Ranking the 10 Worst Offseason NHL Trades Since 2000

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The NHL offseason is among the busiest times for trade activity as teams attempt to improve their rosters. Some seek quick fixes, while others have longer-term plans in mind. The salary cap can also become a factor as clubs with limited space make cost-cutting moves.

A number of significant offseason trades have occurred since the turn of this century. While every general manager tries to make the best deal they can, sometimes a player swap that looked good on paper can have unexpectedly terrible results.

Some entailed moving an established superstar like Jaromir Jagr. A few involved players on the cusp of stardom at the time of the deal. Others saw a promising young player blossom into a star with his new team.

The following is our ranking of the 10 worst offseason NHL trades since 2000. The caliber of talent and the return, plus the consequences of each deal, factored into this compilation. Feel free to voice your views in the comments section.

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The New York Rangers were trying to shed some salary at the end of the 2008-09 season. Meanwhile, the Montreal Canadiens were seeking offensive depth after managing just six goals as the Boston Bruins swept them from the opening round of the 2009 playoffs.

On June 30, 2009, the two clubs swung a major six-player trade. The Canadiens acquired center Scott Gomez and minor leaguers Tom Pyatt and Mike Busto from the Rangers in exchange for center Christopher Higgins and prospect defensemen Ryan McDonagh and Pavel Valentenko.

Winner of the Calder Memorial Trophy in 1999-2000 and a two-time Stanley Cup champion with the New Jersey Devils, Gomez had signed a seven-year, $51.5 million contract with the Rangers on July 1, 2007. Though he reached 70 points for the fourth time in his career in his first season in New York, his struggles the following season turned him into a trade candidate.

Gomez had a respectable 59-point campaign in his first season with the Canadiens, but his production steadily declined over the next two years. In 2013, his tenure with the Habs ended following a compliance buyout of his contract.

McDonagh developed into a top-two defenseman with the New York Rangers, becoming their captain in 2014. Shipped to the Tampa Bay Lightning at the 2018 NHL trade deadline, he helped them win the Stanley Cup last season and reach the Final again this season, squaring off against the Canadiens.

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The Boston Bruins and Dallas Stars stunned the hockey world on July 4, 2013, with a seven-player trade sending Tyler Seguin to the Stars. Forward Rich Peverley and defenseman Ryan Button join Seguin heading to Dallas while the Bruins received forward Loui Eriksson and prospects Reilly Smith, Joe Morrow and Matt Fraser.

Seguin, selected second overall in the 2010 NHL draft by the Bruins, was considered a rising but troubled star. He helped Boston win the 2011 Stanley Cup and reach the 2013 Cup Final. At the time of the deal, reports emerged of Bruins management criticizing Seguin's maturity, professionalism and off-ice behavior.

The Bruins had signed Seguin to a six-year, $34.5 million contract extension the previous September. Given their concerns about the young forward over the course of 2012-13, management was worried about that long-term investment.

That trade, however, brought out the best in Seguin. Skating alongside Stars captain Jamie Benn, he tallied a career-high 84 points in his first season in Dallas. He followed that up with five seasons of at least 72 points as one of the league's most proficient scorers during that period. He remains an invaluable member of the Stars' core.

The deal didn't work out as well for the Bruins. They declined over the following four seasons, missing the postseason twice. Peter Chiarelli, who made the Seguin deal, was replaced as general manager by Don Sweeney in 2015. Every player they received in that trade was no longer with the team by 2017.

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After seven seasons with the Minnesota Wild, Brent Burns was turning into a talented NHL defenseman. In the 2010-11 season, Burns was at his best to that point, tallying what was then a career-high 17 goals and 46 points while earning a trip to the 2011 All-Star Game.

Hosting the 2011 NHL draft, the Wild surprised their fans by shipping Burns and a second-round pick in 2012 to the San Jose Sharks. In return, they received forward Devin Setoguchi, prospect Charlie Coyle and the Sharks' first-round pick (28th overall) in the 2011 draft.

Burns was a year away from unrestricted free-agent status at the time of the trade and in line for a significant raise. With the Wild having missed the postseason for the third straight year, management sought to shake things up.

