Every NHL team has made some trades that have gone down as great for their franchise… and they’ve all made trades that changed their team for the absolute worst. But many of the most one-sided trades in NHL history have actually taken place recently. More specifically, the past 10 years have been home to some of the most amazing trades that shifted the history and landscape of the NHL.
Take a look at every Stanley Cup winner since 2011: they’re all beneficiaries of some awful trades that brought in players to help them win the championship. What made it better, of course, is the fact that the pieces they sent away didn’t even pan out as expected.
As you go through this article, you’ll see how each of these trades made significant impacts in the NHL, but only one team benefited in the deal. Here’s a look at the 15 most one-sided NHL trades since 2006.
15. Flyers Acquire Scott Hartnell And Kimmo Timonen, 2007
The Flyers were a perennial playoff team in the 1990s and 2000s, but they hit a snag in 2007 and finished as the NHL’s worst team. In a market used to competitive teams and spring hockey, the team wasted no time making significant changes.
With Scott Hartnell and Kimmo Timonen set to become free agents, the Flyers traded for both players, sending the 23rd overall pick to the Nashville Predators. They later used that pick to select promising defenceman Jonathan Blum, but he hasn’t established himself so far.
Timonen was instantly one of the Flyers’ top blueliners, playing with them from 2007-08 to 2014-15, before he was traded to the Chicago Blackhawks where he won a Stanley Cup. Hartnell was no slouch himself, putting up five 20-goal seasons with Philly, including a 37 goal campaign in 2011-12. Both men led Philly to the 2010 Stanley Cup Final, though the ‘Hawks took them down.
Still, both men helped the Flyers rise from the ashes by becoming one of the top teams in the East.
14. Sharks Steal Dan Boyle From Lightning, 2008
The Sharks finished the 2008 season with a disappointing second round exit, while the Lightning won the Steven Stamkos sweepstakes. They had traded Brad Richards earlier in the year and decided it was time to rebuild, so they traded superstar blueliner Dan Boyle to the San Jose Sharks.
It made sense, as Boyle didn’t have a long-term future with the Lightning, who had to tear it all down. What they did wrong was not demand enough in return. They got decent blueliner Matt Carle, but he has never come close to performing like Boyle. They also got Ty Wishart and a pair of draft selections, but the Sharks won this trade by a mile.
Though they never reached the Stanley Cup with him, the Sharks were still one of the most dominant teams during Boyle’s six years there. He reached the 50 point mark in his first three seasons and won a gold medal with Team Canada in 2010. Maybe if the Lightning set the asking price higher, they could have added more pieces to speed up the rebuilding process.
13. Blackhawks Give Away Dustin Byfuglien, 2010
To be fair to Chicago Blackhawks GM Stan Bowman, everyone knew Dustin Byfuglien and other ‘Hawks were on their way out after the team won the 2010 Stanley Cup. Jonathan Toews and Patrick Kane were in line for huge extensions, while Brent Seabrook, Duncan Keith, Patrick Sharp, and Marian Hossa took up too much cap space. Bowman was forced to trade away a handful of studs.
In the summer of 2010, Bowman dealt Byfuglien, Brent Sopel, Ben Eager, and Akim Aliu to the Atlanta Thrashers (now Winnipeg Jets) for bottom-six forwards Marty Reasoner, Joey Crab, failed prospect Jeremy Morin, and a pair of draft selections that didn’t mount to any roster players.
Chicago could have easily asked for a nice prospect or two, but they got nothing substantial out of the return. Not that it matters, as they won a pair of Cups after this trade. But the Jets look loaded for years to come, thanks to Byfuglien being a key cog on their blueline who’s constantly hitting or getting close to 20 goals.
12. Penguins Surrender Little For Marian Hossa and Pascal Dupuis, 2008
The Penguins were doing better than many expected in the 2008 season. All that was missing was a proven veteran star to carry young guns Sidney Crosby, Evgeni Malkin, and Marc-Andre Fleury to the next level.
