Phil Kessel and The 5 Worst NHL Trades Of The Decade

James CriderCorrespondent IFebruary 6, 2011

Phil Kessel and The 5 Worst NHL Trades Of The Decade

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    The Phil Kessel drama continues.

    A year after the Toronto Maple Leafs' General Manager acquired the star sniper from the Boston Bruins, things continue to deteriorate.

    Not only is Kessel on pace for another low-50's point total, but the Leafs as a whole continue to struggle heavily and once again find themselves in the bottom of the Eastern Conference.

    And now it comes out in the media that Kessel and Leafs head coach Ron Wilson aren't on speaking terms.

    Yikes.

    As talented of a player as Kessel is, few will deny the trade has been a complete debacle for the Maple Leafs as, for the second season in a row, the arch-rival Boston Bruins will be drafting high in the first round using one of the Leafs' draft picks.

    And with that, let's take a look at the worst moves of the past 10 years, and where the Kessel trade fits in.

5. Boston Bruins and San Jose Sharks (2005)

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    The Bruins will come out on top in a later trade, but this one was downright ugly for them.

    In a stunning move, the Boston Bruins traded franchise center Joe Thornton to the San Jose Sharks in exchange for forwards Marco Sturm, Wayne Primeau and defenseman Brad Stuart.

    The move came a day after then-Bruins general manager Mike O'Connell traded a dollar for two quarters and a nickel.

    This trade could have been alot worse had O'Connell's replacement (you didn't think he kept his job, did you?) Peter Chiarelli got big return on free agent center Marc Savard in the following off-season. However, the short term implications of the move were disastrous.

    Not only did Thornton lead the league in scoring and win the Hart Trophy as league MVP thanks to an insane 92 points in 58 games with the Sharks, but the players the Bruins received were largely busts.

    All three players found success with the Bruins in the short term, scoring 23, 6, and 10 goals (respectively), but Stuart and Primeau's play both took nose dives the following season and they were subsequently shipped to the Calgary Flames.

    Sturm ended up having four 20+ goal seasons with the Bruins, which is more than respectable. But for the price of Joe Thornton? Come on.

4. Florida Panthers and Vancouver Canucks (2006)

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    When you're one of the worst franchises in the NHL and haven't made the playoffs in half a decade, it isn't wise to trade your best player (who's perhaps the best goaltender in the league).

    But that's what the Florida Panthers did. In the 2006 off-season, they dealt goaltender Roberto Luongo, defenseman Lucas Krajicek, and a sixth-round draft pick in 2006 (Sergei Shirokov) to the Vancouver Canucks for forward Todd Bertuzzi, defenseman Bryan Allen, and goaltender Alex Auld.

    No first-round pick. No top prospect. No star player.

    The Panthers traded away one of the most dynamic goaltenders in the game for depth players.

    Todd Bertuzzi, arguably the most valuable player heading Florida's way, only managed to play seven games due to back problems, and was traded to the Detroit Red Wings at the NHL trade deadline.

    Alex Auld, expected to be Florida's starting goaltender heading forward, was supplanted on the depth chart by a 42-year-old Ed Belfour. Auld would finish the season with seven wins and a 3.35 goals against average.

    Brian Allen remains on Florida's roster, but is no more than a depth defenseman.

    It's obvious Luongo would have never had the 47-win season he had in 2006-2007 if he were still playing in Florida, but that season—along with guiding Vancouver to three division titles—puts in perspective the type of player Florida practically gave away.

3. New York Islanders and Ottawa Senators (2001)

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    This trade happened a decade ago, and the Islanders organization still hasn't recovered from it.

    At the 2001 NHL entry draft, New York Islanders general manager Mike Milbury made a blockbuster trade to acquire star forward Alexei Yashin from the Ottawa Senators. He then signed Yashin to a mammoth 10-year, $87 million deal.

    Yashin never managed to duplicate his totals from his Senator years, eclipsing 30 goals once (his first year with the Islanders), and never managing more than a point per game in any given season.

    After seven frustrating years in which the Islanders failed to win a playoff series, Yashin's contract was eventually bought out.

