Hockey fans love debating trades. Many notable deals still arouse fascination to this day. Who can forget the day the Edmonton Oilers shipped Wayne Gretzky to the Los Angeles Kings in 1988, or when the Philadelphia Flyers sent a plethora of players and picks to the Quebec Nordiques for Eric Lindros in 1992? How about the ridiculously one-sided Joe Thornton trade from Boston to San Jose in 2005? Those deals were either famous or infamous, depending on where your allegiance lies.

Of course, the Thornton trade was not the only lopsided trade in league history. Teams are routinely involved in trades, and many get burned, while others come out on top. It seems that some teams have not learned from history. This list takes a look at some of the most lopsided trades over the past five years in the NHL. It explores why the Bruins gave up Tyler Seguin in 2013, and why the Washington Capitals traded Filip Forsberg in 2014.

These deals cannot be undone, but in hindsight, these GMs probably wish they hadn’t pulled the trigger. Five years is usually the waiting period to see who really won a trade, but less than five years in, these deals already look one-sided.

15. Anthony Duclair traded to Arizona for Keith Yandle

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When the New York Rangers acquired Keith Yandle at the 2015 trade deadline, many fans hoped they picked up the missing piece for a deep playoff run. They dealt away defenseman John Moore, forward Anthony Duclair, and two draft picks for Yandle.

While Yandle performed respectably in his year-and-a-half tenure with the Rangers, he eventually signed with the Florida Panthers in 2016. Meanwhile, Duclair tallied 20 goals and 44 points in 81 games for Arizona, finishing tenth in the Calder Trophy race for the NHL’s top rookie. To be fair, Duclair’s production declined rapidly last season, to the tune of five goals and 15 points in 58 games.

Despite Duclair’s struggles last season, he is still just 22 years old. Coyotes GM John Chayka instilled a vote of confidence in Duclair, calling him “as talented as they come in this league.”

The deal had another upside for Arizona. They traded the two conditional picks from the Rangers to Detroit for the rights to Pavel Datsyuk and the team’s 2016 first-round pick. That pick was used to select young defenseman Jacob Chychrun.

14. Matt Moulson to the Wild in 2014

AP Photo/Seth Wenig

Matt Moulson’s tenure in Minnesota did not last as long as the Wild would’ve hoped. However, Wild GM Chuck Fletcher may have had no choice in bringing him from the Buffalo Sabres at the 2014 trade deadline. Fletcher dealt forward Torey Mitchell and two second round picks for Moulson and Cody McCormick. Mitchell allegedly requested a trade, although he later denied that rumor.

Moulson had 17 goals and 38 points in 55 games at the time of the trade, but only scored six goals in 20 games with the Wild. Meanwhile, McCormick scored two points in 14 games. Both players returned to Buffalo at season’s end.

Torey Mitchell didn’t make much of an impression in Buffalo and was shipped to Montreal at the 2015 trade deadline.

The downside for Minnesota was that they gave up two second round picks. The Sabres traded the 2014 pick to the Washington Capitals for two picks in that same draft. They selected forward Eric Cornel and defenseman Brycen Martin. More notably, they traded the 2016 pick to Montreal to acquire defenseman Josh Gorges.

13. Kris Russell to the Dallas Stars for Jyrki Jokipakka, Brett Pollock, and a 2nd round pick in 2016

Jerome Miron-USA TODAY Sports

The Dallas Stars needed a defensive upgrade at the 2016 trade deadline, and got their man in Kris Russell of the Calgary Flames. In exchange for Russell, the Stars gave Calgary young defenseman Jyrki Jokipakka, prospect Brett Pollock, and a conditional second round pick.

Russell went goalless in 11 regular season games (and 12 playoff games) with the Stars. His skating style never quite gelled in Dallas’ fast-paced system He signed with the Edmonton Oilers before the 2016-17 season, where he paired well with Andrej Sekera.

