NHL Trades: 10 Worst Trades in Modern NHL History (2005-Present)

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On the eve of free agency, there have been several big trades in the NHL, notably two involving the Philadelphia Flyers, as teams attempt to remake their rosters for the upcoming season.

With all respect to Brad Richards, this is a rather lacklustre crop of unrestricted free agents hitting the market on July 1, particularly when it comes to forwards.

Expect to see more than the usual amount of trades over the July long weekend as teams decide trading is less expensive than getting into a bidding war over the few decent free agents.

General managers usually make foolish decisions when signing free agents on July 1. Will we see some foolish or lopsided trades as well?

With that in mind, here is a look at some of the worst trades in modern NHL history.

I'm intentionally limiting it to trades that happened in the salary cap era, but if I missed one you think is significant, feel free to mention it in the comments.

Chris Pronger (2006)

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In 2005, Chris Pronger helped lead the Oilers to the Stanley Cup Finals.

Shortly afterwards, he demanded a trade out of Edmonton for reasons that still haven't been officially confirmed by either party.

The Oilers traded Pronger to the Anaheim Ducks, picking up a pair of prospects (Joffrey Lupul and Ladislav Smid) as well as a pair of first rounders and second rounder.

Now on the one hand, Edmonton did do fairly well out of this deal, despite their hand being forced by Pronger's public demands.

However, on the other hand, Pronger would go on to lead the Ducks to the Stanley Cup in his first season with his new team. If he had stayed in Edmonton, could they have done the same?

Also his trade demand helped cement Edmonton's reputation as a place that free agents should avoid.

Loser: Edmonton

Todd Bertuzzi (2006)

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In 2006, the Florida Panthers traded Roberto Luongo to the Vancouver Canucks in exchange for Todd Bertuzzi (There were other players involved, but these two were the key.).

In the Panthers' defence, they were having problems attempting to sign Luongo to a contract extension.

But Bertuzzi would be a spectacular bust for them.

Bertuzzi did put up seven points in his first seven games, but then injured his back and didn't play another game for Florida.

Luongo, on the other hand, has had quite a bit of regular season success in Vancouver, and in the postseason, he helped the Canucks to the 2011 Stanley Cup Finals.

Loser: Florida

Ryan Smyth (2007)

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Ryan Smyth was the heart and soul of the Edmonton Oilers team that made it to the Stanley Cup Finals in 2005.

Two short years later, he was traded to the New York Islanders when negotiations for a contract extension broke down.

For a great top line winger who is a playoff performer, the Oilers got a pair of prospects (Robert Nilsson and Ryan O'Marra) and a first rounder.

While those players are still young and could develop further, the Oilers shot themselves in the foot by trading away their most popular and most effective player without getting back a solid NHL player in return.

Loser: Edmonton

Phil Kessel (2009)

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Prior to the 2009 season, the Boston Bruins traded Kessel to the Toronto Maple Leafs. In return, they got two first rounders and a second rounder.

This will go down as one of Brian Burke's worst trades as a GM, as Kessel hasn't lifted the Leafs into a playoff spot (yet), and those picks went on to be a trio of blue chip prospects, notably Tyler Seguin. Seguin, by the way, helped the Bruins win the 2011 Stanley Cup.

Loser: Toronto Maple Leafs

Christian Ehrhoff (2009)

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In the summer of 2009, the San Jose Sharks had gone over the salary cap due to their acquisition of Dany Heatley, and they needed to get back under the cap before the season started.

They ended up trading offensive defenseman Christian Ehrhoff to the Vancouver Canucks for a pair of busted prospects in Daniel Rahimi and Patrick White. Both had been first rounders who hadn't even been able to make the AHL roster, let alone the NHL roster.

This was a totally lopsided trade, as the Sharks essentially gave away a 50-point defenceman for free. And they didn't even trade him outside the conference. 

Loser: San Jose

Scott Gomez (2009)

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Scott Gomez was a great player a decade ago for the Devils teams that won the Stanley Cup in 2000 and 2003. But he isn't that same calibre of player anymore.

Signed to a ridiculous long term contract with a cap hit of $7,357,143, Gomez is an anchor weighing down the Montreal Canadiens.

