This whole list could probably just be trades made by Milbury as Islanders GM

Also, the Leafs trading goaltender Tuukka Rask to the Boston Bruins in exchange for goalie Andrew Raycroft in 2006. The Leafs lost out on that trade big time.

The most widely regarded, lopsided trade in NHL history isn't even on your list. 1967 - CHI trades Phil Esposito, Ken Hodge and Fred Stanfield to Boston Bruins for Gilles Marotte, Pit Martin and Jack Norris

The Selanne trade only happened because the team was selling assets in order to relocate at the lowest cost. Thank you Gary Bettman.

Worst was Chicago sending Esposito, Hodge and Stanfield to Boston for Pit Martin, Marotte and Norris.

WORST trade in NHL History is Eric Lindros trade. Lindros for Steve Duchesne, Ron Hextall, Kerry Huffman, Mike Ricci, the rights to Peter Forsberg, the Flyers' first-round pick in 1992 (seventh overall) and 1993 and $15 million. Only Forsberg himself was way better than Lindros ever was. Quebec later won Stanley cup as Colorado.

Another crazy detail about that Gretzky trade: the Red Wings were in serious talks to bring him on board. Legend has it that Gretzky initially wanted the Wings too since he grew up idolizing Gordie Howe and wanted to play for Gordie's old team, but the prospect of growing the game in LA ended up winning him over.

This list ignores some pretty important context particularly Gretzky and Roy

How the hell did you not include the March 1991 trade where the Hartford Whalers traded Ron Francis, Grant Jennings and Ulf Samuelsson to the Pittsburgh Penguins for John Cullen, Zarley Zalapski and Jeff Parker?! The Hockey News said that the Whalers won the trade; but it turned out to be a lopsided win for the Penguins as they went on to win their first Stanley Cup in May 1991 (with Ulf Samuelsson scoring the cup winning goal) and winning a second in June 1992. The Whalers ultimately faltered and relocated to North Carolina in 1997. Francis became the perfect number two center in Pittsburgh, winning the Selke and Lady Byng Trophies on his way to the Hockey Hall of Fame.

I find it funny how the Habs fans felt betrayed when Roy left them when he was being blatantly mistreated by the new head coach by being left in until the red wings had scored 9 goals on him.

The worst trade of al time is Pittsburgh trading Markus Naslund for Alek Stojanov

No where near as big of a trade, but extremely one-sided: the trade that sent Kris Draper from Winnipeg (the franchise that is now the Coyotes) to Detroit. Detroit got the best third-line center in the league at the time, who consistently made life miserable for the opposing top line. He rarely scored, except when it really mattered, but he led the Grind Line which played a key role in powering Detroit's dynasty of the late 1990's and early 2000's. And what did Winnipeg get in exchange? Exactly $1. Actually, a bit less, because it was a Canadian dollar. I don't know what they spent that dollar on, but I hope that it was important, because they sure gave up a lot to get it!

To be fair, Milbury’s time as GM was mostly due to orders from upper management (specifically their owner Charles Wang) to cut payroll, even if this meant trading highly touted prospects. So not all the blame can be placed on Mad Mike

Habs didn't have much of a choice in the Roy trade. He told them he wasn't playing for them anymore

The Kings traded for a gimp named Rick Martin for a draft pick that wound up being Tom Barrasso... The Kings traded for a sieve named Simmons for the pick that became Ray Bourque...

I'd say the Bruins trading Joe Thorton deserve an honorable mention. Trading him for a bunch of averages players was horrible. I know that Boston blamed Joe for their early playoff eleminations, but they traded a 1ppg big centerman for averages players.

The Flames traded Gilmour to the Leafs in the 1991-92 season, they acquired him from the Blues in 1988

As a SoCal hockey fan who grew up in the 90s, it was definitely fun seeing the duo of Kariya and Selanne and seeing them both get 100 points a season... but the Ducks were mediocre at best because they relied almost exclusively on their first line to produce. The Gretzky trade TO the Kings in 88 ultimately was good for both parties... the Oilers traded Carson (at his request) for players that showed Edmonton they could win another Stanley Cup without the Great One in 90, and the Gretzky led Kings inspired a lot of new hockey fans in a non-traditional market... myself included... and they came close in 93... The Gretzky trade from LA to STL on the other hand... trading the great one for a 3rd liner, two nobodies, and two draft picks that never played a single NHL game.... THAT was one of the worst trades in NHL history. Thanks a lot, McMaster the Disaster!