Setoguchi, a three-time 20-plus goal scorer with the Sharks, struggled through two seasons in Minnesota and was traded to the Winnipeg Jets in 2013. Coyle would become a good two-way center during his seven seasons with the Wild until he was traded to the Boston Bruins during the 2018-19 season.

Burns, meanwhile, remains a popular star with the Sharks and one of the league's best puck-moving defensemen. Between 2014-15 and 2018-19, he reached or exceeded 60 points five times, won the James Norris Memorial Trophy in 2016-17, was named to the First All-Star Team in 2016-17 and 2018-19 and helped the Sharks reach the 2016 Stanley Cup Final.

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Jean-Sebastien Giguere is the greatest goaltender in Anaheim Ducks history. During his tenure with the Ducks from 2000-01 to 2008-09, he backstopped them to two Stanley Cup Finals while winning the Conn Smythe Trophy in 2003 and the Stanley Cup in 2007. He also holds their single-season records of 36 wins and eight shutouts and their all-time records for games played (447), wins (207) and shutouts (32).

The Ducks have the Calgary Flames to thank for that. On June 10, 2000, they shipped Giguere to Anaheim in exchange for a second-round pick in the 2000 draft.

Reviewing the trade in May 2003, The Hartford Courant's Jeff Jacobs reported Giguere was one of five goaltenders in the Flames system at the time. Then-general manager Craig Button had to expose a goaltender in the 2000 expansion draft. He opted to protect Fred Brathwaite, trading Giguere to the Ducks rather than risk losing him for nothing to the Minnesota Wild.

Button would flip that second-round pick to the Washington Capitals at the 2000 NHL draft for winger Miika Elomo and a fourth-round pick. Elomo never played a game for the Flames or any other NHL club after that. Neither would Levente Szuper, the player they selected with that fourth-round pick.

The Flames would offset this error three years later when Button's successor Darryl Sutter acquired Miikka Kiprusoff from the San Jose Sharks. Nevertheless, giving up the promising Giguere for nothing substantial ranks among the worst trades of this century.

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Entering the 2006 offseason, then-Toronto Maple Leafs general manager John Ferguson Jr. was searching for a goaltender after declining to pick up the option year in Ed Belfour's contract. He had two promising goalies in Tuukka Rask and Justin Pogge in the Leafs' system, but neither was ready to become a starting netminder in 2006-07.

The Boston Bruins, meanwhile, had a surplus of NHL-ready goalies in Andrew Raycroft, Tim Thomas and Hannu Toivonen. In an Oct. 2019 interview with The Athletic's Joe McDonald, former Bruins GM Jeff Gorton said he felt Raycroft, winner of the Calder Memorial Trophy in 2003-04, needed a fresh start after struggling on the rebuilding Bruins in 2005-06.

During the 2006 NHL draft, the Leafs acquired Raycroft from the Bruins for Rask. Revisiting that trade in March 2013, the Toronto Sun's Steve Simmons reported Ferguson didn't want to move Pogge as he backstopped Canada to gold at the 2006 World Junior Hockey Championship. Pogge was also under contract, while there was concern Rask could prove difficult to sign.

The deal did nothing to improve the Leafs' goaltending. Raycroft lasted just two seasons in Toronto. His playing career ended in 2011, and he's now the Bruins' studio analyst on NESN. Pogge played just one NHL season (2008-09) and spent the past nine seasons in Europe.

Rask, of course, became an elite goaltender for the Bruins. A backup during their 2011 Stanley Cup run, he backstopped them to two Cup Finals (2013, 2019), won the Vezina Trophy in 2013-14 and shared the William M. Jennings Trophy with Jaroslav Halak in 2019-20. He's also their franchise leader with 560 games played and 306 career wins.

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On June 23, 2011, the Columbus Blue Jackets acquired center Jeff Carter from the Philadelphia Flyers in exchange for winger Jakub Voracek and the Jackets' first- and third-round picks in the 2011 draft. At the time, then-Jackets general manager Scott Howson expected Carter to have many productive seasons in Columbus. He didn't even last for one.

Reviewing the trade three years later, the Hockey News' Jason Kay explained the Flyers were coming off a disappointing season after reaching the Stanley Cup Final the previous year. They were also trying to shed salary. Carter was about to start an 11-year, $58 million contract in 2011-12. The Blue Jackets, meanwhile, wanted to prove to then-captain Rick Nash they were serious about improving the roster.

