas7933]

Biff Danielson babe bruth to the Yankees for 100 thousand dollars

[@joshw604]

Kyle korver for a photocopier

[@sharangoalvich]

The reason Gretzky was traded was because the team had financial problems and Gretzky had a massive contract

[@stpbasss3773]

He got them four cups so they at least got something out of it, even though if he stayed they could have probably won't ten cups lol but that's is Mark stayed too but we all know how that went 1940 lol.

[@josephcrowe2908]

Gretzky was sold. Make no mistake. Oilers owner was struggling financially and dressed it up like a trade.

[@lucas9929]

As an oilers fan, right now I’d rather have Adam Larson lmao

[@Narnia61]

Hall is now on his fifth team and has been traded 3 times and Larsson is still with the Oilers. I don't think the Hall-Larsson trade should be on this list.

[@bdhplayer5551]

Montreal trading Chelios for Denis Savard and also giving a 2nd round pick to Chicago. Only good part of that trade was Savard was a Stanley Cup winner after a great career.

[@heatherdeane8218]

Corey ordered Serge to make that deal.

[@ronaldfaler4753]

How can you possibly have this list without discussing the Ron Francis for John Cullen 6 player deal between Hartford and Pittsburg. This trade, by itself, not only drove the franchise into the ditch, but likely sealed the deal for the team to move to Carolina.

[@brandonthomas6280]

That Tyler Seguin trade wasn’t a good trade but wayyy too high on your list. You had Jagr and Roy below him. No wayyyy

[@alexmurphy5289]

No, it's literally one of the worst of all time. If Pevs didn't almost DIE the trade would've been even worse. He was a monster our first year too

[@jmckeown1218]

Seguin to Dallas was overreacted because seguin was apparently having behavior problems

[@heatherdeane8218]

Guys and idiot. Nobody on the Bruins missed him..... on or off the ice.

[@jimmiller6704]

The worst trade ever has to be Toronto when they traded Clark along with 27-year-old defenseman Sylvain Lefebvre, 19-year-old prospect Landon Wilson and the 22nd overall pick in the 1994 draft to Quebec for 23-year-old Sundin, 31-year-old defenseman Garth Butcher, 20-year-old prospect Todd Warriner and the 10th overall pick in the draft. Prior to the trade they had made it to the third round twice in a row. After the trade they didn't win a playoff series for five years. Comparing defencemen involved Garth Butcher gave the Leafs one year then he retired while S. Lefebvre went on to play for 9 years and helped Colorado win a Cup. He's still in Hockey as a coach and could be in the Leaf org. now. Taking both Clark and Lefebvre out took the heart out of one of the toughest teams to play against in the early 1990's and caused a 5 year playoff drought.

[@atarileaf]

Toronto doesn't just make bad trades, they make earth shattering bad trades.

[@Dan-nt2yb]

It’s OK tho because the building has been full for 50 years and will be for the next 50 years.😃👍🏾

[@Yokes27]

Unless i missed it maybe we do a Mike Milbury tribute to awfulness...that Gif tho is priceless. Can see him behind the GM desk doing that right after getting off the phone

[@ryangaskin4938]

I would've found room for Luongo getting traded to Vancouver for Bertuzzi. Lu, became far and away the greatest goalie in franchise history while Bertuzzi played 7 games for the panthers.

[@artvandelay1967]

youre an idiot.

[@tvyyz5604]

Eric Lindros trade on draft day to the flyers has to be on this list ... not just honourable mention to the leafs trading for Tom kurvers

[@gorille151]

Dryden for Guy Allan? 1st OA (Lafleur) from LAK?

[@sebastienlandry7868]

Golden Seals not LAK, but yes I think its the worst

[@appletile2887]

Tony Esposito was one of Sam Pollack's mistakes when he traded Tony O who was one one the best in history

[@loupgarou1317]

One i can think of....Victor Rask to the Wild for Nino Niederreiter to the Hurricanes.....now this is only on the partial season since the trade, but if he pans out like he has so far......

[@jammastajef3766]

You missed the Peter Forsberg / Eric Lindros trade.