It is inconceivable to me that the Esposito/Hodge trade is not on this list.

Im a Bruins fan and undoubtedly one of the worst trades in NHL history was trading Joe Thornton (Right before he was about to turn into a star) for Marco Sturm, Wayne Primeau, and Brad Stuart. The Bruins didnt even bother trying to pluck draft picks away from SJ they were just happy with a collection of pure mediocrity in exchange for one of the bright young stars in the NHL. I still cannot believe the absolute stupidity of the trade.

Selanne trade.......I remember sitting in winnipeg watching a replay of him wearing a Coyote jersey saying his welcome Phoenix intro

a) The Esposito trade that bought 2 Stanley Cups to Boston was a big time heist. b) Rick Middleton for Ken Hodge. Another big time Bruins heist. c) How can I take this site seriously when they can't even pronounce Barry Pederson's name properly?

The Gilmour trade was in 1991 not 1988. Gilmour won a cup with the Flames in 89. I think your getting mixed up with the trade that brought Gilmour to the Flames from the Blues.

Marcel Dionne going from Detroit to L.A was pretty 1 sided!! Murray Craven going to Philadelphia in exchange for a very over the hill Daryl Sittler was totally 1 sided too!!

1976 Bruins trade Hodge for Rick Middleton! Not to forget the Espo trade that brought Ratelle & Park to Boston. and Savard for McNab.

The chapters saying "Patrick Wa" has me dying laughing

Gilmour was traded in 1992, not 1988 as he was part of the 1989 Stanley cup flames team. Still a terrible trade, Cliff Fletcher (the former flames GM) took the current flames GM (Risebrough ) for a ride.

How could you forget the Russ Courtnall for John Kordic trade?

The Yashin-Chara trade also included what became Jason Spezza, which was a fleecing by Ottawa all its own even without Chara in the equation. that whole trade was a highway robbery.

The reality of the Selanne, Gretzky and Messier trades was that they were all due to money. The Jets simply couldn't afford Keith Tkachuk, Alexei Zhamnov and Teemu Selanne at the same time because they were a small market team. After giving a big raise to Tkachuk (because Chicago offered him a huge contract as an RFA), they had to trade Zhamnov or Selanne, and Selanne had a much higher potential return. Unfortunately, they got next to nothing in return for Selanne, who flourished in Anaheim alongside Paul Kariya. The Oilers traded Gretzky and Messier largely because the team's owner, Peter Pocklington, had other businesses that were struggling and he needed cash to stay solvent. The Gretzky trade got him $15 million US, and the Messier trade got him another $5 million US. However, these trades led to Pocklington being despised in Edmonton and eventually selling the team to a group of local investors, shortly after which he fled to Arizona.

I think you got the date wrong on the Gilmore trade as he was still on the Flames in 89 when they won the cup.

Roy was never going to play for Montreal ever again anyways, so it really wasn't that bad of a trade to be honest. They had already lost Roy, at least they got something for him.

Some trades can’t really be listed as the worst ever when you factor in circumstances Patrick Roy….in the middle of the season said he would never play another game for Montreal again. They had no choice and teams knew this. There was zero chance Montreal was going to get a good return because they had no leverage Wayne Gretzky…He requested the trade and if memory serves me he requested L.A. for family reasons. You also can’t consider this a bad trade when Edmonton won a cup without Gretzky and the Kings didn’t win one with him.

Love the videos! Always interesting info.

Phil Esposito …… come on .

2:09 i’d say that’s an understatement. he scored 76 goals as a rookie in 93.

The Cam Neely trade included Vancouver's first round draft pick in the 1987 draft. The Bruins selected Glen Wesley. So, Neely and Wesley for Barry Pederson. Pretty good trade for Boston.

Philadelphia trading for Lindros. They gave up Peter Forsberg, Mike Ricci, Ron Hextall, Steve Duchesne, Kerry Huffman, future considerations and two first round picks for a guy who was always injured. Quebec/Colorado went on to win the cup.

