NHL: Worst Trades of the Salary Cap Era

Worst Trades of the Salary Cap Era

The Salary Cap Era began with the 2005-06 season, and so much attention lately has been on some awful trades being made, particularly highlighted by the Oilers and Chiarelli in particular. There have been a lot of trades that have worked out well for both teams and some that have been very one-sided. I’ve been seeing a lot of people talking about certain trades on Twitter the last little bit, which made me want to dive into a lot of them and see exactly how they’ve worked out for both teams. I’m excluding any trades that were simply picks for picks, too many of those to sort through. These are not ranked in any specific order of which one is worse, but here we go. I found a great site listing all of the trades I’m talking about here http://www.nhltradetracker.com/user/trade_list_by_season, check it out:

June 24th, 2006 – Toronto Maple Leafs and Boston Bruins

Toronto Acquires – Andrew Raycroft – GM was John Ferguson Jr.

Boston Acquires – Rights to Tuukka Rask – GM was Peter Chiarelli

Raycroft won the Calder trophy is his first full year in the NHL in 2003-2004, with 29 wins in 57 games played. He followed that up with a lackluster 8 wins in 30 games played, which for some ridiculous reason tempted Toronto to trade for Raycroft. They had 2 goalie prospects in Justin Pogge and Tukka Rask, and clearly the Leafs valued Pogge more, keeping him and shipping out Rask. Since the trade, Raycroft played 173 games, winning only 70 of them. Pogge played in a total of 7 NHL games, winning 1 game! Rask, on the other hand, has played 395 NHL games, won a Stanley Cup in 2011, and a Vezina Trophy as the top-goaltender in 2014. This could easily be one of the more lopsided trades in Leafs history. This is one of the rare instances where Peter Chiarelli has come out on top in a trade.

Winner: Bruins fans are probably still laughing at this one, while Leafs fans are likely still crying.

Feb 25th, 2007 – Montreal Canadiens and San Jose Sharks

Montreal Acquires – Josh Gorges & 1st round pick in 2007 (Max Pacioretty) – GM was Bob Gainey

San Jose Acquires – Craig Rivet & 5th round pick in 2008 (Julien Demers) – GM was Doug Wilson

Rivet was a much more established defender at that time, but only went on to play 91 games for the Sharks in just over 1 season. The Sharks didn’t make it past the 3rd round of the playoffs that year when they made this trade, but Rivet played well for them. The flip side however is what Montreal acquired from this trade. Gorges played a whopping 457 NHL games for the Canadiens, before they then traded him to Buffalo for a 2nd round pick. The pick San Jose gave to Montreal turned into Max Pacioretty… who’s currently the captain of the team, and has 411 points in 562 games since being drafted. He’s scored over 200 goals, and been the Canadiens go-to player for offensive since 2011. This trade is looking worse and worse as the days go on.

Winner: Montreal, by a mile

June 18th, 2007 – Philadelphia Flyers & Nashville Predators

Philadelphia Acquires – Scott Hartnell & Kimmo Timonen – GM was Paul Holmgren

Nashville Acquires – 2007 1st Round pick (Jonathan Blum) – GM was David Poile

Hartnell is your ideal power-forward – big body, hits & fights, and can score. After coming off of back-to-back 20+ goal seasons, Nashville decided it was time to ship him out of town. To make matters worse, Nashville also added in Kimmo Timonen, who at the time was a top-pairing d-man in his own right. Timonen would go on to play in 8 more NHL season, before injuries derailed his career. Either one of this players would be better than what Nashville ended up with, as the pick turned into Jonathon Blum, who played in a measly 110 NHL games.

