As the NHL trade deadline approaches, each team is trying to make a deal that will help their club improve.
Sometimes these moves work and sometimes they backfire.
Here is a look at the worst trade in each team's history, a deal that was one-sided and did not work out for one of the clubs that made it.
Some organizations were tough to choose for because they had so few bad deals, and some had too many to consider. Others didn't make too many horrific trades over the years.
Feel free to disagree and point out a trade that was worse, but explain why you feel your choice belongs on our list.
March 5, 2001: The Ducks send Teemu Selanne to San Jose for Jeff Friesen, Steve Shields and 2003 second-round pick (Vojtech Polak).
The Ducks dealt their best player ever to San Jose and didn't get a lot in return. Friesen lasted a little more than one season in Anaheim and scored just 17 goals.
Shields served as a backup goalie for one season and was 11 games under .500 despite having a solid 2.67 GAA.
The second-round pick turned into Vojtech Polak who played only five career NHL games before heading back to his native Czech Republic.
Selanne had two good, but not great, seasons in San Jose and one disappointing season in Colorado before returning to Anaheim and again becoming a productive goal scorer.
In the end, the Ducks didn't get enough for a top scorer like Selanne and were fortunate he returned to Anaheim a few years later.
February 3, 2007: Bruins get Brandon Bochenski from Chicago for Kris Versteeg and a conditional fifth-round pick (not exercised).
At the time, it didn't seem like a major deal, but the Bruins dealt a young forward named Kris Versteeg to the Blackhawks for Brandon Bochenski.
Bochenski played in parts of two seasons in Boston, totaling a mere 51 games in which he scored 11 goals. He has spent the last three seasons in the KHL.
Versteeg has gone on to have 20 or more goals in four seasons and, when healthy, is still a part of the Panthers top line.
The Bruins don't have a history of making too many terrible trades, but this one was not a great one.
November 12, 1988: Sabres send Tom Barrasso and a 1990 third-round pick (Joe Dziedzic) to Pittsburgh for Doug Bodger and Darrin Shannon.
This trade gave the Pittsburgh Penguins the starting goalie who would help win them Stanley Cup titles in 1991 and 1992. In fact, Barrasso spent a decade in Pittsburgh, nearly all of it as their starter. In addition to winning two Cups, he became the first American-born goalie to win 300 NHL career games.
In return, the Sabres got a steady but not spectacular defenseman in Doug Bodger and a prospect in left wing Darrin Shannon who never quite panned out.
The former first-round pick scored just 10 goals in 52 games for the Sabres before moving on to an undistinguished, but steady, career with the Jets/Coyotes organization.
June 10, 2000: The Flames send goalie J.S. Giguere to Anaheim for a second-round pick (Matt Pettinger).
The Flames traded young goalie J.S. Giguere to Anaheim in exchange for a second round pick in the summer of 2000.
Giguere went on to lead the Ducks to two Stanley Cup Finals in nine fine seasons with the club. He won the Conn Smythe Trophy as playoff MVP in 2003 when the Ducks lost to the Devils in the finals and then led Anaheim to their first and only championship in 2007.
Meanwhile, the Flames took the pick they got from Anaheim and dealt it to the Washington Capitals in exchange for a fourth-round pick and Finnish left wing Miika Elomo who played in only two career NHL games.
In the end, the Flames had little to show for trading away a Stanley Cup-winning goaltender.
March 4, 1991: Whalers send Ron Francis, Grant Jennings and Ulf Samuelsson to Pittsburgh for John Cullen, Jeff Parker and Zarley Zalapski.
This was the trade that took away the heart and soul of the Whalers franchise and gave the Penguins the final pieces they needed to win back-to-back Stanley Cups in 1991 and 1992.
Francis provided Pittsburgh the perfect second-line compliment to Mario Lemieux and leadership skills to boot while Samuelsson added solid play in his own zone and the ability to get under opponent's skin. Francis was inducted into the Hockey Hall of Fame in 2007.
