The 25 Worst Trades in Montreal Canadiens History – #1-5

Trades #1-5 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, #16-20, #11-15, #6-10

The Montreal Canadians have a long and storied history in the NHL.  They have won many Stanley Cups, and they have had many great players.  But 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 going without a Stanley Cup victory in 20 years (a drought Leafs fans would be happy to 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, Montreal draft picks that failed to pan out, and a failure to make the most of the players/assets in the long-term.

If you haven’t had the chance to read the previous articles in the series yet (links are at the top of this article, just above the logo), let’s revisit the trades that ranked #6-25 on the list:

  • #25: Bob Berry to the Los Angeles Kings for cash (October 1970)
  • #24: Gerald Diduck to the Vancouver Canucks for a 1991 4th Round Pick (Vladimir Vujtek) (January 1991)
  • #23: Craig Ludwig to the New York Islanders for Gerald Diduck (September 1990)
  • #22: John Van Boxmeer to the Colorado Rockies for a 1979 3rd Round Pick (Craig Levie) (November 1976)
  • #21: Darcy Tucker, Stephane Richer and David Wilkie to the Tampa Bay Lightning for Patrick Poulin, Igor Ulanov and Mick Vukota (January 1998)
  • #20: Andre Boudrias, Bob Charlebois and Bernard Cote to the Minnesota North Stars for a 1971 1st Round Pick Chuck Arnason (June 1967)
  • #19: The Oakland Golden Seals claim Carol Vadnais from Montreal in the 1968 Intra-League Draft (June 12th, 1968)
  • #18: Mark Hunter, Michael Dark, a 1985 2nd Round Pick (Herb Raglan), a 1985 3rd (Nelson Emerson), a 1985 5th (Dan Brooks) and a 1986 6th (Rick Burchill) to the St. Louis Blues for a 1985 1st Round Pick (Jose Charbonneau), a 1985 2nd (Todd Richards), a 1985 4th (Martin Desjardins), a 1985 5th (Tom Sagissor) and a 1985 6th (Donald Dufresne) (June 1984)
  • #17: 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 (Columbus selected Kiel McLeod) (August 2004)
  • #16: Sylvain Lefebvre to the Toronto Maple Leafs for a 1994 3rd Round Pick (Martin Belanger) (August 1992)
  • #15: Alex Campbell, Denis DeJordy, Glenn “Chico” Resch, and Future Considerations (Germain Gagnon) to the New York Islanders for a 1973 2nd Pick (Glenn Goldup) and cash (June 1972)
  • #14: Danny Grant, Claude D. Larose, and Future Considerations (Bob Murdoch) to the Minnesota North Stars for a 1972 1st Round Pick (Dave Gardner), Future Considerations (Marshall Johnston) and cash (June 1968)
  • #13: Lyle Odelein to the New Jersey Devils for Stephane Richer (August 1996)
  • #12: Mike Ribeiro and 2008 6th Round Pick (Matt Tassone) to the Dallas Stars for Janne Niinimaa and a 2007 5th Round Pick (Andrew Conboy) (September 2006)
  • #11: Pavel Valentenko, Ryan McDonagh, Doug Janik and Christopher Higgins to the New York Rangers for Scott Gomez, Tom Pyatt and Michael Busto (August 1992)
  • #10: Andrew Cassels to the Hartford Whalers for a 1992 2nd Round Pick (Valeri Bure) (September 1991)
  • #9: Craig Conroy, Rory Fitzpatrick and Pierre Turgeon to the St. Louis Blues for Murray Baron, Shayne Corson and a 1997 5th Round Pick (Gennady Razin) (October 1996)
  • #8: Mark Recchi to the Philadelphia Flyers for Dainius Zubrus, a 1999 2nd Round Pick (Matt Carkner) and a 2000 6th Round Pick (Scott Selig) (March 1999)
  • #7: Jyrki Lumme to the Vancouver Canucks for a 1991 2nd Round Pick (Craig Darby) (March 1990)
  • #6: Claude Lemieux to the New Jersey Devils for Sylvain Turgeon (September 1990)

And with that, here are the trades that ranked #1-5: the five absolute worst trades in the modern history of the Montreal Canadiens.


