The NHL is such a great league because of its unmatched parity. While leagues such as the NBA, NFL, and La Liga generally see the same teams having success year in and year out lately, the NHL has seen a different Stanley Cup Champion in four of the last six seasons. The main reason for this parity is the fact that the league has a hard salary cap, but there are also so many ways for bad team to get better. Free agency and draft picks are great ways to improve, but the real mastery of a GM's job comes in the form of making trades. Whether a deal involves players, draft picks, or both, there is usually an intent for one team to be a "buyer" who is building up for a playoff run and the other to be a "seller" who is trying to build up young talent and draft picks to improve for the future.
Trades are also fun from a fan's perspective, as it is always entertaining to analyze the deal to determine who came out as the winner and who came out as the loser. While some trades actually end up working out well for both teams involved, there has been a great number of lopsided deals over the years. Whether it's evident immediately or could be considered "regretful" after ten years of hindsight, each franchise has its fair share of bad deals. The worst trade in all 31 NHL franchises' history can be found below, with a description of why they are so regretful. Enjoy!
31 Arizona Coyotes (Winnipeg Jets)
The Trade: Teemu Selanne, Marc Chouinard, and 4th Round Pick to Anaheim for Chad Kilger, Oleg Tverdovsky, and 3rd Round Pick
Teemu Selanne is the 15th-highest point producer and 11th-highest goal scorer in NHL history. He went on to win a Stanley Cup and Rocket Richard Trophy with Anaheim. He also participated in eight All-Star games as a Duck and became one of their key franchise players for the better part of 15 years. While Marc Chouinard only put up 23 points over parts of three seasons in SoCal and the 4th-rounder never materialized into anything for the Ducks, those two pieces of the trade are basically non-factors anyway.
Meanwhile, Chad Kilger put up 6 points in parts of two seasons in Winnipeg/Phoenix before moving on to Chicago, making him basically useless to the team. Tverdovsky fared a little bit better, recording 107 points over 241 games with the Jets/Coyotes organization. This is obviously nothing in comparison to what Selanne did in Anaheim. The 3rd-rounder, like the 4th-rounder going the other way, turned out to be a bust, meaning the Jets basically gave up a first-ballot Hall-of-Famer for a third-liner that only stuck around for four seasons.
30 Anaheim Ducks
The Trade: Chris Kunitz and Eric Tangradi to Pittsburgh for Ryan Whitney
Ryan Whitney seemed like a great piece for a Cup-hungry Ducks team in need of defensive depth. In hindsight, what they gave up to acquire him was a terrible idea. Who knows what Kunitz would have done if he had’ve stayed in Anaheim and never got the chance to play with Sidney Crosby, but the Ducks must regret shipping the Canadian Olympian away. Whitney was good for the team in the short term, putting up a respectable 38 points in 82 games with the club and helping them to the second round of the playoffs. However, this two-season stretch is all he could muster with the team, as he was again shipped away.
On the other hand, Chris Kunitz went on to find a deep chemistry with Penguins star Sidney Crosby and put up 388 points over nine seasons with the club. He was a main piece in three Stanley Cup wins in Pittsburgh and even earned a spot on the 2014 Olympic-champion Canadian squad. Tangradi had a so-so spurt, recording 5 points in 45 games in Pittsburgh before moving on to Winnipeg, Montreal, and finally Detroit, mostly as an AHLer. The trade really comes down to Kunitz for Whitney, which is absolutely no contest.
29 Boston Bruins
The Trade: Ken Dryden and Alex Campbell to Montreal for Guy Allen and Paul Reid
Ever heard of Campbell, Allen, or Reid? No? That’s probably because none of them even had a sniff at the NHL. I’m sure, though, that you have heard of the legendary Ken Dryden. When Boston made this trade in 1964, they had just picked the 16-year-old Dryden in the NHL Entry Draft and he actually opted for college hockey, making it unclear whether he would even make it back to the NHL. After three years at Cornell, he finally signed with the Habs and the rest is history. Through 8 NHL seasons, Dryden had an outstanding 2.24 GAA, six All-Star appearances, five Vezina Trophies, and six Stanley Cups. Though no one could have known at the time of the trade, it ended up as one of the most one-sided in league history - a first-ballot Hall-of-Famer for two nobodies.