In exchange, the Whalers received Cullen, who played one full season and parts of two more in Hartford before moving on. Parker played in only four games for the Whalers before suffering a career-ending knee injury. Zalapski was a high-risk, high-reward defenseman who spent a little more than three seasons with the Whalers. He scored 20 goals in 1991-92 but was horrible in his own zone and a frustrating player for coaches.
The Penguins won two Stanley Cups and became the dominant team of the early 1990s while the Whalers fell deeper into mediocrity as a result of this trade. It's value is measured in intangibles almost as much as in statistics, but the Penguins won the trade both ways.
The Whalers moved to Carolina in 1997.
May 15, 1967: Blackhawks send Ken Hodge, Phil Esposito and Fred Stanfield to Boston in exchange for Jack Norris, Pit Martin and Gilles Marotte.
This turned out to be one of the most one-sided trades in NHL history. The Bruins got one of the greatest goal scorers of all-time in Phil Esposito, who would set a new record for goals in a season with 76 and would win five Art Ross Trophies as the league's top point-getter. He was inducted into the Hockey Hall of Fame in 1984.
Hodge became Esposito's wing on the Bruins top line and scored more than 40 goals in three different seasons including a career-best 50 goals in 1973-74.
Stanfield had six seasons of 20 or more goals and became a steady force on the Bruins third line.
As a group, the Bruins won the Stanley Cup in 1970 and 1972 and reached the finals again in 1974 (although Stanfield had left the team after the 1972-73 season).
Pit Martin became a steady second-line center for the Blackhawks, but Marotte was nothing more than a journeyman defenseman, and Norris played just 10 games over two seasons in net for the Blackhawks.
This trade gave the Bruins what they needed to become champions while the Blackhawks got very little in return by comparison.
March 8, 2006: The Avalanche send David Aebischer to Canadiens for Jose Theodore.
The Avalanche haven't made too many awful trades in their history, but acquiring Theodore didn't quite work out the way management had intended.
Theodore had played quite well for the Canadiens, but in 2006, he failed to ignite the Avs in the playoffs, and they were eliminated in the second round.
The following year, Theodore was below .500, his GAA ballooned to 3.26, and his save percentage fell below .900.
After a bit of a bounce back season in 2007-08, Theodore left Colorado and signed with the Capitals as a free agent.
Aebischer had two partial seasons as a backup in Montreal and honestly didn't do much either, although expectations were much higher for Theodore.
In the end, this deal didn't do much for either team, but the Avalanche were a lot more disappointed.
June 23, 2011: Blue Jackets acquire Jeff Carter from Philadelphia for Jakub Voracek, 2011 first-round pick (Sean Couturier) and 2011 third-round pick (Nick Cousins).
Jeff Carter was supposed to help lead a resurgence in Columbus but it never worked out that way.
He played only 39 games for the Blue Jackets before being dealt to the Kings later in the 2011-12 season. He scored 15 goals and 25 points in just 39 games after missing the early part of the season due to injury. The Blue Jackets finished with the worst record in the league.
Meanwhile, Jakub Voracek has been a steady contributor for the Flyers. The best part of the deal for Philadelphia, however, was the first-round pick, which they turned into Sean Couturier who had a strong rookie season for the Flyers. At 20, Couturier has his best hockey ahead of him.
Nick Cousins remains in juniors but topped the 100 point mark this season in the OHL.
March 19, 2002: Stars send Jamie Langenbrunner and Joe Nieuwendyk to New Jersey for Jason Arnott, Randy McKay and 2002 first-round pick (Daniel Paille).
This trade paid off for the Devils one year later as Langenbrunner and Nieuwendyk contributed to a Stanley Cup championship for New Jersey.
Arnott had three fairly productive seasons in Dallas while McKay played all of 14 games in a Stars uniform before moving on to Montreal. The first-round pick was later traded to Buffalo who selected Daniel Paille.
