NHL General Managers have an incredibly difficult job. They must assemble a team of eighteen players and two goalies that fit the desired style of the coach, all while staying under a league-mandated salary cap. GMs are always under criticism and can be easily fired if their team is not successful. Because of these reasons, GMs must be savvy with their signings, draft picks, and, most importantly, their trades. While some trades work out well for both teams such as the Ryan Johansen-Seth Jones deal between Nashville and Columbus in 2016, others make one General Manager look like a genius and the other a chump. Critics love to debate “winners” of every trade that takes place, and in some cases that winner is blatantly obvious. Many trades involve draft picks and when these picks turn into stars, the deal can seem lopsided in hindsight. Unsurprisingly, a few of these trades were made by notorious trade-loser Mike Milbury. More surprisingly, future Hall-of-Famers Jaromir Jagr and Roberto Luongo were each involved in two questionable trades, proving that anyone is available if a GM is desperate enough. With the benefit of hindsight, as many of these trades happened over ten years ago, this list will analyze the most obviously one-sided trades of the 21st century so far.

15. Matt Niskanen and James Neal (Dallas) for Alex Goligoski (Pittsburgh)

via defendingbigd.com / via theigloolockerroom.co

The Niskanen and Neal for Goligoski deal orchestrated by Pittsburgh Penguins GM Ray Shero and Dallas Stars skipper Joe Nieuwendyk is the most recent trade on this list. When the deal was done in early 2011, the players involved were all still relatively unproven, each under the age of 25. Neal had put up the third most points on a not-so-good Stars team and Niskanen had become the squad’s premier point-producing defenceman. Goligoski, on the other hand, was still proving his worth and was projected as a top-four defenceman in the near future.

The deal really didn’t make much sense at the time, as a Niskanen-for-Goligoski trade in itself would have been considered reasonable. As the next season wore on, though, the one-sidedness of the deal became even more apparent. Neal became a star in the Penguins’ black and gold, posting what is still a career-high 40 goals and 81 points. Niskanen, meanwhile, put up 21 points as a solid defensive-defenceman. Goligoski totaled 30 points himself, proving that Pittsburgh had won the deal big-time.

14. Jean-Sebastien Giguere (Calgary) for a 2nd Round Pick (Anaheim)

via thestar.com

The deal that sent Giguere to the Mighty Ducks of Anaheim for a 2nd Round Pick in 2000 was very one-sided. The 2000-01 season was Giguere’s rookie season, wherein he earned a 2.57 GAA and a .911 SP in 34 games. In the following season he was re-signed and played his first full season. This time having an astonishing 2.13 GAA and .920 SP in 53 games. The 2002-03 season he posted his first winning season, creating a career high of 8 shutouts and posting a 34-22-6 record.

From here, the Canadian goalie, still in his prime, went on to have a great career with the Mighty Ducks, winning them a Stanley Cup and taking home Conn Smythe honours. Meanwhile, the Calgary flames traded the second round pick they received for him to the Washington Capitals who selected Matt Pettinger. Pettinger is a very underwhelming player. He spent the first few seasons of his career between the Capitals and their AHL affiliate, the Portland Pirates, before achieving a full-time spot with the Capitals in 2003-03. Pettinger’s career high was in the 2005-06 season, where he recorded 20 goals, 18 assists, and 38 points. He then was traded and only played 68 games before leaving the NHL for the DEL in Europe. This trade shows that Calgary’s decision to trade away Giguere for a 2nd round pick was terrible when comparing Giguere’s and Pettinger’s careers.

13. Roberto Luongo and Olli Jokinen (New York Islanders) for Mark Parrish and Oleg Kvasha (Florida)

via hfboards.hockeysfuture.com

The first of two Roberto Luongo deals on the list, this one can be forgiven slightly more than the other. “Lou” was only 21 at the time and the Islanders had just taken Rick DiPietro with the first overall pick in the NHL Draft. The inclusion of Jokinen to the deal just puts it over the edge, though. When the trade went down in mid-2000, Luongo was unproven and Jokinen had already played two full NHL seasons, recording just 21 points in each. Parrish had also only played two years but had fared much better, totalling 81 points, while Kvasha had posted 50 points in two full seasons.

While the deal looked good at the time, further analysis 17 years down the road proves that a career cannot be predicted simply on the first two seasons’ statistics. Luongo went on to become one of the best goalies in NHL history, a likely Hall-of-Famer once he retires. Jokinen went on to post seasons of 71, 89, and 91 points with the Panthers, becoming their franchise linchpin for much of the 2000s. Parrish and Kvasha, meanwhile, were less-than-impressive. Parrish and Kvasha spent the majority of their careers as fourth-liners and were out of the league by 2012 and 2006, respectively. The Panthers won this deal, hands-down.