Winner: Flyers come out on top in this one

August 11th, 2007 – Phoenix Coyotes & Chicago Blackhawks

Phoenix Acquires – Radim Vrbata – GM was Don Maloney

Chicago Acquires – Kevyn Adams – GM was Dale Tallon

Adams played his final year in the NHL with the Blackhawks after this trade, scoring 2 points in 27 games. On the other side of the trade, Vrbata has played 10 more seasons, scoring 204 goals and 439 points. Vrbata is one of the rare consistent goal scoring wingers in today’s game, who has averaged 24 goals/82 games played since this trade, while Adams had a whopping 8 points in the year prior to be traded. It’s hard to imagine that Tallon couldn’t have gotten more for Vrbata.

Winner: Phoenix wins this one, easily.

June 24th, 2008 – Boston Bruins & Colorado Avalanche

Boston Acquires – Johnny Boychuk – GM was Peter Chiarelli

Colorado Acquires – Matt Hendricks – GM was Francois Giguere

This was back when Chiarelli appeared to know what he was doing, as he traded career-4th-liner Matt Hendricks for Johnny Boychuk, who played in the top-4 for Boston for 5 seasons. Hendricks has never been more than a 4th line player in his career, and has actually been outscored by Boychuk throughout his career.

Winner: Rare Chiarelli win for Boston

June 30th, 2009 – Montreal Canadiens & New York Rangers

Montreal Acquires – Tom Pyatt, Scott Gomez, Michael Busto – GM was Bob Gainey

Rangers Acquire – Ryan McDonagh, Pavel Valentenko, Doug Janik, Chris Higgins

It’s hard to imagine what Bob Gainey was thinking when you look back on this trade, as yes Gomez was coming off a 58 point campaign, but that was for a much better New York Ranger team. To say he struggled in Montreal would be a vast understatement, as after one good season, he fell off a cliff in terms of production, never scoring more than 7 goals in a season for the remainder of his career. Meanwhile, Busto never played an NHL game and Pyatt is nothing more than a bottom-6 depth forward. For New York, they received future captain and top defender Ryan McDonagh. Janik and Valentenko did not pan out as hoped, but Higgins played in 711 NHL games after being traded, and was more productive than Gomez alone. This could be one of the worst trades in this article.

Winner: There once was a website tracking how long it had been since Gomez scored a goal, which eclipsed a year. So yeah, New York is the clear-cut winner here.

July 21st, 2009 – Arizona Coyotes & Tampa Bay Lightning

Arizona Acquires – Radim Vrbata – GM was Don Maloney

Tampa Bay Acquires – Todd Fedoruk & David Hale – GM was Brian Lawton

Another trade for Vrbata heading to Arizona/Phoenix that is a solid win for that organization. I’ve already spoken about his scoring prowess over his career, and he definitely is much better that the combined two players he was traded for. Fedoruk played one last season after being traded, scoring 6 points in 50 games. Hale played in two more NHL season, only totaling 64 games over those two years, and 9 points.

Winner: Vrbata again the best part of a trade to Arizona.

June 25th, 2010 – St. Louis Blues & Ottawa Senators

St. Louis Acquires – 2010 1st rounder (16th overall – Vladimir Tarasenko)

Ottawa Acquires – David Rundblad – GM was Bryan Murray

Ottawa decided they wanted to go after a young, recently drafted player in Rundblad, after he had 13 points in 47 games in the SEL. Rundblad did not develop into an everyday NHL player, topping out at a career-high 49 NHL games in 2014-2015. The pick the Sens gave up turned into one of the most feared goal-scorers in today’s game – Vladimir Tarasenko. One goal shy of back-to-back 40 goal seasons, Tarasenko has scored 70+ points in 3 straight seasons, and looks like he has no plan to stop. At only 25 years old, Tarasenko will be a dominant force in the NHL for years to come.

Winner: Tarasenko is arguably the second-best scoring winger in today’s NHL. Sorry Sens fans.