28 Buffalo Sabres
The Trade: Dominik Hasek to Detroit for Vyacheslav Kozlov and 1st Round Pick
Another case of a team acquiring a franchise goalie for chump change, this one is a bit less forgivable than Boston’s draft-day deal. Hasek had already won six Vezina Trophies in Buffalo, so they knew his value. While his age may have been well past the point that most professional athletes can call their “prime”, there was no sign of him regressing. Hasek went on to spend four years in Detroit, helping them to two Stanley Cups and posting an outstanding 2.13 GAA before finally retiring on top at age 43.
Kozlov spent just a single season in Buffalo, putting up a paltry 22 points, before moving on to Atlanta where he spent the remainder of his career. The 1st-rounder was used to select Jim Slater, who was also moved to Atlanta before playing a single NHL game in Buffalo. The Sabres gave up one of the best goalies in league history, while still in the best years of his career, for basically nothing.
27 Calgary Flames
The Trade: Brett Hull and Steve Bozek to St. Louis for Rob Ramage and Rick Wamsley
This might have been an okay trade for Calgary in the short-term, as it netted them veteran defenseman Rob Ramage, who was a huge part of their Stanley Cup run in 1988-89. In the long term, though, giving up Brett Hull to acquire him was a bad idea. Hull went on to become a legend in St. Louis, scoring 936 points over 11 seasons as a Blue. He even got the Cup he missed out on in Calgary, scoring the controversial winning goal in 1999. Hull sits 4th in goal-scoring in NHL history and earned himself a Hall of Fame induction in 2009. Who knows what Calgary could have done in the years following ‘89 if they had the young Hull around still?
Bozek and Wamsley were both bit players for the remainder of their careers, making their relevance in this trade almost nil. Bozek had zero points in 7 games in St. Louis while Wamsley put up a rather sad 3.21 GAA and .878 SP over 5 seasons with the Flames.
26 Carolina Hurricanes (Hartford Whalers)
The Trade: Ron Francis, Ulf Samuelsson, and Grant Jennings to Pittsburgh for John Cullen, Jeff Parker, and Zarley Zalapski
This huge 6-player trade becomes a lot easier to analyze when you eliminate the irrelevant players. Grant Jennings never scored more than 13 points in a single season during his eight-year NHL career and Jeff Parker recorded 0 points in just 4 games played in Hartford. Basically, the trade comes down to Francis and Samuelsson for Cullen and Zalapski. The two Cups that Francis and Samuelsson brought to the Penguins super-team of the early '90s are enough on their own to make this trade a huge win for Pittsburgh. Add in the fact that Francis contributed 613 points over 533 games in the Steel City and Samuelsson stabilized their blueline with a +76 rating over five years, and you have the recipe for an incredibly lopsided deal.
Cullen and Zalapski weren’t exactly useless in Hartford, as Cullen put up a solid 102 points over his short 109-game stay as a Whaler and Zarley produced a respectable 165 points in parts of four seasons with the club. Neither of these totals even remotely stack up to what Francis and Samuelsson contributed to Pittsburgh, making this the worst trade in Hartford/Carolina franchise history.
25 Chicago Blackhawks
The Trade: Phil Esposito, Ken Hodge, and Fred Stanfield to Boston for Gilles Marotte, Jack Norris, and Pit Martin
A classic case of a team giving up on a young player too soon, Chicago’s 1967 trade is the definition of regretful. Phil Esposito was just 24 at the time and had produced a respectable 174 points in 235 contests with the Black Hawks. Seeing potential in a trio of young Bruins players, the Hawks dealt Esposito and fellow youngsters Hodge and Stanfield. Phil Esposito went on to become one of the best NHLers of all-time in Boston, racking up a ridiculous 1012 points in 625 games. His presence alone would make this trade lopsided, but when you also factor in Hodge and Stanfield’s contributions to the Bruins - 1100 points in 1083 games - it just becomes embarrassing on Chicago’s part.
