Top 25 Worst Trades in NHL History

The old saying of “The grass is always greener…” is a good way to describe NHL general managers. GMs always see players performing well for other teams and want them to take the ice for their squad. Or maybe it’s a case of a selling GM has a player that’s going to be a free agent after the season. They always want to get a good return for that player rather than lose them with no compensation at all. So trades are made that each GM thinks is going to improve his team. But there are risks that come with each deal that is made. Some may work out very well while some may work out pretty badly. In some cases both happen on the same trade. In a single trade one team can get an outstanding return while the other team gets screwed for years. That’s what we will take a look at today. Here are the 25 worst trades ever completed in the history of the NHL.

25 Ilya Kovalchuk for 3 players and 2 draft picks 

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The New Jersey Devils have a rich tradition of putting together winning squads over the last twenty years. They have made a lot of trades during that time and while a lot of them make you scratch your head, they always seem to work out in the end for them. But then out of the blue in 2010 they traded for Ilya Kovalchuk and all of that went out the window. While it looked like a major addition for the team at the time of the deal, it ended up quite the opposite.

New Jersey sent Johnny Oduya, Niclas Bergfors, Patrice Cormier, and a first and second round draft pick to the Atlanta Thrashers for Kovalchuk, Anssi Salmela and a second round pick.

After a couple of seasons with the Devils that could be considered OK at best, Kovalchuk left the NHL and went back to Russia to play in the KHL. He had 12 years left on his newly signed contract with New Jersey that was worth around $77 million. One day he just walked away from it. The rest of what the Devils received didn’t amount to anything and most of what went to Atlanta didn’t work out for the Thrashers either. Oduya has continued to be a top defenseman and was part of a Stanley Cup winning team in Chicago. But overall this deal was a bust for both sides.

24 Ryan Smyth for two players and a 1st round draft pick 

For twelve years Ryan Smyth played solid hockey for the Edmonton Oilers. He earned the nickname of “Captain Canada” for his hard play. In 2007 the Oilers shocked the league when they sent him to the New York Islanders for Ryan O’Marra, Robert Nilsson and a first round draft pick that ended up being Alex Plante.

This is another trade that didn’t work out for either team as Smyth helped the Islanders sneak into the playoffs that year but didn’t stick around on the island. He played for two other teams before ending up back in Edmonton four years later. What the Oilers got amounted to nothing as O’Marra played in only 33 games in Edmonton and then went to play in Norway. Plante went to play in Austria and Nilsson went to play in Russia. So this deal basically amounted to the Oilers giving up their best player so that a few other teams could use his services for awhile, and for it they got nothing in return.

23 Miroslav Satan for Craig Millar and Barrie Moore 

In 1997 the Oilers made another trade that they would feel for many years to come. They weren’t happy with how Miroslav Satan was developing so they traded him to the Buffalo Sabres for Craig Millar and Barrie Moore.

Satan turned into one of the league’s top snipers as he scored more than 30 goals in a season three different times. He reached the 29 goal mark in a season on two other occasions and he put together a 75 point year in 2003.

On the other side of the deal it took Millar three seasons to reach the 36 games played mark and he had a total of only six points during that time. But it’s better than what Moore did. He played in just four games for the Oilers and does not have an NHL point to his credit.

22 Pavol Demitra for Christer Olsson 

Via minnesota.cbslocal.com

This was a horrible deal for the Ottawa Senators. In late 1996 they traded Pavol Demitra to the St. Louis Blues for Christer Olsson. Olsson played in only 25 games for Ottawa and totaled up two goals and three assists for just five points. He ended up going to play in Europe.

Demitra grew into a star with the Blues scoring more than 20 goals in a season in seven of his eight years in St. Louis. Three times he tallied more than 30 goals and he was consistently one of the top point scorers in the NHL.

21 Marian Hossa for 3 players and a 1st round draft pick 

Via commons.wikimedia.org

In 2008 the Atlanta Thrashers were led by Marian Hossa but the team could not win hockey games. Whatever Hossa put up offensively, Atlanta gave up double defensively. So they sent him to the Pittsburgh Penguins along with Pascal Dupuis for Colby Armstrong, Angelo Esposito, Erik Christensen, and a first round draft pick that turned out to be Daultan Leveille.

