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Worst Trade in Every NHL Team's History

"Once you’re a winner, you keep improving on perfection. You keep making trades and changes that will strengthen their team, even if they aren’t popular at the time. You go about your business." Th

"Once you’re a winner, you keep improving on perfection. You keep making trades and changes that will strengthen their team, even if they aren’t popular at the time. You go about your business."

Those are the words of the legendary Sam Pollock, arguably the greatest general manager in the history of the NHL. He's the man who brought Ken Dryden, Guy Lafleur, Larry Robinson, and Bob Gainey to Montreal, among many others. He built a Canadiens dynasty that won the Stanley Cup nine times during his 14-year tenure as GM. He's also the same man who let Hall of Fame goaltender Tony Eposito go in an intra-league draft, traded Vezina Trophy winner Rogie Vachon for practically nothing, and drafted Mark Napier over Mike Bossy.

Even the best in the business make mistakes sometimes. It's the price you pay for trying to build a team that can consistently win championships. Often you have to take big risks to make your team better even, as Pollock said, if it isn't the popular decision at the time. The difference between a bad manager, a good manager, and a great manager is knowing which risks are worth taking and keeping your failures to a minimum. But sometimes even the most calculated of risks can blow up in your face.

Every NHL team has, at one point or another in their history, made a trade that left fans shaking their heads. The great teams all found ways to recover from those trades and turn lemons into lemonade. Others have tried to fix their own blunders, only to make matters worse. Some of these trades have been forced by financial or personal decisions. Others are just completely baffling and leave you wondering how the person in charge ever got hired in the first place. Here's a look at every NHL team's worst trade. Note: the trades also take into account the franchises' entire histories, meaning some old Jets, Nordiques and Hartford Whalers trades will come up.

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30 Anaheim Ducks

via battleofcali.com

- Teemu Selanne for Jeff Friesen, Steve Shields and 2nd Rounder

Midway through the 2000-01 season the Ducks traded leading scorer Teemu Selanne to the San Jose Sharks for Jeff Friesen, Steve Shields, and a second round draft pick. Friesen and Shields each played just one unspectacular season in Anaheim before being shipped elsewhere. Selanne's two full seasons in San Jose weren't the most productive of his career, but he still led the Sharks in goals both years. After one forgettable season in Colorado, Selanne returned to Anaheim following the 2004-05 lockout. Perhaps Selanne could have been the missing piece in the Might Ducks run to the Stanley Cup Final in 2003.

29 Arizona Coyotes (Winnipeg Jets)

via nhl.com

- Teemu Selanne, Marc Chouinard and 4th Rounder for Chad Kilger, Oleg Tverdovsky and 3rd Rounder

Of course, the Ducks aren't the only team to regret trading away the Finnish Flash. Selanne scored a rookie record 76 goals and 132 points for the original Winnipeg Jets in the 1992-93 season. However, 51 games and 71 points into his fourth NHL season - the Jets final season before the move to Phoenix - Selanne, Marc Chouinard, and a fourth round draft pick were traded to the Mighty Ducks for Chad Kilger, Oleg Tverdovsky and a third round draft pick.

Tverdosky got his tenure in Phoenix off to a nice start, posting a career high 55 points in his first season, but he was never able to establish himself as a top defenseman and was traded back to Anaheim after three season with the Coyotes. Kilger, meanwhile, was never able to justify his selection as the 4th overall pick in the 1995 NHL draft and spent most of his career as a third or fourth line winger. As for Teemu, he finished his career as the Ducks' all time leader in games played, goals, and points.

The moral of these last two entries? Don't trade Teemu Selanne.

28 Boston Bruins

John E. Sokolowski-USA TODAY Sports

- Tyler Seguin, Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, Matt Fraser and Joe Morrow

Following the 2013 Stanley Cup Playoffs, the Bruins were upset with 21-year-old Tyler Seguin for behaving like a 21-year-old and shipped the former 2nd overall pick to the Dallas Stars along with Rich Peverley and Ryan Button for Loui Eriksson, Reilly Smith, Matt Fraser and prospect Joe Morrow. Fraser and Smith are no longer with the Bruins and Morrow has yet to establish himself as a regular NHL defenseman.