12. Zdeno Chara, Bill Muckalt, and a 1st Round Pick that became Jason Spezza (New York Islanders) for Alexei Yashin (Ottawa)

via TheSportster.com

Besides being the tallest man to ever play in the NHL, Chara also has many other big accomplishments. Muckalt did not remain in the NHL long after being traded but the 1st-round pick the Islanders gave up turned into Jason Spezza, another huge player currently in the NHL. After the 2001 draft day deal, Chara began to rise as an elite defenceman and posted career highs of 30 assists and 39 points, becoming one of Ottawa’s top two defenders. Now he is the captain of the Boston Bruins. In the 2010-11 season, he led the team to their first Stanley Cup Championship since 1972. Muckalt only spent one season with the Senators before signing as a free agent. Spezza went on to play 33 games during his debut season where he scored 21 goals. Although having run-ins with injuries, Spezza has had a pretty respectable career in the NHL, recording 316 goals and 546 assists in 911 games.

The player who the two future All-Stars were traded for was Alexei Yashin. Yashin was traded from the Senators to the New York Islanders to an enormous 10-year deal. When Yashin joined the Islanders, his points dropped. The team made him captain after trading away their existing captain, and began to build the team around him. His performance continued to decline even after becoming the Islanders captain. In 2007, the Islanders bought out his contract and after no other NHL teams wanted him he went to the KHL and eventually retired following the 2011-12 season. This trade shows one of the most one-sided trades. Trading away a declining performance player for two soon-to-be All-Stars  was a great decision by the Sens.

11. Jaromir Jagr and Frantisek Kucera (Pittsburgh) for Kris Beech, Michal Sivek, Ross Lupaschuk, and cash (Washington)

via nhl.com

While this trade may have seemed reasonable at the time as Jagr looked to be past his prime, the fact that the Czech legend is still producing at the age of 45 makes the deal seem silly now. After being a perennial three-digit point-producer throughout the ’90s, Jagr began to slow down at the turn of the century. The Penguins were no longer as competitive as they were in the early-’90s and were looking to begin a rebuild. Thus, they traded Jagr and fourth-liner Kucera for three of Washington’s top prospects at the time. Beech was selected 7th overall, Sivek 29th overall, and Lupaschuk 34th overall, all in 1999.

Of the three players Pittsburgh received, Beech is the only one who managed any significant NHL experience, playing 198 games and posting 67 points. The other two combined for just 41 games and 6 points, while Jagr went on to appear in 905 more games, recording 835 points and putting himself 2nd on the NHL’s all-time scoring list.

10. Dan Boyle (Florida) for a 5th Round Pick (Tampa Bay)

via tampabay.com

During Boyle’s career, he posted great numbers with different NHL teams throughout for 17 seasons. After being traded from the Florida Panthers to the Tampa Bay Lightning for a 5th round pick, he had a good run with his new NHL home in the Sunshine State. Following Boyle’s first full season in the NHL, Boyle helped the team win the 2004 Stanley Cup Championship. Boyle went on to have a great career, scoring 164 goals and 605 points in 1093 NHL games.

The 5th round pick that Boyle was traded turned out to be Martin Tuma. Tuma, a Czech native, was drafted 162nd overall in the 2003 NHL Entry Draft by the Panthers. He only lasted a few seasons stateside, playing on the Panthers’ ECHL and AHL squads before returning to his homeland to play in the Czech pro league. This trade was great for Lightning’s and not so great for the Panthers’. With Tampa Bay gaining a top-pair defenceman for a player who never played an NHL game, the trade was definitely one sided.

9. Ryan McDonagh, Christopher Higgins, Pavel Valentenko, and Doug Janik (Montreal) for Scott Gomez, Tom Pyatt, and Michael Busto (New York Rangers)

Eric Bolte-USA TODAY Sports

When the dust settled after this huge seven-player deal, the New York Rangers and their General Manager, Glen Sather, looked like geniuses compared to Montreal Canadiens GM Bob Gainey. Gomez and Higgins were established NHL scorers and a one-for-one deal between the two would have been fair. While Pyatt, Busto, Valentenko, and Janik never materialized into much for either squad, the inclusion of then-prospect Ryan McDonagh put the Rangers miles ahead.

McDonagh quickly turned into the Rangers’ franchise defenceman and continues to be to this day. He was only 20 at the time of the trade and spent just one more season in the minors before being called up to the big league squad. He has since posted 212 points in 467 games, very respectable for a defenceman, and, more importantly, has led the Rangers on deep playoff runs in most of his seven seasons. Higgins only played one season with the blueshirts, posting 14 points in 55 games, and Gomez was equally unimpressive, recording 87 total points in three seasons with the Habs. Still, the Rangers, thanks to McDonagh’s strong development and career, made this a one-sided trade by a landslide.

