Trades have become more sparse in recent years. With the salary cap becoming more difficult to manage, it takes a lot more maneuvering for a team to be able to strike a deal. It also makes it tough for both teams to get fair value in a trade. It's very rare that a trade happens and a few years later people say to themselves, "well, that worked out for both teams". More often than not, there is a winner and a loser in a trade.
However, certain trades really result in a landslide, where one team absolutely fleeces another. Here, we will explore 15 trades that left one team as a clear victor of the deal and one team as a clear loser. The only rule is that at least one player in each entry on this list has to be an active NHL player.
Some of these deals occurred before the salary cap era, where there were seemingly one or two significant trades every month, while some have happened in the cap era. No matter what way you look at these trades though, it's clear one team came out on top.
Here are the top 15 one-sided trades involving active NHL players.
15 Toronto Lands JVR For Luke Schenn
If you were to ask any NHL GM in the league, odds are they would take James van Riemsdyk as a top six forward. While he hasn't quite lived up to his billing as a second overall pick, he's a steady point producer and slots in well with a top centerman.
Luke Schenn meanwhile, is nowhere close to the player he was projected to be and usually slots in as a third pairing defenseman. So it's pretty easy to see who won this deal when the Leafs sent their former 2008 first round pick to the Flyers for their 2007 first round pick.
JVR is on pace for his best season yet in Toronto, while the Flyers have already moved on from Schenn, trading him to L.A. last year, along with Vinny Lecavalier for Jordan Weal and a third rounder.
14 Ben Bishop To Tampa For Cory Conacher
At the time, this seemed like a fair deal. The Senators had several capable goaltenders and they felt Ben Bishop was expendable. On the other hand, the Lightning didn't have a franchise goalie and Cory Conacher just seemed to be another skilled winger they could afford to part ways with.
Conacher was one of the league's hottest rookies in 2013 while Bishop was showing signs he could be a no.1 goalie. It seemed like a win-win for both Ottawa and Tampa Bay, but it's clear now that the Lightning fleeced the Sens. Conacher only scored 20 points in his full season in Ottawa and has since returned to Tampa after bouncing around several teams.
Bishop helped lead the Lightning to the 2015 Stanley Cup Final and even if he leaves as a UFA this summer, the Lightning can say they won this deal hands down.
13 Jeff Carter To Columbus AND Jeff Carter To L.A.
After the 2010-11 season, the Flyers decided they needed to change the core of their team and they sent Mike Richards to L.A. and Jeff Carter to Columbus in the span of a few hours.
In return for Carter, the Flyers received Jakub Voracek, a 2011 first-round pick (Sean Couturier) and a 2011 third-round pick (Nick Cousins).
You can say that was a fair return for the Flyers, so that's not why Carter is included here. Instead, it's due to the deal the following winter where Carter was traded to L.A. for Jack Johnson and a first round pick. Just why did the Jackets give up on Carter so early? Well, Carter would go on to help the Kings to two Stanley Cups and is still a great scoring center.
Jack Johnson is a solid defenceman but he's not the game breaker Carter is. Just imagine if Carter was still in Columbus today with their current lineup.
12 Spezza To The Stars
Just one season after naming Jason Spezza captain, the Ottawa Senators found themselves in tricky situation where Spezza requested a trade. On July 1, 2014, the Sens sent Spezza along with Ludwig Karlsson to Dallas for Alex Chiasson, Alex Guptill, Nicholas Paul and a second round pick. None of those pieces have paid huge dividends for Ottawa. Meanwhile Spezza is still producing around 60 points a season. He's in an ideal situation where he gets to be a second line center in Dallas.
You have to wonder why the Sens didn't seek more in a trade for Spezza. Sixty-point centers aren't on the market often, so the price should be a premium when they are. Somehow the Stars got a top-2 center for below market value.
11 Marian Hossa Lands In Pittsburgh
In 2007-08, the Penguins were really emerging as an NHL powerhouse. Around the trade deadline, they were seeking some final pieces on what would be a Stanley Cup Finals run later that spring. Marian Hossa was a pending UFA and was easily the biggest asset available on deadline day.
