Montreal Canadiens: Five Trades That Ruined Habs Latest Dynasty Before It Started

The Montreal Canadiens have not won a Stanley Cup since 1993. If not for these five trades, that could have been the start of another dynasty, and not the end of their title runs.

The Montreal Canadiens have the greatest history in hockey. They have won more Stanley Cups, inducted more people into the Hall of Fame, and have won the most individual trophies of any team in the history of the sport. They are, by far the most decorated team and the banners hanging in the rafters of the Bell Centre are a reminder of their great past.

The Habs have not won a championship however, since 1993. It has been 27 years since they were crowned the kings of the National Hockey League and though no team is even close to catching them on the leaderboard of most titles, fans tend to get restless during such a dry spell.

The Canadiens can thank some of the greatest dynasties in sports history for all their success. They won five straight Stanley Cups from 1956-60, four more in a span of five years to close out the 1960’s and won four more consecutively to close out the 1970’s.

These were teams led by Hall of Fame players like Maurice Richard, Jean Beliveau, Doug Harvey, Jacques Plante, Guy Lafleur, Ken Dryden, Larry Robinson among many others who have rightfully had their names placed in the rafters of the Bell Centre, their jersey numbers never to be worn again.

We haven’t seen an extended run of greatness from the Montreal Canadiens since 1979. They did win a Stanley Cup in 1986 with some of the old guard still around from the 1970’s dynasty, and then won again in 1993 while leaning heavily on Patrick Roy to carry them to greatness that season.

However, that is just two Stanley Cup titles in over 40 years now. It is not the worst record over the past 40 years in the NHL, but it is the least amount of winning done in Montreal over any 40 year span in their history. Now, with far more teams than there used to be in the league you would expect a team to win less frequently, but just two in 40 years is quite the dry spell after winning 15 times in the previous 24 years.

In the era of 31 teams, NHL Drafts, free agency and salary caps, it is hard to imagine a team ever going on a run like the Habs did in the 1970’s. No one will make it to ten straight Cup finals like the Habs did from 1951-60, but the Canadiens could have had one last dynastic run recently.

Maybe they would not have won four Stanley Cups in a row, but if not for these five trades, we would have seen a Stanley Cup parade in Montreal more recently than 1993.

5. Chris Chelios traded to the Chicago Blackhawks for Denis Savard

The general manager of the Montreal Canadiens for their last two Stanley Cups was Serge Savard. He made some great trades that helped make those championships happen. He acquired Bobby Smith who was key to winning in 1986. He also traded for Vincent Damphousse, Kirk Muller and Brian Bellows who led the team offensively to their 1993 championship.

One trade he made that he surely would have liked to have back was Chris Chelios being dealt to the Chicago Blackhawks for Denis Savard. The Habs even threw in a second round draft pick in the deal that was put together in June of 1990.

At the time, Chelios was already a dominant two-way defenseman who played a punishing defensive style that would make Chris Pronger blush. In his last full season with the Habs, Chelios scored 73 points in 80 regular season games and added 19 more points in 21 postseason games. He won the Norris Trophy and would have been a candidate for the Conn Smythe as well had the Habs downed the Calgary Flames that year.

Chelios would continue to be a dominant defender through the 1990’s and did not retire from the NHL for another 20 years after being traded from Montreal. Savard, on the other hand, saw his impressive offensive totals from the 1980’s drop off dramatically. He had 70 points in 77 games in 1991-92, but by the time the Habs won the Cup a year later he was reduced to a spare part that was dealing with severe injuries.

Savard left Montreal to play with the expansion Tampa Bay Lightning in 1993-94. Chelios won another Norris in 1993 and took home a third in 1996. He averaged over 30 minutes of ice time per game in 1998 and was simply one of the best two-way defenseman in the league for the entire decade. The Habs won one Cup without him, but he could have been the cornerstone of a few more titles in 1990’s if he stayed in Montreal.