The Chara- Yashin trade is nowhere near on of the worst trades. It turned out to be a BAD deal. But one of the worst? Nowhere near

I have my serious doubts if Gretzky´s trade was worse than Messier´s. I mean, the Oilers still won a cup without Gretzky, and he did not win another Stanley Cup after the trade, he was the dominating force in the league, but didnt reach the carreer heights he had in the Oilers, and unlike the other trades mentioned here, it wasnt a situation improvement, he was almost the real loser of the trade, instead of the Oilers or the KIngs. In the other hand, Messier´s move was almost a ruinous event for the Oilers, and he went to win even more stuff with the Rangers.

There is never a guarantee that a player's performance in any given environment would have necessarily happened somewhere else. That's why lines get shuffled - to find combinations that work. Yes, there are standout players, but that doesn't make a team (ie Gretzky never winning a cup in LA)

As an avs fan, the Roy trade was a great trade.

Tbh, Habs trading Roy and Jets trading Selänne AND calling them bad is debatable. Roy already had decided that he's done with Montreal = They needed a new goalie which they got in Thibault. Bad trade as a trade ofc, but they were pretty much forced to it. Just as Jets trading Selänne. Forced to dump value to get relocation cost down.

i wouldnt consider the Patrick Roy trade to be a normal "trade". After montreal got blown out by detroit one game and the montreal coach didnt pull Roy, essentially allowing roy to let in something like 7 goals. Roy was seen pretty much telling his coach off after he was finally pulled. Apparently at that point, Roy refused to play another game there

I know the flames trade wasn't great, but they went on to win the Stanley Cup the very next year, so it can't really be considered that bad.

i think the Tom Kurvers to Toronto trade is pretty bad too, New Jersey ended up getting Scott Niedermeyer from the pick Toronto gave them for Kurvers.

Chicago have a made a string a bad trades first in the mid to late 90's trading away all their talent (Roenick, Chelios, Amonte, Belfour) and then again from 2016 onwards when Stan made a knee jerk reaction when they lost in the first round.

Gretzky wasn't blindsided..he knew all along what was happening

Only want to predict before I was almost need to have the Duchene, Turris and Avs trade. I mean it’s a win since I’m an Avs fan but man what a deal that was

Roy was a brutal trade as we got a not ready goalie & not even a star like Sakic or forsburg back...../ but worse than the Roy trade was recchi for Desjardins Dionne & LeClair then we trade rechhi back to Philly for zubrus...so essentially zubrus for recchi / LeClair/ Desjardins/ & dionne.

Worst trade made has to go to the Leafs for trading Wendal Clark S. Lafavre trade for Sundin. The Leafs went from a team that had made it to the third round two years in a row to a team that didn't win another playoff series for 5 years. They made two quick playoff exits followed by two years of no playoff appearances at all. It took them 5 years to recover. Clark would have played easily 50 games a year, got them into the playoffs year after year, looking at his record after the trade that's how many games he played. I checked. They were wrong about his back. 50 games a year would have got them into the playoffs year after year and likely winning several series. Maybe a Stanley Cup. Mats played mostly all season long, almost every game, they didn't make it out of the first round for 5 years. Without the trade they would have made it farther than being out of the first round and been contenders. A few small tweaks was all that team needed. But it wasn't just Clark and Mats in the trade. Stephen Lefavre was involved and he was as important a player as Clark and Sundin. After the trade up went Toronto's goals against. They had lost a great defenceman in that trade. That was the killer part of the deal. Stephen Lefavre who played another 9 years while the guy we got, defenceman Butcher played a year and retired. Up went their goals against. Yes they gave up too much to get Clark back-at that point he had lost his heart because of the trade and was no longer the same player. That's on poor Leaf mgt. for trading him when they were so close to being contenders. I'm looking at the whole deal, not just Clark and Sundin when I say it was one of the worst trades in league history. Stephen Lefavre played a bigger role than many realized in it. They made it to the third round two years in a row prior, after they didn't win a series for five years. I stand with my assertion "It was one of the worst trades in League history".

just to note, i hate when people call it "worst trade" because for one team it's "best trade", better word to use is: "most lopsided trade"

Wayne Gretzky was not traded by the Oilers. He was sold to LA for $15,000,000. The trade was McSoreley and Krush for the 5 assets. But even so, this still hurt the Oilers.