Hossa went to the Stanley Cup Finals that year with the Penguins and the following year he did the same with the Detroit Red Wings. He fell short in his bid for a championship but later won two Stanley Cups with the Chicago Blackhawks. Dupuis flourished with the Penguins while playing with Sidney Crosby.

Esposito and Armstrong were highly touted prospects that never amounted to anything and Christensen and Leveille amounted to less than that. Atlanta had a real chance to improve their franchise by moving Hossa, but they failed miserably and the team isn’t even in the United States anymore.

20 Markus Naslund for Alek Stojanov 

In 1996 Markus Naslund was finally finding his groove in the NHL with the Pittsburgh Penguins. The team was disappointed that it took him that long to start producing on the ice so they decided to take a chance on another prospect. They traded Naslund to the Vancouver Canucks for Alek Stojanov.

Stojanov was the #7 overall draft pick in the 1991 NHL Draft and Pittsburgh thought they had a future star coming back for Naslund. But it didn’t turn out as they had hoped. The highly regarded prospect played in only 107 games in the NHL and notched a disappointing total of just seven points. Vancouver however received one of the best players in the history of their franchise.

Naslund became a star for the Canucks for 12 years and spent a great deal of time as the captain of the team. In 2003 he scored a career high of 104 points and after he retired the Canucks retired his #19 jersey. This deal was one of the best in Vancouver’s history while it was one of the worst in the Penguins’ history. Luckily Pittsburgh had several other stars on the team so it was easy for them to get over the mistake.

19 Butch Goring for Billy Harris and Dave Lewis 

When the New York Islanders were preparing for their playoff run in 1980, they made a trade with the Los Angeles Kings that would seal their fate for the next several years. In a good way. They sent Billy Harris and Dave Lewis to the Kings for Butch Goring. Goring was already a star in Los Angeles having won the Bill Masterson trophy and the Lady Byng trophy. His addition would lift the Islanders to four Stanley Cups in a row while Lewis and Harris didn’t do much with the Kings.

Harris was good when he was playing hockey on the island but he couldn’t keep it going once he moved out to the west coast. Lewis played for the Kings for a few years but was never a star and didn’t really make a good name for himself until he started coaching.

18 Tom Kurvers for a first round draft pick 

Via sportsnet.ca

The Toronto Maple Leafs have a long history of bad luck in drafts and in trades. This one transaction covered both bases in one shot. In 1990 Toronto was off to a slow start to the season. They felt that their defense needed to be stronger so they made a trade with the New Jersey Devils for defenseman Tom Kurvers. They send their first round draft pick to the Devils in the next draft. The previous year Kurvers had the best season of his career scoring 66 points. He finished that season with 52 points for the Maple Leafs, which wasn’t a bad year at all. The only problem was that the team never started winning hockey games and that first round pick turned out to be the #3 overall pick.

New Jersey used that #3 overall pick to select Scott Niedermayer who went on to a great career that featured four Stanley Cup rings, three with New Jersey. His jersey #27 was eventually retired by the team and it currently hangs from the rafters at The Prudential Center.

Kurvers was traded to the Vancouver Canucks for Brian Bradley. The Leafs then didn’t protect Bradley and he was chosen by the Tampa Bay Lightning in the expansion draft. His first year with the Lightning he scored 42 goals.

This trade has haunted Toronto for years. It was the beginning of several losing seasons after that. It’s amazing the long coming repercussions that can be felt from just one bad decision.

17 Jerry Korab for a 1st round draft pick (Phil Housley)

Via ebay.com

Sometimes things work out in trades and sometimes they don’t. At the trade deadline in 1980 the Los Angeles Kings sent a first round draft pick to the Buffalo Sabres for Jerry Korab. The Kings got a physical defenseman that was well past his prime and they overpaid for him. And it cost them dearly.

Buffalo used that first round draft pick, which turned out to be #6 overall, to choose Phil Housley. He only became one of the best ever offensive defensemen in hockey history. He played in seven all star games and was king of the point at the offensive blue line for 21 years.

