Hockey fans love to play the role of general manager when it comes to trades. Whether they’re bragging over their team landing a big-name star, or complaining about the blue chip prospects they traded away, every fan has an opinion.
Some of the biggest deals in history (Gretzky to the Kings, Messier to the Rangers, Roy to the Avalanche) have polarized fan bases and sparked debate. Some discussions still endure to this day.
However, as the new millennium arrived, big-time trades in the NHL continued. For instance, the Sabres dealt franchise goalie Dominik Hasek to Detroit, and the Ducks shipped superstar Teemu Selanne to San Jose. While the Red Wings and Sharks each benefitted from these trades, the Sabres and Ducks certainly lost out.
For every trade winner, there is a loser. Every “smart” GM who wins a trade needs to have taken advantage of another GM’s ill-advised decision. A GM may “fleece” another in a deal, but of course, there has to be a GM getting fleeced, if you catch my drift.
Case in point, New York Rangers GM Glen Sather came out on the winning end of the lopsided “Scott Gomez-for-Ryan-McDonagh” trade in 2009. Montreal GM Bob Gainey got the short end of the deal. What turned out being a great move for the Rangers was a disaster for the Canadiens.
That is just one instance. Here is every NHL team’s worst trade since 2000.
30 Anaheim Ducks - Trading Teemu
Teemu Selanne retired from the Anaheim Ducks in 2014 as the franchise’s leading scorer. He helped the team capture its only Stanley Cup Championship in 2007.
“The Finnish Flash” registered two 50+ goal seasons during his initial run in Anaheim in the late 90s. Surely, the Ducks would never trade him, right?
Midway through the 2000-01 season, the Ducks dealt their leading scorer to their neighbors in San Jose. In return, the Sharks sent Jeff Friesen, Steve Shields, and a second-round pick.
The deal failed in hindsight, as Friesen and Shields each played just one season in Anaheim before being traded. Friesen was shipped to the Devils, and Shields went to the Bruins.
29 Arizona Coyotes - Briere To Buffalo
Daniel Briere has enjoyed a successful career in the NHL despite initial concerns over his diminutive size. He stood at 5-foot-9, but registered more than 300 goals and nearly 700 points over an 18-year career.
Briere began his professional career with the Phoenix Coyotes in the late ‘90s, and by the 2001-02 season, registered his first 30-goal, 60-point season. His totals dropped the following season to 17 goals and 46 points, respectively, and his defensive coverage was suspect.
The Coyotes needed a strong, physical forward, and thus, shipped Briere to the Buffalo Sabres for Chris Gratton at the 2003 trade deadline. The teams also swapped mid-round draft picks in 2004. The trade was criticized and came back to bite the Coyotes. Briere went on to play well for the Sabres, scoring 65 points in his first season en route to being named team captain in February of 2004.
28 Boston Bruins - Seguin To The Stars
The infamous Joe Thornton trade to San Jose was a definite contender for this spot. However, the Bruins still received a few decent players in that deal in Wayne Primeau and Brad Stuart.
The 2013 Tyler Seguin trade was disastrous, not only because of the bonafide superstar Seguin became but the lack of return on investment the Bruins received.
Boston general manager Peter Chiarelli believed Seguin needed a change of scenery and dealt his young star to Dallas for Loui Eriksson, Reilly Smith, Matt Fraser, and Joe Morrow.
Eriksson and Smith proved to be the only quality pieces in that trade for Boston. Most notably, Eriksson scored 62 goals and 147 points in three seasons with the team. However, both players no longer play in Boston. Smith was traded to Florida in 2015, and Eriksson signed in Vancouver in 2016.
27 Buffalo Sabres - Hasek To Hockeytown
Dominik Hasek holds one of the greatest legacies in Sabres history. He led the team to the Stanley Cup Final in 1999 and is the franchise record holder for wins, games played, shutouts, and goals-against-average.
Unfortunately, by 2001, Hasek had grown impatient with the direction of the team and requested a trade to a contender.
The Sabres dealt Hasek to the Detroit Red Wings in the early morning hours of July 1, 2001. The return? Forward Slava Kozlov, a 2002 first-round pick and future considerations (Jim Slater).
