The 25 Worst Trades in Montreal Canadiens History – #16-20

Trades #16-20 of the 25 Worst Trades in the modern history of the Montreal Canadiens

Links to the other individual articles in this series: Intro, #21-25, #11-15, #6-10, #1-5

The Montreal Canadians have a long and storied history in the NHL.  They have won many Stanley Cups, and a large number of Hall of Fame hockey players have worn their colours.  However, they have also made their share of outright bone-headed trades (the bulk of which occurred in the 1990s and early 2000s), which has resulted in their failing to win a Stanley Cup victory in 20 years (a drought Leafs fans would happily accept instead of our 46-and-counting tally).  I have taken a look at Montreal’s trades in the Modern Era of the NHL (post-1967), and compiled a list of the 25 Worst Montreal Canadiens Trades of All Time.  One thing to mention as a qualifier: I largely ignored whomever the Canadiens’ trading partner selected with the draft pick received, as there is no guarantee the Canadiens would have chosen that player.  I put the most weight on ex-Habs who went on to great things (post-Montreal), Montreal draft picks that didn’t pan out, and the failure to make the most of players/assets in the long-term.  With that, here are the trades that ranked #16-20.

#20: Montreal trades Andre Boudrias, Bob Charlebois and Bernard Cote to the Minnesota North Stars for a 1971 1st Round Pick (Chuck Arnason) (June 6th, 1967)
The Montreal Canadiens’ dynasty of the 1970s was built in large part due to their success in trading mid-level veteran players to the 1967 expansion teams for first round picks in the Entry Draft.  This trade however was one of the few that failed to benefit the Habs (directly, anyways).  Chuck Arnason was a bust: he scored 2 points in 19 games for the Canadiens before being dealt to the Atlanta Flames (which later became the Calgary Flames).  Arnason eventually scored 196 points in 384 games after leaving Montreal.  In dealing Arnason, Montreal did receive a first round pick.  They chose Rick Chartraw, whom they later sent to Los Angeles in exchange for a second round pick.  THAT pick turned into Claude Lemieux, but this entire process took more than fifteen years to pay off (Lemieux was selected in the 1983 Entry Draft).

Three players went to Minnesota.  Bernard Cote was a dud; he never played in the NHL.  Bob Charlebois played just seven games for the North Stars, and then left for the WHA.  So the only one who played in the NHL was Andre Boudrias.  He scored 53 points in 74 games for Minnesota in ’67-68, and then dropped off to 13 points in 53 games before being dealt to Chicago with Mike McMahon Jr. for Tom Reid and Bill Orban.  Boudrias then had short stints with Chicago and St. Louis before hitting his stride in Vancouver, where he had five seasons in the 60-78 point range.  During that span he had three seasons of 25-30 goals.  In all, he scored 150 goals and 485 points in 655 games, and he managed a healthy -7 rating despite playing for some very weak teams.  That’s a pretty decent offensive career over a fairly extended period of time, and his secondary scoring would have benefited the Habs.  They still made out fairly well in the 1970s (they won six cups between 1971 and 1979), but that doesn’t change the fact that this trade bombed for them.

#19: Montreal allows the Oakland Golden Seals to claim Carol Vadnais in the 1968 Intra-League Draft (June 12th, 1968)
While this is technically not a trade, it follows the general theme of this list: the Canadiens had the option to leave anyone they wanted available in Intra-League Draft, and they chose to expose Carol Vadnais.  They opted to let him go to another team.  Oakland happily snapped him up, and he had a decent four-season run with the team.  As a defenseman on a fairly terrible team, Vadnais had back-to-back 40-point seasons for the Oakland Seals (including 24 goals in ’69-70).  They became the California Golden Seals, and his luck turned; he dressed for 94 games over the next two seasons, although he still managed 60 points during that time.  In total, he scored 63 goals and 146 points in 246 games for the Seals, along with 560 penalty minutes.  He was sent to Boston in a deal that brought the tremendously talented Reggie Leach to California.  Unfortunately, Leach was soon flipped to Philadelphia, where he became a tremendous goal scorer (his career high was 61 goals in a single season).  Vadnais went on to play another 799 games after leaving California, scoring 105 goals and 436 points, along with 1,187 PIM.  In total, he played 1,045 regular season games post-Montreal.  And he was even better in the playoffs, scoring 50 points in 104 games.  It’s hard to justify walking away from a 1,000-game player.  Admittedly it didn’t really impede the Canadiens during the 1970s, but I find it difficult to believe that Vadnais wouldn’t have been a productive member on their blueline corps.

#18: Montreal trades Mark Hunter, Michael Dark, a 1985 2nd Round Pick (Herb Raglan), a 1985 3rd Round Pick (Nelson Emerson), a 1985 5th Round Pick (Dan Brooks) and a 1986 6th Round Pick (Rick Burchill) to the St. Louis Blues for a 1985 1st Round Pick (Jose Charbonneau), a 1985 2nd Round Pick (Todd Richards), a 1985 4th Round Pick (Martin Desjardins), a 1985 5th Round Pick (Tom Sagissor) and a 1985 6th Round Pick (Donald Dufresne) (June 15th, 1984)
This was an oddly large deal that looks to be much more complex than it actually is.  It essentially boils down to the Canadiens trading Mark Hunter and Michael Dark to the St. Louis Blues in exchange for the Blues’ first round pick… the rest of the deal is just noise from the Habs and Blues (for some reason) swapping four picks each between rounds 2-6.