The sad part is, the Canadiens willingly took on the contract in 2009 as part of a seven player trade after Gomez had signed it with the New York Rangers in 2007, and has been a bust there for two years.

Does Ranger GM Glen Sather have blackmail pictures of someone in the Montreal organization? I can't think of any other reason why the Canadiens would have taken on this horrible contract.

Loser: Montreal (And the rest of the NHL, since Sather was absolved of responsibility for his bad contract, and then he promptly did it again with Marian Gaborik)

Ilya Kovalchuk (2010)

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At the trade deadline, otherwise smart general managers sometimes make rash decisions.

At the 2010 trade deadline, the New Jersey Devils traded two NHL players (Niclas Bergfors and Johnny Oduya), a blue chip prospect (Patrice Cormier), a first round pick and a second round pick for Ilya Kovalchuk.

If they had given up all that for a proven playoff performer, it might have made more sense. Kovalchuk hadn't won an NHL playoff game in his life at this point in time.

The Devils managed to get him that first playoff win, but that was it, as they lost in five games during the first round of the playoff.

Sometimes you gamble and win, but this time, the Devils got burned. They probably could have managed to lose in the first round without giving up that rich package to land Kovalchuk.

Loser: New Jersey

Dan Hamhuis (2010)

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BC born shutdown defender Dan Hamhuis was scheduled to hit free agency on July 1st, 2010.

He was going to be a hot commodity come July 1, so the Philadelphia Flyers tried to get a jump on the competition and traded prospect Ryan Parent to the Nashville Predators for the rights to Hamhuis just days before free agency.

Hamhuis would decline their contract offers, so his rights were then traded to the Pittsburgh Penguins for a third round pick.

Hamhuis would again decline the contract offers from the Penguins.

On July 1, he promptly signed with the Canucks for less money than the Penguins and Flyers had reportedly offered.

The problem here is that the Flyers and Penguins didn't do their homework.

Hamhuis is from BC, played his junior hockey in BC and repeatedly said to the press that he would like to play in BC again. 

Doesn't that sound like a guy who wants to head home as a free agent and take a hometown discount for the team he grew up cheering for? 

Why bother trading away picks and prospects to get negotiating rights to a player that has already stated in the media where he is going?

Loser: Philadelphia and Pittsburgh

Kris Versteeg (2011)

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Kris Versteeg was part of the 2010 Stanley Cup winning Chicago Blackhawks, and then he was part of the salary cap purge the following summer.

Ending up in Toronto, Versteeg was then traded at the 2011 trade deadline to the Philadelphia Flyers for a first round pick and a third round pick.

That is a fair price for a good second or third line player with playoff experience at the deadline.

The stupid thing was that Philadelphia didn't need another forward. They already had tons of great forwards. What they needed as a goalie.

Imagine if Philadelphia had instead traded those draft picks for Thomas Vokoun of the Florida Panthers, or Dwayne Roloson of the New York Islanders?

Or had they simply asked for Toronto's J.S. Giguere instead of Versteeg?

All three were on the market, and Roloson was moved at an even cheaper price to the Tampa Bay Lightning, who went all the way to Game 7 of the Eastern Conference Finals, largely on the strength of his goaltending.

Well, at least now Flyers fans can console themselves with the knowledge that the team has finally acknowledged that a bullpen of three AHL goalies doesn't cut it in the playoffs.

Loser: Flyers

Christian Ehrhoff (2011)

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Unable to come to terms with the Vancouver Canucks, Christian Ehrhoff was traded to the New York Islanders just days before becoming a free agent in return for a fourth round draft pick.

Now while obviously money was an issue in Vancouver, Ehrhoff had also said repeatedly to the media that he wanted to play for a contender. 

With that in mind, did Garth Snow really think he could fool Ehrhoff into thinking the Islanders were going to be contenders?

Ehrhoff would turn down a reported six million dollar offer from the Islanders, who in turn shipped him to the Buffalo Sabres in return for a fourth round pick.

The only problem is that the Sabres are going to be significantly higher in the standings than the Islanders, so essentially, Garth Snow traded down roughly 10 spots in the draft in an attempt to sign a player who he should have known wouldn't want to play on Long Island.

Loser: New York Islanders