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)…
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