I don’t put any stock in the players St. Louis selected (as there is no guarantee the Habs would have chosen any of these players), but here’s how they turned out.  Herb Raglan played in 235 games over parts of six seasons, but only scored 65 points.  He was dealt to Quebec with Andy Rymsha and Tony Twist for Darin Kimble in a nothing trade.  Nelson Emerson did well: he scored 23 goals and 59 points in ’91-92 and then improved to 22 goals and 73 points in ’92-93.  He was then flipped to Winnipeg with Stephane Quintal for Phil Housley, whom St. Louis smartly dealt to Calgary in exchange for Al MacInnis (an absolutely fantastic chain of asset management).  Their other two picks (Brooks, Burchill) never made the NHL.  So of all the picks, really Emerson was the only one that made an impact, and he set off a chain of intelligent trades to maximize St. Louis’ value out of that third-round pick.

The Habs meanwhile squandered all of their draft picks.  Tom Sagissor never made the NHL.  Martin Desjardins and Todd Richards each played eight NHL games, but Desjardins was the only one to play for Montreal.  Jose Charbonneau played 25 games with the Habs (scoring just one goal), and was then traded to Vancouver for Dan Woodley (who never played for Montreal).  The lone worthwhile asset the Habs got out of this was Donald Dufresne, and he was hardly a star.  He played in 119 games over parts of five, only once playing more than 32 games in a season.  He was dealt to Tampa Bay in June 1993 to fulfill the Future Considerations from Montreal’s acquisition of Rob Ramage at the 1993 trade deadline.

Even ignoring all the Blues’ draft picks, this deal was still a massive clunker.  Montreal traded Mike Dark and Mark Hunter for 31 points in 152 games from all of the players they selected with those draft picks.  Dark didn’t amount to much, scoring 11 points in 43 games with a +6 rating over two seasons.  But Hunter was fantastic: over a three-year stint with the Blues, he scored 112 goals and 206 points in 218 games, along with 476 penalty minutes.  His best season was his first (’85-86): he scored 44 goals and 74 points, and then added 14 points in 19 games during their lengthy playoff run.  Hunter and Dark were eventually sent to Calgary along with Steve Bozak and Doug Gilmour for Mike Bullard, Craig Coxe and Tim Corkery, which was a stinker in its own right.  But Hunter was still a fantastic acquisition, and the parts Montreal acquired (especially Charbonneau) amounted to absolutely nothing of value.

#17: Montreal trades Vincent Damphousse to the San Jose Sharks for a 1999 5th Round Pick (Marc-Andre Thinel), a 2000 1st Round Pick (Marcel Hossa) and a 2001 2nd Round Pick (later traded to Columbus, who selected Kiel McLeod) (August 18th, 2004)
As Montreal’s struggles mounted in the early 2000’s and Damphousse’s production slowed, the Canadiens decided to flip their Captain as part of a rebuilding movement.  The problem with a rebuild is you need to develop assets that you can… y’know… build with.  Marc-Andre Thinel never played in the NHL.  The Habs sent the second-round pick to Columbus.  In exchange, Columbus agreed to select Frederic Chabot in the Expansion Draft, allowing Montreal to retain a player whose identity I was unable to determine.  The Blue Jackets used the draft pick on Kiel McLeod, who never played in the NHL.  The final piece of the trade for Montreal was Marcel Hossa, who was an absolute bust (and nowhere near the talent level of his brother Marian Hossa).  Marcel scored 19 points in 59 games over parts of three seasons before being traded to the New York Rangers for Garth Murray.  Meanwhile, Vincent Damphousse was rejuvenated in San Jose.  He scored at a point-per-game clip after being acquired (13 points in 12 games, followed by 5 points in 6 playoff games).  He then maintained at that pace over the next two seasons (70 points in ’99-00 and then 46 points in 45 games during ’00-01), and continued to be a productive player over his final three NHL seasons.  In total, he scored 92 goals and 289 points in 385 games for the Sharks, as well as 38 points in 53 playoff contests (including 14 points in 17 games during his final playoff run in 2004).  He even managed a healthy +14 rating during that time.  He ended up with three 20+ goal seasons, each of which saw him score 58-71 points.  So much for his being “done” when the Habs dealt him.

#16: Montreal trades Sylvain Lefebvre to the Toronto Maple Leafs for a 1994 3rd Round Pick (Martin Belanger) (August 20th, 1992)
This was just a straightforward dud of a deal.  Martin Belanger never played a game in the NHL, while Sylvain Lefebvre became one of the better stay-at-home defensemen in the league.  He had two solid seasons in Toronto, posting a +41 rating in 165 games (along with 25 points).  He was key contributor to the Leafs’ back-to-back trips to the Conference Finals in 1993 and 1994, before being dealt to Quebec in the Mats Sundin-Wendel Clark trade.  Lefebvre won a Stanley Cup with the Colorado Avalanche in 1996, and finished his NHL career with the New York Rangers.  He played 580 games post-Toronto, recording 106 points along with a +51 rating.  And the Habs quite literally gave him up for nothing (zero NHL games from Belanger).

We’re getting into the middle of the list now… it only gets worse from here.  Or better if you don’t like Montreal, it’s all about perspective.  Click here to see Trades #11-15!

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