Eriksson posted just 10 goals and 37 points in his first season in Boston. He improved upon that with 22 goals and 47 points in 2014-15, but his numbers still don't compare to the three straight 70 point seasons he posted in Dallas prior to the 2012-13 lockout. Meanwhile, Seguin has posted back to back 37 goal seasons for the Stars, has averaged more than a point per game, and is quickly establishing himself as one of the game's premier point producers.

27 Buffalo Sabres

via nhl.com

- Dave Andreychuk, Daren Puppa and 1st Rounder for Grant Fuhr and 5th Rounder

Dave Andreychuk scored a career high 41 goals and 91 points for the Sabres in 1991-92 and had 29 goals and 61 points in 52 games midway through the 1992-93 season when he was traded, along with Daren Puppa and a first round draft pick, to the Toronto Maple Leafs for a 30-year-old Grant Fuhr and a fifth round pick. Andreychuk scored 25 goals and 38 points in 31 games following the trade and scored 12 goals and 19 points in 21 playoff games in the Maple Leafs run to the 1993 Conference finals. He followed that up with 53 goals and 99 points in 1993-94.

Toronto used the first round pick on Kenny Jonsson who would later be traded to the Islanders and become one of their top defensemen. Fuhr played just 64 games for the Sabres across three seasons and was quickly relegated to backup behind Vezina Trophy winner Dominik Hasek.

26 Calgary Flames

via nhl.com

- Doug Gilmour, Ric Nattress, Kent Manderville, Jamie Macoun andRick Wamsley for Gary Leeman, Craig Berube, Alexander Godnyukk, Michael Petit and Jeff Reese

On January 2, 1992 Maple Leafs general manager Cliff Fletcher swung a massive 10 player deal with his former team, sending Gary Leeman, Craig Berube, Alexander Godynyuk, Michel Petit, and goaltender Jeff Reese to Calgary for Doug Gilmour, Ric Nattress, Kent Manderville, Jamie Macoun and goaltender Rick Wamsley. The deal paid immediate dividends for Toronto. In Gilmour's first full season in Toronto he picked up a franchise record 95 assists and 127 points while taking home the Selke Trophy and was the runner up for the Hart Trophy.

The deal was instrumental in building a Maple Leafs team that made a run to the 1993 Conference finals. As for the players who went to Calgary, none of them produced as expected and all were out of Calgary within three years.

25 Carolina Hurricanes (Hartford Whalers)

via sportslogos.net

- Ron Francis, Ulf Samuelsson and Grant Jennings for Jeff Parker, Zarley Zalapski and John Cullen

Current Hurricanes general manager Ron Francis was part of the franchise's worst trade when the Hartford Whalers traded him, Ulf Samuelsson and Grant Jennings at the 1991 trade deadline to the Pittsburgh Penguins for Jeff Parker, Zarley Zalapski, and John Cullen. Francis was the team's number one centre and held many of the franchise's records, but had already been stripped of his captaincy and was in the final year of his contract when the trade took place.

The trade gave the Penguins the ideal the number two centre behind Mario Lemieux and helped the Penguins to back-to-back Stanley Cup victories in 1991 and 1992. Cullen was the centrepiece of the deal for the Whalers, but played just one full season in Hartford before being traded to the Maple Leafs. Zalapski played parts of four seasons in Hartford and recorded seasons of 37 and 51 assists but didn't produce much beyond that. Perker played only four games for the Whalers before disappearing from the NHL.

24 Chicago Blackhawks

via suntimes.co.uk

- Phil Esposito, Ken Hodge and Fred Stanfield for Pit Martin Jack Norris and Gilles Marotte

During a 1967 Blackhawks team party, a drunken Phil Esposito said to Chicago general manager Tommy Ivan and coach Billy Reay, “We’ve got a great team here, you could almost have a dynasty, but you two are gonna screw it up.” He was right. That offseason the Blackhawks traded Esposito, Ken Hodge, and Fred Stanfield to the Boston Bruins for Pit Martin, Jack Norris, and Gilles Marotte. Of the three players Chicago got in the deal, only Martin made any real contributions, reaching the 30 goal mark three times and the 70 point mark four times, including a career high 90 points in 1972-73. However, those numbers pale in comparison to what they gave up.