The Penguins pried Hossa from the Atlanta Thrashers along with Pascal Dupuis for Angelo Esposito, Colby Armstrong, Erik Christensen and a first round pick. Hossa would come as advertised for Pittsburgh, helping them reach the Cup final. Even though Hossa left that offseason, Dupuis stayed in Pittsburgh and was a key contributor to the Pens' 2009 championship.
Meanwhile, none of the aforementioned pieces helped the Thrashers climb out of the NHL basement. When you trade one of your organization's most valuable assets, you'd better make it count.
10 Dustin Byflugien Leaves Chicago In 2010 Firesale
This entry is not included to indite Chicago, because they really didn't have a chance in acquiring fair value for Dustin Byfuglien. Following their 2010 Stanley Cup, the Hawks were forced to move various pieces to preserve some salary cap space. Among their most prized assets was hulking Dustin Byflugien who was coming off a tremendous 2010 playoff.
Byfuglien was sent to Atlanta with Brent Sopel, Ben Eager and Akim Aliu for a first and second round pick, Marty Reasoner, Joey Crabb and Jeremy Morin. Neither of those draft picks amounted to roster players and none of the above players contributed much to the Blackhawks.
Byfuglien became a staple on the Atlanta blue line and continus to be the franchise's top defenceman today, albeit now as a Winnipeg Jet.
9 Taylor Hall For Adam Larsson
When this trade occurred last summer, experts were blown away that Taylor Hall was traded in a straight up one-for-one deal for Adam Larsson. Granted, Edmonton needed help on the blue line and it was expected that they would trade one of their star forwards to get one, but the talent gap is high between the two.
Taylor Hall has had an 80-point season while Larsson hasn't proven to be a no.1 defenceman. So far this season, the trade seems to be working out fine for Edmonton, as they're now contending for a playoff spot, but that has more to do with young phenom Connor McDavid leading the way.
We might need a few more years to really say who won this deal, but Larsson just doesn't seem to have the upside Hall does.
8 Tuukka Rask For Andrew Raycroft
Leafs fans are still miffed at this one. The Leafs drafted Tuukka Rask in the '05 draft, but had goaltender Justin Pogge in their system and felt he would be the team's future starter. Meanwhile, Bruins' goaltender Andrew Raycroft hit a sophomore slump after winning the Calder Trophy in 2003-04, so the Bruins shipped him to Toronto and took a chance on Rask.
Well, it didn't take long for the Leafs to regret the trade, as Raycroft's career continued to go in a downward spiral north of the border. While it took a while for Rask to take Boston's starting job from Tim Thomas, he's since become one of the NHL's better goaltenders and has a Vezina trophy to show for it. Where's Raycroft these days?
7 Luongo Returns To Florida
Roberto Luongo has been traded three times in his NHL career and they've all been lopsided trades. First, after the Islanders drafted Rick DiPietro, they sent their 1997 first round pick, Luongo, to the Panthers along with Olli Jokinen for Mark Parrish and Oleg Kvasha. Luongo became one of the league's best young goaltenders, while DiPietro proved to be a bust.
Prior to the 2006-07 season, Luongo was traded to Vancouver with Lukáš Krajíček and a sixth rounder for Todd Bertuzzi, Bryan Allen and Alex Auld. Ask Florida how that deal worked out for them.
Finally, after a year of speculation, the Canucks traded the second piece of their once formidable goaltending duo to the Panthers for Shawn Matthias and Jacob Markstrom. The Canucks also have maintained part of Luongo's salary.
What does the lesson seem to be here? If you have Luongo, don't trade him.
6 Zdeno Chara And Jason Spezza To Ottawa For Alexei Yashin
The Islanders once had a chance to build a core that would have featured players like Luongo, Zdeno Chara and Jason Spezza. But they let every young asset of theirs slip away.