The duo of Marotte and Martin combined for a decent (but measly in comparison) 700 points in 932 games. Norris, a goaltender, played just 10 games with the Hawks (and just 191 total in his NHL career), struggling to a 4.42 GAA. One of the best players ever for three who were mediocre at best? Not a great move by Chicago.
24 Colorado Avalanche (Quebec Nordiques)
The Trade: Mats Sundin, Garth Butcher, Todd Warriner, and 1st Round Pick to Toronto for Wendel Clark, Sylvain Lefebvre, Landon Wilson, and 1st Round Pick
After this terrible trade, it’s just short of a miracle (or a bad Flyers trade that can be found later in this list) that the Nordique/Avalanche franchise went on to win two Stanley Cups within a decade. Mats Sundin was just a young pup when he was dealt away, and the Swede went on to become the face of the Leafs for the better part of 13 years, racking up 987 points in 981 games with the club. Butcher and Warriner were basically irrelevant in the trade, as both produced less than 85 points in the Blue-and-White. The first rounder that went to the Leafs was also irrelevant, as it turned out to be Nolan Baumgartner, a career AHLer who never played a game for Toronto.
Clark was supposed to be the big piece going the other way and he did play pretty well, recording 30 points in 37 regular season games and a further 3 points in Quebec’s one-round playoff run, but that was as long as Clark lasted as a Nordique. He was shipped to New York in the offseason and was back in Toronto again within a year of the original trade. Lefebvre and Wilson were relative nobodies in Quebec/Colorado, putting up a combined 76 points in 367 games. Even the 1st-rounder that went to Quebec turned out to be a dud as the player never even made it to the AHL. In the end, Colorado gave up a franchise player for half-a-season of Wendel Clark.
23 Columbus Blue Jackets
The Trade: Jakub Voracek, 1st Round Pick, and 3rd Round Pick to Philadelphia for Jeff Carter
As far as total trade packages go, this is one of the most lopsided on the list, as all three players that went to Philly had more of an impact than Carter did in Columbus. Voracek has gone on to become one of the faces of the Flyers, alongside Claude Giroux. The Czech native has compiled a solid 354 points over six seasons. The 1st-round pick Philly got was used to select Sean Couturier, who has become a perfect middle-six centreman. Couturier has 191 points in his 6 seasons in Philadelphia, while also earning an outstanding +35 rating on a so-so Flyers squad. The 3rd-rounder was used on Nick Cousins, who has had slightly less offensive impact than the other two, but has still managed 27 points in 107 games.
Carter, who was supposed to be a huge piece in Columbus, lasted just 39 games as a Blue Jacket. He did produce a decent 25 points over that span, but in the grand scheme of things he had almost no impact on the franchise while Philly has used their returns for him in their everyday lineups for the better part of six seasons.
22 Dallas Stars
The Trade: 1st Round Pick to Anaheim (that ended up being Corey Perry) for two 2nd Round Picks
Draft pick-for-draft pick trades are hard to predict, but the outcome of this one must be hugely regretful for Dallas. The first rounder they sent to Anaheim was used to select none other than Corey Perry, who has gone on to become the face of the franchise and arguably the 2nd-best player in Ducks history. Perry had almost immediate impact, as he was a strong part of the Ducks’ 2007 Stanley Cup run, and he has not slowed since. The Peterborough native has racked up 717 points in 886 games in Anaheim, becoming one of the premier snipers in the league for the better part of a decade.
The two 2nd-rounders that Dallas got in return were used on Vojtech Polak and B.J. Crombeen. Polak lasted a measly 5 games in the NHL, recording a grand total of zero points. Crombeen fared slightly better, though the best years of his short career weren’t even spent in Dallas. He recorded just 7 points in 23 games as a Star. That’s a total of 7 points vs. Perry’s 717 points.