Esposito played parts of nine seasons in Boston and reached the 50 goal mark five times, the 60 goal mark three times, and scored a whopping 76 goals in 1970-71. He won the Art Ross Trophy five times, the Hart Trophy and Lester B. Pearson Award twice each, and the Stanley Cup twice. He is the tenth leading scorer in NHL history. As for the players who accompanied him to Boston, Stanfield played six seasons for the Bruins and produced three 70 point seasons. Hodge played nine seasons for the Bruins and reached the 40 goal mark three times, including one 50 goal season, and the 100 point mark twice before he was traded in another one of the league's worst deals.

23 Colorado Avalanche (Quebec Nordiques)

via espn.com

- Mats Sundin, Garth Butcher, Todd Warriner and 1st Rounder for Wendel Clark, Sylvain Lefebvre, Landon Wilson and 1st Rounder

The Quebec Nordiques had the first overall pick in three straight drafts from 1989-91, but by the time the team won its first Stanley Cup in Colorado, all three of those players had been traded away. While it's hard to argue with the results, the return for 1989's pick, Mats Sundin proved to be underwhelming. At the 1994 Draft, the Nordiques dealt Sundin, Garth Butcher, Todd Warriner, and a first round pick to the Maple Leafs for Wendel Clark, Sylvain Lefebvre, Landon Wilson, and a first round pick.

The two draft picks never accomplished much and Lefebvre and Wilson's contributions were minimal, while Clark only played one season for the Nordiques before being traded again. Sundin went on to have a Hall of Fame career in Toronto, where he played 13 seasons and became the first European born captain in NHL history and the Maple Leafs' all time leader in goals and points.

22 Columbus Blue Jackets

Eric Hartline-USA TODAY Sports

- Jakub Voracek, 1st Rounder, 3rd Rounder for Jeff Carter

Rumors were running rampant leading up to the 2011 NHL Draft that the Philadelphia Flyers were shopping stars forwards Mike Richards and Jeff Carter. After trading Richards to the Los Angeles Kings, they reached a deal to send Carter to the Blue Jackets for Jakub Voracek, the eighth overall pick, which the Flyers used to draft Sean Couturier, and a third round pick.

The Blue Jackets were hopeful that Carter would finally provide the team with another elite forward alongside Rick Nash. However, Carter was never happy with Columbus and injuries limited him to just 39 games before he was reunited with Mike Richards in a trade to the Kings. From Philadelphia's perspective, Voracek has developed into one of the league's premier playmakers, posting a career high 81 points in 2014-15, and Couturier has become one of the game's best young defensive forwards.

21 Dallas Stars

via zimbio.com

- James Neal and Matt Niskanesn for Alex Goligoski

The Stars were a young team with plenty of forward prospects and in need of some talent on the back end heading into the 2011 trade deadline when they dealt James Neal and Matt Niskanen to the Pittsburgh Penguins for defenseman Alex Goligoski. Goligoski has yet to produce the type of offensive numbers the Stars were hoping for, while James Neal quickly found a home on Evgeni Malkin's wing. He scored 40 goals in his first full season with the Penguins and played at nearly a point per game pace over three full seasons in Pittsburgh before being traded to Nashville. Niskanen improved upon his offensive numbers for the Penguins and in 2013-14 the defenseman scored a career high 46 points - more than Goligoski's best season - before leaving via free agency.

