1. Mar. 18, 1983: The Kings traded Larry Murphy to the Capitals for Brian Engblom and Ken Houston
The Capitals stole Larry Murphy at 22 for a ridiculous price. Houston played only 33 more games in the NHL after the trade. Engblom was similarly unimpressive, though he played 3.5 more seasons.
2. Mar. 4, 1991: The Whalers traded Ron Francis, Ulf Samuelsson, and Grant Jennings to the Penguins for John Cullen, Jeff Parker, and Zarley Zalapski
This trade, though one-sided, doesn’t make the list because at the time, Cullen was a dominant player. At the time of the trade, he was 27 and had 94 points in just 65 games. Nobody could have guessed he would fall apart two years later.
10. Oct. 4, 1991: Edmonton trades Mark Messier and Jeff Beukeboom to the Rangers for Bernie Nicholls, Steven Rice, and Louie Debrusk
Even if Edmonton was rebuilding after its dynasty, it’s hard to rationalize this trade. Messier was one of the best players in the NHL, and Edmonton was compensated with 30-year old Bernie Nicholls (a good player, but useless for a rebuilding team) and two prospects that never panned out (Steven Rice and Louie Debrusk).
There was an interview on WFAN (the New York City sports radio station) with former Rangers GM Neil Smith which touched on this trade. Smith explained that at the time, those interested in Messier were worried about the wear and tear on his body.
For the past 13 years, Messier had missed very few games and played deep into the playoffs in almost every season. In addition, he had appeared in several grueling Canada Cups. According to Smith, NHL GM’s going after Messier all believed this so fully that it drove down Messier’s value.
9. March 20, 1996: Vancouver Canucks traded Alek Stojanov to the Pittsburgh Penguins for Markus Naslund
This trade makes my list because of the staggering disparity between the two players. Many of the trades on this list involve one good player switching teams in exchange for packages of young players who did not pan out.
This deal is different. During the 1995-96 season, Stojanov had recorded no goals and one assist in 58 games. And no, he wasn’t a defenseman, he was supposed to be a power-forward. It’s hard to rationalize placing any value at all on a winger with that sort of statline. Stojanov finished his career with two goals and five assists in 108 games.
Also, this is not a case of two teams giving up on under-performing top prospects. Naslund was having a breakout season, and already had 52 points in 66 games at the time of the deal!
8. 1976: The Rangers traded Rick Middleton to the Bruins for Ken Hodge
This trade foreshadows the Rangers of the late 1990’s and early 2000’s: they traded Rick Middleton—a budding star—after his sophomore season for a washed-up scorer at the end of his career (Hodge).
Middleton went on to score 898 points in 881 games over 12 successful seasons with the Bruins. Hodge spent one full season with the Rangers, scoring 62 points. The next season, he faltered and was sent down after 18 games, never to return to the NHL.
7. June 6, 1986: The Canucks traded Cam Neely and a first-round pick to Boston for Gary Pederson.
This one still hurts Canucks fans. You could try to argue against blaming the Canucks’ management for the trade because Neely had scored only 39 and 34 points in his two seasons with the team, but that was between the ages of 19 and 21. Pederson—a star who had previously had seasons of 92, 107 and 116 points—only had two more successful seasons after the trade.
6. June 23, 2006: Florida traded Roberto Luongo, Lukas Krajicek, and a sixth round pick to Vancouver for Todd Bertuzzi, Bryan Allen, and Alex Auld
Kevin Lowe criticized Brian Burke for his tenure as Vancouver GM, saying that the team would have been in the cellar a long time ago had Dave Nonis not conned the Panthers out of Roberto Luongo. I think he’s right, and this is one of the most lopsided deals since I’ve followed hockey.
There’s no excuse for giving up Luongo for Bertuzzi. It’s true that Bertuzzi had scored 95 points three seasons before the deal, but his scoring had clearly declined somewhat by 2006. Worse yet, his value was further diminished because he was being booed in every arena including Vancouver due the Steve Moore incident.