21 Detroit Red Wings
The Trade: Marcel Dionne and Bart Crashley to Los Angeles for Dan Maloney, Terry Harper, and 2nd Round Pick
Like Chicago did with Esposito eight years earlier, Detroit traded a future legend while he was still in his developing years. Unlike Phil, though, Dionne had just compiled a 121-point season as a Red Wing. Anyhow, Detroit shipped Dionne, who went on to put up an outstanding 1307 points in 921 games as a King, earning a spot in the Hall of Fame. Crashley had almost no impact in L.A., only playing 4 games and recording a single point.
Dan Maloney was respectable over a short three-year stint in Detroit, putting up 137 points. Harper managed just 70 points over four years as a Wing, and the 2nd rounder was used on Jim Roberts, who played zero games as a Red Wing. Los Angeles got a Top-100 All-Time player who stuck around for 12 years in exchange for two second-liners who lasted less than four years each.
20 Edmonton Oilers
The Trade: Mark Messier and Jeff Beukeboom to New York for Bernie Nicholls, Steven Rice, Louie DeBrusk, and David Shaw
This trade was huge in that it was a main contributor to the Rangers’ first Stanley Cup in 53 years. Messier became a legendary leader while also still putting up points at an outstanding rate. Though he played in New York through his 30s and into his mid-40s, where most players usually see a decline, Messier still managed 691 points in 698 games. Beukeboom also served as a solid defenseman for the Rangers for eight seasons, earning a +63 rating.
Bernie Nicholls, the main piece in the return for Messier, did contribute well in Edmonton, racking up 89 points, but he only lasted stayed an Oiler for about a season and a half. DeBrusk only managed 31 points over parts of six seasons in Edmonton and Shaw contributed just 2 points over a short 12-game stint as an Oiler. Seeing as both players New York received turned into solid centrepieces that lasted almost a decade each, the lack of production and longevity the Oilers received in return is utterly regretful.
19 Florida Panthers
The Trade: Roberto Luongo, Lukas Krajicek, ad 6th Round Pick to Vancouver for Bryan Allen, Alex Auld, and Todd Bertuzzi
This is another trade that is easier to analyze after removing the unimportant pieces. Lukas Krajicek spent just a year and a half in Vancouver, recording almost four times as many penalty minutes as he did points and the 6th-rounder was used on Sergei Shirokov, who played just 8 NHL games and recorded a single point. Basically, the Panthers traded Bobby Lou for the package of Allen, Auld, and Bertuzzi. Luongo went on to become the best goaltender in Canucks history and a likely Hall of Famer during his eight years in Vancouver, where he also led the team to a pair of President’s Trophies and a trip to the Stanley Cup Finals.
Allen and Bertuzzi played a combined 291 games in Florida, recording just 74 points between them. Auld served as a backup for just one season as a Panther, appearing in 27 games and struggling to a 3.34 GAA. Florida gave up a franchise goalie for two short-term third-liners and a short-term backup.
18 Los Angeles Kings
The Trade: Wayne Simmonds and Brayden Schenn to Philadelphia for Mike Richards
Philadelphia did a great job of transitioning their two veterans - Jeff Carter and Mike Richards - into a great core of five young players. As listed earlier, they landed Voracek, Couturier, and Cousins for Carter, and just hours later they managed to rob L.A. of Simmonds and Schenn for Richards. Simmonds has emerged as a solid second-line power forward for the Flyers, perfectly fitting the “Broad Street Bullies” moniker. Schenn is more of a finesse centreman and fits into the third-line slot perfectly. The two have combined for a solid 551 points in 871 games as Flyers.
Richards contributed well in the short-term for the Kings, ranking as one of their top scorers during their 2012 Stanley Cup run. He really fell off after just two seasons in L.A., though, and lasted another two before being moved to the Capitals. In total, Richards put up just 87 points over four seasons as a King. Respectable, sure, but nothing compared to the impact that Simmonds and Schenn have had in Philly.
17 Minnesota Wild
The Trade: Brent Burns to San Jose for Charlie Coyle and Devin Setoguchi
To be fair, no one could have expected Brent Burns to emerge as the Norris Trophy-winning offensive dynamo that he has become in his late 20s. This has to hurt for the Wild in hindsight, though, considering what they got in return for the hairy behemoth. Burns has gone on to produce 316 points in 426 games in San Jose, awesome numbers for a defenceman. On top of that, he has earned a +39 rating and was a huge part of the team’s trip to the Stanley Cup Finals in 2016.