The deal was a dud for Buffalo. Kozlov spent just one season with the team, scoring nine goals and 13 assists in 38 games before a mid-season trade to the Atlanta Thrashers. The team used that first round pick to trade up and select Daniel Paille. Paille never excelled in Buffalo and later found a niche in Boston. Slater, meanwhile, never played for the Sabres.
26 Calgary Flames - Giguere Goes South
Calgary truly “flamed out” with this trade. They dealt young goalie Jean-Sébastien Giguère to the Ducks for a second-round pick (Matt Pettinger) in the summer of 2000.
Giguere went on to lead the Ducks to two Stanley Cup Finals appearances in nine seasons with the club, while the Flames eventually traded Pettinger to the Capitals for a fourth-round pick and left winger Miika Elomo.
Elomo never ended up playing a game for the Flames, while Giguere became one of the greatest goaltenders in Ducks franchise history.
25 Carolina Hurricanes - Mr. Game 7 Goes To Hollywood
Justin Williams loves scoring the big goal, especially in the playoffs. He has a league-record seven Game 7 goals, and 14 Game 7 points. Yet, that didn’t stop the Carolina Hurricanes from shipping him to the Los Angeles Kings at the March 2009 trade deadline in exchange for Patrick O’Sullivan and a second-round pick.
Carolina didn’t lose out entirely, as they later traded O’Sullivan to Edmonton for Erik Cole and a fifth-rounder. However, after a few successful seasons in Carolina, Cole signed in Montreal in 2011. Meanwhile, Williams won two Stanley Cups with the Los Angeles Kings, winning the Conn Smythe Trophy as playoff MVP during the team’s 2014 championship run. He signed with Washington in 2015 and continues to be a key contributor to the Caps’ offensive attack.
24 Chicago Blackhawks - Vrbata To The Desert
The Blackhawks haven’t faltered much over the past decade. The team has captured three Stanley Cups championships and is a routine contender year in and year out.
However, in 2007, then-general manager Dale Tallon was still working out his roster, trying to wheel and deal and give birth to the team we know today.
Tallon made the curious decision to trade forward Radim Vrbata after less than two full seasons in the Windy City. After a promising 34 points in 45 games in 2005-06, Vrbata’s production faltered the following season. Tallon shipped him to Phoenix before the 2007-08 season for Kevyn Adams.
If you needed to run a quick search on that name, you’re not alone. Adams played 27 games for the Blackhawks that season, scoring two assists. He never played in the NHL again. Vrbata went on to record 56 points in 76 games for the Coyotes in 2007-08. He has turned into a solid top-six forward for both the Coyotes and Canucks,
23 Colorado Avalanche - Drury To Calgary
Alex Tanguay nearly took this spot, but then again, the Avalanche received a decent return for the play-making forward. The same can’t be said for their trade of Chris Drury before the 2002-03 season. Drury won the Calder Trophy after a 44-point rookie campaign and developed a knack for scoring clutch goals. He potted 11 playoff goals during the Avs’ 2001 cup run.
That didn’t stop Colorado from trading Drury to Calgary (along with two-way forward Steven Yelle) in exchange for Derek Morris, Dean McAmmond, and Jeff Shantz.
The deal soon snowballed into a disaster for the Avalanche. Morris spent less than two seasons in Colorado before leaving for Phoenix at the 2004 trade deadline. McAmmond played a mere 41 games before a mid-season trade back to Calgary. Shantz signed in Europe after the 2002-03 season.
22 Columbus Blue Jackets - Columbus Gets One Year Of Carter
The Blue Jackets are arguably the hottest team in the NHL right now. They appear to be enjoying a revival this season after several seasons of non-contention.
However, back in 2011, the team was still struggling to find its identity, and their questionable trade moves reflected that.
The Jackets traded for Philadelphia Flyers sniper Jeff Carter. In return, Columbus sent Jakub Voracek, a first-round pick (Sean Couturier) and a third-round pick (Nick Cousins) to Philadelphia.
Talk about a doomed trade. Carter was largely dissatisfied with the Blue Jackets’ system and culture. Less than one year into his Blue Jacket tenure, Carter was traded to Los Angeles for Jack Johnson and a first-round pick (Marko Dano).