So, Ray Shero went out and sacrificed what appeared to be plenty of future superstardom players and got Atlanta Thrashers standout Marian Hossa. Not only that, they added Pascal Dupuis, who became one of Sidney Crosby’s favourite linemates and a key part of their 2009 Stanley Cup championship winning team.
All Pittsburgh had to give up was Colby Armstrong, who’s no longer playing, along with a first round pick, roster player Erik Christensen, and elite prospect Angelo Esposito. None of those players lasted long in Atlanta and the Penguins made it to the Stanley Cup Final with Hossa’s services.
To make matters better, Hossa rejected an extension and landed in Detroit the following season. Pittsburgh would avenge the Stanley Cup Final loss the year before (against Detroit) by beating Hossa’s Wings in seven games.
11. Flyers Dump Mike Richards To Kings, 2012
Many were shocked when the Philadelphia Flyers traded away their two franchise players, Jeff Carter and Mike Richards, in the summer of 2011. Looking back, everything made sense.
The Los Angeles Kings were on the rise and needed a proven veteran to lead, so they sacrificed a TON to get Richards: Power forward Wayne Simmonds, prized prospect Brayden Schenn, and a second round selection in 2012.
Richards lasted just three seasons in LA, and his career high would be 18 goals and 44 points there, a far cry from the man who had a pair of 30 goal seasons and an 80 point campaign in Philly. Oddly enough, Kings fans may not regret the trade, as they won two Cups with Richards on the roster. However, he simply wasn’t a key part of any of those championships and it’s safe to say the Kings would have likely still won those without him.
Schenn and Simmonds have become cornerstone players in Philly since. The latter has hit 28+ goals in four of his five years with Philly and Schenn is coming off a career high 26 goal, 59 point season.
10. Canadiens Gamble And Lose On Scott Gomez, 2009
Scott Gomez got paid big-time by the New York Rangers despite just one terrific season in his career – a 33 goal and 84 point 2005-06 campaign with the New Jersey Devils. That didn’t stop Glen Sather from handing him a seven-year, $51.5 million contract.
Gomez had a pair of solid seasons with the Blueshirts and the Montreal Canadiens thought he could rejuvenate their team. So in a seven-player trade, they gave up quality top-six forward Chris Higgins and prospect blueliner Ryan McDonagh to get Gomez.
McDonagh has since become one of the NHL’s best leaders and is effective at both ends of the ice. As for Gomez? His best season in Montreal was a 12 goal, 59 point season. He even went a full year without scoring a goal in the NHL. They were lucky that the new CBA included a pair of amnesty buyouts and they got rid of the league’s worst contract. They bought him out in 2013. But the trade hurts years later, as McDonagh and P.K. Subban…err..Shea Weber, would be a great duo.
9. Calgary Flames Steal Franchise Defenceman Dougie Hamilton, 2015
The Boston Bruins were trying to regain faith from their fans. Their idea of doing that was firing GM Peter Chiarelli in 2015 after the team missed the playoffs and having former franchise player Don Sweeney take over for him.
It was hard for fans to believe in Sweeney and it still is to this day. With Zdeno Chara on his last legs, the B’s at least knew they had Dougie Hamilton on the rise to take over as the team’s top blueliner. Instead of giving into Hamilton’s contract needs, Sweeney dealt him to the Calgary Flames for three draft picks in 2015. Time will tell how they pan out.
But it’s virtually impossible to see how this makes sense. Hamilton was 22 at the time of the trade, coming off of an impressive season of 10 goals and 42 points. Hamilton is big at 6’6″ and 210 pounds, and the Flames surrendered very little to add a guy who’ll contend for the Norris Trophy in the long-run.
8. Senators Land Kyle Turris, 2011
Kyle Turris was hyped as a can’t-miss prospect when the Arizona Coyotes drafted him third overall in 2007. However, the team made a huge mistake in not giving him proper ice time or paying him. No way a guy of his talents should have been kept off the ice so much.