February 9th, 2011 – Toronto Maple Leafs & Anaheim Ducks

Toronto Acquires – Joffrey Lupul, Jake Gardiner, conditional 4th rounder – GM was Brian Burke

Anaheim Acquires – Francois Beauchemin – GM was Bob Murray

Beauchemin was a good defender for Anaheim, as he played in the better part of 4 seasons for Colorado, scoring 20 points 3 times. Lupul had two good seasons for the Leafs after being traded, but has since succumbed to injuries. The kicker in my opinion is giving up Jake Gardiner, as he has developed into a great puck-moving defenseman. He played more than any other defender for the Leafs in their playoff appearance this year, and looked great while doing so. Anaheim was a team trying to win now, and didn’t want to wait on Lupul and Gardiner, but looking back they should have been able to get more had they waited on Gardiner just a little while longer.

Winner: Leafs, as Murray was trying to win a Cup when bringing in Beauchemin, but he gave up a little too much to do so.

February 18th, 2011 – Boston Bruins & Atlanta Thrashers

Boston Acquires – Rich Peverley, Boris Valabik – GM was Peter Chiarelli

Atlanta Acquires – Mark Stuart, Blake Wheeler – GM was Kevin Cheveldayoff

Blake Wheeler has developed into one of the best wingers in the game today, and one is usually highly under-appreciated by most. He’s hit 60+ points in 4 straight seasons, including 2 at over 70 points. He’s a big-man, and uses that size to dominate possession for the now Winnipeg Jets. Stuart has been a serviceable d-man since the trade, playing parts of 7 straight seasons for Winnipeg. On the other side of the trade, Peverley had his career cut short due to a scary incident in 2014 in which he collapsed on the bench, while Valabik never played another NHL game. Even if it weren’t for the incident with Peverley, this trade would be incredibly lopsided. Wheeler is a top-10 winger in today’s NHL, and the captain of the Jets alone.

Winner: The beginning of the end for Chiarelli in Boston, as this is a brutal trade.

February 21st, 2011 – Pittsburgh Penguins & Dallas Stars

Pittsburgh Acquires – James Neal, Matt Niskanen – GM was Ray Shero

Dallas Acquires – Alex Goligoski – GM was Joe Nieuwendyk

After scoring at least 20 goals in his first 3 NHL season with Dallas, Nieuwendyk decided it was time to trade him to the Stanley Cup hopeful Penguins. He went on to score 40 goals in his first full season there, and has hit at least 20 in every season since. The other piece sent out by the Stars was Matt Niskanen, who has developed into a top-pairing defender. He himself has surpassed Goligoski in terms of value, who is actually older than Niskanen, which makes this trade even more bizarre. Goligoski is by no means a bad defenseman, he’s just not worth either of Neal or Niskanen in terms of trade value, let alone BOTH.

Winner:  Shero gets the best of Nieuwendyk and the Stars

June 23rd, 2012 – Toronto Maple Leafs & Philadelphia Flyers

Toronto Acquires – James Van Riemsdyk – GM was Brian Burke

Philadelphia Acquires – Luke Schenn – GM was Paul Holmgren

What on earth was Holmgren thinking?! Luke Schenn was rushed into the NHL, likely hurting his development, but he was NEVER an offensive d-man. He was drafted too high back in 2008, but the fact that Brian Burke was able to trade him straight-up for James Van Riemsdyk is mind-boggling. JVR is hands-down the better player in this trade, and it’s not even close. Schenn was barely a 3rd pairing player in Arizona this year, one of the worst teams in the league, meanwhile JVR is a key piece of a strong, young Toronto team.

Winner: Brian Burke pulls of magic for the Leafs.

April 3rd, 2013 – Tampa Bay Lightning & Ottawa Senators

Tampa Bay Acquires – Ben Bishop – GM was Steve Yzerman

Ottawa Acquires – Cory Conacher – GM was Bryan Murray

Conacher scored 24 points in 35 NHL games in his rookie year, prompting Bryan Murray to jump ALLLLL over him, trading out one of the best goalies in today’s NHL in a one-for-one deal. Since the trade, Conacher has fallen all the way to the AHL, over to Switzerland, and back to the AHL before suiting up in 11 NHL games this year, for the team that traded him back in 2013. Bishop, since being traded, has won 133 NHL games, with 17 shutouts. Ottawa had Craig Anderson in the fold at the time, but should have gotten much more for a goalie like Ben Bishop.