[@popetoper]

That wasn't necessarily a bad trade. Both players did very very well.

[@alexandrethibault2482]

@@popetoper Point is that it was far from being a one vs one trade; Nordiques also received Ron Hextall, Mike Ricci, Steve Duchesne, 15 millions, 1st overall pick of 1993 (Adam Deadmarsh)....

[@frankpfaff9675]

Flyers with lindros never won a cup while what the nordiques got in return was a half of the core of the 2 cups they won when they moved to Colorado

[@ryanmoore9276]

Fuckin Forsberg had Sakic and a fuckin goalie , Lindros made who he had all stars , Lindros was far more skillful then Forsberg !!

[@geodrive1882]

@@alexandrethibault2482 Don't forget the best player in the trade! Peter Forsberg.(imo) It was 5 players, 2- 1st round picks and $15 million for just the "Rights to sign" Lindros. Quebec had 52 points that season, The next year with those new players they finished with 104 points.

[@lancecampbell4323]

You missed the. Gilmour for Leeman package (Flames-Leafs). Gilmour had to be run out of town quickly for off ice issues but still, it didn’t have to be that bad

[@mikeappleyard1898]

What were those off ice issues?

[@lancecampbell4323]

@@mikeappleyard1898 He was messing around with his kids teenage babysitter. Same thing that happened in St. Louis

[@mikeappleyard1898]

@@lancecampbell4323 I was living in Calgary as a young kid at the time of that devastating trade. I remember feeling so betrayed, and I remember not being able to find out why exactly they made this lopsided trade so hastily. Nothing was being reported in either the Calgary Herald nor the Calgary Sun beyond just that they had to because they couldn't afford to keep Gilmour going forward due to the fact that they were a small market Canadian franchise with a weak Canadian dollar trying to pay player salaries in American dollars. I do not understand why they wouldn't report this story. Neither Eric Francis (Calgary Sun), or Eric Duhatschek (Calgary Herald) ever reported anything about this story. I guess both of them were more concerned about their own careers than reporting the truth.

[@dayneroman9162]

When you're an oiler fan it feels like watching these is asking a question you already know the answer to.

[@opinionaytedonhockey]

So true

[@reveurs9]

Hi! Thanks for this video. And here are some suggestions: Not only are the Montreal Canadiens doing poorly on the exchange market, but their system for scouting and developing young talents is also one of the most deficient in all the NHL. Over the past 30 years, I've seen the Montreal Canadiens send away elite players you can build a team on. These players become very successful elsewhere and their original team sometimes gets less of their value for them. The equivalent of a stack of hockey sticks, for instance. The first that comes to mind is the one who sent young and still promising defenceman Chris Chelios to Chicago for the declining Denis Savard in 1990. Chelios won two other Norris trophies and played in the NHL until the age of 47 (!!), while Savard only had one good season in Montreal (1991-1992, 70 pts) and was no longer part of the team as of September 2013. The second that comes to mind is the trade that sent elite winger and defenceman John LeClair and Eric Desjardins to the Philadephia Flyers in exchange for Mark Rechi (1995). This was quite a heavy price to pay for a single player. Desjardins was a top defender and leader in "Philly" for over ten years. And LeClair immediately exploded alongside Eric Lindros by achieving three seasons of 50 goals and two others of 40. Last but not least: 1994. Top defensive centerman Guy Carboneau to the Saint-Louis Blues in exchange for - who? -Jim Montgomery. JM only played 5 games in Montreal whilst Carbonneau played until the age of 40, as proved himself quite useful as a defensive forward for the next six years and lead the Dallars Stars to their third Stanley Cup conquest in 1999. ‘’ Honorable’’ mentions: On September 4, 1990, the Canadiens traded Claude Lemieux (RW) to the Devils for Sylvain Turgeon (LW). Lemieux's career resumed and he won three more Stanley Cups elsewhere. As for Turgeon, known history, his best days were far behind. Mike Ribeiro (C): Traded in 2006 to the Dallas Stars for defenceman Janne Niinimaa. Niinimaa was atrocious in Montreal while Ribeiro had a total of 640 points in 798 games after leaving the Habs. So long.