16 Pat Verbeek for Sylvain Turgeon 

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In the summer of 1989 the Hartford Whalers and New Jersey Devils traded snipers. At the time of the deal it looked like a pretty even trade. The Whalers sent Sylvain Turgeon to the Devils for Pat Verbeek.

But Turgeon only played a single season in New Jersey, scoring 30 goals, before he was traded to the Montreal Canadiens. Verbeek had been a star in New Jersey and he continued to be one in Hartford for six more years. He scored 37 or more goals on 4 different occasions and he topped the 75 points in a season mark four times as well.

When New Jersey traded Turgeon to Montreal he had pretty much scored all the goals that he was going to score in his career. Maybe they knew something because they got Claude Lemieux in that trade. Lemieux played for the Devils for five seasons and was a key part of the 1995 Stanley Cup championship team.

It’s hard to tell what New Jersey was thinking when they sent Verbeek to Hartford. At the time he was the single season franchise leader in goals scored. But they got lucky and it worked out in the end.

15 Scott Gomez for Ryan McDonagh and three others 

Via canadiens.nhl.com

After several great seasons with the New Jersey Devils, Scott Gomez bolted across the river to the New York Rangers via free agency. New York gave him a huge contract that averaged out to be more than $7.3 million per season. Gomez had a very good first year with the Rangers and then he fell off the map.

He still had good trade value when the Rangers shipped him and Tom Pyatt, along with Michael Busto to the Montreal Canadiens for the rights to Ryan McDonagh, Christopher Higgins, Pavel Valentenko, and Doug Janik.

Based only on what Gomez did on the ice in Montreal, this is one of the worst deals that Montreal has ever made. His production continued to decline to the point that three years later the Canadiens told him to just stay home and not even bother coming to training camp. Eventually they bought out his contract.

McDonagh turned into one of the top defenseman in the NHL and he still has a lot of great hockey ahead of him.

After some rough years Gomez came back to the NHL and performed decently, but he hasn’t put up anywhere near the numbers that he did at the beginning of his career. It was almost like one day he woke up and just forgot how to play hockey.

None of the other players in the deal were spectacular. Janik was decent but past his prime at that point and Pyatt wasn’t all that bad. The keys were Gomez and McDonagh. The Rangers have made a lot of bad deals over the years but they got this one right.

14 Patrick Sharp for Matt Ellison 

Dennis Wierzbicki-USA TODAY Sports

In December of 2006 the Philadelphia Flyers had a lot of centers in the organization and General Manager Bobby Clarke was looking for another forward that was more versatile. So he traded a young Patrick Sharp and Eric Meloche to the Chicago Blackhawks for Matt Ellison and a third round draft pick.

Ellison played both center and wing and Clarke thought he was the guy that the team needed. He should have done some experimenting within his club because Ellison played a total of just 7 games in two years with the Flyers. Meanwhile Sharp went on to become a star in Chicago, at left wing. Sharp scored 62 points or more five times and won two Stanley Cups with the Blackhawks. Oops!

13 Tuukka Rask for Andrew Raycroft 

Charles LeClaire-USA TODAY Sports

If you are a Toronto Maple Leafs fan this one just flat out pains you. In the summer of 2006 Toronto had a pair of young talented goalies in their system. Rask and Justin Pogge. General Manager John Ferguson Jr. said that he didn’t want to trade Pogge and because of that, Rask was going to be tough to re-sign. So he sent him to the Boston Bruins for another starting goalie in Andrew Raycroft. The deal really didn’t make any sense based on Ferguson’s thought process on trading Rask away. If you have one young goalie that you want to keep because you think he is your future, making the other goalie expendable, why bring in another goalie that is already established? Well just as should have happened, the deal blew up in his face and it’s one of the many reasons that he is no longer the GM in Toronto.

Raycroft had done well with the Bruins. He won the Calder Trophy as the rookie of the year in 2004. But he only stayed with the Leafs for two seasons. And Pogge, who was thought to be the future of the franchise, had an NHL career that consisted of just 7 games.