#5: Montreal trades Rogatien “Rogie” Vachon to the Los Angeles Kinds for Denis DeJordy, Dale Hoganson, Noel Price and Doug Robinson (November 4th, 1971)
I’ll just come out and say it: this trade was an absolute mess on the Montreal side of the ledger.  Doug Robinson played in 239 NHL contests pre-Montreal; but he never played for the Canadiens, and never again played in the NHL.  Noel Price never played for Montreal either, and he was traded to the Atlanta Flames for cash and Future Considerations (and I have no idea what those considerations ended up being, despite my best efforts).  Dale Hoganson DID manage to play in 47 games for Montreal over two seasons, but failed to score a single goal; he had two assist and four penalty minutes before leaving for the WHA’s Quebec Nordiques.  Montreal later traded Hoganson’s rights to the Atlanta Flames for cash.  And finally, Denis DeJordy appeared in seven games for Montreal, going 3-2-1 in net with an awful 4.52 goals-against average.  DeJordy was then dealt to the New York Islanders in the Chico Resch deal (Trade #15 in this series).  So basically the Habs got 54 games and some cash out of the entire trade.

How did the Kings make out?  They only ended up with quite possibly the best goaltender in the history of their franchise.  Rogie Vachon had a bit of a rocky start in L.A., going 6-18-3 in 28 appearances along with a 4.05 goals-against average.  But in the each of the next six seasons, he played in 50+ games, won at least 20 games, had a least four shut-outs, and was .500 or better.  He also had a GAA below 3.00 in five of the six seasons.  He was a Second-Team All-Star in 1975 and 1977, played in the All-Star Games in ’73, ’75 and ’78, and he played for Canada in the 1976 Canada Cup (he even made the tournament All-Star Team).  Vachon signed with the Detroit Red Wings as a free agent after the 1977-78 season, leaving the Kings without a true #1 goaltender until Kelly Hrudey arrived in 1989.  In total, Vachon was 171-148-66 in 389 games along with a 2.86 goals-against average and 32 shutouts.  His talents were wasted on the West Coast to a certain extent, as he left the Kings before Marcel Dionne became a world-class player (Dionne scored 130+ points in each of the three seasons after Vachon left).  In addition to getting much less exposure in the Pacific Time Zone, Vachon never had an extended playoff run, posting a record of 9-16 in just 25 playoff games between 1974 and 1978.  Why Vachon is not in the hall of fame is a mystery to me, as he was one of the best goalies in the NHL during the 1970s.  And certainly worth much more than the pittance Los Angeles paid to get him.

#4: Montreal trades Rod Langway, Doug Jarvis, Craig Laughlin and Brian Engblom to the Washington Capitals for Ryan Walter and Rick Green (September 9th, 1982)
This trade almost single-handedly helped the Capitals transition from a laughing stock to a perennial contender (in the regular season, at least) in the late 1980s and early 1990s.  But before we get into that, I will acknowledge that this trade is a rarity for Montreal on this list: the players acquired had very lengthy stays in Montreal.  Ryan Walter and Rick Green each received Stanley Cup rings as members of the 1986 Canadiens, so clearly the trade didn’t hurt Montreal (on the surface).  Green spent seven seasons in Montreal; he was largely a defensive defenseman, although he did have four seasons in the 10-19 point range and a high of 29 points in ’82-83.  His +/- was up-and-down, but he was +37 overall in 399 along with 89 points.  He also added 19 points in 97 playoff contests.  He was flipped to Detroit for a 5th round pick (Dmitri Motkov, who never panned out) and, after 69 final games, Green was gone from the NHL.  Walter played with the Habs for nearly a decade, from ’82-83 to ’90-91, and he was a solid defensive forward.  His first season in Montreal (where he scored 29 goals and 75 points) was an outlier, but he did manage to hit the 20-goal mark three times, and he cleared 40 points four times.  He was highly disciplined, typically getting 30-50 penalty minutes in a season.  He was strong in the playoffs, but really stepped up during the Canadiens’ attempt to repeat as Stanley Cup champions in 1987 when he scored 19 points in 17 games.  In total, Walter had 141 goals and 349 points along with a +7 rating in 604 games.  He added 48 points in 100 playoff games, and eventually left Montreal for Vancouver as a free agent.  But he was pretty much done at that point; he only played a further 92 games post-Montreal.