At the 2001 draft, the Islanders mortgaged their future to land the enigmatic Senators star Alexei Yashin. While Yashin had proven to be an amazing talent, he came with a lot of baggage and that carried him into Long Island.
The Isles sent young towering defenceman Zdeno Chara, along with Bill Muckalt and their second overall pick in the '01 draft (Spezza) for Yashin. While Yashin provided solid offensive numbers, his massive contract and declining numbers spelled doom for the franchise. The Sens meanwhile, would emerge as a Stanley Cup contender in the early to mid 2000s.
5 Devils Land Cory Schneider
After trying to trade Roberto Luongo and failing, the Canucks threw in the towel and sent the younger and more affordable of their two goalies, Cory Schneider to the New Jersey Devils for a first round pick. The Canucks used the pick to land Bo Horvat. While Horvat has proven to be a very solid NHL player, he's not exactly a star in the league.
Meanwhile, Cory Schneider has been the Devils' workhorse since Martin Brodeur left town. While he's taken a bit of a step back this year, the Devils have their franchise goalie for the foreseeable future and they didn't have to give up all that much to get him.
Moves like this are what eventually got Vancouver GM Mike Gillis fired.
4 Ryan McDonagh To The Big Apple For Scott Gomez
Every Montreal fan knows this trade by heart. In the summer of 2009 after a disappointing centenntial season, the Canadiens traded their top defensive prospect Ryan McDonagh to the New York Rangers along with Chris Higgins, Doug Janik and Pavel Valentenko for Scott Gomez, Tom Pyatt and Michael Busto. Gomez's massive seven year, $51.5 million contract proved to be too much to live up to and his play quickly dipped in Montreal. The Habs eventually bought him out following the 2012-13 lockout.
Meanwhile McDonagh has since become the Rangers' captain, their no.1 defenceman and has led them to a Stanley Cup Finals berth. The Habs are dreaming to this day of what their blue line could have looked like had they not given up on McDonagh so early.
3 The Canucks Landing Both Sedins
In what was a stroke of genius by then Cancuks GM Brian Burke, he managed to land the 1999 draft's only stars when he maneuvered himself in a position to land Henrik and Daniel Sedin back to back. The moves are very complicated, but in the end, all you need to know is that when you look back at that 1999 draft, it's clear the Canucks were the clear winners. The Thrashers were one of the teams involved in this series of trades, and after dealing with the Canucks, they ended up landing the first overall pick. They took Patrik Stefan with that pick, who proved to be a huge disappointment for them.
It turns out every GM should have been doing everything possible to land the Sedin twins, who made it very clear they wanted to play together.
2 Jaromir Jagr To The Capitals
Jaromir Jagr was a Pittsburgh icon, but after the return of Mario Lemieux, he and the Penguins came at a crossroads. The Pens wanted the returning Lemieux to be the leader of the team, while Jagr felt that in Lemieux's absence, the Pens were now his team. After a brief reunion between Jagr and Lemieux, the Penguins traded Jagr to the Washington Capitals for Kris Beech, Michal Sivek and Ross Lupaschuk. None of those players amounted to anything for the Penguins, which really makes you wonder how they possibly traded Jagr without acquiring at least one proven NHL player.
While Jagr's tenure in Washington didn't result in a Stanley Cup, the Capitals essentially got an icon of the game, with many prime years left, for spare parts.
1 Tyler Seguin To The Stars
Boston Bruins fans are cursing this trade to this day. The Bruins landed the 2010 second overall pick in a deal with the Leafs where they traded Phil Kessel, but after three seasons with the Bruins, the team decided Seguin wasn't mature enough. They weren't crazy about his partying ways, so they sent him to the Dallas Stars along with Rich Peverley and Ryan Button to the Stars for Loui Eriksson, Reilly Smith, Matt Fraser and Joe Morrow.
Eriksson was the biggest piece returning in that deal and he's not even a Bruin anymore. Meanwhile Seguin has developed into an elite point producer in Dallas and seems to have an amazing career ahead of him.
Bruins fans can only wonder what Seguin could have done in Boston had the organization been more patient with him.
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