In over 100 years of existence, it is only natural that the Montreal Canadiens have made some bad trades. In fact, they've made some outright terrible ones. I have always held a strong opinion on which trade is currently the worst in team history, but I thought it would be fun to take it to the community.
For the purpose of this exercise, we have chosen five trades so as to narrow down the field a little bit.
Incoming: Denis Savard
Outgoing: Chris Chelios, second-round draft pick (Michael Pomichter)
Habs trade a Norris-winning defenceman for an older star player. I believe we have seen this movie before.... Anyway, amid a slew of rumours about personal issues that he may or may not have had with teammates, Chris Chelios was moved to Chicago for Denis Savard during the 1990 off-season.
Savard ended up being a pretty productive player for the Canadiens over three seasons, and did win a cup in 1993 with the club, but it was still a big fat L on the scoreboard. Chelios went on to win two more Stanley Cups with Detroit, and added another two Norris trophies just for kicks. Bad trade. Very bad trade.
Savard left the team after that Stanley Cup season, and retired in 1997. Chelios played his last NHL game in 2007. They mortgaged the future, and paid a hefty price for doing so.
2. "Le Trade"
Incoming: Jocelyn Thibault, Martin Rucinsky, Andrei Kovalenko
Outgoing: Mike Keane, Patrick Roy
This is a really, really bad one. The legendary Patrick Roy forced the organization's hand when he demanded a trade in 1995, but they received a woefully bad return for him regardless of the circumstances. Almost every Habs fan would tell you that the team is beyond the quarter-century Stanley Cup mark if Roy had finished his career in Montreal.
But he didn't. Instead he won two more cups with the Colorado Avalanche, adding a Conn Smythe in 2002 for good measure. This trade is still a sore spot for Habs fans, and as such, probably the frontrunner in this race. But my next choice may have been partially responsible for setting it up.
3. Mark Recchi
Incoming: Mark Recchi, third-round pick (Martin Hohenberger)
Outgoing: John LeClair, Gilbert Dionne, Eric Desjardins.
This is one that often isn't talked about nowadays. Perhaps because it was just that terrible. This trade came earlier in the 1995 season, before the Roy trade, and sent basically the bulk of the 1993 Stanley Cup team core to the Flyers for Mark Recchi. Yeesh.
This might have been a big reason why the team was bad enough to let nine goals past Roy in the first place. Recchi was a solid, dependable player through his parts of four seasons in Montreal, but he just didn't amount to what they lost. It was a huge sacrifice of depth, and really thinned out the overall roster.
Another good option as a frontrunner here. That is now two from the same season... 1995 really sucked, eh?
4. The Gomez
Incoming: Scott Gomez, Tom Pyatt, Michael Busto
Outgoing: Ryan McDonagh, Doug Janik, Chris Higgins, Pavel Valentenko
Did you think I would leave this one out? Nope. Not a chance. Most of the players not named Ryan McDonagh or Scott Gomez were of medium to little consequence for either team, but the two centrepieces of the deal make it pretty easy to call this one a big loss in hindsight.
Ryan McDonagh is now a legitimate top-pair defender in the NHL, whereas Gomez will be most remembered for going over one year without scoring a goal, and doing so at a $7 million cap hit. Maybe I allowed recency bias to push this one into my top-five, but there is no denying it was quite the stinker.
5. Making Washington great again
Incoming: Ryan Walter, Rick Green
Outgoing: Rod Langway, Doug Jarvis, Brian Engblom, Craig Laughlin
Unlike many of the other trades listed, the Habs did receive a couple of decent players in return. Green managed to surpass the 25-point mark during his first season with the Habs, but it was all downhill from there. Walter also enjoyed his best season with the Canadiens immediately following the trade, reaching 75 points. But like Green, it was all downhill from there. In the highest-scoring era the NHL has ever seen, Walter did not manage to hit 50 points. He was primarily a defensive forward, although to his credit he did manage three more 20-goal seasons following the move to Montreal.
What makes this trade terrible is Langway's impact in Washington. Save for Alex Ovechkin, you could argue that Langway was the most important player in the Capitals' history. Not only did he help them transition from basement-dwellers to contenders, he went on to win the Norris Trophy on two occasions with Washington, and was also named to several All-Star Teams. What makes his Norris wins even more impressive is that he did it on the back of stalwart defense, rather than a high point count.
We probably could have made this an even longer list, as the Canadiens, like most teams, have made some other real stinkers over the years. As usual, if you have an idea for a trade that I didn't include on this list that you feel should be here, please discuss in the comment section.