20 Detroit Red Wings

via espn.com

- Marcel Dionne and Bart Crashley for Dan Maloney, Terry Harper and 2nd Rounder

Marcel Dionne was already a star player on an otherwise lackluster Detroit Red Wings team when a contract dispute following the 1974-75 season led to a trade that sent him and Bart Crashley to the Los Angeles Kings for Dan Maloney, Terry Harper, and a second round draft pick. Dionne played parts of 12 seasons in Los Angeles, scoring 50 goals six times, winning an Art Ross Trophy, the Lady Byng Trophy and Lester B. Pearson Award twice. Dionne is the sixth highest scoring player in NHL history. Maloney, who was the centrepiece of the deal for the Red Wings, played parts of three seasons for Detroit, reaching the 60 point mark just once before he was traded to the Maple Leafs.

19 Edmonton Oilers

via windsorstar.com

- Wayne Gretzky, Marty McSorley and Mike Krushelnyski for Jimmy Carson, Martin Gelinas, three 1st Rounders and $15 million

In the summer of 1988, following the Oilers' fourth Stanley Cup victory in five years, financial trouble prompted Oilers owner Peter Pocklington to agree to a trade with Los Angeles Kings owner Bruce McNall, along with input from The Great One, that sent Wayne Gretzky from Edmonton to Los Angeles, along with Marty McSorley and Mike Krushelnyski. In return the Oilers received Jimmy Carson, Martin Gelinas, three first round draft picks and $15 million.

The Oilers won the Stanley Cup for a fifth time in 1990, but many would argue that if not for the trade, they could've won it a few more times. In ESPN's 30 for 30 documentary about the deal, Kings Ransom, former Oilers general manager and head coach Glen Sather said it best, "I wouldn’t have traded him for an entire organization."

18 Florida Panthers 

Kim Klement-USA TODAY Sports

- Dan Boyle for 5th Rounder

In January of 2002, 25 games into his fourth NHL season, the Panthers traded undrafted defenseman Dan Boyle to the Tampa Bay Lightning for a fifth round draft pick. Boyle quickly became one of the league's top point producing defensemen in Tampa Bay en route to a 2004 Stanley Cup victory. Boyle played parts of six seasons for the Lightning and is the franchise's highest scoring defenseman of all time. The Panthers used the fifth round pick to draft Martin Tuma who, like most late round picks, never made it to the NHL.

17 Los Angeles Kings

David Banks-USA TODAY Sports

- Kimmo Timonen and Jan Vopat for Future Considerations

Following the 1998 expansion draft, the Kings traded prospect Kimmo Timonen and Jan Vopat to the Nasvhille Predators for "future considerations". Under the terms of the pre-arranged deal the Predators received Timmonen and Vopat as compensation for taking goaltender Frederic Chabot in the expansion draft and not selecting defenseman Garry Galley.

Teams who lost a goaltender in the draft were ineligible to lose a defenseman. It also made the Kings ineligible to lose a goaltender in the 1999 Expansion draft. Timmonen would play parts of 16 NHL seasons and was a staple on Nashville's blueline for eight of them. Meanwhile, Galley only played two more seasons for the Kings and one for the Islanders before retiring.

16 Minnesota Wild

via cbsminnesota.com

- Nick Leddy and Kim Johnsson for Cam Barker

At the 2010 trade deadline the Wild traded defense prospect Nick Leddy and 33-year-old defenseman Kim Johnsson to the Chicago Blackhawks for former third overall pick Cam Barker. Johnsson scored three points in eight games for the Blackhawks, but didn't play at all in the postseason during Chicago's Stanley Cup run. However, Leddy became a top four defenseman and was only traded from Chicago for salary cap reasons. He produced a career high 37 points for the New York Islanders in 2014-15.

As for Barker, he quickly proved he lacked the foot speed to play at the NHL level and was bought out following the 2010-11 season.

15 Montreal Canadiens

via sbnation.com

- Patrick Roy and Mike Keane for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko

Canadiens fans everywhere point to this trade as being the main reason for the Habs currently experiencing the longest Stanley Cup drought in the franchise's history. After being humiliated in a game against the Red Wings, in which Roy was kept in nets for nine goals, he stormed past coach Mario Tremblay and told team president Ronald Corey, "it's my last game in Montreal." Four days later, the team traded Roy and captain Mike Keane to Colorado for goaltender Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko.