Charlie Coyle has become a solid middle-six forward for the Wild, contributing a decent 177 points over four-and-a-half seasons in Minnesota. Setoguchi was a huge bust, though, as he declined greatly from his prime days as a Shark, putting up just 63 points in two seasons even though he averaged one of the highest time on ice totals out of all the team’s forwards. The Wild gave up one of the best offensive defensemen of the past decade for a second-liner and two years of below-average Setoguchi.
16 Montreal Canadiens
The Trade: Patrick Roy and Mike Keane to Colorado for Jocelyn Thibault, Martin Rucinsky, and Andrei Kovalenko
Every hockey fan knows the story behind this trade. After being left in net for the entirety of a 9-goal drubbing, Roy requested a move out of Montreal. Even though the Habs had their hand forced, they could have undoubtedly received a better package in return for Roy. The legendary goalie went on to lead the Avs to two Stanley Cups, earning an outstanding 2.27GAA and .918SP over his eight years in the Mile High state. Mike Keane was more of a scrapper, racking up 153 PIMs and just 64 points in 223 games with Colorado.
Thibault lasted just three and a half seasons in Montreal, posting a so-so 2.73 GAA. Rucinsky fared slightly better, recording a respectable 297 points in 432 games as a Hab. Kovalenko, however, lasted just 51 games in Montreal and had 34 points to show for his efforts. These three players contributed to the Canadiens at a decent rate for a couple of years at most, making Roy’s eight-year, Hall-of-Fame-worthy stay in Colorado a sad time for Habs fans and front office executives alike.
15 Nashville Predators
The Trade: Cody Franson and Matthew Lombardi to Toronto for Brett Lebda and Robert Slaney
The outstanding 19-year tenure of David Poile as Nashville’s GM has produced many great trades and very few poor ones. For this reason, we’re really scratching at the bottom of the barrel to find a “regretful” trade in Preds franchise history, so this is as bad as it gets! Franson went on to have a solid four-year stay in Toronto, putting up 115 points in 236 games while often playing as a top-pairing defenseman. Lombardi’s one-year stay in Toronto wasn’t quite as pleasant, as he managed just 18 points.
While this isn’t quite as impressive as the hauls obtained in other trades throughout this article, Franson’s brief impact still outdoes that of the players coming the other way by a mile. Brett Lebda didn’t play a single game for Nashville, moving on to Columbus before he got a chance to. Robert Slaney didn’t play a game for the Preds either, or any NHL club for that matter, as he never made it past the AHL level. While not a terrible move in the grand scheme of things, giving up a top-4 defenceman for two guys who don’t play a single game for your team has to fall into the “regretful” category.
14 New Jersey Devils
The Trade: 1st Round Pick to Vancouver (Bo Horvat) for Cory Schneider
This one is debatable depending on how you look at it, but once again, the Devils franchise simply hasn’t made many bad moves in its 43-year history. It has to be considered “regretful” because, in hindsight, the Devils likely wouldn’t have wanted to give up Bo Horvat, the player that the 1st rounder was used on. Horvat has blossomed into a young leader on the rebuilding Canucks and has even put up a respectable 117 points in his short, three-year NHL career thus far.
Cory Schneider is definitely nothing to scoff at in return, but the Devils have no hope of being competitive whether they have a great goalie or not, so why give up a first-round draft pick to acquire a 28-year-old, relatively unproven goaltender?
13 New York Islanders
The Trade: Zdeno Chara, Bill Muckalt, and 1st Round Pick to Ottawa for Alexei Yashin
To put it lightly, the Islanders overpaid tremendously to acquire Yashin the whiner. Chara had four great seasons in Ottawa, recording 146 points in 299 games and earning an outstanding +109 rating. Muckalt is basically irrelevant in the deal, as he only put up 8 points in 70 games as a Senator. The 1st-rounder that Ottawa acquired was used to select none other than Jason Spezza. The Toronto native went on to spend 11 years in Ottawa as one of the faces of their franchise alongside Daniel Alfredsson, racking up 687 points in 686 games.
