In recent years, the NHL trade deadline has been consistently disappointing. General Managers have no doubt been looking at a history of trade deadline deals playing out badly, the shortsightedness of them resulting in teams parting with long-term plans and promising prospects in favor of immediate impact, which has time and time again played out poorly. Because big trades happen so infrequently in the NHL these days, it's not surprising that there is a long list of deals that just about happened. The reasons for these deals not falling through vary. In most cases, it's because a team put together a decent offer that was then beat by an even better offer from another team. Other times, a miscommunication or even technical problems have gotten in the way of a big trade.
Often, it takes years for fans and analysts to be able to tell how a trade panned out and which team came out as the winner. This is also true of deals that didn't quite materialize. An oft-cited NHL trade that didn't quite materialize was Wayne Gretzky to the Vancouver Canucks back in 1996. That was two years after the Canucks' cup run, and their roster then included Pavel Bure, Alexander Mogilny, Trevor Linden, and Markus Naslund, who was emerging as an elite scorer at that time. Instead Gretzky went to the Rangers, the team that beat the Canucks in the Stanley Cup Finals, and it has been said that the reason Gretzky didn't sign with the Canucks is because Pat Quinn—the Canucks' president and General Manager—was too pushy on the phone, which turned Gretzky off even though he'd made a verbal agreement with the team. There are all sorts of weird examples of monumental trades not quite working out for whatever reason. Let's take a look at fifteen examples that involve active players.
15 Corey Perry to Edmonton for Mike Comrie
Although there have been plenty of contributing factors, part of the Edmonton Oilers' futility in recent years can be traced back to bad trades. Consider the Mike Comrie trade that really should have happened. It can be hard to remember now, but there was a time in which Mike Comrie was a very promising young hockey player. In his first full season in the NHL, he put up 33 goals for the Oilers, but he ran into contract disputes with them, asking for a much larger second contract than they were willing to sign him to.
They thus decided to trade him to the Anaheim Ducks for Corey Perry and a 1st round pick, which, in hindsight, is a very lopsided trade but the Ducks were happy to make the deal.
However, Oilers GM Kevin Lowe also specified that Mike Comrie had to pay his signing bonus back to the Oilers as a way of saving the organization a few bucks. Instead, the Oilers ended up having to trade Comrie to the Flyers for a defensive prospect and two picks that didn't pan out, while Perry has obviously gone on to have about as successful of a career as a guy can hope for, winning a Stanley Cup, two Olympic gold medals, a Hart Trophy and more.
14 Jeff Carter and a first to Toronto for Tomas Kaberle
Jeff Carter was an 11th overall draft pick back in 2003 and he was an immediate impact player for the Flyers, who drafted him. He put up 23 goals in his first season, and in his third season he was on his way to putting up 29 goals when Paul Holmgren started to think about trading him? Why would he do this? The Flyers were absolutely stacked up the middle, with Daniel Briere, at this point in his prime, playing top line minutes as a center, and Mike Richards, an equally promising young player who was better on the defensive end, playing the role of second line center.
So Holmgren decided he would trade Carter to try to get a top-end offensive d-man, which the team then needed. So they offered young Jeff Carter and their first round pick for Kaberle, and the Leafs were willing to make the trade but the blueliner shut the deal down using his no-trade clause, and the Flyers dodged a bullet because Carter emerged as an offensive force the next season, scoring 46 goals, while Kaberle's play began to decline.
The Flyers eventually made a much better trade, trading Carter to Columbus for Jakub Voracek and using that first round draft pick to select Sean Couturier. Aside from Claude Giroux, Voracek and Couturier remain the Flyers' best offensive players.
13 Vincent Lecavalier to Montreal for Tomas Plekanec, Chris Higgins, Josh Gorges and P.K. Subban
Why has P.K. Subban always been so disposable to the Montreal Canadiens? More than maybe any other player in recent memory, Subban has found himself constantly at the center of trade rumors, and even this year, following the Nashville Predators' exit from the playoffs, there has been talk that they'd be willing to send him elsewhere. Is it because his personality is too big and dominant? Is he occasionally a liability? Maybe, but how many point-per-game defensemen are their in the NHL aside from Subban? Almost none.
It's fitting that this deal, which would have made the Tampa Bay Lightning even more formidable in the present day, included another player that was always drowning in trade rumors, Vincent Lecavalier. It makes sense that the Habs badly coveted Vinny in 2009 when this trade almost went down.
Lecavalier was both the best and the most famous Francophone player in the league, which was valued by a market that really wants to support French players.