At the time of the trade, Pollock led the WHL’s Edmonton Oil Kings in scoring, and expressed surprise at Dallas’ decision to deal him. He has since put together a solid first season in the Flames’ minor-league system. Jokipakka notched just 12 points in 56 games as a Flame before being traded to the Ottawa Senators at the 2017 trade deadline.

The Flames used the conditional second-round pick to select WHL center Dillon Dube. He notched 55 points in 40 games last season for the Kelowna Rockets. The Stars, meanwhile, have nothing to show for the Russell deal.

12. Detroit Red Wings acquire Erik Cole and 3rd round pick for Matthias Janmark, Mattias Backman, and a 2nd round pick

via themajors.net

By the time the Detroit Red Wings traded for Erik Cole at the 2015 trade deadline, the former 30-goal scorer was a shell of himself as a player. The Red Wings picked him up from the Dallas Stars (along with a conditional third round pick) in exchange for forward Mattias Janmark, defenseman Mattias Backman and a second round pick.

Cole’s injury history reared its ugly head, as he played just 11 games in Detroit before being sidelined with a spinal contusion. He hasn’t played in the NHL since.

Meanwhile, Backman never played a game in a Stars sweater. He signed in Switzerland in 2017. Janmark fared much better in the NHL. He notched a 15-goal, 29-point rookie campaign in 2015-2016. Unfortunately, he missed the entirety of last season with a knee injury. Still, Janmark is just 24, and has yet to reach his full potential in the NHL.

As for the second round pick the Stars acquired in the Cole deal, they used it to select Finnish forward Roope Hintz. Hintz helped Finland capture the gold medal at the 2016 World Junior Championships, and recently signed a three-year entry-level deal with the Stars in 2017.

11. Eric Staal to the Rangers in 2016

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Just one year after the Yandle deal, the Rangers involved themselves in another disastrous trade deadline debacle. The Carolina Hurricanes fleeced the Rangers for two second-round picks (one in 2016 and one in 2017) and top prospect Aleksi Saarela for captain Eric Staal. On its face, the deal didn’t seem too one-sided. The Rangers were getting a top-six center, whose brother Marc, played on New York’s blueline. The reunited Staal brothers could bring some chemistry to the Rangers for the stretch run.

However, Staal underperformed in New York, scoring six points in 20 regular season games. He went scoreless in the 2016 playoffs and subsequently signed a three-year deal with the Minnesota Wild that July.

Carolina ended up getting the better of the deal in the long run. The Hurricanes traded the 2016 second-rounder to Chicago as part of a deal that brought in Bryan Bickell and Teuvo Teravainen. They selected defenseman Luke Martin with the extra 2017 second round pick.

Saarela signed a three-year entry-level deal with Carolina in 2016, and put up 10 points in nine games in the AHL in 2016-17.

10. Ben Bishop to the Los Angeles Kings in 2017

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Ben Bishop found himself at the center of two trade deadline blunders. The first occurred in 2013 when the Ottawa Senators dealt him to the Tampa Bay Lightning for Cory Conacher and a fourth round draft choice (Tobias Lindberg). The second occurred at the 2017 trade deadline, when Bishop was shipped west to the Los Angeles Kings along with Tampa Bay’s fifth-round pick in 2017. For the sake of “recent deals,” let’s focus on the 2017 deal.

In exchange for Bishop, the Lightning received veteran goaltender Peter Budaj, young defenseman Erik Cernak, and two picks in the 2017 draft. The Lightning traded one of those picks in a deal to acquire Mark Streit. They then dealt Streit to Pittsburgh in exchange for a fourth round pick in 2018.

Bishop went 2-3-2 in seven starts in Los Angeles, failing to get the Kings to the playoffs. The Kings traded him to the Dallas Stars for a fourth-round pick. Meanwhile, Budaj signed a two-year extension with the Lightning after the 2016-17 season. Cernak is developing as a “big, strong, physical” defenseman, according Stacy Roest, Tampa Bay’s director of player development.