Luongo was already established as one of the best goalies in the league, and was clearly in his prime. It’s true that Florida was trying to trade him because he had one year left on his contract and wasn’t going to re-sign, but surely they could have aimed higher...
5. Jan. 2, 1992: The Calgary Flames traded Doug Gilmour, Jamie Macoun, Kent Manderville, Ric Nattres, and Rick Wamsley to the Maple Leafs for Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and Jeff Reese.
At the time of the trade, Doug Gilmour was one of the best players in the NHL, and was in his prime with plenty of time to spare. Calgary traded him, along with two of its most reliable shutdown defensmen (Nattress and Macoun), and a good backup goalie (Wamsley), for an enforcer (Berube), an eighth defenseman (Godynyuk), a declining second liner (Leeman), a suitcase (Petit, the all-time record holder for most times traded last time I checked), and a third string goalie (Reese).
There’s simply no way to rationalize this trade from the Flames’ perspective.
4. Dec. 6, 1995: The Canadiens traded Patrick Roy and Mike Keane to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky, and Jocelyn Thibault
No mystery here. Roy was one of the greatest goalies ever. Without him, I’m not sure Colorado would have won its two Stanley Cups. Kovalenko and Rucinsky were both career second or third line players. Thibault had several good seasons, but has only had three winning seasons since.
Roy demanded a trade after coach Mario Tremblay decided to unkindly leave him in the net after a bad first period. After 20 minutes, Roy had allowed five goals on 17 shots, but Tremblay sent him back out, and he gave up four more goals before finally being yanked, enduring jeers from the fans.
Roy has since said that if Tremblay had not sent him back out, he would not have demanded a trade (see the Wikipedia entry for "Patrick Roy"). Tremblay had taken over from Jacques Demers after the latter was fired fove games into the season.
The Canadiens were not going to fire Tremblay because he had been with the organization even longer than Roy. However, the least they could have done was made a better trade.
3. March 7, 1988: The Flames traded Brett Hull and Steve Bozek to the Blues for Rob Ramage and Rick Wamsley
This one doesn’t require much explanation. The Flames traded Brett Hull towards the end of his rookie season along with a second line winger (Bozek) for a declining defenseman (Ramage) and a goalie St. Louis didn’t need anymore (Wamsley).
Ramage managed only four more full seasons and scored 136 points in 369 games. However, even if he had played as well as in his best season for many more years, the trade would not have been even in the grand scheme.
2. June 23 1975: Detroit traded Marcel Dionne and Bart Crashley to the Kings for Terry Harper, Dan Maloney, and a second round draft pick
This one is pretty simple. Marcel Dionne was 24, and had just scored 121 points. Dan Maloney had some potential, but even with that taken into account, his value should have come nowhere near that of Dionne.
The Red Wings traded one of the highest scorers in history at the age of 24 for a journeyman defenseman and a second-line winger. Dionne proceeded to make them pay by recording 592 goals and 813 assists for 1405 points in 1039 games over the next 14 seasons.
1. May 15, 1967: The Chicago Blackhawks traded Phil Esposito, Ken Hodge, and Fred Stanfield to the Bruins for Pit Martin, Gilles Marotte, and Jack Norris.
Often, when I read a list like this one, the Esposito trade is forgotten. I think it’s hard to argue that this is not by far the most lopsided trade ever made.
Boston acquired Hall-of-Famer Phil Esposito at 25 years old, and he went on to score over 100 points in six of his eight seasons with the Bruins, during which time he shattered the single-season scoring record. Hodge and Stanfield were highly-skilled forwards who both consistently averaged more than a point-per-game with the Bruins.
Hodge did it four out of nine seasons and Stanfield three out of six. All three played major roles in the Stanley Cup victories of 1970 and 1972.
Pit Martin was a solid, scoring winger, about as good as Stanfield. Marotte was a defenseman with some potential, but he never was more than a second-pairing player. Norris was a useless goalie.
Imagine if a team traded Evgeni Malkin (i.e. Esposito), Marian Hossa (Hodge) and Mike Ribeiro (Stanfield) for Vaclav Prospal (Martin), Ian White (Marotte) and Scott Clemmensen (Norris)…