Brett Hull to St. Louis for a second pairing D-man and a backup goalie.

Toronto trading away Tyler Sequin and Dougie Hamilton to get Full Kessel is the worst trade in NHL history, because it didn't need to be made. Many of the trades on your list were made either because the player wanted out or the team couldn't afford to re-sign them.

All bad trades, but in 1992 the Chicago Blackhawks traded Dominick Hasek to the Buffalo Sabres for Stephane Beauregard and a fourth round draft choice. Beauregard played in 29 NHL games after the trade compiling a record of 3-13-1. Hasek, after the trade, won 376 NHL games including 80 shutouts. And he won 6 Vezina Trophies, 2 Hart Trophies, 3 Jennings Trophies, and 2 Stanley Cups. But, go ahead, and not consider this one of the seven worst trades in NHL history.

Nothing Montreal could do to prevent that trade, Patrick Roy wanted out, he demanded it.

It's so obvious Gretzky wanted to be traded. Its no different than the Pronger situation in 06. No way Wayne's american actress girlfriend wanted to live in snowy Alberta forever. Please.

The Roy trade was one sided but he was refusing to play after not getting pulled in a blow out game. He told the GM as he was leaving the ice it was his last game with the team! Gretzky trade was in part because the owner of the Oliers was hurting for cash, you didn't mention the money they received as part of that trade!

452 goals in 393 games for Gilmour with the Leafs? That's pretty good!!

Calgary and Edmonton were low market canadien teams. They were bound to ship their hhof players to cut payroll and when they still could get something in return. In roys case he was done in Montreal. He refused to play. I would instead name trades like, red kelly to toronto, esposito/hodge to boston, näslund vs stojanov, francis to pittsburgh. Marcel dionne to la. As a flames fan the brett hull trade hurts. They got the grit on D they needed to win the cup but they did let go of a future franchise player.

The other important point about the Roy trade: they didn't have a choice. Anybody getting Roy was going to get him at a discount.

No idea why we ever traded Selanne away.

Nice list bud 👍 keep em coming.

Completely missed the most lopsided trade of all time. Toronto acquiring Tom Kurvers from New Jersey for a 1st round pick.

The insane part of course is that the Oilers DID win an other STanley Cup after the Gretzky trade, while the best that the Kings could do was make ONE finals appearance. Still an insanely lopsided trade though!

Your timeline about Doug Gil.our being traded to the Leafs is incorrect, he was pary of the 1989 Stanley Cup winning Flames and wasn't traded to the Leafs until January 1992.

Bruins traded Joe Thornton, Phil Kessel, and Tyler Seigen aii within a few years of each other's and I can't honestly remember one player that they received in exchange.

Griffin Reinhart to Edmonton for the 16th overall pick and a second and a third. The Islanders traded the second and third for the 28th pick which became Anthony Beauvilier and now they turned Beauvilier into Bo Horvat.

Messier guaranteed a lot of things and nearly all of them didn't come closed to true, yet people only remember him guaranteeing that 1 Devils game win.

Wow where is Dominik Hasek trade?!? The best goalie of his era traded for Kozlov (who barely played for Sabres( an prospects that didnt amount to much

I'm surprised the Hasek to Buffalo for a no name 3rd string and pick considering he went on to become a legend

Imagine now days if the oilers did the Gretzky trade but with Connor mc David instead …

Rangers trading Rick Middleton for Ken Hodge. Middleton put in about 400 goals for the Bruins, while Hodge contributed about 20 goals for the Rangers.

I know you are only talking about modern day but the sale of King Clancy to the Toronto Leafs by the old Ottawa Senators ranks up there

Espo trade has to be the worst. Surprised the Thornton trade isn’t on here.

