Some trades look bad right from the start. While others may look good at the time but as time goes on it begins to appear very one-sided. All types of trades appear on this list and I am sure each GM thought he was getting a good deal at the time. There are some teams that appear on this list on both the good and bad side of a trade which shows no team is perfect.
In this list, I take a look at the 15 most one-sided trades that have occurred since the tragic lockout in 2004. You will see some of the biggest names in hockey on this list which shows no one is safe from a bad deal. From teams giving up on a promising player way too soon to some teams that were forced to move on from a star player due to demands or impending free agency.
Hindsight is definitely 20/20 when it comes to all hockey trades but I think everyone can agree that in the 15 trades that are to be listed there was definitely one team that ended up much better off than the other. So without further ado let’s take a look back as we count down the 15 Most One-Sided NHL Trades since the 2004-05 Lockout!
15 Atlanta Thrashers Trade Marian Hossa
The Trade: Atlanta Thrashers trade Marian Hossa and Pascal Dupuis to the Pittsburgh Penguins for Colby Armstrong, Erik Christensen, Angelo Esposito and a 1st round pick.
The Thrashers knew they had to trade Hossa or risk losing him for nothing in the offseason but they received a horrible return for the sniper. Not only that but they gave up Pascal Dupuis who became the regular linemate for Sidney Crosby. None of the players they received was even worth just Dupuis. The pick was a bust, the prospects didn’t work out (Angelo Esposito never even played a regular season NHL game) and Colby Armstrong is just not that great. The team would move to Winnipeg just three years later and never made another playoff appearance while in Atlanta.
14 Los Angeles Kings Acquire Mike Richards, Sacrifice Future
The Trade: the Los Angeles Kings trade Brayden Schenn, Wayne Simmonds, and a 2nd round pick to the Philadelphia Flyers for Mike Richards and Rob Bordson.
This trade looked okay at first as the L.A Kings shocked the NHL by winning the Stanley Cup in 2012. Over time it has become obvious that the Flyers got the best of this deal by far. Wayne Simmonds is one of the premier power forwards in the game and Brayden Schenn was a solid player during his tenure as a Flyer. Mike Richards struggled after that first year and was eventually arrested and had his contract terminated in 2015. Some may argue the Kings won two Stanley Cups with Mike Richards, but Richards wasn't exactly the driving force behind those Cups. It's very likely the Kings still would've won with Simmonds and Schenn and possibly wouldn't have missed the playoffs two of the past three seasons.
13 Edmonton Oilers Trade Ryan Smyth
The Trade: Edmonton trades Ryan Smyth to the New York Islanders in exchange for Robert Nilsson, Ryan O’Marra and a 1st round pick in 2007.
This trade cut the heart and soul right out of the Edmonton Oilers. After some failed contract negotiations, and not wanting to risk losing him for nothing Kevin Lowe traded Ryan Smyth at the 2007 NHL deadline. Robert Nilsson and Ryan O’Marra struggled in the NHL. The Oilers also struck out with the draft pick selecting failed prospect Alex Plante. Nothing good came from this deal and at least Smyth came home to end his career. It's crazy to think that this madness occurred just a year after the Oilers had gone on a magical run to the Stanley Cup Final.
12 St. Louis Blues Trade Chris Pronger
The Trade: The St.Louis Blues trade Chris Pronger to the Edmonton Oilers for Eric Brewer, Doug Lynch, and Jeff Woywitka.
No offense to Eric Brewer who was a solid defenseman in the NHL but in no way does he compare to Chris Pronger. The Blues got fleeced badly in this deal as Pronger would help lead the Edmonton Oilers to the Stanley Cup Final in his only season with the club. Woywitka and Lynch would both not accomplish anything at the NHL level. Brewer became captain of the Blues but struggled to fill Pronger’s big shoes. Unsurprisingly, the Blues finished at the bottom of the NHL and had the first overall pick in 2006, only to pass on Jonathan Toews. Edmonton won this deal going away. If only Pronger stayed in Edmonton for more than one season.