4. Claude Lemieux traded to New Jersey Devils for Sylvain Turgeon

While Serge Savard’s biggest blunder was trading Chelios for Denis Savard, he lost another key piece to possible Stanley Cup runs when he dealt Claude Lemieux to the New Jersey Devils for Sylvain Turgeon in September of 1990.

Lemieux burst onto the scene in Montreal in 1986, scoring ten goals and 16 points in 20 postseason games to help the Habs win the Stanley Cup. He was just a rookie that year, having played only ten regular season games before his playoff performance.

After leaving the Habs, he proved to be a valuable player for championship teams in New Jersey and Colorado. He played a physical, gritty style and had no problem adding plenty of offence. His penchant for coming up big in the playoffs did not end with his rookie year as Lemieux would win the Conn Smythe Trophy in 1995 as playoff MVP with the Devils and then won the Cup again the following year with the Avalanche. He would return to New Jersey and win yet another championship in 2000.

Meanwhile, Turgeon played one and a half underwhelming seasons in Montreal before moving on to the expansion Ottawa Senators. By 1995, he was out of the NHL, and travelled around Europe playing in various leagues, while Lemieux was proving to be a pivotal player on three Stanley Cup champions.

Lemieux set a career high with 81 points in 1993, but was at his best during a handful of playoff runs in the late 1990’s. After winning the Smythe in 1995, Lemieux scored 55 points in 62 playoff games for the Avalanche in the next four years. His 80 career playoff goals are 9th all time, one ahead of Jean Beliveau (though the great Jean Beliveau played less playoff games).

Having Lemieux in the late 1990’s on the Habs would have given them a terrific two-way player and leader who brought his all on every shift and transformed into an elite player each year in the playoffs.

3. John LeClair and Eric Desjardins traded to Philadelphia Flyers for Mark Recchi

Serge Savard was mercifully let go at the end of the 1994-95 season but not before he pulled off another one-sided deal in the wrong direction. John LeClair, a budding star power forward, and Eric Desjardins, an elite right-shot defender were shipped to Philadelphia for high scoring winger Mark Recchi.

In all fairness to Recchi, he was great during his time in Montreal. He arrived in February 1995, which was early in the lockout shortened year and he scored 43 points in 39 games. The Habs made the playoffs the next three years and Recchi was a key reason why. He had 78, 80 and then 74 point seasons and added 24 points in 21 total playoff games during that span.

So, Recchi was good, he just didn’t make up for the loss of LeClair and Desjardins. LeClair scored 19 goals in each of last two seasons with the Canadiens and put up 44 and 43 points. Upon arriving in Philadelphia, he immediately exploded offensively and exceeded what Recchi was doing in Montreal.

Joined on a line with Eric Lindros, LeClair became a fierce power forward for the Flyers and was a key member of the Legion of Doom line with Lindros and Mikael Renberg. LeClair had 49 points in 37 games during his first year in Philly. He followed that up with seasons of 97, 97, 87, 90 and 77 points while putting up five straight 40 goal seasons and three times notching 50 snipes. He was one of the best goal scorers in the league in the late 1990’s.

The Flyers were one of the best teams in the Eastern Conference at that time and Desjardins was leaned on heavily as the team’s best defenseman. Immediately after leaving Montreal, Desjardins was in the top ten for Norris Trophy voting in five of the next six seasons. He never won, but it shows that he was consistently one of the best defensemen in the game from 1995 to 2001.

Now, imagine him on the second pairing in Montreal all those years because Chris Chelios was on the top pair. Not a bad one-two punch on the right side and they would have had a pretty solid goaltender in behind them.

2. Patrick Roy and Mike Keane traded to the Colorado Avalanche for Martin Rucinsky, Andrei Kovalenko and Jocelyn Thibault

This was one of Rejean Houle‘s first trades and the wild thing is, it is debatable whether it was actually his worst or not. He had an awful tenure at the helm of the Habs from 1995-2000 and traded away several key pieces that would go on to have great success over the next few years elsewhere.