Lecavalier was coming off 108 point and 92 point seasons and had recently won a cup, and even though Montreal knew they'd be giving up a lot, it was a price they were willing to pay to bring in a certified winner.
However, Lecavalier shut the deal down because he was happier living in Tampa, and right around that time his production slowed down while Plekanec and Subban emerged as the leaders of the Habs shortly after.
12 Cory Schneider to Columbus for Gilbert Brule
There's a funny trend among NHL teams that have gotten a reputation as being "goalie graveyards". Once they get a world-class goalie or two, they panic and don't know what to do with them. That certainly seems to have been the case for former Canucks GM Dave Nonis, who, once he'd acquired Roberto Luongo, likely the best goalie in the world at the time, immediately started looking to deal Cory Schneider, who was already widely acknowledged as a promising young goalie with the potential to be a top ten goalie in the future.
The Canucks eventually traded Schneider to the New Jersey Devils—a team that certainly isn't a goalie graveyard—for the pick they'd use to select Bo Horvat, their future captain. That was a great trade for both teams, but what wouldn't have been a great trade for the Canucks would have been if this trade with Columbus had it gone through. The Canucks as an organization had the hots for Brule for a number of reasons. First of all, he was a legitimate star in the WHL for the Vancouver Giants, once putting up a ridiculous 169 points in 70 games, so Vancouver's sports media thought of him as one of the NHL's top young prospects.
He failed to live up to anyone's expectations in Columbus and this was attributed to his being rushed into the lineup without time to develop. Now, the Columbus Blue Jackets probably have the best goalie in the world in Sergei Bobrovsky, but looking back they would have liked to have made this trade that they rejected at the time.
11 Claude Giroux to Tampa Bay for Paul Ranger
Claude Giroux's reputation as a player has changed more than any player in recent memory. He was first thought of as a productive playmaker with top-six potential, but everything changed with his breakout season in 2012, where he scored a whopping 93 points, cementing himself as one of the league's best scorers. But then, partially due to injury and for other reasons as well, his play dropped off, and as recently as last year, Claude Giroux was thought of as a player on the decline, whose best days were behind him. And then this year, he came galloping back into the picture, particularly in the latter half of the season, and finished second overall in points.
Back in 2009, right before Giroux's breakthrough, Paul Holmgren offered Giroux to Tampa straight up for D-man Paul Ranger.
Ranger was, at the time, thought of as a solid, stay-at-home guy who could play big minutes in big situations. Tampa said no to the deal, and we all know what happens next as Giroux broke out as a star right after and Paul Ranger played only a handful of NHL games before taking a leave of absence from the NHL for "personal reasons" and spending some time playing in the Swiss league.
Ranger, still only 33, has been retired from professional hockey since 2015, and he recently disclosed in an interview that he was suffering form depression while playing in the NHL and needed to spend some time away from the game.
10 Steven Stamkos to New York for Depth Player Package
What's the deal with how many of these huge almost deals involve the Tampa Bay Lightning? Following their surprising Stanley Cup win back in 2004 and then their dip back into irrelevance with a few truly bad seasons a couple years later, the team faced an identity crisis. They knew they'd picked a future star in Steven Stamkos but not everyone remembers that he didn't look all that good in his first season for the Bolts. In a full season, he scored just 46 points, so while he's now considered to be playing at the same level as guys like Crosby and Ovechkin, he didn't have the same kind of immediate impact that they had on the NHL level.
Apparently, because he scored only seven points in his first twenty-one games for the Lightning, they considered trading him right off the bat.
According the Glen Sather, who has been the President of the New York Rangers since the year 2000, the Rangers and the Lightning had a deal in place where the Lightning could pick and choose which Rangers assets they wanted to exchange Stamkos for. The deal was accepted by Len Barrie, a partial owner of the Lightning, but was shutdown by other controlling forces in Tampa, which they no doubt saw as the smart move at this point, especially with Stamkos as a centerpiece of a thriving squad.
9 Taylor Hall to Ottawa For Cody Ceci
At this point, it's clear to any hockey fan that Taylor Hall for Adam Larsson was a bad trade for the Oilers. The Oilers have a funny history of drafting without consideration as to what their needs are, which is not an entirely surprising strategy. Generally when you've got a first overall pick, it's smart to go with the consensus number one choice in the draft, both because you're more likely to end up with a generational talent, and because it can be hard anyway to predict what your team's needs will be a few years down the line.
But the Oilers' trend of drafting skilled forwards meant, in the past, that they had a glut of talent up front but huge holes on defense and in net, which is why it sort of made sense to trade Hall—who might in the Hart Trophy this year—for Larsson, who was also a high draft pick but hasn't shown any real signs of being an elite player.