The trade essentially handed the Avalanche the 1996 Stanley Cup while the Canadiens failed to get an impact player for an elite goalie with two Conn Smythe trophies to his name. It was bad enough that the Habs traded Roy, but to not get anything of value in return doomed the NHL's most storied franchise.

14 Nashville Predators

Christopher Hanewinckel-USA TODAY Sports

- Cody Franson and Matthew Lombardi for Brett Lebda, Robert Slaney and 4th Rounder

The Predators haven't made many bad trades in their short history, but their two worst trades happened to involve the same player. In the summer of 2011 the Predators traded Cody Franson and Matthew Lombardi to the Toronto Maple Leafs for Brett Lebda, Robert Slaney, and a fourth round draft pick in a deal that was made entirely for financial reasons. Lombardi had just completed the first year of a three year contract in which a concussion had limited him to just two games. In order to dump his contract, the Predators had to part with Franson.

Neither Lebda or Slaney ever played a game for Nashville and Lombardi played 62 underwhelming games for Toronto before he was traded to the Coyotes. Franson developed into a top-four defenseman for the Maple Leafs before he was traded, along with Mike Santorelli, at the 2015 deadline back to the Predators for Olli Jokinen, prospect Brendan Leipsic, and a first-round draft pick. In his second Nashville tenure, Franson recorded just four points in 23 games and two assists in five playoff games before he became an unrestricted free agent.

13 New Jersey Devils

via totalprosports.com

- Pat Verbeek for Sylvain Turgeon

The Devils haven't made a lot of trade blunders in their history, especially in the prime years of Lou Lamoriello's tenure, but there's one move that does sticks out. In the summer of 1989, the Devils traded Pat Verbeek to the Hartford Whalers for Sylvain Turgeon. Verbeek reached the 40 goal and 80 point marks in his first two seasons with the Whalers and posted at least 30 goals and 75 points in four out of his five full seasons in Hartford. Turgeon on the other hand played just one season in New Jersey and scored 30 goals, but only 47 points and never reached the 30 goal mark again. The silver lining here for Devils fans is that after his lone season in New Jersey, Turgeon was traded to the Canadiens for future Conn Smythe Trophy winner Claude Lemieux.

12 New York Islanders

via zenfs.com

- Zdeno Chara, Bill Muckalt and 2nd Overall Pick (Jason Spezza) for Alexei Yashin

The Mike Milbury era was a fun time to be anyone but an Islanders fan. Milbury made a plethora of awful moves while running the Islanders, but his worst move came at the 2001 Draft when he acquired Alexei Yashin from the Ottawa Senators for future Norris Trophy winner Zdeno Chara, along with Bill Muckalt, and the second overall pick. Ottawa used the pick to draft Jason Spezza, who would post four 30 goal seasons and reach the 80 point mark four times with the Senators.

Following the trade, Milbury promptly signed Yashin to a 10 year, $87.5 million contract. Yashin had his moments on Long Island, including three 60 point seasons, but his stint was mired by injuries and inconsistency and never justified the return or the 10 year contract. Following the 2006-07 season the Islanders bought out the final four years of Yashin's deal.

11 New York Rangers

via espn.com

- Rick Middleton for Ken Hodge

The second time Ken Hodge was involved in one of the worst trades in NHL history came in 1976 when the Bruins traded the 31-year-old to the Rangers for Rick Middleton. Hodge scored 21 goals and 62 points in his first season in the Big Apple, but played just 18 games in the 1977-78 season before he was sent down to the minors and retired shorty thereafter. Middleton went on to play parts of 12 seasons in Boston and posted five consecutive 40 goal seasons from 1979-80 to 1983-84, including 51 goals in his Lady Byng Trophy winning 1981-82 season.

10 Ottawa Senators

via nhl.com

- Pavol Demitra for Christer Olsson

In November of 1996, the Senators traded a 21-year-old centre named Pavol Demitra to the St. Louis Blues for defenseman Christer Olsson. Olsson played a total of 25 games for the Senators before returning to his native Sweden.

Demitra became a top line centre for the Blues, reaching 35 goals three times, 70 points four times - including seasons of 89 points and 93 points in 1998-99 and 2002-03 respectively - and taking home the Lady Byng Trophy following the 1999-00 season.