Yashin would spend parts of 5 seasons in New York, recording a solid 290 points (but not-so-solid -24 rating) in 346 games before attitude issues led to his departure from the league. The Islanders gave up a young number one defenceman and a young number one centre for an aging, selfish, one-way player who probably did his team more harm in the dressing room than he did good on the ice.
12 New York Rangers
The Trade: Brad Park, Jean Ratelle, and Joe Zanussi to Boston for Phil Esposito and Carol Vadnais
During the second time Phil Esposito was involved in a bad trade in his illustrious career, he was on the other end as a past-his-prime 33-year-old. While Esposito did go on to produce great numbers in New York, the price that the Rangers paid for him was just too steep. Brad Park went on to put up 417 points in 501 games with Boston, great numbers for a defenceman. He also had an astronomical +229 rating over this time, showing his worth at both ends of the ice. Ratelle had a late-career resurgence in Beantown, compiling 450 points in 419 games there. Zanussi, meanwhile, was basically irrelevant, as he only managed to record 9 points in 68 games as a Bruin.
Vadnais and Esposito were fine on the scoreboard, combining for 650 points in 907 games in New York, but they certainly did not perform well at the other end of the ice, as they also combined for an atrocious -148 rating over that time. New York over-spent on an aging and overrated Esposito, giving up an outstanding defenceman and reliable veteran forward to acquire the defensively-challenged legend.
11 Ottawa Senators
The Trade: Pavol Demitra to St. Louis for Christer Olsson
Yet another case of a team giving up on a youngster too soon, this prospect-for-prospect trade was absolutely terrible in hindsight. Pavol Demitra went on to become a star over his eight seasons in St. Louis. The Czech native racked up 493 points in 494 games as a Blue.
The same cannot be said for the man going the other way. Christer Olsson struggled mightily in Ottawa. The Swede managed to play just 25 games for the Sens, totaling a measly 5 points, before he was out of the NHL for good. Ottawa gave up a franchise pillar for a dud.
10 Philadelphia Flyers
The Trade: Peter Forsberg, Ron Hextall, Chris Simon, Mike Ricci, Steve Duchesne, Kerry Huffman, two 1st Round Picks, and $15M to Quebec for Eric Lindros
One of the most famous trades of all-time, this, like the Roy deal earlier in the list, was partially a result of the Flyers having their hand forced by both the NHL itself, and an arbitrator who oversaw the trade. The NHL forced Quebec to make a deal as they didn’t want a potential star player sitting out any longer. Lindros had been taken first overall by the club in the previous year’s draft but refused to play for them, leading to the NHL basically holding an auction for Lindros’ services. The package that the Flyers put together was deemed to be the best one available, and still an arbitrator added Chris Simon and an additional 1st-rounder to it before it finally went through. We all know how Lindros was forced into retirement after playing just parts of eight seasons with the Flyers (and a further five with other clubs) due to numerous head injuries. He did manage to put up an impressive 659 points during this time, but the lack of actual playing time made the deal incredibly lopsided.
Forsberg went on to play 11 years in Quebec/Colorado, putting up an impressive 755 points in 591 games. Based on these numbers, Philly would have given up too much even if it was just a Forsberg-for-Lindros trade. But, there were so many more pieces to come! Simon, Ricci, Duchesne, and Huffman combined to play 647 games for the Nordiques/Avalanche franchise, recording a respectable 394 points over that period. Hextall played one year in Quebec, struggling to a 3.45 GAA. The first rounders were used on Jocelyn Thibault, who served as a solid backup in Quebec for three seasons and Nolan Baumgartner, who didn’t play a game for Quebec/Colorado. With this plethora of assets PLUS $15 million, it's easy to see how incredibly lopsided this trade was in hindsight and why the Avalanche went on to win two Cups within 10 years of the deal.