21 Dallas Stars - Passing On Perry
It’s never easy to evaluate a team’s trade when it involves draft picks. In these cases, teams can’t predict the careers that these young players might have, so trading them is truly a 50-50 move.
However, that uncertainty came back to haunt the Dallas Stars on Draft Day 2003 when they traded their first round pick (28th overall) to the Anaheim Ducks for two second-round picks. Of course, the Stars didn’t know that the Ducks would use that pick to select Corey Perry.
The Stars selected Vojtech Polak and B.J. Crombeen with the 36th and 54th overall picks, respectively.
Polak played five career NHL games while Crombeen fared slightly better. He remained in the NHL as a bottom-six forward with a penchant for dropping the gloves. He has registered 35 goals and 80 points in 445 career games through the end of the 2015-2016 season. As for Perry? 319 goals and 664 points in 804 games.
20 Detroit Red Wings - Renting Legwand
Much like the Blackhawks, the Red Wings have had great success at drafting and developing young players in recent seasons. For Detroit, this success goes back even further than that of Chicago, as the team drafted late-round gems like Henrik Zetterberg, Pavel Datsyuk, Jimmy Howard, and Dylan Larkin just to name a few.
So when general manager Ken Holland moved top prospect Calle Jarnkrok, fourth-liner Patrick Eaves, and a 2014 second rounder to the Nashville Predators at the 2014 trade deadline, fans hoped they’d see a huge return.
They received Nashville center, David Legwand, brought in as a rental player for a playoff run. Things didn’t go as planned, and Legwand scored four goals and 11 points in 21 games before going scoreless in the team’s five-game playoff run.
19 Edmonton Oilers - So Long, Captain
The Oilers have an exciting young team to build around this season, but despite a recent flurry of top draft picks, haven’t enjoyed the level of success that management had hoped for.
The team’s last major playoff run came in 2006 when they lost a tough seven-game Stanley Cup Final to the Carolina Hurricanes. One of the key pieces to that Oiler team was Ryan Smyth. Smyth spent the first 12 seasons of his career in Edmonton, but couldn’t come to an agreement on a contract extension past the 2006-07 season.
As a result, the team traded Smyth to the Islanders for Ryan O’Marra, Robert Nilsson and a first-round pick (Alex Plante) at the 2007 trade deadline.
18 Florida Panthers - Give Up Luongo's Prime Years
The Florida Panthers knew that they had a great talent in Roberto Luongo. The young goalie made the 2004 All-Star team and was a finalist for the Vezina Trophy and Lester B. Pearson Award that same year.
That didn’t stop then-Panthers general manager Mike Keenan from making one of the worst trades of the decade in 2006. He dealt Luongo, Lukas Krajicek and a sixth-round pick (Sergei Shirokov) to Vancouver for Alex Auld, Bryan Allen, and Todd Bertuzzi.
It’s unclear what Keenan saw in Bertuzzi at that point but he traded away his franchise goalie because of it. More confounding was the fact that Luongo had just set the team record for wins by a goaltender in a single season, with 35.
Bertuzzi ended up playing seven games for the Panthers, scoring eight points before back spasms ended his season.
Luongo went on the cement his status as an elite goaltender in Vancouver, while Bertuzzi bounced between the Flames, Ducks, and Red Wings before his 2014 retirement.
17 Los Angeles Kings - Mortgaging The Future
Mike Richards helped the Kings win a couple of Stanley Cup titles during his tenure on the West Coast, but what the Kings gave up to get him will sting for a while.
The Kings dealt forwards Wayne Simmonds and Brayden Schenn (along with a second-round pick) to Philly in 2011 for Richards and depth forward Rob Bordson.
Over the years, Simmonds and Schenn became mainstays in the Flyers’ top-six rotation, while the Kings released Richards after his June 2015 arrest for drug possession. He scored a career-low 16 points in 53 games during his final season in Los Angeles in 2014-15.
16 Minnesota Wild - Getting Burned
Some of Minnesota’s smarter trades have brought in Devan Dubnyk and Marek Zidlicky. However, that’s not to say the team hasn’t made some “wildly” poor deals. Awful joking aside, the Wild once had a talented defenseman named Brent Burns. He emerged as a top defenseman on the team in 2007-08 with 15 goals and 28 assists for 43 points. Despite having another career in 2010-11 (46 points), the Wild traded Burns to San Jose at the 2011 NHL Draft.