Montreal received 1,003 games of service from a pair of quality NHLers.  So why does this trade qualify as a bad trade, never mind one of their worst?  Because the players Washington received, either directly or indirectly, each helped shape the Capitals into a franchise to be reckoned with.  Doug Jarvis was a top-notch defensive forward, and he spent just over three seasons in Washington.  He scored 112 points in 265 games along with a +9 rating.  While his stay was short, he played a key role in firming up the Capitals’ poor performance in their own zone.  They eventually became known as a solid defensive team.  Jarvis was traded to the Hartford Whalers for Jorgen Pettersson, who didn’t last long in Washington.  Brian Engblom was hardly an impact player.  He scored 27 points in 73 games for the Capitals in ’82-83.  But after six appearances the following season, he was traded to the Los Angeles Kings with Ken Houston for future Hall-of-Famer Larry Murphy, who spent six quality seasons in Washington.  Murphy was traded with Mike Gartner to the Minnesota North Stars for Bob Rouse and Dino Ciccarelli, who eventually became Al Iafrate and Kevin Miller.  All of these players had key roles in the Capitals successes during the 80s and 90s.  As opposed to the more qualitative or indirect impacts of Engblom and Jarvis, Craig Laughlin was a solid player for Washington.  He spent four-and-a-half seasons with the Capitals, scoring 20+ goals three times (including 30 in ’85-86), and scoring 50+ points four times (including 75 in ’85-86).  He left Washington with 110 goals and 283 points in 428 games along with a healthy +22 rating.  He was sent to the L.A. Kings for Grant Ledyard, whom the Capitals later traded to Buffalo (along with Clint Malarchuk and a 6th round pick) for Calle Johansson (plus a 2nd round pick that they used on Byron Dafoe).  Johansson suited up for 983 games with Washington.

So the trade with Montreal gave them some quality seasons from Laughlin, and by extension gave them lengthy tours of service from Larry Murphy, Calle Johansson and Al Iafrate.  Fantastic asset management.  But we have yet to look at the primary asset in this entire deal: Rod Langway.  Rod Langway may in fact be the greatest Washington Capital in history (although that is a title which Alexander Ovechkin may yet seize, especially if he ever achieves any measure of playoff success).  Langway had proven himself capable as a two-way defenseman with the Canadiens; between ’79-80 and ’81-82, he scored a total of 120 points and was a combined +155 in 223 games.  But with Washington, he helped forge an identity for both himself and the team.  Langway spent parts of eleven seasons in Washington, all of it as the team’s Captain, until his retirement.  He scored 30+ points in his first two seasons, but then appeared to concentrate on his defensive game.  It worked, because he ended up as one of the very best defensive defensemen of his era.  He had a positive +/- rating nine seasons in a row, with his lone negative rating coming in his partial (but final) season of ’92-93.  Langway played in 726 games for Washington, scoring 202 points and posting a +117 rating.  He could play physical hockey, but he was very disciplined: he rarely exceeded 60 penalty minutes (totalling 502 PIM).  While the Capitals rarely made it past the first round (outside of a deep run in 1990), Langway still managed to suit up for 78 playoff games (scoring 18 points).  Langway won the Norris trophy as the NHL’s top defenseman in 1983 and 1984, making the First All-Star team both years (he was also named to the Second All-Star team in 1985).  He was arguably the last truly defensive defenseman to win the Norris, which has since been dominated awarded to more offensively-skilled defenseman (such as Ray Bourque, Nik Lidstrom and Chris Chelios).  He was inducted into the Hockey Hall of Fame in 2002.

Langway would have been a valuable part of the Canadiens’ blueline; it is not inconceivable to think he could have been a difference maker when the Habs lost to the Calgary Flames in 1989, and he could have earned a ring in 1993 in place of Rob Ramage.  It’s a shame Langway was never able to have any significant playoff success in Washington, but it is safe to say that the exciting era of Alex Ovechkin, Mike Green and Nicklas Backstrom might not have happened (or at least not in Washington) were it not for Rod Langway’s contributions to that franchise.  Despite the solid contributions of Green and Walter, this trade was absolutely horrible for the Canadiens… and glorious for the Capitals.

#3: Montreal trades Patrick Roy and Mike Keane to the Colorado Avalanche for Jocelyn Thibault, Andrei Kovalenko and Martin Rucinsky (December 6th, 1995)
Of all the trades that pushed the Canadiens into their dark era post-1993, this was the most emotionally devastating.  While I believe that the two trades ranked #1 and #2 on had a greater (negative) impact on the franchise, the “Le Trade” devastated the team’s fanbase and cost the Canadiens its heart.  On December 2nd, 1995, Roy was left in net by Canadiens coach Mario Tremblay despite a terrible performance: Roy allowed 9 goals in 26 shots against the Detroit Red Wings.  When the score was 7-1, Roy made an easy save, and the crowd booed him… but Tremblay left him in for another two goals.  After he was finally pulled, he stormed past Tremblay and told Canadiens’ team president Ronald Corey “It’s my last game in Montreal”.  Four days later, “Le Trade” sent Patrick Roy and Mike Keane to the Colorado Avalanche.