Two things: First, Doug Gilmour was traded in 1992, not 1988. He won his only cup with Calgary in 89, so your information is wrong. Second, Patrick Roy demanded a trade after leaving a game in which his coach Mario Tremblay left him in for 9 goals against Detroit. Montreal was forced to trade him because he told the president that he would not play for Tremblay ever again. May have been a bad trade but the circumstances around it left Montreal with few other options, considering Tremblay was just brought on as head coach.

top 6 hockey, please stop making videos, cause your facts are all wrong!

Gretzky never won another Cup after leaving Edmonton. Martin Gelinas and Jimmy Carson both won the Cup with Edmonton, and were instrumental in the playoffs when they did, playing on "The Kid Line" with Joe Murphy. I don't know how other fans feel, but I'd be happy with a Cup over no Cup.

hard to call the patrick roy trade a bad one when montreal were left with no other choice but to deal him. when a player wants out that bad, you basically have to take bargain deals.

Meh. Most of these are subjective. Gilmore had to be traded. Neely was a nobody at the time (nucks basically got Naslund and Bertuzzi the same way they lost neely). Considering what trades you posted, how do you omit calgary trading Hull?

You gotta feel bad for montreal because they had no leverage trading roy

I haven't watched the list yet but almost every trade the Leafs made up until about 2016 should be on this list. Need a Stanley Cup? Trade for a former Leafs player and win NOW!

Great video - but you may want to add the fact that the Oilers also received 20 million dollars for Gretzky.

Joe Thornton trade is in top 5

Lindros was the worst trade of all time. Haven't watched the whole vid yet but deserves number one. I mean Lindros was amazing but the amount phili gave for him was absolutely insane. Edit: guess I should say in regards to this though, he had to be traded for refusing to play with Quebec. So in that regard it wasn't bad because they had no choice.

Wings trading Marcel Dionne is right up there( or down there).

The Jets couldn't afford Selanne. The return was pretty decent and ended up doing well for the team 😂 the fact that you don't have the Andrew raycroft (who was getting cut by the Bruins) for Tukka Rask on this is hilarious lol.

1st one .... TOTALLY wrong.... What choice do the Habs have when Roy publicly tells the team "this is the last game I play in Montreal".... ? should they have fired the Coach instead..? probably , but Roy forced their hand. They also could have gotten a better return for him. Neely and Wesley for Pederson..... 😅🤣😂- WOW ! .... That IS a steal. But one big trade you missed was the Paul Coffey for Jimmy Carson trade that put Detroit over the hump back in late 1993.

Few things that aren't mentioned, sometimes it's just about money. Can't afford to keep a superstar because of their salary. As well, wasn't Roy angry at MTL and wanted to be traded?

I don't know if the Patrick Roy one deserves to be on this list. I mean, he refused to play another game for them and demanded to be traded.

I almost forgot that Messier had hair at one time. That was long ago.

I don't consider the patrick Roy trade to be a bad trade for Montreal, they didnt have a choice patty literally told them he will never play another game for them. What were they going to do keep him on the team not have him play and still pay him or trade him and hope you get something out of it. You probably should of put the stupid andrew raycroft trade that sent tukka rask to boston where he played 15 seasons won a cup and a vezina and brought raycroft to toronto for 1 full season and 19 games his second year before being traded to Colorado.

As a Habs fan .. i am shocked you didnt mention Gomez trade for McDonah … To me.. worst trade i seen.

Leafs trade the #1 draft pick in 91 for Tom kurvers. The pick ended up being Scott niedermayer

You need to do your homework a little bit more on these trades. Patrick Roy told Montreal he would never play for them again prior to the trade. It wasn't a choice it was a necessity. - prior to the trade Selanne what showing signs of being a dominant player... Yeah he only scored 76 goals in his rookie season...

In the coming years you can add the Timo Meier trade to this list.

Correct me if I’m wrong, but didn’t P. Roy want out of Montreal? Didn’t know C. Neely played for a different team.

When Joseph Stalin- I mean, Bill Wirtz- ran the Blackhawks, he and his mindless cronies had quite the knack for trading talented players in exchange for precisely nothing. I could never figure that one out.

How did you miss the trade Chicago made that rivals all of these for worst ever? Esposito, Hodge, and Stanfield to Boston... Then, several years later, Boston was able to trade Hodge for Rick Middleton