In return for Burns (and a 2012 second-rounder), the Sharks gave the Wild struggling forward Devin Setoguchi, young winger Charlie Coyle, and a first-round pick. Setoguchi scored 32 total goals in two unspectacular seasons in Minnesota, while that first-round pick, Zack Philips, never played a game for the Wild.
Fortunately, Charlie Coyle established himself as a solid power forward with promising potential. He scored a career-best 21 goals and 42 points in 2015-16.
15 Montreal Canadiens - The Scott Gomez Deal
By 2009, New York Rangers general manager Glen Sather knew Scott Gomez's $7.4 million cap hit was an albatross on the team's payroll. The center hadn't played up to expectations, and Sather needed to deal him to save some cap space.
Sather found his suitor in Montreal GM Bob Gainey, who offered defensive prospect Ryan McDonagh and forwards Chris Higgins and Pavel Valentenko for Gomez, Tom Pyatt, and Michael Busto. The Rangers used the cap space they saved in the deal to sign sniper Marian Gaborik shortly after. Gaborik went on to have two 40+ goal seasons, while Gomez was waived in January 2013 after a two-goal, 11-point 2011-12 season with the Habs.
The true steal of the deal was McDonagh, who emerged as the Rangers' best defenseman and eventual team captain. He plays top-pair minutes, runs the power play, shuts down the other team's top-line players, and joins the rush on offense.
14 Nashville Predators - Too Late For Forsberg
Peter Forsberg’s career numbers are nothing short of spectacular. He scored 249 goals and 636 assists for 885 points in just 708 games. Foot injuries sidelined Forsberg for long stretches of his career, and it’s fairly certain that he could've built on those totals had he been fully healthy.
Unfortunately, when the Predators traded for Forsberg before their 2007 playoff run, the Swedish star was a shell of his former self. Given that Nashville traded Scottie Upshall, Ryan Parent, a first and fourth-round pick to Philadelphia in exchange, this deal was fairly lopsided. He still produced at a near point-per-game pace and contributed two goals and four points in five games in the postseason.
13 New Jersey Devils - Willie Mitchell To Minny
The Devils were en route to a second consecutive Stanley Cup Final appearance in 2001 and needed a rental player for the playoff push. Team GM Lou Lamoriello traded for Minnesota Wild defenseman Sean O'Donnell at the March trade deadline.
He sent back another defenseman in return, a young 23-year-old named Willie Mitchell. Perhaps you've heard of him.
While O'Donnell did help the Devils get to a Game 7 of the 2001 Stanley Cup Final (where they lost to the Avalanche), he was nothing more than a short-term piece. He left for Boston the following season, while Mitchell blossomed into a top-pair, stay-at-home defenseman and one of the great leaders in today's NHL. He was a steady blueline presence for the Wild, the Canucks, and the Kings over the next decade.
12 New York Islanders - Milbury Strikes Again
The Islanders created a fiasco of epic proportions when they traded Zdeno Chara in 2001. They dealt the then 24-year-old defenseman alongside Bill Muckalt and a first-round draft pick to the Islanders for Alexei Yashin.
Of course, the deal didn’t sound terrible at the time. Yashin was a star in Ottawa, scoring 491 points in 504 games during his tenure with the Senators. Meanwhile, Chara scored six goals total in his first three seasons on Long Island.
However, the Senators knew that Chara’s formidable 6-foot-9, 250-pound frame would serve him well. While the Islanders limited his power play minutes, the Senators encouraged him to shoot the puck on the power play. This new-found confidence led to Chara potting 10 goals in his first season in Ottawa.
Armed with a massive slap shot, Chara built on his point totals each season, culminating in a 19-goal, Norris Trophy-winning 2008-09 season. He also captained the Bruins to the Stanley Cup in 2011.
11 New York Rangers - Sacrificing Speed
The Rangers have made many boneheaded free agent signings over the past 16 years. From Bobby Holik, to Scott Gomez, to Wade Redden, to Donald Brashear, general manager Glen Sather has also made a few ill-advised trades.