[@duanefrench3500]

What about the Phil Esposito trade?

[@billwindsor4224]

Awesome job on this compilation; keep them coming!

[@chrispswann6825]

Mike Milbury trading young players Bryan McCabe and Todd Bertuzzi to Vancouver for Trevor Linden who was almost 30 and past his prime

[@vaneagles2639]

chris swann and then Vancouver eventually trading a broken Bertuzzi for Luongo and McCabe for the 3d overall pick in 99 that became Henrik Sedin

[@deonal]

McCabe was mostly overrated, why he landed in Toronto where overrated is cool. Bertuzzi remains popular in Vancouver.

[@richardkey4289]

That was a dark time in Van.city; losing the cup in 7 to the rangers, the Griffith's family losing ownership of the team, Keenan & Messier coming to the canucks, & Linden leaving...he was more popular in Van.than god ! One punch after another for Canucks fans....

[@scottjackson1420]

July 23, 1957: Ted Lindsay traded by the Detroit Red Wings with Glenn Hall to the Chicago Black Hawks for Bill Preston, Hank Bassen, Forbes Kennedy and Johnny Wilson. May 27, 1955: Tony Leswick traded by the Detroit Red Wings with Glen Skov, Johnny Wilson and Benny Woit to the Chicago Black Hawks for Dave Creighton, Gord Hollingworth, John McCormack and Jerry Toppazzini. May 20, 1965: Marcel Pronovost traded by the Detroit Red Wings with Aut Erickson, Larry Jeffrey, Eddie Joyal and Lowell MacDonald to the Toronto Maple Leafs for Andy Bathgate, Billy Harris and Gary Jarrett. June 3, 1955: Terry Sawchuk traded by the Detroit Red Wings with Marcel Bonin, Lorne Davis and Vic Stasiuk to the Boston Bruins for Gilles Boisvert, Real Chevrefils, Norm Corcoran, Warren Godfrey and Ed Sandford. February 10, 1960: Red Kelly traded by the Detroit Red Wings to the Toronto Maple Leafs for Marc Reaume. Obviously, I'm not a fan of Jack Adams.

[@thelonegeekboy]

The Capitols actually sent Jagr and half the money for his contract for Carter.

[@jsun6396]

Amazing how you have the Roy trade on here at 10., but arguably the worst trade in NHL History is NOT; The flyers get: Eric Lindros The Nordiques (Then Avalanche) Get: Steve Duchesne Peter Forsberg Ron Hextall (Traded later for Mark Fitzpatrick and Adam Deadmarsh) Kerry Huffman Mike Ricci Jocelyn Thibault (Traded later for Patrick Roy) Chris Simon Nolan Baumgartner 15 Million Dollars Thibault was supposed to be a generation goal tending talent and arguably the centerpiece of the trade, as essentially it was him for Roy. The Roy trade wouldn't have happened had they not had Thibault. Because of this trade the Avalanche won 2 cups... and the Flyers with the spoiled Entitled Lindros? Zero. The Flyers basically handed the Nordiques NE Avalanche 2 cups in exchange for one of the most overhyped, spoiled and arguably most overrated players in NHL history, Eric Lindros

[@PeterKKraus]

Terrible..Brad Park and Jean Ratelle, for Phil Esposito was the worst trade of all time.

[@gerryzaccaria3838]

Exactly!! And actually if that wasn;t bad enough, the Middleton trade may be the worst of any sport all time

[@mrbill4206]

Peter Schiarelli has the distinction of being the gm who traded both the first and second picks of the 2010 draft by trading Tyler Seguin from Boston and later Taylor Hall from Edmonton. Both players were considered trouble for their attitudes and locker room issue rumors.

[@jharris34]

Esposito to Boston duh...

[@appletile2887]

This was the greatest robbery of all time. It turned Boston into a powerhouse.