9. Ryan Miller and Steve Ott to St. Louis in 2014 for William Carrier, Chris Stewart and two future draft picks

via hockeyworldblog.com

Ryan Miller was still on the backend of his prime by the time the Sabres traded him to the St. Louis Blues at the 2014 trade deadline along with Steve Ott. He amassed 15 wins in 40 starts at the time of the trade, and picked up 10 more wins in 19 starts with the Blues. However, the Blues were bounced in the first round by the Chicago Blackhawks. Miller left the Blues that summer, and signed a three-year, $18 million deal with the Vancouver Canucks.

The Blues traded Jaroslav Halak, a solid netminder in his own right, to acquire Miller. They also traded away William Carrier, Chris Stewart, a 2015 first round pick and a 2016 third round pick. The Sabres used that first rounder as part of the blockbuster 2015 trade deadline deal that brought Evander Kane, Zach Bogosian, and Jason Kasdorf to Buffalo. They used the third round pick in a package to acquire Dmitri Kulikov in 2016.

Although Carrier, Stewart, Halak, and Kulikov are no longer on Buffalo’s roster, the Sabres still received the larger haul in the Miller trade. Also, Kane and Bogosian serve important roles for the Sabres. On the other hand, Miller’s tenure in St. Louis lasted just 25 games.

8. Vancouver Canucks trade Roberto Luongo & Steven Anthony to the Florida Panthers for Jacob Markstrom & Shawn Matthias

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Roberto Luongo truly hit his stride in the NHL after the Florida Panthers traded him to the Vancouver Canucks in 2006. He won 252 games with the Canucks, and backstopped them to the 2011 Stanley Cup Final.

By 2014, however, Luongo became expendable. Even with Cory Schneider off the team, Canucks’ GM Mike Gillis needed to shed Luongo’s massive 12-year, $64 million contract. He traded Luongo back to the Panthers for goalie Jacob Markstrom and Shawn Matthias.
Luongo won 69 games in his first two and a half seasons back in Florida, although injuries limited him to just 17 wins in 40 games and last year. Meanwhile, Markstrom has gone 36-53-12 in his career thus far in Vancouver. Matthias enjoyed a career-best 18-goal, 27-point season in 2014-2015, but opted to not re-sign with the Canucks.

While Luongo revitalized his career in Florida, Markstrom has struggled in Vancouver so far. At this point, it seems the Canucks came out on the short end of this deal.

7. Minnesota Wild trade Brent Burns and a 2nd round pick to San Jose for Devin Setoguchi, Charlie Coyle, and a 1st round pick

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Any team that would be willing to trade Brent Burns for Devin Setoguchi would need to re-evaluate their priorities. However, in 2011, that trade might not have seemed so lopsided. The Minnesota Wild dealt Burns and a second round pick to the San Jose Sharks for Setoguchi, Charlie Coyle and a first round pick. By all accounts, the Wild got a solid return.

Fast forward to 2017, and all Minnesota has to show for the deal is Coyle. Setoguchi spent just two seasons with the Wild, notching 32 goals and 63 points in 117 games. He bounced around the NHL and AHL before signing a two-year deal with German hockey club, Adler Mannheim. The Minnesota Wild used that first-round pick from the Sharks to select Zack Phillips, who never suited up for the Wild, and now plays in Europe.

Fortunately, Coyle has developed into a solid franchise center, but that’s all the Wild have to show for the deal. Meanwhile, Burns’ production exploded once he arrived in San Jose. He has scored at least 20 goals in four of his six seasons with the Sharks. He scored a career-high 29 goals and 76 points in 2016-2017 en route to winning the Norris Trophy as the NHL’s top defenseman.