Kay also pointed out Carter was unhappy in Columbus and hampered by injuries. On Feb. 23, the Jackets shipped him to the Los Angeles Kings for defenseman Jack Johnson and a first-round pick in 2012 or 2013. Carter regained his form in Los Angeles, spending almost 10 seasons with the Kings and helping them win two Stanley Cups. He was dealt to the Pittsburgh Penguins at this year's trade deadline.

This deal, and the return they got from the Kings for Carter, failed to improve the Jackets. It also may have contributed to Nash's departure. On July 23, 2012, he was traded to the New York Rangers in a five-player deal.

The Flyers, meanwhile, did well with their return. Voracek turned into a reliable playmaking winger, reaching or exceeding 55 points in seven straight seasons from 2013-14 to 2019-20. They used that first-rounder from the Jackets to select Sean Couturier, who's become one of the top two-way forwards in the league.

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Dominik Hasek cemented his legacy among the NHL's greatest goaltenders during his nine seasons with the Buffalo Sabres. Between 1992-93 and 2000-01, The Dominator won the Vezina Trophy six times, was named to the First All-Star Team six times and took home the Hart Memorial Trophy twice. He also backstopped the Sabres to the 1999 Stanley Cup Final.

By 2001, however, Hasek had yet to add a Stanley Cup to his trophy case. He informed the Sabres he wanted to play one more season but with a contender. On July 1, 2001, they traded Hasek to the Detroit Red Wings in exchange for Vyacheslav Kozlov, a 2002 first-round pick and future considerations.

The Associated Press' John Wawrow reported the Sabres made that move rather than risk losing Hasek for nothing. They wanted to keep him, but he informed them he woulkd retire or return to the Czech Republic if he wasn't traded to a contender like the Wings. They picked up the one-year option in his contract hours before the free-agent deadline to facilitate the trade to Detroit. The Wings signed him to a three-year deal.

Hasek had the Sabres over a barrel, leaving them little choice but to move him. The return, however, did nothing to help them. Kozlov played just one season in Buffalo and was traded to the Atlanta Thrashers. At the 2002 draft, they swapped first-round picks with the Thrashers and selected Daniel Paille 20th overall. A depth forward, Paille spent four seasons with the Sabres and was traded to the Boston Bruins in 2009-10.

With Hasek between the pipes, the Red Wings dominated the regular-season standings in 2001-02 and won the Stanley Cup that spring. He retired later that year but returned for four more NHL seasons. Three of those were with the Wings, helping them win another Stanley Cup in 2007-08.

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The Florida Panthers got a steal of a deal in June 2000 when they acquired Roberto Luongo and Olli Jokinen from the New York Islanders in exchange for forwards Mark Parrish and Oleg Kvasha. While the Panthers struggled to build a playoff contender for the next five seasons, by 2003-04 Luongo had blossomed into an All-Star and a finalist for the Vezina Trophy.

In 2004, Mike Keenan took over as Panthers general manager. Two years later, his relationship with Luongo deteriorated. In 2007, the Globe and Mail's Grant Kerr reported the disagreement had to do with a new contract for the rising star. The club took Luongo to arbitration in 2005 after he rejected a five-year deal. He was awarded a one-year, $3.2 million contract.

With the clock ticking to make Luongo a qualifying offer for 2006-07, Keenan instead shipped the goaltender to the Vancouver Canucks on June 23, 2006, for winger Todd Bertuzzi as part of a five-player swap. Defenseman Lukas Krajicek and a sixth-round pick also went to the Canucks, while goalie Alex Auld and defenseman Bryan Allen headed to Florida.

The Canucks were the big winners as Luongo established himself among the NHL's elite goaltenders. He backstopped them to seven Northwest Division titles from 2006-07 to 2012-13, reaching the Stanley Cup Final in 2011. Traded back to the Panthers in 2014, he remains the Canucks' franchise leader in single-season wins (47) and shutouts (nine) and their career leader with 252 wins and 38 shutouts.