Montreal received a package of three players.  Andrei Kovalenko didn’t amount to much with the Canadiens: he scored 17 goals and 34 points in 51 games in ’95-96.  He was then traded to the Edmonton Oilers for Scott Thornton, who later traded to the Dallas Stars for Juha Lind.  Martin Rucinsky actually fared reasonably well in Montreal.  He had three straight seasons of 20+ goals and 60+ points to start his tenure with the Canadiens, and ended up spending parts of seven seasons in Montreal.  He scored 134 goals and 297 points in 432 games 398 penalty minutes and a decent-enough +/- rating of -8.  With Rucinsky, the Canadiens made the playoffs just twice, and he didn’t help much (he scored 3 goals in 15 games).  He was dealt to Dallas with Benoit Brunet for Donald Audette and Shaun Van Allen, neither of whom did much long-term in Montreal.  Each of Audette, Van Allen and Lind left Montreal once their contracts expired, meaning Montreal received nothing in terms of compensation for their departures.

And then there was poor Jocelyn Thibault.  Imagine being an up-and-coming French-Canadian goaltending prospect with the Quebec Nordiques.  The team moves to Colorado, which helps alleviate some of the pressure.  But then you find out you’re being traded to Montreal, which is incredibly demanding of its goaltenders, especially if they’re Francophone.  Not only that, but you find out you’re replacing “St. Patrick”, the team’s best goaltender since Ken Dryden (not to mention a surefire Hall-of-Famer).  That’s exactly what happened to Monsieur Thibault at just 21 years of age.  Despite the enormous pressure, he held up quite well, and he likely benefitted from Andy Moog’s mentorship in ’97-98.  Thibault went 67-56-24 in 158 games over parts of three seasons with the Canadiens; he had a 2.73 goals-against average and a .908 save percentage along with 7 shutouts.  Fairly solid numbers, and a decent win-loss record.  Unfortunately, he was very weak in the playoffs; he went 2-7 in 11 appearances, with an ugly 3.94 GAA and a poor .885 PCT.  After 10 appearances in the ’98-99 season, he was sent to the Chicago Blackhawks in a six-player trade.  Thibault, Dave Manson and Brad Brown went to Chicago, and in return Montreal received Jeff Hackett, Eric Weinrich, Alain Nasreddine and a 4th round pick that ended up being Chris Dyment.  So while Montreal actually managed a modest return on the initial deal (Rucinsky and Thibault), they failed miserably in the next round of asset management.  Hackett spent a fair amount of time in Montreal, but was dealt to San Jose for Niklas Sundstrom and a draft pick (dead end).  Weinrich was traded to Boston for Patrick Traverse, who became Mathieu Biron (dead end).  Nasreddine went to Edmonton with Igor Ulanov for Christian Laflamme and Matthieu Descoteaux (another dead end).  And Dyment netted them a 5th round pick from Minnesota, which became Jiri Cetkovsky (who never made the NHL).  So within a decade of the deal, Montreal had virtually nothing to show for trading their most popular player (arguably) of the past 30 years.

How did things turn out for Colorado?  Well they won the 1996 Stanley Cup just a few months later, and another in 2001.  So it turned out pretty darned well.  Keane was exactly the kind of quality character player the Avs needed.  He didn’t score a lot (47 points in 136 games), but he was disciplined, defensively responsible and a leader (he was Montreal’s Captain at the time of the trade).  He left after the ’96-97 season and signed with the New York Rangers as a free agent.  Meanwhile, Patrick Roy continued to enhance his reputation as one of the greatest goaltenders of all time.  In his partial season with the Avs after the trade, he went 22-15-1 with a 2.68 GAA and .909 save percentage.  He spent the next seven seasons in Colorado, each of which saw him post better numbers than that partial season.  In the 1996 playoffs, he was stellar; 16-6 in 22 games with a 2.10 GAA and .921 PCT, along with three shutouts.  Between 1996 and 2002, Colorado won two Stanley Cups (‘96 and ‘01), and made it to the Semi Finals on four other occasions (losing to Detroit in ‘97 and ‘02, and losing to Dallas in ‘99 and ‘00).  With Roy in net, Colorado played in 22 playoff series over eight seasons, winning 15 of them.  That’s playoff series, not games.  Roy was vital in putting Colorado over the top in ’96, and he won the Conn Smythe trophy as Playoff MVP in 2001 (the third of his career; he is the only player in NHL history to win it more than twice).