6. New Jersey Devils trade Adam Larsson to Edmonton for Taylor Hall

Perry Nelson-USA TODAY Sports

The 2016 offseason saw two blockbuster trades occur in the NHL. One had Devils GM Ray Shero send top defenseman Adam Larsson to the Oilers for sniper Taylor Hall in late June. The other saw the Canadiens send P.K. Subban to the Predators for Shea Weber. While the Canadiens/Predators trade was a wash, the Oilers/Devils trade was a bit more one-sided.

At the time, the Devils had a need for a skilled left-winger like Hall, as they were thin at the position. Larsson would help sure up Edmonton’s spotty defense. In his first season with the Devils, Hall certainly made his presence felt. According to stats database, Corsica Hockey, New Jersey’s shot attempts per 60 minutes increased from 45.5 with Hall off the ice to 57.4 with him on the ice. Goals per 60 minutes also increased from 1.61 to 2.08 by the same measure when Hall took the ice.

Yet, Larsson’s contributions meant more to his team’s overall success. Larsson’s play indirectly helped the Oilers reach the Western Conference Final. Hall’s scoring unfortunately couldn’t even help the Devils secure a playoff spot.

Hall put up 20 goals and 54 points, but he had a -9 rating in his first season, and saw his hit, shot block, and takeaway totals decline. Larsson’s steadiness on the blue line was apparent, as he put up a career-high +21 rating and averaged over 20 minutes of ice time. He also established career highs in hits (253), shot blocks (160) and takeaways (28).

This wasn’t the most one-sided trade for Edmonton, but one year in, it seems they got the better of the deal with New Jersey.

5. New York Islanders trade Matt Moulson, a 1st and 2nd round pick to Buffalo for Thomas Vanek

Anthony Causi/bloguin.com

Matt Moulson makes his second appearance on this list for his involvement in the October 2013 trade that saw him shipped north from Long Island to Buffalo. The Islanders acquired Thomas Vanek in exchange for Moulson and a first and second round pick in 2015.

The deal seemed alright on paper, as Vanek scored 44 points in 47 games as an Islander. However, as the trade deadline approached, it appeared Vanek was set on testing the free agent market. Islanders GM Garth Snow realized he had given up one of his top forwards (Moulson) and two future draft picks for a player who could bolt after less than one season.

In an attempt to salvage some sort of return for Vanek, Snow traded him to the Montreal Canadiens, along with a fifth round pick, for Sebastian Collberg and a 2014 second round pick. The Islanders eventually waived Collberg in May of 2016.

Meanwhile, the Sabres used that first round pick from the Islanders in a trade with the Senators at the 2015 draft to acquire Robin Lehner and David Legend. They selected defenseman Brendan Guhle with their second round pick.  Moulson returned to Buffalo in the summer of 2014, after a brief tenure in Minnesota.

4. Boston Bruins trade Dougie Hamilton to the Calgary Flames

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In just two seasons in Calgary, Dougie Hamilton emerged as a talented puck-moving defenseman for the Flames. He has scored 25 goals and 93 points in 163 games as a Flame since the start 2015-16 season. His success likely haunts the Bruins, who traded him away to Calgary in 2015 for a first round pick and two second round picks. The Bruins took OHL sniper Zachary Senyshyn in the first round, and took Jakob Forsbacka-Karlsson and Jeremy Lauzon in the second round. These prospects have NHL potential, but have just one game of NHL experience between the three of them. Senyshyn and Forsbacka-Karlsson have yet to make their Bruins debuts.

The Bruins justified the trade as a means of salary cap relief. Hamilton was an impending restricted free agent and, quite deservingly, wanted a raise. He signed a six-year, $34.5 million deal with the Flames shortly after the trade.

As stated, he blossomed into a stud defenseman alongside T.J. Brodie. He left a void on the Bruins’ blueline that they still have not filled.