9 Pittsburgh Penguins
The Trade: Markus Naslund to Vancouver for Alex Stojanov
Like the Senators trade from two points back, this was a straight-up prospect-for-prospect deal. The two teams were both playoff-bound, though Pittsburgh was a much better club, still riding their dynasty of the early 1990s. Naslund had already proven himself to be a decent player at this point while Stojanov hadn’t, but the Pens’ scouts seemed to have seen some upside in the youngster. Boy, were they wrong. Naslund went on to quickly become the best player in Vancouver’s franchise history to that point (before the Sedins came along), racking up an impressive 756 points over 12 seasons with the Canucks.
Stojanov could only ever dream of that kind of longevity, as the Ontarian lasted just 45 games with the Penguins and produced a miniscule 6 points before losing his NHL job and never gaining it back again. The Penguins traded a franchise player for a minor leaguer, one-for-one.
8 San Jose Sharks
The Trade: Josh Gorges and 1st Round Pick (Max Pacioretty) to Montreal for Craig Rivet and 5th Round Pick
A one-for-one trade of Gorges for Rivet would have been fair, but the fact that the Sharks threw in a FIRST-ROUND PICK tips the scales mightily in Montreal’s favour. Gorges went on to become one of the best defensive defensemen in the league for a short stint while in Montreal, earning a +34 rating and a ridiculous 1,042 blocked shots over eight years as a Hab. The 1st-rounder that San Jose so foolishly gave up was used on a youngster named Max Pacioretty, who has blossomed into the leader of the Canadiens, both on the scoreboard and in the dressing room. The 28-year-old has racked up 411 points through parts of nine seasons in Montreal thus far, and he seems to be dedicated to the team for years to come.
Rivet, on the other hand, stuck around in San Jose for a mere year-and-a-half before departing for Buffalo. The defenceman recorded a respectable 43 points over that time period, but his lack of longevity while Gorges and Pacioretty lasted so long in Montreal is embarrassing for the Sharks. The 5th-rounder they received will not relieve that embarrassment either, as it was used on Julien Demers, who never even made it to the minor-league level before fizzling out as a University of Ottawa Gee-Gee. Two decade-long tenures from solid players for a season-and-a-half of Craig Rivet… bad move, San Jose.
7 St. Louis Blues
The Trade: Doug Gilmour, Steve Bozek, Mark Hunter, and Michael Dark to Calgary for Mike Bullard, Tim Corkery, and Craig Coxe
This trade is just mind-blowing. Most of the deals on this list at least made some sense on the day they were made and then ended up being regretful in hindsight, but this one was bad from the day it happened! Gilmour was just 24 at the time and had already put up 354 points in 384 games in St. Louis. He went on to continue that success in Calgary, where he racked up an impressive 295 points in just 266 games. Bozek also saw his career as a grinding winger take off in Calgary, where he recorded 143 points in 261 games. Hunter produced at a decent pace as well, putting up 60 points in 133 games as a Flame. Dark never played a game in Calgary.
In exchange for these three very solid players, the Blues received Bullard, Corkery, and Coxe, who played a combined 61 games for St. Louis and put just 23 points on the scoresheet. Calgary got a future superstar and two decent middle-six players in exchange for three nobodies.
6 Tampa Bay Lightning
The Trade: Brad Richards and Johan Holmqvist to Dallas for Mike Smith, Jussi Jokinen, Jeff Halpern, and 4th Round Pick
This was another part in the dismantling of Tampa’s core three players from the early-mid 2000s - Vincent Lecavalier, Martin St-Louis, and Brad Richards. The Lightning didn’t get nearly enough for what they gave up, though. Richards went on to have a great four seasons in Dallas, recording 227 points in 220 games. Holmqvist was basically irrelevant, only playing 2 games for the Stars.
Mike Smith did not have his best years in Tampa, winning only 43 games over four seasons and recording a not-so-great 2.85 GAA. Jokinen and Halpern combined to play just 192 games with the Lightning, putting up a lowly 81 points between them. The 4th-rounder never made it to the NHL, actually only managing 8 AHL games. Giving up a point-per-game player for two bottom-six forwards and a backup-quality goalie does not look good on the Lightning.