8. Braydon Coburn (Atlanta) for Alexei Zhitnik (Philadelphia)

via libertycitys.com

Coburn was traded to the Philadelphia Flyers for Alexei Zhitnik in 2007 after already playing for four years with the Atlanta Thrashers. When Coburn went to the Flyers, he became one of their top defenders in the 2006-07 season. In the 2007-08 season, Coburn potted 8 goals and 26 points while playing for the Flyers. He provided them with reliable minutes for nine seasons, becoming one of the team’s defensive lynchpins.

Up to the point when the trade occurred and the Thrashers obtained Zhitnik, he had had a fairly successful career. Playing with the Los Angeles Kings in his rookie season, Zhitnik finished second among rookie defeseman with 48 points and was an important part of the Kings’ playoff run to the Stanley Cup Finals. After being traded to the Buffalo Sabres, he became one of the team’s best players. When he finally was traded to the Thrashers, his game play was fairly abysmal and the team decided to rebuild. This led to Zhitnik getting bought out and becoming a free agent. Zhitnik then returned to the Russian league.

Notably, this is one of the most one-sided trades in recent Flyers history, as Coburn went on to be a top defender and Zhitnik’s career came to an end shortly afterwards.

7. Marian Hossa and Pascal Dupuis (Atlanta) for Colby Armstrong, Angelo Esposito, Erik Christensen, and a 1st Round Pick (Pittsburgh)

via pens initiative.com

This 2008 deal between Ray Shero’s Pittsburgh Penguins and Don Waddell’s Atlanta Thrashers served to solidify the Pens into the Cup contenders they were in 2008 and 2009 and also to push the lowly Thrashers towards their eventual relocation to WInnipeg. Hossa, who was arguably Atlanta’s biggest star at the time, and Dupuis, who was a solid top 9 forward for the Thrashers were swapped for the oft-injured Armstrong, draft bust Esposito, career 4th-liner Christensen, and a 1st rounder that turned into Daultan Leveille, who never played an NHL game.

Hossa helped the Pens to a Stanley Cup Finals appearance in 2008 and Dupuis went on to become a top-line winger to Sidney Crosby for many years in Pittsburgh, including during their Cup win in 2009. Meanwhile, Armstrong played just 179 games for the Thrashers over three seasons, recording 39 points. Esposito, who was considered a top prospect at the time, never materialized into much, not even making it to the big leagues. Christensen played only 57 games for the Thrashers, putting up 16 points. In essence, the Penguins received two first-liners for two fourth-liners and two AHLers, making this trade incredibly one-sided.

6. Joe Thornton (Boston) for Wayne Primeau, Brad Stuart, and Marco Sturm (San Jose)

Kelley L Cox-USA TODAY Sports

Thornton was part of a four-player trade between the Boston Bruins and the San Jose Sharks. With the Bruins struggling in the 2005 season, captain Thornton was traded to the Sharks for Primeau, Stuart and Sturm. During Thornton’s time with the organization he had 454 points in 532 games. His record was pretty good but the organization wanted to build their team around youngster Patrice Bergeron.

Primeau, an NHL centreman, bounced around from team to team. After being traded to the Bruins, he had only 29 points in 101 games. Stuart’s time with the Bruins was also very underwhelming. In his two seasons with the squad, he posted 48 points in 103 games. Both Primeau and Stuart were traded to the Calgary Flames after only two seasons. Sturm, on the other hand, stayed with the Bruins for 5 seasons. He had 193 points in 302 games. Although not bad, comparing him to Thornton who has gone on to win various trophies and led the Sharks to the Stanley Cup Finals in 2016 shows the unevenness of the trade.

At the age of 37, this Canadian-born player has reached 1,000 assists as a playmaking centreman, becoming the 13th player in NHL history to reach that milestone. The Bruins traded away an All-Star (and likely Hall-of-Famer) for three men that they traded away two to five years later. The Sharks definitely won this incredibly one-sided trade.

5. Roberto Luongo, Lukas Krajicek, and a 6th Round Pick (Florida) for Todd Bertuzzi, Alex Auld, and Bryan Allen (Vancouver)

via thestar.com

This Luongo trade is a lot less forgivable, as he had proven that he was a top-tier NHL goalie at this point of his career. While Krajicek and the 6th rounder, who turned out to be Sergei Shirokov, were non-factors as NHLers, the return that the Panthers received for “Lou” is sad. Bertuzzi was past his prime and was quickly traded away after playing only 7 games for the team. Auld served as a less-than-capable backup goalie for the Panthers for just one season after the trade. Allen was the most productive of the three outgoing Canucks, as he became a reliable top-four defenceman for the Panthers, even posting career-high numbers with them the season after the trade, recording 25 points in 82 games.