Winner: Another loss for Bryan Murray and the Sens.

April 3rd, 2013 – Washington Capitals & Nashville Predators

Washington Acquires – Michael Latta, Martin Erat – GM was George McPhee

Nashville Acquires – Filip Forsberg – GM was David Poile

This, in my opinion, could be one of the worst trades in recent history. Erat was sitting at 21 points in 36 games when he was traded for, and managed al of 2 goals, 25 points in 62 games for Washington in his 1.5 seasons there. Latta is now playing in the AHL, after putting up even smaller numbers for the Capitals. Forsberg has since developed into an elite winger for the Predators. Trading an 11th overall pick for two players who lack offense is always a risky move, but this turned out to be far worse than expected.

Winner: Poile is likely still laughing at this one, as are Preds fans.

July 4th, 2013 – Boston Bruins & Dallas Stars

Boston Acquires – Loui Eriksson, Joe Morrow, Reilly Smith, Matt Fraser – GM was Peter Chiarelli

Dallas Acquires – Tyler Seguin, Rich Peverley, Ryan Button – GM was Jim Nill

Chiarelli has had some bad trades on his resume, but this one is the worst for me. In the 4 seasons since being traded, Seguin has scored 306 points. He’s one of the best young centres in today’s NHL, and doesn’t look like he’ll slow down anytime soon. Smith played well in his two years in Boston, but was shipped out for Jimmy Hayes, who was disappointing for Boston. Eriksson had 1 good year for Boston, but still never hit the numbers Seguin did, before they lost him to free agency. Morrow hasn’t established himself as an NHL d-man, playing 65 games stretched over 3 seasons, and has since signed in Montreal. Fraser was waived after playing 28 games for Boston. All of this means, Boston traded away a true number 1 centremen, at the age of 21, and have nothing left to show for it.

Winner: Seguin is a core building block for Dallas, an exciting young team. Boston has nothing to show for it. Tough call…

July 8th, 2013 – Ottawa Senators & Anaheim Ducks

Ottawa Acquires – Bobby Ryan – GM was Bryan Murray

Anaheim Acquires – Jakob Silfverberg, Stefan Noesen, 2014 1st round pick (Nick Ritchie) – GM was Bob Murray

Bob Murray continues his streak of bad trades. Not only is this trade awful for Ottawa, but Murray then signed Ryan to a massive 7 year extension, with an AAV of $7.25 million. He managed “OK” in this first few seasons in Ottawa, in-and-around the 50 point mark, but Silfverberg himself has already established that kind of production, not to mention the remaining pieces they received in Noesen (now in New Jersey), and Ritchie (more points than Ryan this year).

Winner: Ottawa loses another.

July 1st, 2014 – Ottawa Senators & Dallas Stars

Ottawa Acquires – Alex Chiasson, Alexander Guptill, Nicholas Paul, 2015 2nd rounder – GM was Bryan Murray

Dallas Acquires – Jason Spezza, Ludwig Karlsson – GM was Jim Nill

It must seem like I’m picking on the Sens here, but I swear I’m not. Everyone thought the Sens would trade Spezza in this offseason, but the Sens got basically NOTHING for him. Chiasson was a dud, with 30 points totaled over 2 seasons. Guptill has yet to play an NHL game, and Paul has played all of 25 games. The pick was traded to the Devils in an exchange of picks, with no promising prospects coming from them. Spezza has continued to thrive in Dallas, scoring 30 goals in his second year there, while hitting 60+ points twice, and 50 in the other.

Winner: Surprise, surprise – Ottawa loses another trade.