Roy proved he was a Hall-of-Famer in every sense of the word.  In his next seven full seasons with Colorado, he won 30+ games (including 40 in ’00-01), had a GAA no higher than 2.39 (including 1.94 in ’01-02), and had a save percentage of at least .913.  He also had 4+ shut-outs six times in seven seasons (he had two in ’99-00).  He ended his in Colorado with a record of 262-140-65 in 478 games.  His line read 2.27 GAA, .918 PCT and 37 shutouts.  He even chipped in 17 assists and 152 PIM.  In the playoffs he was even better: 81-52 in 133 games, with a 2.18 GAA, .922 PCT and 18 shutouts (along with 7 assists and 20 PIM).  In addition to his 2001 Conn Smythe, he was a First-Team All-Star in 2002, and he won the William Jennings trophy when the Avs had the fewest goals allowed in the 2000-01 season.  He was definitely the greatest goalie of the 1980s, and arguably the best goaltender of his era (with the only true competition being Dominik Hasek and Martin Brodeur).  And his exit from Montreal is an absolute shame; not only in the way he left (with anger and hurt pride), but also because his departure failed to benefit the franchise in any measurable way.  As someone who followed the Toronto Raptors during the Vince Carter era, I can sympathize.  Roy really should have retired as a member of the Canadiens.  Or at the very least, the Habs should have waited more than a few days before dealing their best player.

#2: Montreal trades Eric Desjardins, Gilbert Dionne and John LeClair to the Philadelphia Flyers for Mark Recchi and a 1995 3rd Round Pick (Martin Hohenberger) (February 9th, 1995)
This was the trade that truly sent the Habs on a downward spiral after their Stanley Cup hangover.  It also kicked off a frightening 21-month period that ran through to October 1996: during that time, the Habs made four separate trades that appeared in the Top 13 of this list.  They traded away John LeClair, Eric Desjardins, Patrick Roy, Pierre Turgeon and Lyle Odelein.  That’s one hell of a core.  Mark Recchi was the only notable player they got back, as the rest of their “core” returns (Jocelyn Thibault, Martin Rucinsky, Shayne Corson and an aging Stephane Richer) failed to measure up.  Not only that, but the “next wave” of assets (i.e. the players received after trading Thibault et al) consisted of Jeff Hackett, Scott Thornton, Donald Audette, Shaun Van Allen, Danius Zubrus, and Patrick Poulin.  Does that sound even REMOTELY on par with the talent of the first group I mentioned (Roy, Turgeon, etc.)?  It’s no wonder the Habs had a losing record five times in seven season from ’96-97 to ’02-03 (missing the playoffs four times in the process).  They also missed the playoffs three years in a row (1999 to 2001), the first and only time in the 100+-year history of their franchise that that has occurred.

But I digress.  This trade with Philadelphia was all about one thing: acquiring an offensive superstar.  The Habs entered the ’93-94 season as the defending Stanley Cup champions, and had a solid 96-point regular season.  However, they were eliminated in the first round by the Boston Bruins in seven games.  Vincent Damphousse scored 40 goals and 91 points that year, while Brian Bellows had 33 goals and 71 points.  However, no other Hab hit either the 25-goal or 60-point marks.  After the ’94-95 lockout, the shortened season didn’t start off very well.  Although a few players from the 1993 team were already gone (including Guy Carbonneau), the core was still largely intact.  But the team was struggling offensively, and Mark Recchi was made available in Philadelphia.  The Habs quickly jumped at the chance to have a true all-star up front.