Tuukka Rask however, went on to become an elite goalie in the NHL and went to a Stanley Cup Final in 2013 with Boston. The following season he won the Vezina Trophy as the best goalie in the NHL. Every time that Rask takes the ice in Toronto wearing a Bruins jersey it reminds Leaf’s fans of the horrible deal.

12 Dan Boyle for a 5th round draft pick 

In January of 2002 the Florida Panthers sent little used defenseman Dan Boyle to the Tampa Bay Lightning for a fifth round draft pick. That picked turned out to be Martin Tuma who never played a shift in the NHL. As a matter of fact he never even played a full season in the AHL.

Boyle became one of the top offensive defensemen in the NHL and was a major force on the Lightning blue line for six years before being traded to the San Jose Sharks. He was a major part of the Lightning’s 2004 Stanley Cup championship.

11 Brad Richards for 3 players and a draft pick 

Via thehockeywriters.com

The Tampa Bay Lightning had new owners at the time of this deal and during their brief time of controlling the team they made several questionable deals. Most of them had to do with money. They didn’t want to have to pay any out. The worst of the deals that they made was when they sent Brad Richards and Johan Holmqvist to the Dallas Stars for Mike Smith, Jussi Jokinen, Jeff Halpern, and a fourth round draft pick.

Richards was under a new five-year contract that was worth $39 million and at the time of the deal, while everyone was shocked that Tampa moved their long-time star, it looked like a decent deal. But as time went by, it became obvious that Tampa Bay had made a huge mistake. Richards continued to be a star with Dallas and put up a 91 point season in 2010. He proved to be well worth the money over the course of his contract. Holmqvist never did much before or after the deal.

Tampa Bay thought that they were getting the starting goalie that they had been looking for in Mike Smith. While he did become the starter, he didn’t do it with any success in Tampa Bay. He didn’t start winning games consistently again until he moved on to Phoenix. Jokinen turned out to be a decent role player for a couple of other teams after leaving the Lightning and Halpern did the same. But none of the players that came to the Lightning in the trade did anything to improve the team and they sorely missed Richards’ production. This may be the worst trade the team has ever made.

10 Brett Hull for Rick Wamsley and Rob Ramage 

Brett Hull finally found his way in the NHL in 1988 with the Calgary Flames. It wasn’t until that season that he was known as something other than his father’s son. But the Flames traded him to the St. Louis Blues anyway, along with Steve Bozek for Rick Wamsley and Rob Ramage. The next season the Flames won the Stanley Cup but neither Wamsley nor Ramage played a major role on the team. Hull went on to have 11 great seasons with the Blues and he won two Stanley Cups, one with the Red Wings after winning one a few years earlier with the Stars. During the height of his career he was the premier sniper in the NHL. And the Flames gave him away for a backup goalie and a defenseman that was past his prime.

9 Ron Francis and Ulf Samuelsson for three players 

Via blog.triblive.com

In March of 1991 the Hartford Whalers made a trade with the Pittsburgh Penguins that turned Pittsburgh into a back to back Stanley Cup Champion, while at the same time dooming the Whalers franchise. The deal saw Ron Francis, Ulf Samuelsson and Grant Jennings go to Pittsburgh for John Cullen, Zarley Zalapski, and Jeff Parker.

The three former Whalers played major roles in the Penguins winning the next two Stanley Cups.

Hartford didn’t get anywhere near the same return however. Parker got into 4 games as a Whaler and Cullen had one good year in Hartford before he was traded to Toronto. Zalapski had his best years with the Whalers before they traded him to the Flames two years later. He could score some points but he was horrible in his defensive zone, and that's not something you want from a defenseman.

Just 6 years later the Hartford Whalers were no longer in Hartford as the franchise moved to Carolina to become the Hurricanes. To this day Whalers fans say that this was the trade that killed the franchise.

8 Jaromir Jagr for Kris Beech and two others 

Via espn.go.com

For some reason in 2001 Jaromir Jagr didn’t want to play for the Pittsburgh Penguins anymore. He had put together a great career there and he just finished a season that saw him score 121 points. But he wanted to move on. His trade value was sky high but the Penguins couldn’t capitalize on it. They traded him along with Frantisek Kucera to the Washington Capitals for Kris Beech, Michal Sivek, and Ross Lupaschuk.