9 Philadelphia Flyers

via gofansgo.com

- Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Chris Simon, two 1st Rounders and $15 Million for Eric Lindros

When the first overall pick in the 1991 NHL Draft, Eric Lindros, refused to play for the Quebec Nordiques, many teams were lining up to trade for "The Next One". The Flyers ended up winning the bidding war, dealing Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Chris Simon, two first round draft picks, and $15 million to the Nordiques for Lindros. Although he became the dominant power forward of his era and won the Hart Trophy following the 1994-95 season, Lindros' career was cut short by concussions and he was never able to bring a Stanley Cup back to Philadelphia.

As for the boatload Quebec received in return, one of those first round picks became Jocelyn Thibault, who was a key piece in the trade to bring Patrick Roy to Colorado, after the Nordiques moved. That along with Peter Forsberg's Hall of Fame career in Colorado, were instrumental in bringing the Avalanche two Stanley Cup victories.

8 Pittsburgh Penguins

via espn.com

- Markus Naslund for Alek Stojanov

At the 1996 trade deadline, the Penguins were an offensively gifted team looking to add more toughness. So they traded 22-year-old Markus Naslund, who had 52 points in 66 games, to the Vancouver Canucks for Alek Stojanov and his one point in 58 games. Naslund went on to play parts of 12 NHL seasons in Vancouver, eight of them as captain, and retire as the Canucks' all time leader in both goals and points. Stojanov, meanwhile, played just 45 games for the Penguins, posting two goals and six points in his only taste of NHL hockey following the trade.

7 San Jose Sharks

via wikimedia.org

- Josh Gorges and 1st Rounder for Craig Rivet

Heading into the 2007 NHL trade deadline, the Sharks acquired 31-year-old defenseman and pending unrestricted free agent, Craig Rivet from the Montreal Canadiens for defenseman Josh Gorges and a first round draft pick. Rivet played 17 games for the Sharks that season, recording eight points, and was rewarded with a four-year, $14 million contract contract extension. However, he'd only play one of the four years in San Jose, before being traded to Buffalo.

Meanwhile, Gorges became a top four defenseman for the Canadiens and played parts of eight seasons in Montreal, while the first round draft pick was used to draft three-time 30 goal scorer and current Canadiens captain Max Pacioretty.

6 St. Louis Blues 

via espn.com

- Joe Mullen, Terry Johnson and Rik Wilson for Eddy Bears, Charles Bourgeois and Gino Cavallini

Joe Mullen already had a 92 point season under his belt and was in the midst of his third straight 40 goal season when the Blues shipped him, Terry Johnson, and Rik Wilson to the Calgary Flames for Eddy Beers, Charles Bourgeois, and Gino Cavallini in February of 1986.

Mullen reached the 40 goal mark in each of the three seasons following the trade, including a career best 51 goals and 110 points in 1988-89, and won the Lady Byng Trophy in 1987 and 1989. He put up 16 goals and 24 points in 21 games during the Flames 1989 Stanley Cup run. Beers scored 18 points in 24 games for the Blues following the trade, but suffered back injury that put an end to his career in training camp of 1986. Bourgeois never scored more than two goals in a season in St. Louis, while Cavallini topped out at 20.

5 Tampa Bay Lightning

via nhlsnipers.com

- Brad Richards and Johan Holmqvist for Jussi Jokinen, Jeff Halpern, Mike Smith and 4th Rounder

Brad Richards, Martin St. Louis, and Vincent Lecavalier led the Lightning to the last Stanley Cup championship in the pre-salary cap era in 2004. However, in a salary cap world the trio's high-priced contracts prevented the Lightning from adding depth to their lineup and by 2008, the team came to grips with the fact that they would have to move one of them.