Recchi was actually a solid acquisition for Montreal, something that Habs fans tend to forget.  He scored 14 goals and 43 points in 39 games for the Habs, although he did have a -3 rating.  Unfortunately, the wheels were falling off around him.  As the team struggled, management became increasingly desperate.  In April, the team sent fan favourite Kirk Muller and talented defenseman Mathieu Schneider (along with spare part Craig Darby) to the New York Islanders for Pierre Turgeon and Vladimir Malakhov.  While Turgeon was a talented player (and I believe an excellent acquisition), it failed to give the team a jolt: they went 11-18-3 in their final 32 games.  How bad were things in Montreal?  It was the first time in Patrick Roy’s career that he lost more games than he won.  And 1995 marked the first time since 1970 that the Canadiens missed the playoffs.  Recchi was solid over the next three seasons, helping the Habs to rebound and make the playoffs each year.  Despite a flurry of trades sending key players out of town (Roy, Turgeon, Odelein), Recchi was good for an average of 31 goals and 77 points a season.  He also represented the Canadiens at the 1997, 1998 and 1999 All-Star games.  But late in the ’98-99 season, the Habs were struggling again, and it was now obvious a quick fix wouldn’t work.  Recchi’s production had also slumped, and he had 47 points in 61 games.  He was traded back to Philadelphia in exchange for Zubrus, and a pair of draft picks that became Matt Carkner and Scott Selig (see Trade #8 in this series).  Recchi finished his Habs career with solid-if-unspectacular numbers: 120 goals and 322 points in 346 games, a +23 rating, and 222 PIM.  He was also strong in his limited playoff time; although the Habs won just one of the four series Recchi played in, he scored 11 goals and 24 points in 21 games.  The Canadiens used the draft pick on Martin Hohenberger, who never made the NHL.

How about the Flyers?  Let’s look at the backstory for a moment.  After losing to the Canadiens in the 1989 Conference Finals, the Flyers missed the playoffs each year from 1990 to 1994.  Despite the presence of superstar Eric Lindros, things weren’t coming together.  But then this trade happened, and the team suddenly clicked: the Flyers were 3-7-1 prior to the trade, then went on a tear and finished the season on a 25-9-3.  They made the playoffs that year, and went all the way to the Conference Finals.  They made the playoffs each year for the next ten seasons, making it as far as Stanley Cup Finals in 1997, as well as the Conference Finals in 2000 and 2004.  Over that 10-year span, they won 40+ games nine times; their worst season saw them finish with “just” 37 wins and 93 points.

Gilbert Dionne was a nothing acquisition; he played just 22 games for the Flyers over two seasons, recording seven assist along with a -1 rating.  He left for the Florida Panthers as a free agent, and played just five more NHL games after leaving Philadelphia.  Desjardins on the other hand became a crucial part of the Flyers blueline for more than a decade, spending parts of 11 seasons in Philadelphia.  He was durable, playing at least 65 games for eight consecutive seasons.  He scored 12+ goals four times, recorded 30+ assists five times (hitting 40+ assists twice), and scored 40+ points five times (eclipsing 50+ points twice).  He had a positive +/- rating in 9 of 11 seasons, and was never worse than -3.  He also never recorded more than 56 penalty minutes in a season.  In total, he had 303 assist and 396 points in 738 games, along with a +143 rating and 406 penalty minutes.  He was even better in the playoffs, scoring 51 points in 97 games (including a stellar 12 points in 18 games during the 2000 playoffs).

And then there is John LeClair.  He combined with Lindros to be one of the most formidable duos in the NHL in the late 1990s.  For a time they were joined by Mikael Renberg to form the famed “Legion of Doom” line, one of the most dominant lines in recent memory.  LeClair absolutely exploded in Philadelphia, scoring 25 goals and 49 points in 37 games along with a +21 rating.  That pace would have seen him score 54 goals and 106 points in an 80-game season.  He became a First-Team All-Star, and helped lead the Flyers to the playoffs for the first time in six seasons.  LeClair then decisively proved that he was no fluke; he scored 50-51 goals in each of the next three seasons, and then recorded 40-43 in each of the next two.  While he was slowed by injuries during his final few seasons in Philadelphia (he missed most of the ’00-01 season, and never again hit the 30-goal or 60-point marks), he was arguably the best power forward in hockey from ’94-95 to ’99-00.  During that span he scored 260 goals and 497 points in just 441 games, along with a staggering +160 (he never had a negative +/- rating in Philly).  He was a First-Team All-Star in 1995 and 1998, and a Second-Team All-Star in 1996, 1997 and 1999.  He also appeared in five consecutive All-Star games from 1996 to 2000.  His other accolades included being the NHL’s +/- leader in 1997 (+44) and 1999 (+36), as well as being a part of the U.S. team that won the World Cup in 1996 (LeClair also made the tournament All-Star team).

