NHL Trades: The 15 Most Ridiculous Trades in NHL History

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Trades in sports are always a risky proposition. You never know what you're going to get or what you are giving up. You can do all the research, crunch all the numbers, ask all the experts and still walk away looking like a fool, just as easily as you can walk away looking like a genius.

What follows are 15 examples of NHL trades where one side looked like a group of dunces, while the other walked away looking like the smartest guys in hockey. I know that hindsight is 20/20, but really, some of these trades seemed to lack foresight or, really, any sight at all.

15. Marcel Dionne to the Los Angeles Kings

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The Detroit Red Wings had a young, up-and-coming star in Marcel Dionne, a player that they drafted with the second pick in the 1971 NHL entry draft. The problem for Dionne was that the team wasn’t very deep and he was unhappy on the club.

Dionne had no interest in staying in Detroit, so the Wings traded Dionne and Bart Crashley to the Los Angeles Kings for Terry Harper, Dan Maloney and a second-round pick.

Neither team would be especially successful following the trade, and Dionne would eventually tire of playing and losing for the Kings as well.

Dionne was an extremely talented player that had the misfortune to play for two under-performing teams for the majority of his career. Even without much support, he racked up 1,771 points over 1,348 regular-season games.

14. Larry Murphy to the Detroit Red Wings

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Larry Murphy's tenure with the Toronto Maple Leafs was not going well during his time with the Leafs. Things got so bad during the 1997 season that they traded him to the Detroit Red Wings for essentially nothing (future considerations) and agreed to pay some of his salary. That's how bad the team, as well as many of the fans, wanted Murphy out of Toronto.

The trade worked out well for the Red Wings, as Murphy, the player the Leafs gave up on, played five years in Detroit, putting his name on the Stanley Cup twice and adding an All-Star game appearance for good measure.

13. Ron Francis to the Pittsburgh Penguins

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Perhaps one of the biggest trades made in the history of deadline day. On March 4, 1991, the Hartford Whalers sent Ron Francis, Grant Jennings and Ulf Samuelsson to the Pittsburgh Penguins in exchange for John Cullen, Jeff Parker and Zarley Zalapski.

The trade would give the Penguins the players that would score two Stanley Cup-winning goals for the Penguins. 

To this day this trade is baffling. 

12. Patrick Roy to the Colorado Avalanche

Patrick Roy had a terrible night on December 2, 1995, giving up nine goals in less than two full periods. When he made his may to the bench, he stopped and said something to Canadiens president Ronald Corey. We later learned that Roy had told Corey he would never play for the Canadiens again, and he didn't. 

Four days later, he was traded along with Mike Keane to the Colorado Avalanche in exchange for Jocelyn Thibault, Martin Ručínský and Andrei Kovalenko.

It's hard to tell if this trade would have happened if Canadiens coach Mario Tremblay had pulled Roy between the first and second periods; it would be mere speculation to ponder that situation. What we do know is that the Canadiens' loss was the Avalanche's gain.

11. Roberto Loungo to the Florida Panthers

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Someone could have a field day examining the missteps that Mike Milbury made as the general manager of the New York Islanders. One of his most misguided decisions was selecting Rick DiPietro as the No. 1 selection in the 2000 NHL entry draft.

When Milbury made that pick, he already had a hot prospect in one Robert Luongo, a player the Islanders took with the fourth overall pick in the 1997 draft. Convinced that DiPietro would be a better goaltender for the team, he shipped Luongo and Olli Jokinen to the Florida Panthers in exchange for Mark Parrish and Oleg Kvasha. 

DiPietro has proven to be one of the most injury-prone players in the game, playing only 315 games, while Luongo has played almost double that at 727 and has taken his current team, the Vancouver Canucks, to the Stanley Cup Final. DiPietro has four playoff games to his name.

10. Dominik Hasek to the Buffalo Sabres

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It’s no secret that defensemen and goaltenders often take longer than forwards to mature and develop. With that in mind, trading one of these players early in their careers is always risky and can come back to bite the trader in the butt.