At the 2008 trade deadline Tampa Bay traded Richards, along with Johan Holmqvist, to the Dallas Stars for Jussi Jokinen, Jeff Halpern, Mike Smith, and a fourth round draft pick. Richards played parts of four seasons in Dallas, tying his career high with 91 points in the 2009-10 season and following that up with a career high 28 goals, to go along with 77 points, in 2010-11. Of the three players Tampa Bay acquired, only Jeff Halpern produced for the Lightning. Halpern scored 10 goals and 18 points in 19 games following the trade. He followed that up with just 16 points in 52 games the following season. By the end of the 2010-11 season, all three players were gone from Tampa Bay.

4 Toronto Maple Leafs

via leagueittous.com

- Tuukka Rask for Andrew Raycroft

At the 2006 NHL Draft, Maple Leafs general manager John Ferguson, Jr. was looking for a starting goaltender. With 2006 World Junior Gold Medal winning goaltender Justin Pogge also in the system, Ferguson was willing to trade his top goaltending prospect, Tuukka Rask, to the Boston Bruins for Andrew Raycroft. Raycroft had struggled for the Bruins in the first season following the 2004-05 lockout, but the Maple Leafs were confident that the 2004 Calder Trophy winner could regain his form in Toronto. He didn't.

Even though he played 72 games and picked up a franchise record tying 37 wins in 2006-07, Raycroft's play in Toronto was abysmal, to the point that it prompted the team to make another extremely shortsighted trade for a goaltender at the 2007 draft. Rask on the other hand, developed into one of the league's top netminders and took home the Vezina Trophy following the 2013-14 season. What makes matters worse, is that Justin Pogge played just seven NHL games for the Maple Leafs and has since bounced around the minor leagues, Italy, and Sweden.

3 Vancouver Canucks 

via espn.com

- Cam Neely and 1st Rounder for Barry Pederson

The Canucks took Cam Neely with the ninth overall pick in 983, but after three seasons the Canucks felt his development had stagnated and they were unimpressed with his defensive play. They shipped Neely and a first round draft pick to the Boston Bruins for Barry Pederson. Pederson posted back-to-back 70 point seasons for the Canucks, but his play quickly dropped off and by 1992 he was out of the league. In Boston Neely became one of the game's premier power forwards, posting three 50 goal seasons and scoring 50 goals in 44 games in the 1993-94 season. The Bruins used the Canucks' draft pick on Glen Wesley, who became a top defenseman in Boston and along with Neely, helped the Bruins to Stanley Cup Final appearances in 1988 and 1990.

2 Washington Capitals

James Guillory-USA TODAY Sports

- Filip Forsberg for Martin Erat and Michael Latta

Filip Forsberg was a consensus top five pick heading into the 2012 NHL Draft, so it seemed like a steal to many observers when the Swede fell to the Capitals at the 11th pick. However, it took less than a year for the Capitals to fall out of love with Forsberg and at the 2013 trade deadline he was dealt to the Nashville Predators for a disgruntled Martin Erat and Michael Latta.

Erat scored just two goals in 62 games and zero points in four playoff games for the Capitals before he was traded again, while Latta had just one goal in 70 career games heading into the 2015-16 season.

Forsberg finished the 2014-15 season third among rookies with 63 points, fourth in voting for the Calder Trophy, and looks as though he'll be the Predators number one centre for years to come.

1 Winnipeg Jets (Atlanta Thrashers)

via broadstreetbullies.com

- Braydon Coburn for Alexei Zhitnik

Prior to the move to Winnipeg, the demise of the Atlanta Thrashers was due in large part to management's inability to ice a winning team. However, their worst trade came in the lone season that they did qualify for the Stanley Cup Playoffs. Sitting in first place in the Southeast Division at the 2007 trade deadline, the Thrashers dealt rookie defenseman Braydon Coburn to the Philadelphia Flyers for 34-year-old Alexei Zhitnik.

Zhitnik began his tenure in Atlanta by posting 14 points in 18 games, but he was held scoreless in the team's first round sweep at the hands of the New York Rangers. Zhitnik was a complete disappointment the following season, resulting in the Thrashers buying out the remainder of his contract. Coburn, on the other hand, became a top pairing defenseman for the Flyers, where he played parts of nine seasons.

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Worst Trade in Every NHL Team's History