Overall, the Devils got the better of the deal and won a Stanley Cup. The Stars won exactly one playoff series over the next three seasons and missed the playoffs altogether in 2002.
June 15, 1989: Red Wings send Paul MacLean and Adam Oates to St. Louis for Bernie Federko and Tony McKegney.
The Red Wings haven't made too many bad trades, especially recently, but this 1989 deal was not their finest moment.
The key to the deal was Adam Oates, who went on to form one of the most dynamic duos in NHL history when teamed with Brett Hull in St. Louis. The next two seasons, Oates went over 100 points and had better than an assist per game over his Blues career.
Paul MacLean (current coach of the Senators), scored 34 goals for the Blues in his first season with the club.
The Red Wings got a veteran presence in Federko who scored 17 goals in 73 games in his only season in Detroit, while McKegney played only 14 games in a Red Wings uniform and scored three points.
March 18, 1997: Oilers send Miro Satan to Buffalo for Craig Millar and Barrie Moore.
The Oilers dealt a young Miro Satan to Buffalo where the Slovakian winger spent more than seven productive seasons. Satan scored more than 30 goals three times with Buffalo and twice had 29 goals in a season.
Meanwhile, the two players the Oilers got in return did very little. Defenseman Craig Millar played 36 games for Edmonton over three seasons and had only six points. Barrie Moore played only four games for the Oilers and never registered an NHL point.
January 7, 2002: Panthers send Dan Boyle to Tampa Bay for a 2003 fifth-round pick (Martin Tuma).
This deal was extremely one-sided. Martin Tuma never played an NHL game and never even played a complete season in the AHL.
Meanwhile, Boyle went on to play six seasons in Tampa Bay and became their top defenseman. He was a major part of the Lightning's 2004 Stanley Cup win.
In 2006-07, Boyle scored 20 goals and was named to the second-team postseason all-star team.
October 18, 1983: Kings send Larry Murphy to Washington for Ken Houston and Brian Engblom.
Larry Murphy was a very productive defenseman for the Kings, but they dealt him to the Capitals at the beginning of the 1983-84 season.
Murphy continued to play at a high level for Washington for six seasons including two more seasons with 20 or more goals and an 81-point season in 1986-87.
The Kings got back Houston who played 33 games for Los Angeles before retiring at the end of the season, and Engblom who played just two and a half seasons for the Kings as a steady, but unspectacular, defensive defenseman.
August 26, 2005: Wild send Zbynek Michalek to Phoenix for Erik Westrum and Dustin Wood.
Zbynek Michalek went on to become a steady top four defenseman for the Coyotes for five seasons and now has returned to Phoenix this season.
Erik Westrum had one assist in 10 career games for the Wild, while Dustin Wood never played a game in the NHL.
June 30, 2009: Montreal sends Pavel Valentenko, Ryan McDonagh, Doug Janik and Chris Higgins to the New York Rangers for Tom Pyatt, Scott Gomez and Michael Busto.
Despite all the names involved in this deal, there are actually two key names involved: Scott Gomez and Ryan McDonagh.
Gomez carried a salary of more than $7 million per year and never came close to living up to expectations with Montreal. Worse yet, his high salary hurt Montreal's salary cap where he took up a lot of room and provided precious little production. The Habs bought out his contract prior to the start of this season.
Meanwhile, McDonagh developed into a solid, top four defenseman for the Rangers. He is only 23 and still has lots of quality hockey ahead of him.
June 18, 2007: Predators acquire a 2007 first-round pick (Jonathan Blum) from Flyers for Scott Hartnell and Kimo Timonen.
The Predators gave up a lot to acquire a first-round draft pick in 2007, which they used on defenseman Jonathon Blum. Blum has become a decent NHL defenseman but nothing more thus far.
Meanwhile, Hartnell, who already has a pair of 30-plus goal seasons, has become a steady and productive forward for the Flyers, while Timonen has scored more than 35 points in each of his four full seasons in Philadelphia.