In addition to being dominant during the regular season, LeClair also came up big come playoff-time.  In his first three seasons with the Flyers, he scored 20 goals and 44 points in 45 playoff games, including 21 points in 19 games during their run to the 1997 Finals.  He ended his Philadelphia Flyers’ career with 333 goals (5th all-time among Flyers players) and 643 points (7th all-time) in 649 games.  He also had a +197 rating.  Although he was a big player who could play a physical game, he was quite disciplined: he only once exceeded 60 PIM, and finished with 337 overall.  He also finished with 35 goals and 74 points in 116 playoff games.  He left as a free agent for the Pittsburgh Penguins following the ’04-05 lockout, and he played his final 94 games with the Pens.  LeClair for Recchi alone would qualify this trade for the Worst-Of list; factoring in Desjardins and the Habs inability to turn Recchi into further meaningful assets means this trade is almost (but not quite) the worst trade in Canadiens history.

#1: Montreal trades Chris Chelios and a 1991 2nd Round Pick (Michael Pomichter) to the Chicago Blackhawks for Denis Savard (September 4th, 1990)
After the emotional departure of Patrick Roy and the post-Montreal ascension of John LeClair, there is only one trade left that qualifies as a worse transaction in the modern history of the Montreal Canadiens: Chris Chelios for Denis Savard.  Thanks to a trade with the Colorado Rockies (which did absolutely nothing for that franchise), Montreal had the first overall pick in a fairly weak 1980 Entry Draft.  Montreal was apparently considering QMJHL superstar Denis Savard, a skilled, French-Canadian star from the Montreal Juniors.  It was a match made in heaven… until the Canadiens opted to select Doug Wickenheiser from the Regina Pats of the WHL instead.  Wickenheiser did have fantastic juniour stats, so it is at least understandable why the Canadiens went that way.  But they should have followed their gut and chosen the hometown boy.  Wickenheiser was a bust; his best season was ’82-83, where he scored 25 goals and 55 points.  He ended his career with 111 goals and 276 points in 556 games.  Savard meanwhile became a superstar with Chicago, recording five 100+ point seasons (including a high of 131 in ’87-88).  He even has a move named after him: the “Savardian Spin-o-Rama”.

Savard spent 10 seasons in Chicago, but had missed 42 games over two seasons in ’88-89 and ’89-90.  Montreal had just lost Bobby Smith and Mats Naslund at the end of the ’89-90 season, and so they were looking for some fresh offensive talent.  Montreal jumped at the chance to acquire Savard, trying to rectify a mistake made 10 years earlier at the draft.  Unfortunately, it was too late for both Savard and the Canadiens.  Savard was well past his prime, and he was no longer the offensive dynamo he was with Chicago.  He put up a respectable 28 goals and 59 points and a -1 rating in ’90-91; not superstar figures, but decent enough. He stepped up in ’91-92, scoring 28 goals and 70 points along with a +6 rating.  He was solid for the Habs in the playoffs. In each of 1991 and 1992, they won their first round series and then lost to the Boston Bruins in the second round.  Savard was stellar, scoring 25 points in 24 games.  His production continued to decline though, as he scored 50 points in 63 games during the’92-93 season.  His production (and ice time) in the playoffs fell off as well; although the Habs won the Stanley Cup, Savard only dressed for 14 games (recording zero goals and five assists).  Montreal allowed him to leave for the Tampa Bay Lightning as a free agent; he spent parts of two seasons there before one last tour of duty with Chicago.  He retired as a member of the Blackhawks following the ’96-97 season… and as Chris Chelios’ teammate, no less.

As for Chris Chelios, he merely became one of the greatest defensemen in the history of the Chicago Blackhawks.  He was incredibly durable, never missing more than 10 games in a season during his nearly nine-year run with Chicago.  He was at his best in the 1992 playoffs, scoring an amazing 21 points in 18 games while the Blackhawks made it all the way to the Stanley Cup Finals (where they lost to Mario Lemieux and the Pittsburgh Penguins).  Chelios was consistently outstanding; he could score (five seasons of 10+ goals), he could pass (three seasons of 50+ assists, four seasons in the 60-73 point range), he was tough (seven seasons of 100+ PIM, including three over 200) and he was responsible defensively (in seven of his nine seasons, he was +12 or better).  Chicago was consistently a contender with him in the line-up; they made the playoffs from 1991 to 1997, winning six playoff series during that time.  Chelios finished his stint in Chicago with 92 goals and 487 points in 664 games, a +120 rating, and 487 penalty minutes.  He was just as good in the playoffs, with 48 points in 65 playoff appearances.