Such was the case with the Chicago Blackhawks when they unloaded Dominik Hasek to the Buffalo Sabres in exchange for Stephane Beauregard.

Once established as the Sabres' starting goalie, he took home a fair amount of hardware, earning the following:

- Six Vezina Trophies

- Two Hart Trophies

- Two Lester B. Pearson Trophies

Hasek would never win the Stanley Cup in Buffalo, but he would take the team to the finals, falling to the Dallas Stars in 1999 on a controversial goal that is still discussed to this day.

9. Alexei Yashin to the New York Islanders

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When Mike Milbury had it in his mind that the New York Islanders needed a player, he would focus in on that player and not rest until he landed his prize, even if it meant trading off skilled and developing assets.

A perfect example of this was when he had to get Alexei Yashin from the Ottawa Senators. And what did he give up to land Yashin in a trade on draft day in 2001? Zdeno Chara, Bill Muckalt and a draft pick that turned into Jason Spezza.

The payoff for the Islanders was a player that they bought out in June 2007, paying him $17.63 million just to go away. 

8. Phil Esposito to the Boston Bruins

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Phil Esposito is remembered as one of the greatest players to ever wear a Boston Bruins jersey, but if not for a ridiculous trade, he would have never played for the Bruins.

Esposito played the first four seasons of his NHL career with the Chicago Blackhawks, centering a line that included the great Bobby Hull. Surprisingly, Esposito, along with Ken Hodge and Fred Stanfield, were sent to the Bruins in 1967 in exchange for Pit Martin, Jack Norris and Gille Marotte.

Once Esposito suited up for the Bruins, he would take things to the next level, becoming the first player to crack the 100-point plateau. He also held the record for most goals in a season (76) until Wayne Gretzky came along to shatter that and many other NHL records.

In his eight full seasons in Boston, Esposito failed to hit 100 points only twice, missing the mark in his first season with the Bruins and in 1970 when he put up 99 points.

7. Markus Naslund to the Vancouver Canucks

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The Pittsburgh Penguins have built a pretty good team around the draft in recent years. Core players Sidney Crosby, Evgeni Malkin, Marc-Andre Fleury, Brooks Orpik and Kris Letang were all Penguins draft picks. No one can deny that those were all wise picks, but one great pick from the past slipped away when they made an ill- advised trade.

On March 20, 1996, the Penguins shipped their first-round pick (16th overall) from the 1991 draft, Markus Naslund, to the Vancouver Canucks in exchange for the seventh pick in that year’s draft, Alek Stojanov.

Naslund would play more than 950 games for the Canucks and become the Canucks' all-time leading scorer and one of the most beloved players in the history of the team before retiring after the 2010 season.

Stojanov would play 45 games for the Penguins before ending his career in the minors during the 2001-02 season.

6. Cam Neely to the Boston Bruins

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Cam Neely was drafted ninth overall by the Vancouver Canucks in the 1983 NHL entry draft. Neely would play three seasons with the Canucks, never cracking the 40-point plateau in his time with Vancouver.

The Canucks shipped Neely along with the first-round draft pick that would become Glenn Wesley to the Boston Bruins in exchange for Barry Pederson. When Neely hit Boston he exploded, racking up 72 points in his first season and defining the position of “power forward” for all those that came after him.

When Neely was healthy, he was a monster on the ice. He treated the opposition as a nuisance, running over them, intimidating them and fighting when needed. In his first four seasons in Boston, he never scored less than 69 points, topping out at 92 during 1990.

Sadly, Neely’s career was shortened by injury and although he never lifted the Stanley Cup as a player, he was lucky enough to do so as Bruins team president in 2011.

5. Ken Dryden to the Montreal Canadiens

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The fact that Ken Dryden was not always a member of the Montreal Canadiens is often overlooked, but a glance at the list of players drafted during the 1964 NHL entry draft will show that with the 14th pick, the Boston Bruins selected one Ken Dryden.