June 19, 1989: Devils send Pat Verbeek to Hartford for Sylvain Turgeon.
While Lou Lamoirello has made a lot of good deals for the Devils over the years, this one didn't work out as he had hoped.
Verbeek had five very productive seasons in Hartford, scoring more than 40 goals twice and adding seasons of 39 and 37 as well.
Meanwhile, Turgeon played only one season in New Jersey with Cy Young-like numbers (30 goals but just 17 assists).
June 25, 2000: Islanders send Olli Jokinen and Roberto Luongo to Florida for Oleg Kvasha and Mark Parrish.
This deal haunts the New York Islanders to this day. In order to clear the way for Rick DiPietro, the Isles traded a young Roberto Luongo and Olli Jokinen to Florida.
Bobby Loo was a solid starter for the Panthers for five seasons before being even better with the Canucks. Jokinen meanwhile spent four seasons in Florida including a 36-goal campaign in 2002-03.
Kvasha spent five seasons on Long Island but never scored more than 15 goals in any year. Parrish was more productive, topping 20 goals four times including a 30-goal season in 2001-02, but the bottom line is that the Panthers got the better of this deal.
May 26, 1976: Rangers send Rick Middleton to Boston for Ken Hodge.
Simple math shows how one-sided this trade was. Ken Hodge scored 23 goals in 96 games for the Rangers and then was demoted to the AHL.
Rick Middleton played 12 seasons for the Bruins and 402 goals and 898 points for the Bruins including five straight seasons of 40 or more goals.
November 27, 1996: Senators send Pavol Demitra to St. Louis for Christer Olsson.
The Senators lost out on this deal. Pavol Demitra went on to play eight seasons for the Blues including seven seasons with more than 20 goals and three with more than 30.
Meanwhile, defenseman Christer Olsson played all of 25 games for the Senators, scoring two goals and five points before returning to Europe to finish his career.
December 5, 2005: Flyers send Eric Meloche and Patrick Sharp to Chicago for Matt Ellison and a 2006 third-round pick (Ryan White).
Eric Meloche was a journeyman forward who never played a game for the Blackhawks, but Patrick Sharp was the key to this deal. Sharp has had three seasons of more than 30 goals for Chicago and four seasons with more than 60 points.
In return, Philadelphia got Matt Ellison who played seven games for Philadelphia and picked up one assist and a draft pick that was traded to the Montreal Canadiens and became Ryan White.
The Blackhawks clearly got the better of this trade.
March 10, 2003: Coyotes send Daniel Briere and a 2004 third-round pick (Andrej Sekera) to Buffalo for Chris Gratton and a 2004 fourth-round pick (Liam Reddox)
The Coyotes made a mistake when they sent Daniel Briere to Buffalo in 2003. Briere had three seasons in Buffalo including a 95-point season in 2006-07.
Meanwhile, Chris Gratton scored only 32 points in 82 games for the Coyotes over one full season and one partial one.
The draft pick the Coyotes received was traded to the Edmonton Oilers.
March 20, 1996: Penguins send Markus Naslund to Vancouver for Alek Stojanov.
This deal was about as one-sided as it gets.
Naslund played a decade for the Canucks and retired as the franchise's all-time leading scorer with 756 points in 884 games. He was selected to play in five NHL All-Star Games and named to three postseason all-star teams.
The Penguins received winger Alek Stojanov in return, who scored two goals and six points in just 45 games with Pittsburgh before finishing his career in the minor leagues.
November 14, 2003: Sharks send Miikka Kiprusoff to the Flames for a 2005 conditional second-round pick (Marc-Edouard Vlasic).
Sure, Marc-Edouard Vlasic has played six good seasons on defense for the Sharks, but that's hardly close to the value the Flames received in this deal.