January 14th, 2015 – Minnesota Wild & Arizona Coyotes

Minnesota Acquires – Devan Dubnyk – GM was Chuck Fletcher

Arizona Acquires – 2015 3rd rounder – GM was Don Maloney

I questioned putting this one in, because Dubnyk was struggling at this point in his career. He was coming off a season in which he only played 19 games, with a 9-5-2 record. After the trade however, he put up a record of 27-9-2, with a SV% of 0.936 and a GAA of 1.78. Those are remarkable numbers. He’s become one of the best goalies playing in today’s NHL, and the fact that the Wild were able to get him for a 3rd round pick is phenomenal.

Winner: The Wild win this one

June 26th, 2015 – Edmonton Oilers & New York Islanders

Edmonton Acquires – Griffin Reinhart – GM was Peter Chiarelli

New York Acquires – 2015 1st rounder (Matt Barzal), 2015 2nd rounder (Mitchell Stephens) – GM was Garth Snow

Yes, the Oilers desperately needed NHL defensemen at this point in time. The problem is, they gave up 2 great draft picks for an AHL defenseman. Griffin Reinhart was widely viewed as a bust, after failing to live up to his 4th overall selection in 2012. Whatever prompted Chiarelli to trade a 16th overall pick, plus a 2nd rounder, in what was a deep draft for Reinhart will never make sense to me. The two players who were taken with this picks are likely going to have much better NHL careers than Reinhart. To make this trade look even worse, Reinhart played a total of 37 games for Edmonton and was then claimed by Vegas in the expansion draft.

Winner: The Oilers are still looking for defenders…

June 26th, 2015 – Colorado Avalanche & Buffalo Sabres

Colorado Acquires – Mikhail Grigorenko, Nikita Zadorov, JT Compher, 2015 2nd rounder – GM was Joe Sakic

Buffalo Acquires – Ryan O’Reilly, Jamie McGinn – GM was Tim Murray

O’Reilly has been a leader on Buffalo since being acquired, and been consistently near the top of their leader board for points. McGinn had a good year for Buffalo in 2015-2016, before being traded for a 3rd round pick. Coloardo has wound up with much less in this trade, with Grigorenko scoring less than 30 points in his two seasons, and has departed for the KHL now. Compher made his NHL debut this year but struggled, while they traded away the 2nd round pick. The lone bright spot is Zadorov, and the jury is still out on him, if he truly is a top-4 defender or not. This is one Sakic would like to take back, and likely while he’s being cautious with trying to trade Duchene.

Winner: Buffalo wins this one

July 18th, 2016 – Ottawa Senators & New York Rangers

Ottawa Acquires – Derick Brassard, 2018 7th rounder – GM was Pierre Doiron

New York Acquires – Mika Zibanejad, 2018 2nd rounder – GM was Jeff Gorton

LOL Hi Sens fans! The picks have yet to be made, but let’s look at the two players’ 2016-2017 seasons. Brassard had 14 goals, 39 points in 81 games. Zibanejad had 14 goals, 37 points in 56 games. The fact that the Rangers got the better player, and upgraded a 7th rounder into a 2nd round pick is just hilarious. No clue what Ottawa was doing here, as the two had basically identically points in the previous season. Brassard is 6 years older as well, so not like they upgraded for youth.

Winner: Looks like Doiron really did learn everything he knows from Bryan Murray. Good trade by the Rangers.

July 27th, 2016 – Edmonton Oilers & New Jersey Devils

Edmonton Acquires – Adam Larsson – GM was Peter Chiarelli

New Jersey Acquires – Taylor Hall – GM was Ray Shero

Ohhhhh Chiarelli. How is this man in charge of an NHL team!! Yes, Larsson is an upgrade to what they had on defense, but you gave up Taylor Hall! For Larsson! 1 for 1!! Oilers fans could be the worst in the league, as they have been defending this trade since it happened. How you can possibly do that is beyond me. Hall is one of the best wingers in the NHL, while Larsson isn’t a true number 1 defender. This is bad, really bad.