3. Chicago trades Marko Dano, a 1st rounder, and a conditional 3rd rounder to Winnipeg for Andrew Ladd, Matt Fraser and Jay Harrison

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In hindsight, Andrew Ladd’s return to the Chicago Blackhawks at the 2016 trade deadline could’ve been a feel-good story. Ladd was a top-six forward, returning to the team with which he had won a Stanley Cup in 2010. He was arriving from Winnipeg in time for the Blackhawks’ playoff run, and played alongside captain Jonathan Toews.

It wasn’t so much Ladd’s offense that made this trade regrettable for Chicago. It was the return Winnipeg got for Ladd. Winnipeg landed Marko Dano, a 2016 first-round pick, and a conditional 2018 pick in exchange for Ladd, forward Matt Fraser and defenseman Jay Harrison. Ladd notched 12 points in the remaining 19 games that season, but struggled in the playoffs as Chicago fell to the Blues in a seven-game first-round series.

Ladd left Chicago at season’s end and signed a seven-year deal with the Islanders. Fraser spent last season playing in Europe, while Harrison never played a game in a Blackhawks sweater.

As for Winnipeg, they traded that first-round pick to the Flyers for the chance to move up and draft Logan Stanley 16th overall in 2016. Marko Dano also remained in Winnipeg, signing a one-year deal with the Jets last June.

2. Boston Bruins trade Tyler Seguin to Dallas in 2013

Sergei Belski-USA TODAY Sports

There is little doubt that the Joe Thornton trade ranks among the worst in Bruins franchise history. However, for the sake of recent deals, let’s focus on another regrettable deal: The 2013 Tyler Seguin trade to Dallas.

At the time of the deal, Bruins GM Peter Chiarelli believed Seguin had grown disgruntled in Boston and needed a change of scenery. He engaged in preliminary trade talks with the Buffalo Sabres, but opted to deal him to Dallas instead. He included forward Rich Peverley and defenseman Ryan Button in the deal. In return, the Bruins received Loui Eriksson, Reilly Smith, Matt Fraser, and Joe Morrow.

The trade was a flop for the Bruins. Seguin became a star in Dallas, netting three straight 30+ goal, 70+ point seasons for the Stars from 2013-2016. He capped off a 26-goal, 73-point season in 2016-2017.

The Bruins managed to get some solid offensive production out of Eriksson. He scored 62 goals and 147 points in three seasons with the team before signing with the Vancouver Canucks in 2016. Reilly Smith was shipped to Florida in 2015 as part of a package to acquire Jimmy Hayes. The Bruins waived Fraser in December of 2014. Morrow signed with the Canadiens in June of 2017.

Seguin continues to excel in Dallas alongside Jamie Benn, while none of the four players the Bruins received in that 2013 trade remain on the team.

1. Capitals trade Filip Forsberg to Nashville for Martin Erat and Michael Latta

Kim Klement-USA TODAY Sports

The Washington Capitals have chosen wisely at the NHL draft. Since 2006, they have selected Niklas Backstrom, Semyon Varlamov, Karl Alzner, John Carlson, Evgeny Kuznetsov, Filip Forsberg, Andre Burakovsky, all in the first round.

Wait, the Capitals selected Filip Forsberg? Why isn’t the Swedish star skating on Washington’s top line today? Well, it all goes back to an ill-advised trade with the Nashville Predators in April of 2013.

Washington traded Forsberg to Nashville for veterans Martin Erat and Michael Latta, who they hoped would help them in their playoff run. To say the trade backfired would be the understatement of the decade. Erat played just 62 games for Washington, scoring two goals and 27 points before the Capitals saw enough and traded him to the Arizona Coyotes at the 2014 trade deadline. Latta left Washington in June of 2016 to head west and sign with the Los Angeles Kings.

Meanwhile, Forsberg’s fame skyrocketed as he became one of Nashville’s franchise players. He capped off his second straight 30+ goal season in 2016-17, and was a key offensive force for the Predators during their run to the Stanley Cup Final in June. Look for his star to continue shining bright in Music City for years to come.

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