Goalie Miikka Kiprusoff meanwhile, has won a Vezina Trophy and led the Flames to the 2004 Stanley Cup finals during his nine seasons with the team. In fact, "Kipper" has been one of the two best players on the Flames during his tenure with the club.
Februrary 1, 1986: Blues send Terry Johnson, Joe Mullen and Rik Wilson to Calgary for Eddy Beers, Charles Bourgeois and Gino Cavallini.
This deal helped the Flames reach the Stanley Cup Final in 1986 and win their only championship in 1989.
Joe Mullen played five seasons in Calgary after the trade and topped 36 goals in each of his four complete seasons. He also had a career-best 51 tallies in 1988-89, the Flames championship season. Neither Rik Wilson nor Terry Johnson accomplished much for the Flames.
Meanwhile, Ed Beers played 24 games for St. Louis before retiring while Gino Cavallini was steady but unspectacular.
The Flames made two trips to the finals and acquired a 50-goal scorer, while the Blues received less than they gave up.
February 26, 2008: Lightning acquire Jeff Halpern, Jussi Jokinen, Mike Smith and a 2009 fourth-round pick (Kyle Bigos) from Dallas for Brad Richards and Johan Holmqvist
Brad Richards was the key player in this deal. He had three complete seasons in Dallas and had seasons of 77 points and 91 points there.
Meanwhile, Mike Smith was the best player Tampa Bay got back, and he was an inconsistent netminder who never established himself as a bona fide NHL starter.
October 16, 1989: Leafs send first-round pick in 1991 (Scott Niedermayer) to New Jersey for Tom Kurvers.
This was one very uneven trade. The Maple Leafs traded a first-round draft choice to New Jersey for defenseman Tom Kurvers.
Kurvers played one full season and part of another in Toronto, scoring 15 goals and 55 points, while the first-round draft choice became Scott Niedermayer, who played more than a decade in New Jersey and was a major part of three Stanley Cup wins for the Devils.
Kurvers was good but not great. Niedermayer will be in the Hall of Fame shortly after he becomes eligible later this year.
June 6, 1986: Canucks send Cam Neely and a 1987 first-round pick (Glen Wesley) to Boston for Barry Pederson.
This deal was doubly painful for the Canucks.
Neely went on to become one of the greatest power forwards of all-time, had three seasons with 50 or more goals and is in the Hockey Hall of Fame.
The first-round pick became Glen Wesley, who became a very good defenseman that spent seven productive seasons in Boston, played more than 1,400 NHL games and won a Stanley Cup with the Hurricanes later in his career.
In return, Vancouver received Barry Pederson. Injuries derailed his career and he faded after two early productive (70-plus points) seasons with the Canucks.
January 23, 2004: Capitals acquire Anson Carter from the Rangers for Jaromir Jagr.
This one was pretty one-sided, even if Jaromir Jagr wanted out of Washington and wasn't playing his best hockey there.
Jagr set a Rangers franchise record with 123 points in his first season on Broadway and later became captain of the club.
Washington got back Anson Carter who scored five goals in 19 games for the Caps before being dealt to the Kings.
February 26, 2008: Thrashers acquire Colby Armstrong, Erik Christensen, Angelo Esposito and an '08 first-round pick (Daultan Leveille) from Pittsburgh for Marian Hossa and Pascal Dupuis.
The Atlanta Thrashers (now the Winnipeg Jets) dealt Marian Hossa and Pascal Dupuis to Pittsburgh but didn't get much in return.
Hossa helped the Penguins reach the Stanley Cup Final after scoring 12 goals and 26 points in 20 playoff games. Dupuis remains a solid contributor for the Penguins and helped them win a Stanley Cup in 2009.
The Thrashers got back Armstrong who had one 20-goal season with Atlanta, Erik Christensen who scored seven goals in 57 games with Atlanta and Angelo Esposito who has yet to play in an NHL game.
The first round pick they got became Daultan Leveille who is now playing in the ECHL and also never played for the Thrashers/Jets organization.