The best player he traded away was definitely Patrick Roy. There is no denying Roy’s incredible talents in goal and he is arguably the best goaltender to ever strap on the pads in the history of the NHL. He was amazing for the Habs for ten seasons and basically carried them to their two most recent Stanley Cups. With a little more time in Montreal, he likely could have helped them win more.

Roy was traded to the Avalanche in December of 1995 because he was having a rift with head coach Mario Tremblay. The coach was in over his head and, along with Rejean Houle, decimated the team because he could not get along with any of their star players.

Roy went on to Colorado and immediately helped them, along with Claude Lemieux and Mike Keane, to a Stanley Cup title in 1996. Roy was exceptional, as always, in the postseason, putting up a 2.10 goals-against average and a .921 save percentage.

Roy would continue his dominance of the NHL for eight seasons in Colorado. He started between 60 and 65 games every year, finished in the top eight of Vezina Trophy voting every year he was in Colorado and was top five on five occasions. He won the Conn Smythe as playoff MVP in 2001 and even earned some Hart Trophy votes for league MVP three different seasons.

There is no question, any team that had Patrick Roy in their net had a chance to win every game in the late 1990’s and into the 2000’s until he announced his retirement in 2003. Had he stayed in Montreal, they would have been a serious Stanley Cup contender throughout the rest of that decade and even into the early 2000’s.

Mike Keane was a great penalty killer and provided a lot of leadership for the teams he played on after leaving Montreal. He won a Cup with the Avs in 1996 and again with the Dallas Stars in 1999. Martin Rucinsky, Andrei Kovalenko and Jocelyn Thibault were all decent NHL players at the time, but their contributions paled in comparison to what Patrick Roy brought late in his career.

1. Pierre Turgeon, Craig Conroy and Rory Fitzpatrick traded to St. Louis Blues for Shayne Corson and Murray Baron

Finally, the last trade chronologically that completely derailed a potential dynasty. Rejean Houle went back to work to pull off this dandy deal. He traded Pierre Turgeon and threw in a couple of decent young prospects for an aging Shayne Corson and a hard-nosed third pairing defender in Murray Baron.

Turgeon’s tenure with the Habs is not remembered that fondly by fans it seems, but he has the second highest points-per-game of all-time in a Habs sweater. He only played one full season in Montreal, but also played parts of two others between stints with the New York Islanders and St. Louis Blues. However, that one full season saw him score 96 points which is still the highest by a Canadiens player since Vincent Damphousse had 97 in 1993.

In total, Turgeon played 104 games and scored 127 points with the Canadiens. After leaving Montreal very early in the 1996-97 season, Turgeon played five years with the Blues and scored 355 points in 327 games during that time. He didn’t get all the accolades because there were other centers like Joe Sakic, Steve Yzerman and Wayne Gretzky dominating the headlines, but Turgeon quietly was a terrific scorer at that time.

Turgeon did have a terrific power forward winger who could score 50 goals in Keith Tkachuk playing on his left side, but if the Habs avoided these trades, Turgeon would have had John LeClair on his line in Montreal.

The Blues had a hard time in the Western Conference getting past the Detroit Red Wings and Colorado in the postseason, but Turgeon scored 35 points in his last 35 playoff games in St. Louis. Craig Conroy was a decent player for the Blues in the late 1990’s, scoring 43 points in 1997-98 and 39 the following year.

Meanwhile, Corson had a solid year in Montreal in 1997-98, scoring 21 goals and 55 points in 62 games. His offence fell off a cliff after that as he continued to be a valuable depth player that killed penalties and provided leadership, but he didn’t score more than 12 goals again in his career. Murray Baron was a typical late 1990’s defenseman. He was big and could get 100 penalty minutes no problem, but he could not skate well and had a hard time passing ten points in a season.

Though Corson did have one solid season in Montreal, Turgeon was dominant for five more years after the trade and would have been the team’s top center for the next half-decade if the Habs were wise and kept him in town.