However, it was almost even worse for the Oilers, as they apparently had a deal in place in send Hall to Ottawa in exchange for Cody Ceci, who is by any metric a much less impressive player than Larsson. Bureaucracy came to the rescue in this case, as the deal had to be cleared with the Sens' management and before this could happen a deal materialized with the Devils.
8 P.K. Subban to Vancouver for 5th overall pick
There seems to be an unusually high number of Canadian teams on this list, which we think can be explained by the fact that no Canadian team has won a Stanley Cup since the year 1993. There's a kind of desperation among Canadian teams—with Calgary, Edmonton, Vancouver, and Ottawa all making the Stanley Cup finals with recent memory, to no avail—so unexpected moves are common from these franchises, who are simply looking to shake things up and perhaps catch other teams off guard.
P.K. Subban to Vancouver is a hard move to imagine, especially because Vancouver is now in a kind of rebuilding phase where they're looking to add picks and prospects rather than established players but apparently they came extremely close to landing P.K. only two years ago. What happened was that the Montreal Canadiens greatly coveted Pierre-Luc Dubois in the draft and there was a chance he'd fall to fifth in the draft, which was the picks the Canucks held.
If so, there was a deal in place in which the Canucks would give the pick to the Habs in exchange for Subban.
Instead, Dubois was unexpectedly picked up at third overall. The Canucks ended up with defenseman Olli Juolevi, who looks promising but hasn't played an NHL game yet.
7 Matt Duchene to The New York Islanders For Travis Hamonic and 1st round pick
This trade is a bit hard to keep track of now because the pieces it involves have been scattered all over the place. However, back when Matt Duchene was an unhappy member of the Colorado Avalanche, there was a rumor floating around that the Islanders had offered Travis Hamonic and a first round pick in exchange for the speedy centerman. He ended up having a pretty good season for the Ottawa Sentators this year considering the controversy that surrounded his long-awaited trade.
From the Duchene trade the Colorado Avalanche ended up receiving three picks and prospects, but apparently they were unwilling to accept simply Hamonic and a first pick.
Meanwhile, Hamonic was traded to the Flames in exchange for a first round pick and two second round picks. We're still years away from seeing how this all plays out. Hamonic so far hasn't been as good for the Flames as he was for the Islanders but he's also playing on a better defensive team with fewer responsibilities.
Duchene has not been as good for the Senators as he was for the Avalanche when he was at his best but he's also much better than he was when he was at his worst for the Avs. This failed trade is the freshest of the bunch which means it's the hardest to say who would have benefited most.
6 Roberto Luongo to Toronto
It's hard to say how Roberto Luongo would have fared in Toronto if this deal had gone through. On one hand, the pressure of playing in Vancouver–a smaller and less intense market than Toronto—seemed to get inside Luongo's head, but on the other hand, he's one of the best goalies of his generation and does have a history of pulling through in the clutch.
We'll never know what Toronto offered for Luongo in the first place but it has been well-documented that in 2013, around the time of the NHL draft, the Toronto Maple Leafs had an offer on the table for the Vancouver netminder. No doubt in part because Dave Nonis, who'd been General Manager of the Canucks, was General Manager for the Toronto Maple Leafs.
Luongo rejected the trade to the Leafs because he'd heard through the grapevine that the Florida Panthers were also preparing an offer, this was more attractive to him because his family was based in Florida and he spent his summers there anyway. The trade to Florida ended up being for Jakob Markstrom—a serviceable goalie who isn't elite by any standards—and Shawn Matthias, who has been bouncing around the league in recent years.
5 Tomas Vanek to Boston for Tyler Seguin
The Boston Bruins are one of the most resourceful and successful NHL teams of the last decade but that doesn't mean that they're immune from the sting of a bad trade. Three years after selecting Tyler Seguin second overall in the draft, they were unhappy with his production and decided to trade him to Dallas for a bunch of guys, including Loui Eriksson and Reilly Smith.
Now, five years after that trade, the Boston Bruins do not have a single player on that roster from that deal. Meanwhile, Seguin flourished in Dallas, becoming an elite-level talent who you can always count on for a point-per-game season.
Because the Bruins were so desperate to get rid of Seguin, they also almost traded him to Buffalo for Tomas Vanek, which would have been an equally disappointing deal.
While Vanek was a great, dynamic goal scorer for the Sabres early in his career, in recent years he has revealed himself to be a floater who takes games off and isn't really willing to contribute on the defensive end. Apparently, the Bruins were looking for another piece or two to bolster the trade, and the Sabres were unwilling to commit. It's interesting to think of how a guy like Seguin would have helped the development of the Sabres or how they may have stunted his career.