    That's the bad news. The really bad news is that the Islanders traded the second overall pick in the 2001 draft—who turned out to be Jason Spezza—forward Bill Muckalt, and a young defenseman by the name of Zdeno Chara for Yashin.

    Ouch.

2. Boston Bruins and Toronto Maple Leafs (2009)

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    Tyler Seguin is an NHL rookie who, as of now, has accomplished zilch in the NHL. And Phil Kessel is undoubtedly more valuable to an NHL franchise than a first-round draft pick.

    Neither fact changes what a disaster of an acquisition Kessel has been for the Toronto Maple Leafs.

    Giving up first-round draft picks in 2010 and 2011, as well as a second-round draft pick in 2010, the Maple Leafs tried a quick rebuild around the endlessly talented Kessel and through big free agent signings like Mike Komisarek and Francois Beauchemin.

    So far, that plan has blown up in the face of Leafs General Manager Brian Burke.

    Not only has Kessel not lived up to expectations—55 points last season, and on pace for a similar total—but the Leafs as a team have been one of the worst in the NHL, finished 29th a season ago and currently sit 26th.

    For a team who'd just lost their franchise player of a decade and a half (Mats Sundin), the last thing the fading Leafs roster needed was to give up its most valuable assets—its draft picks.

    The three picks could have helped the Leafs reestablish a dried-up prospect pool. Instead, they're left trying to compensate through the free agent market.

    There's no doubt Kessel is currently a better player than Seguin, and may always be so. There's also no doubt Kessel's struggles are largely a part of the players he's paired with, many of whom would be checking line players on the majority of other NHL teams.

    And that's where the problem lies. It's not Kessel's fault he's struggling, it's the situation around him. Kessel is ready to win now, but the team around him isn't. They're too young, too inexperienced, and frankly, too mediocre.

    With Tyler Seguin, Nazem Kadri, Luke Schenn, and whoever they would have taken with what will likely be a top five pick this coming draft, the Leafs would have had a stable young group of players to build around.

    Instead, they're a franchise in complete disarray.

1. Tampa Bay Lightning (2008-2009)

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    The logic here is mind blowing, especially considering part of the reason for the trade was a dislike between Dan Boyle and then-Lightning Co-Owners Oren Koules and Len Barrie.

    Despite re-signing Dan Boyle to a six-year, $40 million contract, the Lightning shipped him (along with defenseman Brad Lukowich) to the San Jose Sharks in exchange for defensemen Matt Carle, Ty Wishart, a first-round pick in 2009 and a fourth-round draft pick in 2010.

    Ignoring the fact that they just traded away one of the best puck-moving defensemen in the NHL, not the worst return in the world. But while the initial deal was over, a new set of deals began to spawn.

    In an attempt to replace Boyle (how about not trading him to begin with?), the Lightning traded defensemen Filip Kuba, Alexandre Picard, and the first-round pick acquired from San Jose for defenseman Andrej Meszaros.

    Additionally, after a shaky first 12 games for Matt Carle, the defenseman was dealt to the Philadelphia Flyers for forward Steve Downie and Steve Eminger. At the trade deadline, they then moved Eminger to the Florida Panthers for minor league defenseman Noah Welch and a third-round draft pick in 2009.

    Needless to say, the Lightning had a lottery pick after the conclusion of the 2008-2009 season. Andrej Meszaros, the best player they ended up with, finished with two goals and 16 points despite being known as an offensive defenseman.

    Steve Eminger and Matt Carle, also known as puck movers, combined for 5 goals and 25 points in their 62 combined games.

    In terms of what they already had on their roster, the Lightning traded away Dan Boyle, Brad Lukowich, Filip Kuba, and Alexandre Picard in exchange for Andrej Meszaros, Steve Downie, Noah Welch, Ty Wishart, a third-round pick in 2009 and a fourth-round pick in 2010.

    In terms of what they actually gave up, the Lightning dealt away Dan Boyle, Brad Lukowich, Matt Carle, Filip Kuba, Alexandre Picard, Steve Eminger, and a first-round pick in 2009 for the above return.

    And that, by far, is the worst trade of the past decade.