When you consider that Krajicek, Shirokov, Auld, and Bertuzzi each had virtually no effect on their respective new teams for much longer than one season, the deal becomes a Luongo-for-Allen trade. Luongo went on to lead the Canucks as their franchise goalie for eight years, taking them all the way to the Stanley Cup Final in 2011. Comparing the careers of the future Hall-of-Famer to the defensive-defenceman Allen proves that this deal was incredibly lopsided in Vancouver’s favour.

4. Patrick Sharp and Eric Meloche (Philadelphia) for Matt Ellison and a 3rd Round Pick (Chicago)

Dennis Wierzbicki-USA TODAY Sports

In the Sharp and Meloche for Ellison and 3rd round pick trade, Sharp was the primary player involved. Meloche was a non-factor in this trade, spending most of his career in the AHL afterwards. Meanwhile, Sharp went on to become alternate captain and a core member of the Blackhawks’ dynasty, helping them to Stanley Cup Championships in 2010, 2013, and 2015.

Ellison, a Canadian player, is another who is fairly unrecognizable. After being traded to the Flyers, he spent most of his time in the AHL during his four years with the team. In the seven games that he played in the NHL, he only had one point. The 3rd round pick was flipped to the Montreal Canadiens, and turned out to be Ryan White, an underwhelming 4th-liner. This one-sided trade was one of the keys to the Blackhawks’ future success, as they got a steal, nabbing Sharp for a career AHLer.

3. Jaromir Jagr (Washington) for Anson Carter (New York Rangers

via thesportster.com

The second of Jagr’s career trades is a real head-scratcher. The one-for-one deal saw the Capitals send one of the game’s best point-producers to the Rangers for a fourth-line grinder. Jagr’s production had dropped from the triple digits to a point-per-game type player. He was still a game-changing player, but the Capitals were having financial troubles and needed to get rid of his $11M contract. They unloaded him to one of the only willing recipients, and even still had to agree to pay $4M per year of his contract while he wasn’t even playing for them.

Jagr has gone on to solidify his status as a shoo-in Hall-of-Famer, and had four productive years with the Rangers, posting 319 points in 277 games with them. Meanwhile, Carter only played parts of two seasons with the Rangers, recording just 11 points in 54 games. This is truly one of the most one-sided trades in NHL history.

2. Josh Gorges and a 1st Round Pick that became Max Pacioretty (San Jose) for Craig Rivet and a 5th Round Pick (Montreal)

Eric Bolte-USA TODAY Sports

The trade that led to the arrival of two key Montreal Canadiens players, Gorges and Pacioretty, occurred when the San Jose Sharks traded them for Craig Rivet and a 5th-round pick in the 2008 NHL Draft. Gorges spent 8 seasons with the Canadiens, becoming a top defender and leading the league in blocked shots in the 2011 season. He is also widely exalted for his performance for the team in the 2010 Stanley Cup Playoffs. Pacioretty has turned into the team’s top forward and is currently the captain of the Canadiens. Pacioretty has played his entire career with the Habs, putting up 411 points in 562 games.

On the other side of the trade was, Rivet, a defenceman. He only spent two seasons with the Sharks, totalling only 43 points in 91 games. He was then traded to the Sabres then the Blue Jackets. The 5th-round pick turned into Jason Demers. For a 5th rounder, he actually became decently useful for the team, going on to play with the Sharks for 6 seasons. During his time, he appeared in 300 games, posting only 98 points. This trade has turned out to be largely one-sided. Both Gorges and Pacioretty went on to become great players in Montreal while the Sharks received two mediocre players that did not perform or last long with the squad.

1. Tuukka Rask (Toronto) for Andrew Raycroft (Boston)

Marc DesRosiers-USA TODAY Sports

The worst Leafs trade in recent memory, the Rask-for-Raycroft deal still haunts their fans to this day, as the squad had struggled to find a solid starting goalie for 10 years until the deal for Frederik Andersen this past offseason. The trade did make some sense at the time, as the Leafs had A+ prospect and Canadian World Junior hero Justin Pogge in their system already. Based on this fact, Leafs GM John Ferguson believed that Rask was expendable and swapped him for the reigning rookie-of-the-year, Boston’s Andrew Raycroft.

Pogge turned out to be a dud, only getting into 7 NHL games before leaving for Europe. Raycroft also failed to come through on his potential, quickly losing steam and only lasting two seasons with the Leafs and four more after that with other squads before also leaving for Europe in 2012. Rask, on the other hand, has become the Bruins’ franchise ‘tender and one of the best goalies in the NHL. He has posted career numbers of 2.24 GAA and .923 SP, both outstanding statistics, and to make matters worse, he was on the other end of the Leafs’ epic playoff collapse against the Bruins in the 2013 playoffs. Considering that the Leafs have gone through eight first-string goalies since the trade and Rask has been the main man in the Bruins’ crease since Tim Thomas moved on, this is a terribly one-sided deal in favour of then-Bruins GM Peter Chiarelli.

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