4 Gabriel Landeskog To Boston for Brandon Carlo and More
This almost-trade is a good example of how quickly things can change in a year. Last year, the Colorado Avalanche had a terrible season and people were wondering how they could possibly get things back on track. The solution seemed to involve trading their captain, Gabriel Landeskog for some reason. They had a deal on the table to trade him to Boston in exchange for Brandon Carlo and another pick and prospect or two. Now, more than a year later, Brandon Carlo has failed to have any kind of real impact on an NHL level, whereas the Avalanche rapidly turned things around with Nathan MacKinnon this season establishing himself as one of the best players in the world and the Avalanche making the playoffs. He's quelling any feelings that they should sell the farm.
While it's certainly true that the Avalanche were outclasses by the Nashville Predators in the first round this year and never really seemed to have much of a chance of winning that series, it's clear now to Avalanche fans that the solution won't be found in trading key pieces away. They instead can slowly build towards a stronger future by continuing to add contributors to their already-solid core.
3 New York Islanders Offer All Their 2012 Draft Picks for Ryan Murray
If you Google some combination of the phrases "Garth Snow" and "fired" you'll quickly see that there's a general sentiment around the league that he's made too many suspect moves for too long and some time soon the New York Islanders will have to cut ties with him, setting him free. He has also won awards for some surprisingly savvy moves, and it's hard to say whether his decision to offer every single one of the New York Islanders' draft picks in 2012 for the second overall pick—which he planned to use to draft defenseman Ryan Murray.
It might have been a solid move or another boneheaded wildcard decision.
One can argue that if you add up the average number of NHL games played by a second overall pick compared to every other lower pick from a lower-drafting team, you'd get more impact overall out of the second overall pick. That may be, but it's also true that going all-in on a single player is a risky proposition.
The 2012 NHL entry draft seems to be the weakest in recent memory, with a first round full of busts in Nail Yakupov, Griffin Reinhart, Derrick Pouliot and many more.
2 Any Trade At All for Dan Hamhuis
Back around the time of the 2016 NHL trade deadline, Dan Hamhuis was one of the most sought-after defensemen on the market, and for good reason. He has a balance of good puck-moving ability with reliable defensive play, which made him a legitimate top-pairing d-man for years. He played on the top pairing in Nashville with Shea Weber, and on the top line in Vancouver with Alex Edler but when Vancouver became a team that wasn't making the playoffs anymore, it was clear that Hamhuis should be moved at the deadline. Both to give him a chance to win and to give the Canucks a decent return on such a key asset, lest he be lost for nothing to free agency.
A wide number of trades were discussed. Some of them, very optimistic on the part of Vancouver fans. It included Hamhuis being traded to a contender for a playoff run but then re-signing with Vancouver the next season. Other proposals involved picking up a draft pick or a prospect for Hamhuis, who is now 33.
However, in a stunning display of futility, the Canucks instead did nothing, allowing the Stars to sign Hamhuis to a very reasonable contract of less than $4 million per year without giving up any of their assets. The Hamhuis example provides a counterpoint to the overzealous trading teams out there. While there's no need to make a risky move just for the sake of it, you also have to know when it's foolish not to pull the trigger.
1 Andrei Markov, Jose Theodore and Two First Rounders to Atlanta for Kovalchuk
This truly would have been one of the biggest trades in NHL history if you consider the impact all of the players involved had on the league. It's strange to think of the butterfly effect as it pertains to hockey and how the inclusion of a single prospect on a trade can shape an organizations' future. It's fair to ask, "Isn't this article about current players? Aren't all of these players not current NHLers?" And this is true, but perhaps not for long. There has been big time media speculation that Ilya Kovalchuk is eyeing a return to the NHL. He has been playing in Russia since 2013 but he has stated his interest in rejoining the New Jersey Devils, who own his rights in the NHL for the foreseeable future.
It's a little disingenuous to say that this package was offered for Kovalchuk, though. What happened was that at the entry draft in 2001, Canadiens' General Manager Andre Savard offered this combination of players for the first overall pick, which Atlanta used to draft Kovalchuk, who had an immediate impact in Atlanta. The deal was turned down because Don Waddell, the Thrashers' GM, wanted goaltender Mathieu Garon rather than Jose Theodore, though Theodore would go on to win both the Hart Trophy and the Vezina Trophy the very next season.
Meanwhile, Kovalchuk was kind of buried in the disinterested hockey market of Atlanta and it's interesting to think of how Habs fans would have responded to having a frequent 50 goal scorer in their lineup.