The Rangers’ 1999 trade of Marc Savard to Calgary backfired. However, as far as post-2000 deals are concerned, the worst was shipping speedy forward Carl Hagelin to Anaheim in 2015 along with two draft picks. New York received forward Emerson Etem and a 2015 second-round draft pick.
The Rangers hoped Etem could replace Hagelin’s speed and penalty-killing prowess but were greatly disappointed. Etem failed to produce at the level Hagelin had on the third line, and he was traded to Vancouver mid-season after going goalless in 19 games.
10 Ottawa Senators - Booting Bishop
The Senators were in a bit of a dilemma with their goaltending situation in 2013. They had a solid, veteran goaltending option in Craig Anderson, but also had young netminders in Ben Bishop and Robin Lehner. Only one could earn the backup role, and Ottawa opted to go with Lehner.
Thus, the Senators traded Bishop to the Lightning in April of 2013 for Cory Conacher and a fourth-round draft pick. The Senators never thought that Bishop would develop into one of the best goalies in the NHL. He won 112 games for the Lightning in his three full seasons with the team and was a two-time Vezina Trophy finalist.
9 Philadelphia Flyers - Sharp To Chi-Town
Patrick Sharp has been such a valuable piece to the Blackhawks’ championship teams, that it’s easy to forget he was once a Philadelphia Flyer.
However, Sharp spent much of his tenure in the City of Brotherly Love playing for the Flyers’ AHL affiliate. He scored five goals and eight points in 22 NHL games before the team decided to trade him to Chicago in December of 2005. The Flyers sent Sharp and Eric Meloche to the Chicago Blackhawks for Matt Ellison and a third-round draft choice in 2006.
Sharp found his scoring touch with the Blackhawks, scoring 20 goals in his first full season in the Windy City. By 2007-08, he was emerging as a star, recording career-highs of 36 goals, 26 assists, and 62 points. He also led the team in power play goals (nine) and game-winning goals (seven). Sharp scored at least 20 goals in five of his next seven seasons in Chicago. He now plays in Dallas.
8 Pittsburgh Penguins - Mr. Jagr Goes To Washington
I consider the Markus Naslund trade in 1995 to be the worst in Pittsburgh franchise history. However, since that deal was made pre-2000, it doesn't qualify for this list. The worst post-millennium deal for the Penguins was the 2001 trade of superstar winger Jaromir Jagr to the Washington Capitals.
To be fair, Jagr put Pittsburgh's management in a tough position, since he demanded a trade in the first place. He grew dissatisfied with the perceived disrespect he faced from the organization after Mario Lemieux's return.
The team dealt him to the Capitals along with Frantisek Kucera in July 2001 for centers Kris Beech and Michal Sivek, defenseman Ross Lupaschuk and future considerations.
Beech played in 100 games for the Penguins and scored 10 goals and 17 assists. Sivek scored just six points in 38 games, and Lupaschuk went pointless in three career NHL games.
7 San Jose Sharks - Heatley x2
The Sharks’ worst post-2000 deal is, in fact, two separate deals involving the same player: Dany Heatley. The Sharks coveted the high-scoring Senators winger, and in 2009, sent forwards Milan Michalek and Jonathan Cheechoo to Ottawa in return.
Heatley played very well in his first season in San Jose, scoring 39 goals and 82 points in 82 games. He notched another 13 points in 14 playoff games.
However, his second season in the Shark Tank saw his production dip to 26 goals and 64 points. Heatley’s massive contract and cap hit hampered the Sharks, so they traded him for another top-six forward, Martin Havlat, in July 2011.
6 St. Louis Blues - Goaltending Rental Fails
Don't get me wrong, Ryan Miller is a great goaltender. He averaged 30 wins or better in every season as the Buffalo Sabres' starter. Yet, the Blues overpaid for him in February of 2014, dealing starting goalie Jaroslav Halak, young forward Chris Stewart, William Carrier, a first-round pick in 2015, and a third-round pick in 2016.
The trade gave Blues fan optimism that they had their missing piece to a long Stanley Cup run. Unfortunately, it was not to be.
The Blues lost to the Chicago Blackhawks in the first round of the 2014 playoffs, with Miller posting a .897 save percentage and 2.70 goals-against-average. The Blues re-signed netminder Brian Elliott that offseason, and let Miller walk as a free agent.