[@bluebear1985]

There was one trade involving a few players once in 1971, the most important part being the California Golden Seals sending that year's first round pick to the Montreal Canadiens. The pick, which turned out to eventually be first overall that year, would be used to select junior star Guy Lafleur. He would spend fourteen years there, winning five Stanley Cup championships along the way, while winning three Art Ross trophies as scoring champion, two Hart trophies as MVP, and a Conn Smythe as playoff MVP.

[@holoholopainen1627]

He was originally Californias Golden #1 Seal - Draft Pick ?

[@bluebear1985]

@@holoholopainen1627 He technically wasn't their pick at the start, but anyone who had the first selection that year would have wanted Lafleur, considering the numbers he was putting up in juniors. Even though the Seals were struggling, they somehow agreed to this deal with the Habs by sending them the first overall pick. Big mistake.

[@greghaines2770]

No Doug Gilmour from Calgary to Toronto for Gary Leeman? Easily one of the biggest fleecings of all time.

[@sixclocks]

leeman was very good but had been injured and never recovered. if he had it would have been a fair trade.

[@ECESW]

Sundin toToronto was an even bigger steal. Especially when you consider Wendal just came back the next summer.

[@Leafsdude]

@@ECESW Actually the Clark trade back to Toronto could go on this list as one of the worst trades from the Leafs perspective. The Isles got Kenny Jonsson and the pick that became Roberto Luongo for him. One of the rare Milbury trades that he won (until the threw away Luongo for peanuts, of course). Leafs did get Mathieu Schneider in that trade as well, who turned into Alexander Karpovtsev and then Bryan McCabe, so maybe the Leafs did wind up coming out fine on that one in the end...

[@ECESW]

@@Leafsdude Given that they got both Schneider and Clark in that trade with Islanders, it wasn't that bad. Although by that time Clark did have his major back trouble. I believe Schneider was traded from Toronto cause of a contract dispute. He will eventually make it to the HoF.

[@chuckruckus3648]

Every NY ISLANDER trade Milbury made.

[@chrisod22]

Rick Middleton for Ken Hodge

[@andrewnicholas9672]

2, involving the rangers. 1- Jean Ratelle and Brad Park for an aging Phil Esposito. 2- Aging Guy Lafleur for a 5th round pick that was used to draft Sergei Zubov.

[@michaeldipietro5010]

as a Caps fan i can say the Gartner for Dino Ciccarelli. Gartner would later (as a Ranger) score his 500th career goal against the Caps. then there was the unloading of my favorite Cap, Peter Bondra, to Ottawa. in exchange the Caps got Brooks Laich (3rd/4th line grinder) and i draft pick (if i remember right). thankfully Bondra did not score his 500th career goal against his former franchise. he was with Chicago at the time. the Forsberg shit trade still stings. lord knows what the kid could be doing in DC. though Trotz probably would had kept him in the AHL.

[@scottbinns318]

Teemu Selanne from Winnipeg to Anaheim for Oleg Teverdovsky. Worst trade of all time made by one of the worst GMs of all time, Mike Smith.

[@maidadutcher8923]

Good game for good season. Waiting for that clash. BTW Im watching on ScreenVariety this year.

[@glensmuglin8912]

Thanks!!

[@pbabs3389]

Should have gone deeper into the Neely trade. Pick turned into glen westley, who turned into 2 picks Kyle mclaren and Sergei Samsonov, who turned into Milan lucic, 25 years of returns

[@jijipuff4697]

how is getting reilly smith and loui eriksson for seguin (8th on this list) a worse deal than getting phil kessel for tyler seguin and dougie hamilton (not on this list)?

[@WaddickLawnCare]

Kessel wasn’t traded for either of those players though? He was traded for picks

[@je7055]

Dunno that the Jagr/Carter trade is even bad in context, much less one of the all-time worst >_> The Caps were tanking for Ovy (or Malkin, or Crosby the year after, etc.) They unloaded not just Jagr but Lang, Gonchar and Bondra. Their core was all guys who were late in their primes or past their prime, guys who they knew would command decent money in free agency. It was a roster horribly prepared to deal with the upcoming salary cap and the front office knew it, they knew they had to burn it down while they had a chance and position themselves to get a young star to build around.