Dryden let the Bruins know that he was going to pursue his degree and play at Cornell instead of turning pro, and in one of the most shortsighted moves in the history of the game, the Bruins traded Dryden’s rights along with Alex Campbell to the Montreal Canadiens in exchange for Paul Reid and Guy Allen.

Dryden would earn his B.A. from Cornell and eventually join the Canadiens, where he would run up quite the list of accolades:

- Conn Smythe Trophy

- Calder Trophy

- Five Vezina Trophies

- Six Stanley Cups

- Five First-Team All-Star selections

- Elected to the Hockey Hall of Fame in 1983

4. Ted Lindsay and Glenn Hall to the Chicago Blackhawks

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With the current CBA talks being one of the hottest topics in the NHL, it’s hard to imagine that not too long ago, there was no NHLPA. In order to get the ball rolling toward that goal, some players needed to step up and risk their careers. One of those players was Detroit Red Wings captain Ted Lindsay.

Lindsay’s actions did not sit well with Red Wings owner Jack Adams, who shipped Lindsay and Glenn Hall to the Chicago Blackhawks in exchange for Johnny Wilson, Forbes Kennedy, Hank Bassen and Willian Preston. The move was basically made to punish the players.

Hall would lead the ‘Hawks to the 1961 Stanley Cup. He would also capture the Vezina in 1963 and 1967.

Hall’s other claim to fame is one NHL record that will never be broken—his 502 consecutive games started in net.

3. Kris Draper to the Detroit Red Wings

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As far as return on investment goes, you would be hard-pressed to find a trade with a better return than the one that sent Kris Draper to the Detroit Red Wings. 

Draper was originally selected by the Winnipeg Jets in the third round of the 1989 NHL entry draft, but he would only play 20 games for the team before they would ship him off to the Wings in exchange for one dollar.

Draper would play more than 1,000 games for the Red Wings before hanging up his skates in the summer of 2011. Draper joins a very select group of players to have played 1,000 games or more for the Wings. The only other players to do so were Gordie Howe, Alex Delvecchio, Steve Yzerman, Nicklas Lidstrom and Tomas Holmstrom.

2. Wayne Gretzky to the LA Kings

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If you have the greatest player to ever play the game of hockey on your club and he is still playing at a high level, wouldn’t you do everything you could to keep him on the team? 

Not if you were Edmonton Oilers owner Peter Pocklington.

If you were Pocklington, you would ship Gretzky, Marty McSorley and Mike Krusheinyski to the Los Angeles Kings in exchange for Jimmy Carson, Martin Gelinas, first-round draft choices in 1989, 1991 and 1993 and $15 million.

Even more insane than that trade, which makes no sense other than to put some cash into Pocklington’s coffers, was the fact that he would make the trade again!

1. Eric Lindros to the Philadelphia Flyers

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Today, the idea that a team would trade eight players and $15 million for one player is almost laughable, but in June 1992, the Philadelphia Flyers did just that, sending Peter Forsberg, Ron Hextall, Chris Simon, Mike Ricci, Kerry Huffman, Steve Duchesne, two first-round picks and a stack of cash to the Quebec Nordiques in exchange for Eric Lindros.

The Flyers would get a player that many claimed was the next “Great One.” He wasn’t. When healthy, he was a beast on the ice, taking the power forward position that Cam Neely cast the mold for and kicking it up a notch. The problem was that he was also reckless. In his younger days, he was always the biggest and the baddest and that may have led to bad habits, namely skating with his head down.

That act put a target on him and players such as Scott Stevens and Darius Kasparaitis were more then willing to hone in on that target.

Lindros would never lead the Flyers to the Stanley Cup, but the Avalanche, with the help of Peter Forsberg, would eventually win hockey's holy grail.

In hindsight, this trade is the definition of the ridiculous trade.