The young centre held out during the 2011-12 season, and the Coyotes would trade him to Ottawa for promising blueliner David Rundblad and a second-round pick. Though many thought Rundblad was on his way to big things, he has yet to find full-time minutes in the NHL. As for Turris? Well…
Aside from an injury-filled 2015-16 season, he’s been a true number one centre with the Senators. He had 26 goals and 58 points in 2013-14 and followed it up with a 24 goal, 64 point season. With Jason Spezza out of the way, Turris stepped in and became a legitimate number one centre. Highway robbery for Bryan Murray.
7. Senators Surrender Jason Spezza to Stars, 2014
The Ottawa Senators had missed the playoffs for the first time in three seasons after the 2013-14 season and centre Jason Spezza didn’t see much of a future in the nation’s capital, so he demanded a trade. It was a prime opportunity for Ottawa to acquire much-needed assets for their rebuild.
The Anaheim Ducks, St. Louis Blues, and Dallas Stars were the three front-runners. Anaheim traded for Ryan Kesler and the Blues signed Paul Stastny to a four-year deal, so Dallas became the last logical option and it worked to their advantage. Bryan Murray willingly took anything they offered him.
All Ottawa got in return for a bonafide franchise star was Alex Chiasson (no longer with the team), Alex Guptill, Nicolas Paul, and a second round pick. None of them have contributed significantly to the roster. There’s no way that you should get four little pieces for a big weapon like Spezza. Murray clearly never set the asking price high enough and the team got almost nothing for him.
6. Jackets Trade for Jeff Carter, Then Flip Him, 2011/2012
After years of rebuilding, the Blue Jackets decided it was time for a major move. They sent the promising Jakub Voracek, their first-round selection (used to select two-way stud Sean Couturier), and a third-round pick for Jeff Carter.
It seemed like a good trade for both teams. The Flyers needed to get rid of a major contract and the Jackets needed a new star immediately. Coming off of three-straight seasons where he notched 30 goals and 60 points, Carter was everything the Jackets wanted and had hoped for.
He struggled immediately, posting 15 goals and 25 points in 39 games. So the Jackets decided to trade him for Jack Johnson and a first-round pick. Carter has become a key part of the Kings’ two Stanley Cup rings and the Jackets didn’t even get much in return.
Johnson isn’t close to a Norris-calibre defenceman, as he’s a solid number two or three blueliner. Given everything Columbus surrendered to get Carter, they should have been more patient with him.
5. Canucks Give Away Cory Schneider, Franchise Netminder, 2013
The Vancouver Canucks once had a problem that all 29 teams could only dream of having: two franchise netminders. On one hand, they had Roberto Luongo, in the midst of a 12-year pact. He had won two Olympic gold medals with Team Canada. Despite his inconsistencies in the playoffs, the Canucks would have been absolutely nothing from 2006-2013 without him, where he was a terrific netminder.
But the logical choice would have been to keep Cory Schneider, who was seven years younger and more consistent than Bobby Lou. When the 2013 NHL Entry Draft came, nobody knew what would happen.
GM Mike Gillis, likely facing intense pressure from the ownership to trade one goalie, chose to give up Schneider. Maybe if the Canucks got a good haul in return, the trade would be easier to understand. All they got was the ninth pick, which turned out to be Bo Horvat.
Now Horvat has made significant strides in his last two seasons, but he probably isn’t more than a number two centre. The Canucks, had they thought this out more, would have gotten at least one young roster player entering his prime and a pair of elite prospects. Not one guy who may never be a top-six forward.
Oh, and Luongo was traded to Florida the following year. So two franchise goalies gone in less than a year. No wonder Gillis was let go in 2014.
4. Canucks Get a Franchise Netminder For Little, 2006
The Canucks finished 2005-06 outside of the playoffs for the first time since 2000 and it was clear that a franchise goalie was needed. Todd Bertuzzi was on the decline and Alex Auld/Dan Cloutier weren’t cutting it out any more as number one starters.