11 Ottawa Senators Give Away Ben Bishop
The Trade: The Ottawa Senators trade Ben Bishop to the Tampa Bay Lightning for Cory Conacher and a 4th round pick.
There is nothing redeemable about this deal at all for the Senators. They had three goalies on the roster at the time that showed NHL potential and they just moved the wrong one. Bishop developed into a great goalie in the NHL hitting a career high 40 wins in 2014-15. He even led the Lightning all the way to the Stanley Cup Final. Conacher on the other hand never reached his potential and has bounced around the league since the deal. Just not a good move for a Sens team that could have used Bishop! Yes, Craig Anderson has since filled the role nicely, but if the Sens got a decent return for Bishop, they may have had the missing piece they needed in this year's playoffs.
10 The Edmonton Oilers Trade Chris Pronger
The Trade: The Edmonton Oilers trade Chris Pronger to the Anaheim Ducks for Joffrey Lupul, Ladislav Smid, and 2 draft picks.
After coming within one game of winning the cup Pronger forced his way out of Edmonton. The Oilers had no choice but to move him and didn’t get a strong return. Smid became a good shot blocker but Lupul struggled in Edmonton. One of the picks became Jordan Eberle who is now a member of the New York Islanders after an up and down career with the Oilers. In fairness to the Oilers, their hands were tied, but perhaps they should have been a little more patient in shopping Pronger around.
The Oilers defense is just now starting to become a strength again after being torn apart in this deal.
9 Washington Capitals Trade Filip Forsberg
The Trade: The Washington Capitals trade Filip Forsberg to the Nashville Predators for Martin Erat and Michael Latta.
The Capitals were gearing up for a deep playoff run in 2013 when they pulled off this deal. Filip Forsberg had not yet played for the Capitals as he was selected 11th overall in the 2012 draft. Forsberg was however a highly touted prospect with great offensive ability. That ability has been on full display in Nashville scoring over 30 goals the last two seasons. Erat lasted 66 games over 2 seasons only scoring 2 goals. The Capitals lost in round one in the playoffs, so the deal didn't even benefit them in the short term. If Forsberg's career continues going the way it has, this may very well go down as the worst trade of the cap era.
8 Florida Panthers Trade Roberto Luongo To Vancouver
The Trade: Florida trades Roberto Luongo, Lukas Krajicek, and a 6th round pick to the Vancouver Canucks for Todd Bertuzzi, Bryan Allen, and Alex Auld.
Wow was this a horrible move by the Panthers. Roberto was one of the best goalies in the NHL at the time of this deal and the best piece they got for him was an over the hill Todd Bertuzzi. Bertuzzi was not the same player in Florida and struggled with back injuries. Luongo quickly proved he could be an elite goalie helping the Canucks become one of the best teams of the late 2000s- early 2010s. The Panthers would wind up trading for Luongo again a few years ago, but they missed out on the best years of his career.
7 Philadelphia Flyers Trade Sergei Bobrovsky
The Trade: The Philadelphia Flyers trade Sergei Bobrovsky to the Columbus Blue Jackets for a 2nd round draft pick, and two 4th round picks.
Oh boy do the Flyers do a horrible job when it comes to goaltenders. After using him as a backup the Flyers moved Bobrovsky in June of 2012. Bobrovsky would flourish with the Blue Jackets. He has now won two Vezina Trophies (2013 and 2017) while the Flyers still struggle to find the answer in net.
If the 2nd round pick they received (Anthony Storlaz) ends up being as good as advertised at least they may finally have their answer in net. It's just crazy that the Flyers FINALLY got a goalie of the future, only to let him slip away.
6 Montreal Canadiens Acquire Scott Gomez For Ryan McDonagh
The Trade: The Montreal Canadiens trade Ryan McDonagh, Chris Higgins, Doug Janik and, Pavel Valentenko to the New York Rangers for Scott Gomez, Tom Pyatt, and Michael Busto.