5 Tampa Bay Lighting - Richards To Dallas
Brad Richards was instrumental in guiding the Tampa Bay Lightning to its only Stanley Cup Championship in 2004. He won the Conn Smythe Trophy as playoff MVP with 26 points in 23 games as the Lightning doused the Flames in an epic seven-game series.
So when the Lightning traded Richards to the Dallas Stars in 2008, Bolts fans wondered what management’s thinking was. They must’ve been even more flabbergasted when they saw the terms of the deal. The Lightning dealt Richards and goaltender Johan Holmqvist to the Dallas Stars for goaltender Mike Smith, winger Jussi Jokinen, and center Jeff Halpern. They also threw in a fourth-round pick in the 2009 draft.
It’s safe to say the deal didn’t work out for Tampa Bay, and they missed the playoffs in the three seasons since the trade. Smith and Jokinen struggled through disappointing tenures, before finding success in Arizona and Carolina, respectively.
4 Toronto Maple Leafs - Steen To St. Louis
In 2008, Toronto GM Cliff Fletcher knew he needed to shake up the team roster before Brian Burke came in as his replacement. He traded forwards Carlo Colaiacovo and Alex Steen to St. Louis in exchange for Lee Stempniak.
At the time, the deal didn’t seem too outrageous. Colaiacovo had struggled with injuries for much of his Toronto tenure, and Steen had just four points on the season to that point. Meanwhile, Stempniak had 13 points through the Blues’ first 14 games.
As it turned out, Stempniak’s and Steen’s career trajectories went in two very different directions. Stempniak turned into the serviceable fourth-line forward that Steen had been in Toronto, while Steen went on to become the player the Leafs had hoped Stempniak would be.
3 Vancouver Canucks - Who Needs Goaltending?
The 2011-12 Vancouver Canucks sported one of the most fearsome goalie tandems in the entire NHL: Roberto Luongo and Cory Schneider. Schneider took over the starting job from Luongo after a November 2011 injury sidelined Luongo for a spell.
Schneider went on to set team records for goals-against average and save percentage during the 2011-12 season and started the team’s first-round playoff series against the Los Angeles Kings that spring.
However, after a year of trying to trade Luongo, the Canucks realized Schneider could fetch them a better return, given his recent streak of quality play.
The problem was, they didn’t get an equal return. The Canucks sent Schneider to the Devils in 2013 for the ninth overall selection in the 2013 draft (Bo Horvat).
2 Washington Capitals - Forking Over Forsberg
The Washington Capitals have no shortage of talented young stars on their roster. They've developed Nicklas Backstrom, Evgeny Kuznetsov, Braden Holtby, and others into core pieces of the team's success.
Another prospect the Caps could've used in their youth movement is 22-year-old Filip Forsberg. Yet, Washington traded Forsberg to Nashville at the 2013 trade deadline for 31-year-old Martin Erat and center Michael Latta.
1 Winnipeg Jets/Atlanta Thrashers - Hosed For Hossa
The Winnipeg Jets are doing their best to re-establish themselves after relocating from Atlanta in 2011. Winnipeg has a team full of young talents like Mark Scheifele and Patrik Laine, and a rabid fan base for support.
Yet, they endured serious hardships before their relocation from Atlanta. One such disaster was the lopsided 2008 trade that shipped star forwards Marian Hossa and Pascal Dupuis to Pittsburgh for Angelo Esposito, Colby Armstrong, Erik Christensen, and a first-round pick (Daulton Leveille).
Sure, the Penguins gave up a lot in terms of quantity but maximized on the quality in this deal. Hossa and Dupuis helped the Penguins reach the Stanley Cup Final that season. Hossa, in particular, notched 26 points in 20 playoff games.
On the other hand, neither Esposito nor Leveille played a single game for the Thrashers. Esposito was traded to the Panthers in 2011. Christensen scored seven goals and 23 points in less than two seasons in Atlanta. Armstrong was the only player to contribute on some level during his during his two years with the Thrashers.
Fortunately, moving to a new city creates opportunities to forge a new identity. The Jets would be happy to move on from the shadow of their former franchise and forget about this botched trade.
Leave A Comment
Looking for an AD FREE EXPERIENCE on TheSportster?Get Your Free Access Now!