5 Toronto Maple Leafs
The Trade: 1st Round Pick to New Jersey (Scott Niedermayer) for Tom Kurvers
Why Toronto thought it would be worth it to give up a 1st-rounder for Kurvers, who had already played six years in the league and carved out a niche as a power play specialist with poor defensive ability, is anyone’s guess. The 1st-round pick was used by New Jersey to select one of the most successful players to ever play the game of hockey, Scott Niedermayer. Niedermayer went on to play 13 seasons as a Devil, playing a large part in their three Stanley Cup victories and earning an awesome +172 rating over 892 games. He also won everything there was to win at the international level and the individual awards level, earning a Hall of Fame induction for his efforts.
Kurvers, on the other hand, played a measly 89 games with Toronto, recording a -20 rating before moving on to Vancouver the following year. As a one-for-one deal, this franchise player for brief second-pairing defenceman trade takes the cake as one of the most regretful ever.
4 Vancouver Canucks
The Trade: Cam Neely and 1st Round Pick to Boston for Barry Pederson
Even as a one-for-one deal between Neely and Pederson, this was a terrible idea on the Canucks’ part. Add in the 1st rounder, and you have the recipe for the most regretful trade in franchise history. Pederson lasted just three-and-a-half seasons as a Canucks, recording a pedestrian 197 points in 233 games during an era when scoring was at an all-time high. He did so as a centreman.
Neely, as a defenceman, recorded 590 points in 525 games as a Bruin. He also earned a tremendous +138 rating, meaning that he was just as successful in his own end of the rink. The 1st-rounder was used to select Glen Wesley, who spent a solid seven years in Boston, totaling 307 points and a +40 rating. Why, Canucks GM Jack Gordon, why?
3 Vegas Golden Knights
The Trade: Marcus Kruger to Carolina for 5th Round Pick
It's slim pickings for this one, as Vegas has made just three proper trades (not counting their expansion draft deals) in their short three months as an actual NHL team. Marcus Kruger has had an okay career to this point, primarily playing as a third-line centre on a deep Blackhawks squad. When the Golden Knights acquired him from Chicago, it looked as if he would fit nicely into the young team’s top-six as a reliable veteran presence.
Instead, the Knights offloaded him to Carolina for nothing more than a 5th round selection in 2018’s NHL Entry Draft, which will more-than-likely land Vegas an AHLer, at best. This is not a great way to start your new franchise, Golden Knights.
2 Washington Capitals
The Trade: Filip Forsberg to Nashville for Martin Erat and Michael Latta
Washington is another franchise that has not made very many bad trades in its history. This one, however, is the definition of regrettable. Forsberg has gone on to become a star in Nashville. The 22-year-old Swede has tallied 185 points over his first three full seasons as a Predator, emerging as the team’s driving offensive force.
Erat and Latta have not had the same success as Capitals, combining to put up just 44 points in 175 games before Erat retired and Latta was sent down to the AHL. The Caps gave up a young, first-line sniper for an aging depth forward and an underwhelming prospect.
1 Winnipeg Jets (Atlanta Thrashers)
The Trade: Marian Hossa and Pascal Dupuis to Pittsburgh for Colby Armstrong, Erik Christensen, Angelo Esposito, and 1st Round Pick
This trade is indicative of the entire Thrashers franchise during their 12 years in Atlanta. Hossa went on to play just 12 regular season games in Pittsburgh but was a huge part of their 2008 Stanley Cup Final run, posting 26 points in 20 games. Dupuis, on the other hand, was around for the long-run. He played for nine seasons in Pittsburgh, becoming a responsible linemate of Sidney Crosby for a number of years and recording a respectable 247 points in 452 games. His two-way play helped the Pens win their 2009 Stanley Cup.
Colby Armstrong and Erik Christensen combined to put up just 103 points over 236 games in Atlanta. Esposito never even made it past the AHL, failing to play a single NHL game despite being a first round draft pick. The 1st-rounder that the Thrashers received never managed to play in the NHL either, spending most of his career in the ECHL. Pittsburgh received two solid top-six forwards, one of whom became a franchise favourite, for almost nothing.