Chelios absolutely racked up the accolades in Chicago.  He had already won a Norris Trophy as the NHL’s most outstanding defenseman in 1986 with the Habs, and he won two more in Chicago (1993 and 1996).  He was a First-Team All-Star in 1993, 1995 and 1996, as well as a Second-Team All-Star in in 1991 and 1997.  This means that he was found to be one of the top four defensemen in the NHL five times in his nine seasons with Chicago.  He also represented Chicago at the all-star game seven times: 1991 to 1994, and 1996 to 1998.  He only missed two all-star games (1995 and 1999).  On top of that, he was also a major presence for the U.S. in international competitions: he represented the U.S. at the 1991 Canada Cup, and helped them win the 1996 World Cup.  He was also named to the tournament All-Star team each time.  Chicago won this trade so badly it’s almost comical.  Savard scored 179 points in 210 games during his three-year stint in Montreal.  During that same span (’90-91 to ’92-93), Chelios scored 193 points in 241 games.  And even when considering the playoffs (again during that same span), Savard had 30 points in 38 games, while Chelios had 31 points in 28 games.  Although Savard did get a Ring in 1993, Chelios outperformed Savard in every possible way.  And Chelios was a defenseman.  Thankfully Mike Pomichter never made the NHL, because any success he had would have made the trade look even worse to Canadiens’ fans (he was eventually sold to Toronto).

Late in the 1999 season, Chicago opted to go cheaper and younger, resulting in Chelios being shipped to the rival Detroit Red Wings.  It was understandable, as Chelios was 37 years old and probably done.  Except it turns out he wasn’t almost done.  He played another 578 games for the Red Wings, and then a final seven-game stint with the Atlanta Thrashers.  He had a pair of 30+ point seasons for the Wings, including 39 points in ’01-02.  Chelios scored 152 points in his final 585 NHL games, along with a fantastic +156 rating.  He also played in 103 playoff contests post-Chicago, recording 28 points.  2001-02 was arguably his last “great” season: he represented Detroit at the 2002 All-Star game, lead the league in +/- (+40), scored 39 points, and then added 14 points in 23 playoff games as the Wings won the Stanley Cup.  He failed to record a point when the Wings won in 2008, but he did appear in 14 games (as well as 6 games during their run to the Finals in 2009, where they lost to the Pittsburgh Penguins).  His production slowed after that, but he was still had a positive +/- rating every season from ’02-03 to ’09-10.  He retired from the NHL in August 2010 at the age of 48.  Most players would be lucky to hit 40, and Chelios almost made it to 50 years of age.  His first NHL game occurred during the ’83-84 season; a player born during the 1983 offseason would have been 27 years old when Chelios retired.  Chelios in his prime on the Canadiens’ team with Damphousse, Muller and Roy would have made for a supremely entertaining franchise.  A top pair on the powerplay of Desjardins and Chelios?  Yes please!  Instead, Chelios finished what is sure to be a Hall-of-Fame career with more games played in each of Detroit and Chicago than in Montreal, which is a shame.  Which makes it the worst trade in the modern history of the Montreal Canadiens.

Logo - 100 Seasons Years Logo - 100 Seasons

I hope you enjoyed this trip down memory lane.  And if you’re a Habs’ fan, have no fear; I have begun doing research into the Best Canadiens trades in an attempt to reach karmic balance.  Much as I did with the Toronto Maple Leafs’ trade history.  As a Leafs fan, I am supremely jealous at the wealth of great trades in the history of the Canadiens.  Using Oakland’s draft pick on Guy Lafleur, picking up Bobby Smith from Minnesota, acquiring Vincent Damphousse from Edmonton… plenty of material work with.  It should be a blast.  Feedback is always welcome, and I’m hoping to one day have a Best of/Worst of list for each of the Canadian NHL franchises.  Thanks for reading, and I hope you enjoyed your visit.


6 thoughts on “The 25 Worst Trades in Montreal Canadiens History – #1-5

  1. The Scott Gomez trade has definitely worked it’s way into the top 5 by now. It has clearly surpassed the Rogie Vachon trade at this point. Keep in mind, the Habs had Ken Dryden at the time. They also dumped Tony Esposito around that time period and he was a better goalie than Vachon.

    • That Gomez trade is like a fine wine, it just gets better with age. Like the Raycroft-Rask trade for Toronto.

      Even with Ken Dryden making Vachon expendable, they failed to get fair value for him (one of the few trades L.A. WON with Montreal).

      I completely forgot about Esposito, thanks for flagging that one!

  2. best trades for karmic balance, I’ll salute that!
    looking forward to it, great analysis, hard to find too!
    cheers from a Habs fan in Australia

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