Those three players combined to score 13 goals in the NHL for Pittsburgh, 10 of which came from Beech in 2002. That total was about an average month of play for Jagr. He went on to score more than 500 more points in his continuing NHL career.

7 Jaromir Jagr for Anson Carter 

Via en.wikipedia.org

After a few years with the Washington Capitals, Jagr didn’t want to play there anymore either. And his on ice performance had dropped considerably so it made the decision to trade him pretty easy. So the Caps dealt him to the New York Rangers for Anson Carter.

Carter played 19 games in Washington, scoring five goals, before they traded him to the Los Angeles Kings. Jagr on the other hand decided that he liked New York and he set a Rangers franchise record by scoring 123 points in his first year there. He was named captain of the team before he moved on to continue the Hall of Fame career that he is still playing today.

6 Roberto Luongo and Olli Jokinen for two players 

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In the summer of 2000 the New York Islanders had a goalie problem. They had a young Rick DiPietro and a young Roberto Luongo. So a decision had to be made on which one to move. They chose wrong when they sent Roberto Luongo and Olli Jokinen to the Florida Panthers for Mark Parrish and Oleg Kvasha. The Islanders are still to this day looking for a franchise goalie.

Parrish was a good player as he scored 30 goals in 2002 and he scored more than twenty goals on four different occasions. Kvasha played on the island for five seasons but his best year was a 15 goal campaign.

Jokinen scored 36 goals for the Panthers in 2003 and he played in Florida for four years before moving on. His career didn’t turn out all that bad. Luongo however will be going to the Hall of Fame when his career is finished. He was the number one goalie with the Panthers for five years before they traded him to Vancouver, where he got even better.

5 Roberto Luongo for Todd Bertuzzi 

Via en.wikipedia.org

In the summer of 2006 Luongo was involved in a bitter contract dispute with the Panthers. So General Manager Mike Keenan sent him, along with Lukas Krajicek, and a sixth round draft pick, to the Vancouver Canucks for Todd Bertuzzi, Bryan Allen, and goalie Alex Auld. Ouch!

Krajicek was an ok player but Luongo became the face of the Vancouver franchise for almost ten years and he led the Canucks to the Stanley Cup Finals in 2011. Vancouver became a powerhouse in the Western Conference for many years because of his play. He was traded back to the Panthers in 2015 but he spent the prime of career as the leader of the Vancouver Canucks and is a definite Hall of Famer.

Bertuzzi was a marginal player who liked to use his stick for hitting everything except the puck. He missed most of the next season in Florida because of an injury and he was then traded away. He has played for four other teams since then, none with any success.

Auld only played one forgettable season with the Panthers while Allen spent five years with them, but mostly as an ineffective 7th defenseman. The Panthers robbed the Islanders when they got Luongo, but then they got robbed of him by the Canucks. What goes around comes around.

4 Phil Esposito and two others for 3 players 

Via bleacherreport.com

It’s not very often that one player can get traded twice in his career and have one trade feature him as the steal, and the other trade feature him as a bust. But that’s what happened to Phil Esposito, one of the greatest scorers in the history of the NHL. In 1967 the Chicago Blackhawks played a very physical game of hockey. But Espo was more of a finesse player and he didn’t want to play the style that they played in Chicago, and he had no problem in saying so. So Chicago started to look for a new home for him.

The Boston Bruins sent Pit Martin, Jack Norris, and Gille Marotte to Chicago for Phil Esposito, Fred Stanfield, and Ken Hodge. That’s right they flat out robbed Chicago at gun point.

Pit Martin went on to put together a decent career in Chicago, Marotte did nothing at all, and Norris played goal for all of ten games over two seasons.

On the other hand the trade turned the Bruins into instant winners. Hodge scored 105 points in a season with Boston twice and Stanfield played the third line for six years. He scored over 20 goals in a season six different times. During his time in Boston he averaged almost a point per game. Hodge reached 40 or more goals in three seasons and scored 50 in 1974. And then there was Espo.