Winner: Not even close, Devils win by a mile.

June 22nd, 2017 – Edmonton Oilers & New York Islanders

Edmonton Acquires – Ryan Strome – GM was Peter Chiarelli

New York Acquires – Jordan Eberle – GM was Garth Snow.

It might be a little early to have this one in here, but here’s another instance where Chiarelli did not get full value for the player he was trading away. You can’t keep trading away players and not getting full value back and expect it to all work out, even if your team has McDavid. Sure Eberle struggled in the playoffs this year, but he still scored 20 goals in the regular season, which was actually his lowest total since 2012-2013. Strome’s career best is 17, and then he followed that up with 8 the following season. The kicker here is that Edmonton was making this trade to free up cap space, or so they say. What did they do with this cap space? They signed Kris Russell to 4 years at $4 million per…

Winner: Edmonton will continue to hope McDavid saves them from all of these disastrous trades.

 

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Trade Candidates – Dec ’16

December has just come to a close, and while we’re only a little over a third of the way through the season, it’s becoming more evident who will likely be sellers come the deadline at the end of February. Here is my take on the top 10 players who appear like they could be on the move:

10) Sedin Twins – eventually, one would hope the Canucks realize they’re not built like a playoff team, and accept the rebuild. This would require moving the Twins. This will be quite difficult, as they have another year left after this at a high cap hit. If they wish to stay together, that will only make things more difficult. 

Where to?:  Minnesota, Nashville, Montreal

9)  Jaromir Jagr –  Jagr is not likely to move, as Florida still hopes to make the playoffs, and he enjoys playing there. However, if Florida continues to struggle, I’m sure teams will come calling. 

Where to?: Montreal, San José, Dallas

8) Ryan Miller – Miller still plays at a high level, and can be that extra factor to push a team over the top. Can we see him on the move again near the deadline? All depends again on the Canucks willingness to accept the rebuild. He can help many teams who could use a better 1-2 punch. 

Where to?: Dallas, Edmonton, Los Angeles

7) Radom Vrbata – Enjoying a bounce back year, Vrbata can provide secondary scoring at a very low cap hit. He should have many interested suitors the closer we get to the deadline, and Arizona again far away from a playoff spot. 

Where to?: San José, Chicago, NY Rangers

6) James Van Riemsdyk – Big, skilled wingers are hard to come by. Soft hands down low, and with a cheap cap hit for this year and next make him a highly valuable target. Lots of rumours that the Leafs are willing to move him. 

Where to?: Rangers, Minnesota, Nashville

5) Thomas Vanek – Another winger singed out of camp that is having a bounce back year. Vanek, much like Vrbata, can help provide a secondary scoring punch to a team in need. 

Where to?: NY Rangers, San José, St. Louis

4) Jarome Iginla – Iginla is surely towards the end of his career, time to give it another shot at a Cup. That won’t be happening in Colorado. 

Where to?: Pittsburgh, Tampa Bay, Montreal

3) Dennis Seidenberg – Here’s a guy who almost had no place to play this year if it wasn’t for a strong showing at the World Cup. He’s having a decent season on a lackluster team. He’s cheap, and can improve almost any current D-core. 

Where to?: Dallas, Edmonton, NY Rangers

2) Dmitry Kulikov – Teams looking to add on defense will likely have a hard time finding players available. Kulikov could be one of the few names floating around the market. He can add depth to a team in need. 

Where to?: Dallas, Edmonton, NY Rangers

1) Ben Bishop – many would have predicted Tampa move Bishop this past offseason, but with the expansion draft looming closer and closer, it would make most sense to move Bishop at the deadline for a piece that could push Tampa over the top as they push for Cup. 

Where to?: Buffalo, Vancouver, Colorado