So, Dave Nonis made an extremely bold trade. He gave up bottom-pairing defenceman Bryan Allen, fading power forward Todd Bertuzzi, and Alex Auld for Roberto Luongo, Lukáš Krajíček, and a sixth-round selection. Luongo would go on to become the franchise’s all-time leader in wins (252), shutouts (38), while posting a 2.36 GAA, and .919 save percentage. Only Schneider has better numbers, but he played 98 games against Luongo’s 448.
Say what you want about his playoff performance, but the Canucks won six Pacific Division titles, two Presidents Trophies, and were one win away from the Stanley Cup championship in 2011. Without Luongo, they would have remained a laughingstock in the league. He revived a fan base that was losing hope with its team before he arrived.
And they didn’t have to pay much to get it.
3. Chris Pronger To Anaheim For Juice Boxes And Goldfish Crackers, 2006
I remember my dad telling me how Chris Pronger was a huge impact player for this reason: he got Edmonton to the Cup Final in his first year with them (2006), Anaheim (2007), and Philadelphia (2010).
Well, Pronger was a huge reason Edmonton was a win away from taking it all in 2006. He and Scott Niedermayer formed arguably the greatest defensive pairing of the last 20 years en route to a Cup win in 2007. You get the idea. He’s one of the best players ever and he was a huge impact on the ice.
There’s a reason the Oilers haven’t made the playoffs since that Cinderella run in 2006: They should have gotten way more in the Pronger trade. They got Joffrey Lupul (a nice top six forward, but failed in Edmonton), mediocre blueliner Ladislav Smid, and two draft picks, though one of them became Jordan Eberle.
Unless Eberle becomes a 40-goal scorer who leads the Oilers to the Stanley Cup, you can’t expect Edmonton to ever look back and be happy about this. If the Oilers win a Cup with their current core, Eberle will be a part, not the heart of it all.
2. Leafs Give Up Two Major Assets For Phil Kessel, 2009
When the Maple Leafs traded for Phil Kessel, many thought this was the trade that would end the rebuilding stage. The price was hefty: Their first-round selections in 2010 and 2011. The trade was a huge gamble enough, but doing business with division rivals, the Boston Bruins, was a little too insane.
Kessel had four 30 goal seasons with Toronto and the other two saw him reach the 20-goal plateau. He was everything Toronto wanted, but they failed to build around him, reaching the playoffs just once (and you know how that turned out). And even if Kessel had the supporting cast to turn them into a contender, remember those picks they gave up. They turned out to be Tyler Seguin (a top five NHL scorer by far) and franchise blueliner Dougie Hamilton.
The Leafs traded him to Pittsburgh last summer and they did get some promising young players in that deal. Even if they turn out great, we’ll assume they’re not going to be like what Seguin and Hamilton could have been. Auston Matthews and Seguin together? Yes, please.
1. Then Boston Trades Seguin (2013)
If it’s any consolation for Leafs fans, Boston managed to trade away both Seguin AND Hamilton, without getting equal value in return. Amazingly enough, the Bruins take the top spot on our list for giving up far too early on the young centre.
The reports go that Boston didn’t like Tyler Seguin’s party lifestyle and routine of breaking curfew frequently, so they traded away a 21-year-old who was just coming into his own. So here is the return the Big Bad Bruins got in a deal that also gave Dallas Rich Peverley and Ryan Button:
-Loui Eriksson: Inconsistent first two years with Boston, became 30-goal scorer in last year. Now a member of the Vancouver Canucks after signing for six-years earlier this month.
-Reilly Smith: Flipped for Jimmy Hayes last year. Was a 20-goal scorer in his first year with Boston.
Matt Fraser: Bottom-six player.
Joe Morrow: Promising blueliner that hasn’t reached his potential. If he does, he still won’t be as impactful as Seguin.
And there you have it. Seguin’s posted 107 goals and 234 points in 223 games with Dallas through three seasons. Here’s the other catch: Boston has missed the playoffs twice since trading Seguin, and Dallas has qualified twice.
That’s all you need to know as to why this was a major disaster for the Bruins.
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