This is one of the most moves in Montreal Canadiens history. Scott Gomez was a huge bust in MTL, actually going a full 12 months without a goal at one point. Higgins for Gomez would have been fair at this point, but when you add in McDonagh this trade skews greatly towards the Rangers. McDonagh is the captain of the team and one of the better defensemen in the NHL. The Habs paid Gomez a lot of money and he didn’t do much for the club. Many Habs fans have said this trade was even worse than the Patrick Roy trade, given this kind of trade was made in the salary cap era.
5 Minnesota Wild Trade Brent Burns
The Trade: The Minnesota Wild trade Brent Burns and a 2nd round pick for Charlie Coyle, Devin Setoguchi, and a 1st round pick.
What were the Minnesota Wild thinking? At the time Brent Burns had already shown flashes of the offensive ability he possessed. He didn’t quite fit into their defensive minded system and so he was moved to the Sharks. The 1st round pick was wasted, Devin Setoguchi was past his prime, only Charlie Coyle has been a redeeming factor in this deal. Burns though is on a different level and is one of the elite defensemen in the NHL and that was proven more than ever this season, as he took home the Norris Trophy. Coyle alone is not enough to save this deal.
4 Boston Bruins Trade Joe Thornton
The Trade: Boston trades Joe Thornton to San Jose for Wayne Primeau, Brad Stuart, and Marco Sturm.
Joe Thornton was the captain of the Boston Bruins heading into the lockout. Thornton was constantly criticized then (and now) for failures in the playoffs. The Bruins decided it was time to move on from the embattled star during the 2005-06 season and agreed to send him to the Sharks. None of the players Boston received accomplished much of anything. Thornton would win the Hart and Art Ross that season and continues to star for the Sharks consistently among the league leaders in points. Yes, the Bruins have won a Stanley Cup since the trade and the Sharks haven't, but you have to think the Bruins would have figured out a way to win multiple cups with Jumbo Joe being joined by the likes of Bergeron and Chara.
3 Toronto Maple Leafs Trade Tuukka Rask
The Trade: The Toronto Maple Leafs trade Tuukka Rask to the Boston Bruins for Andrew Raycroft.
This trade hurts Leafs fans for many reasons. The Bruins initially wanted Justin Pogge but the Leafs offered up Rask instead. The Leafs felt that Pogge and not Rask was their goalie of the future. To make matters worse the Bruins were planning to release Raycroft anyway which means the Leafs could have had him for nothing. Raycroft struggled to find his game in Toronto while Rask became one of the elite goaltenders in the NHL. With all the struggles the Leafs have had in net over the years it must hurt that they had a stud prospect that they gave away for nothing. Thankfully, they seem to have competent people in charge now.
2 Toronto Maple Leafs Acquire Phil Kessel For Two 1st Round Picks
The Trade: The Toronto Maple Leafs trade 2010 1st and 2nd round pick, 2011 1st round pick to the Boston Bruins for Phil Kessel.
Leafs GM Brian Burke was so sure that Phil Kessel was the answer to all his problems that he placed no exceptions on either of the two first round picks. He didn't account for the fact that his team might be bad for a couple of years, which would make those picks all the more valuable. The Leafs struggled and picked 2nd overall in 2010 which got the Bruins Tyler Seguin. In 2011 the Leafs struggled again picking 9th and gifting the Bruins stud defenseman Dougie Hamilton. Toronto would continue to struggle, Burke would be fired and Kessel is now busy winning Cups in Pittsburgh. But it's okay Leaf fans, all the sucking got them Auston Matthews.
1 The Boston Bruins Trade Tyler Seguin
The Trade: The Boston Bruins trade Tyler Seguin, Rich Peverley, and Ryan Button to the Dallas Stars for Loui Eriksson, Reilly Smith, Matt Fraser and Joe Morrow.
Tyler Seguin liked to party; that was his big crime with the Boston Bruins. They were sick of his partying ways and moved him on to the Stars where he has become one of the best scorers in the NHL. Loui Eriksson was the best piece that they got back but he is nowhere near the player that Seguin is. Dallas was more than happy to deal with a slowly maturing Seguin and Boston is just left with regret. They have seemingly regressed as an organization the past few years and Seguin hasn't even hit his prime yet.