Phil Esposito played with the Bruins for 8 years and he led the NHL in scoring five times. He scored 100 points or more in a season on six different occasions and he won the Art Ross Trophy five times. He also added a Hart Trophy while leading the Bruins to a pair of Stanley Cup championships. Espo set the league record at the time by scoring 76 goals in a season, a record that would stand until Wayne Gretzky entered the NHL. This deal is one of the most lopsided in the history of the NHL.

3 Phil Esposito for Brad Park and Jean Ratelle 

Via espn.go.com

In the summer of 1975 the New York Rangers were rebuilding their team. After falling short in the playoffs the previous two seasons they wanted to make some changes. Their first move was letting Eddie Giacomin go via waivers. The goalie was picked up by the Detroit Red Wings and went on to a Hall of Fame career. But they followed that horrible move with another by sending Brad Park, Jean Ratelle, and Joe Zanussi to the Boston Bruins in exchange for Phil Esposito and Carol Vadnais. Several year earlier Esposito was the gem in a steal of a deal by the Bruins, but this time around he was the dud in the deal acquired by the Rangers.

Esposito wasn’t the same elite scorer that he had been in Boston and Vadnais had a solid yet unspectacular time with the Rangers. But on the other side Brad Park and Jean Ratelle went on to great careers with the Bruins. They are as much icons in Boston as Espo was when he was there. It took the Rangers a very long time to recover from these two disastrous transactions.

2 Eric Lindros for six players, two draft picks, and cash 

Via grantland.com

If one single player could be responsible for the demise of a franchise it would be Eric Lindros. After being drafted by the Quebec Nordiques with the #1 overall draft pick in 1991, Lindros refused to play for Quebec. He hadn’t played a single shift in the NHL and he was dictating where he would and would not play. In all honesty nobody should have traded for him and just let him sit home and think about the opportunity that he threw away.

But Quebec found a suitor in the Philadelphia Flyers. Philly sent their first round draft pick Peter Forsberg, Kerry Huffman, Mike Ricci, Steve Duchesne, Ron Hextall, Chris Simon, a pair of draft picks, AND $15 million cash to Quebec for Eric Lindros. A player that was 100% unproven in the NHL. The trade proved to be the end of the Quebec Nordiques and they soon moved to Colorado and became the Avalanche. Later one of the draft picks acquired in the Lindros deal was traded by Colorado to Montreal for Patrick Roy. Trading Lindros away turned the Avalanche into instant winners and they won two Stanley Cups. All because of that trade. Those poor fans in Quebec.

Lindros wasn’t horrible in Philadelphia but they didn’t win any Stanley Cups so the deal has to be considered a bust of major proportions. The Flyers basically made the Quebec/Colorado franchise into a powerhouse that lasted for several years.

1 Wayne Gretzky for players, 3 1st round picks, and cash 

Via sportsnet.ca

On August 9, 1988 the sports world was changed forever. On that day it became obvious that no player is untouchable or unmovable, no matter how good they are. That day the saying was born that has been repeated many times over the years: “If Gretzky can be traded, so can I.”

The Edmonton Oilers traded the best player to ever put on skates in the world, along with Marty McSorley, and Mike Krushelnyski to the Los Angeles Kings for Martin Gelinas, Jimmy Carson, three first round draft picks (1989, 1991, and 1993), and $15 million cash. After the deal was completed, Oilers owner Peter Pocklington received death threats from all across Canada, especially in the Edmonton area.

The Oilers did win a Stanley Cup without The Great One, but the deal signaled the end of a dynasty and the franchise soon fell to the bottom of the standings to stay. On the other hand it also created a buzz for hockey on the west coast and in more nontraditional hockey markets.

Edmonton followed the Gretzky trade by trading away Jari Kurri, Mark Messier, Grant Fuhr, Glenn Anderson, Kevin Lowe, Esa Tikkanen, and Craig MacTavish over the next few years. If the Gretzky trade was never made and the team stayed together there is no telling how many Stanley Cups they could have totaled up.

None of the players or draft picks that went to the Oilers amounted to much of anything, and when you consider they gave away the greatest player in history, who was still in his prime, it very well could be the worst deal of all time.

Sources: bleacherreport.com, sportsnet.ca, wikipedia.org

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