A big power forward coming off six straight seasons with at least 50 points with the Canucks, Bertuzzi played only seven games with the Panthers before undergoing season-ending back surgery. He spent the next seven seasons with the Anaheim Ducks, Calgary Flames and Detroit Red Wings.

Krajicek was out of the NHL by 2010. Auld spent just one season with the Panthers and went on to play with six other clubs between 2007-08 and 2011-12. Allen played nine seasons with the Panthers, Carolina Hurricanes and Montreal Canadiens.

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Mike Milbury made several questionable deals during his tenure as New York Islanders general manager from 1995-96 to 2005-06. The notable players he traded away included Roberto Luongo, Todd Bertuzzi, Olli Jokinen, Zigmund Palffy, Wade Redden and Brian McCabe.

Milbury's worst trade, however, occurred during the 2001 NHL draft. In a stunning move, he shipped defenseman Zdeno Chara, winger Bill Muckalt and the second overall pick in that draft to the Ottawa Senators for center Alexei Yashin.

Chara, at the time, was considered a promising but still developing blueliner. Yashin was a talented center with two 40-plus goal seasons on his resume. However, he missed the 1999-2000 campaign because of a contract holdout.

Signed by Milbury to a 10-year, $87.5 million contract soon after joining the Islanders, Yashin had some early success, including a 75-point performance in 2001-02. By 2006-07, however, his production was in decline. His NHL career ended in 2007 when Milbury's successor, Garth Snow, bought out the remainder of his contract.

Chara became an elite defenseman during his four seasons in Ottawa. He helped them win the Presidents' Trophy in 2002-03 and was the runner-up for the James Norris Memorial Trophy in 2003-04. Signing with the Boston Bruins in 2006, Chara served 14 years as their captain, winning the Norris Trophy in 2009 and the Stanley Cup in 2011. He completed his 23rd NHL season in 2020-21 with the Washington Capitals.

As for that second overall pick, the Senators used it to select Jason Spezza. He became one of the top players in franchise history, sitting second all-time with 251 goals, 436 assists and 687 points. He's also their single-season leader with 71 assists in 2005-06 and 105 points in 2006-07. After 11 seasons in Ottawa and five with the Dallas Stars, he's signed for a third season with the Toronto Maple Leafs. 

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It was one of the most stunning offseason trades in NHL history. It was also the worst since 2000, becoming a rare deal that turned out badly for the two clubs involved.

On July 11, 2001, the Pittsburgh Penguins traded winger Jaromir Jagr and defenseman Frantisek Kucera to the Washington Capitals. At the time, Jagr was one of the greatest players in Penguins history. He had been named to the First All-Star Team six times, was a five-time NHL scoring champion, a two-time Stanley Cup champion and winner of the Hart Memorial Trophy in 1998-99.

Jagr, however, was unhappy in Pittsburgh during the 2000-01 campaign and had requested a trade. The New York Rangers were reportedly the front-runners, but then-Penguins GM Craig Patrick wanted a return of younger players. He got prospects Kris Beech, Michal Sivek and Ross Lupaschuk from the Capitals.

Capitals owner Ted Leonsis was seeking a big-name star to raise his money-losing club's profile. He hoped the addition of Jagr would address that issue.

The trade was a disaster. After reaching 121 points in his final season with the Penguins, Jagr's stats tumbled to 79 and 77 points in this first two seasons in Washington. The Capitals missed the playoffs in 2002-03 and were bounced from the opening round the following season by the Tampa Bay Lightning. Midway through 2003-04, the Capitals sent Jagr to the Rangers for right wing Anson Carter.

Beech, Sivek and Lupaschuk failed to develop for the Penguins. Beech played 198 NHL games with the Penguins, Capitals and three other clubs. Sivek played 38 games for the Penguins in 2002-03 and Lupaschuk just three. The club would miss the playoffs four straight seasons amid rumors of relocation until they drafted franchise savior Sidney Crosby in 2005.

Leonsis had to wait until the 2004 NHL draft to land his franchise player in Alex Ovechkin. Jagr went on to play four seasons with the Rangers, spent three years in the KHL and returned to play seven more NHL campaigns with five clubs. He returned to his native Czech Republic in 2018 to finish his playing career with his hometown team, Rytiri Kladno.

Stats and player info via NHL.com and Hockey Reference.