The 8 Best And 7 Worst Moves In Montreal Canadiens History

Every NHL team has had their share of good and bad moves in regards to trades, signings, etc... And when a team has been around for over a century, they will have certainly had their fair share of brilliant and questionable acts.

There’s no question that the Montreal Canadiens have had an incredible history beginning in 1909 when they were first founded and continuing to this very day. They have won the most Stanley Cups of any NHL team with 24 of them. And of course great success always comes with having tremendously talented players such as Maurice Richard, Jean Beliveau, Guy Lafleur, Ken Dryden and Serge Savard just to name a few.

But behind the scenes, every team’s management works full time to try to create the best team in the league by trading players, signing free agents, hiring the most qualified coach to direct the players, and of course choosing the most talented prospects at each year’s draft.

While the Canadiens’ management team hasn’t always made the best choices, they have also made some incredibly great moves that Habs fans will always remember. Here is a list of the eight best and seven worst moves in the history of the Montreal Canadiens.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Best: Taking A Chance On Alexander Radulov

Adam Hunger-USA TODAY Sports

The last time Alexander Radulov played in the NHL was in 2012 with the Nashville Predators. He had a bit of a tarnished reputation for breaking curfew and getting suspended by his own team. He did, however, have a phenomenal career overseas in the KHL, earning well over a point a game and developing into one of the greatest players in that league.

Then in July 2016, the Montreal Canadiens announced that they had signed the free agent Radulov to a one-year contract. They took a chance on him and it sure paid off. He played 76 games with the Habs and produced 54 points, along with a +10 plus/minus rating. He led the team with 36 assists, most of which were helpers on Max Pacioretty’s goals. There’s no doubt that Radulov and Pacioretty played fantastic together.

The Canadiens and Radulov are currently in talks over a new contract. Let’s hope they can come to an agreement.

14 Worst: Drafting David Fischer

via bleacherreport.com

The Montreal Canadiens had the 20th-overall choice at the 2006 NHL Entry Draft and selected David Fischer.

At the time of the draft, this defenseman was playing for Apple Valley High School in Minnesota and was averaging nearly a point a game. However, he never did make it to the National Hockey League. He spent four seasons playing for the University of Minnesota, followed by two seasons in the ECHL with the Florida Everblades. He also played two games with the Houston Aeros of the American Hockey League in 2011-12, but that’s as far as he made it. He has since been playing overseas.

If the Canadiens would have passed on Fischer, they could have drafted one of the other prospects who turned out to have great careers such as Claude Giroux (drafted 22nd), Patrik Berglund (drafted 25th), and Nick Foligno (drafted 28th).

13 Best: Drafting Patrick Roy

via SI.com

In November 1983, the Montreal Canadiens traded Robert Picard to the Winnipeg Jets in exchange for a 3rd-round pick in the 1984 NHL Entry Draft. And with that pick, they chose Patrick Roy 51st overall. The Habs were extremely lucky that no other team had chosen Roy and their decision to draft him turned out to be one of the best moves in franchise history.

He ended up spending 12 seasons with the Canadiens between the 1984-85 and 1995-96 seasons. He produced 289 wins (including 29 shutouts), 175 losses and 66 ties, along with a 2.78 goals against average in 551 regular season games. He then played in 114 playoff games and earned 70 wins. He helped the Canadiens win the Stanley Cup in 1986 and 1993.

During his career between Montreal and Colorado, he was awarded three Vezina Trophies, five William M. Jennings Trophies, and three Conn Smythe Trophies. He was inducted into the Hockey Hall of Fame in 2006 and then on November 22, 2008 the Montreal Canadiens retired his number 33 jersey.

12 Worst: Drafting Jarred Tinordi

Jean-Yves Ahern-USA TODAY Sports

The Montreal Canadiens had the 22nd-overall draft pick at the 2010 NHL Entry Draft and chose defenseman Jarred Tinordi.

Since he is 6 feet 6 inches tall and 230 pounds, you’d think that he would be a force to be reckoned with, but that’s not how this defenseman played. He was only mediocre when it came to delivering hits and blocking shots. And in 46 regular season games played, he tallied just 6 assists, along with a -5 plus/minus rating.

He had a difficult time earning a permanent spot with the Canadiens so he spent the majority of his time playing in the AHL. Then in January 2016, he and Stefan Fournier were sent to the Arizona Coyotes in exchange for Victor Bartley and John Scott.

I’m pretty sure the Habs are regretting their decision to draft Tinordi, especially since they could have chosen the talented Evgeny Kuznetsov who has been thriving at the NHL level with the Washington Capitals.

11 Best: Craig Rivet For Josh Gorges And A 1st-Round Draft Pick

Adam Hunger-USA TODAY Sports

Craig Rivet spent twelve seasons with the Montreal Canadiens between 1994-95 and 2006-07. During that time, this defenseman recorded 151 points, 795 penalty minutes (including 35 majors) and a -1 plus/minus rating in 653 regular season games. Then in February 2007, he was traded, along with a 5th-round draft pick, to the San Jose Sharks for Josh Gorges and a 1st-round draft pick.

The Habs sure got their money’s worth for Rivet because in 2007 they drafted Max Pacioretty 22nd overall. In the nine years that Pacioretty has been with the Canadiens, he has led the team in points for the last six consecutive seasons from 2011-12 to 2016-17.

Josh Gorges ended up spending eight seasons with the Canadiens from 2007 to 2014 and led the entire team during that time with an overall plus/minus rating of +34. He also led them with 1,048 blocked shots and ranked second with 611 hits.

10 Worst: John Leclair And Eric Desjardins For Mark Recchi

via hfboards.hockeysfuture.com

On February 9, 1995, the Montreal Canadiens traded Eric Desjardins, Gilbert Dionne and John LeClair to the Philadelphia Flyers for Mark Recchi and a 3rd-round draft pick. It’s not hard to figure out who came out on top in this trade.

There’s no doubt that Recchi was a great player with having produced 322 points and a +23 plus/minus rating in 346 regular season games with the Canadiens, but they should have received more than just him and a draft pick. And they ended up trading him back to the Flyers in 1999. As for their third round draft pick, the Habs chose Martin Hohenberger, who never even played a game in the NHL.

The Flyers definitely received a lot more. Leclair spent 10 seasons with them and racked up 643 points, along with a phenomenal +197 plus/minus rating, in 649 regular season games. Desjardins spent 11 seasons with them and earned 396 points, along with a fantastic +143 plus/minus rating, in 738 regular season games. Dionne, however, only played 22 regular season games and tallied 7 assists.

9 Best: Drafting Carey Price

Adam Hunger-USA TODAY Sports


The Montreal Canadiens had the 5th-overall choice at the 2005 NHL Entry Draft and chose goaltender Carey Price. At that time, the Habs had Jose Theodore, followed by Cristobal Huet who were both putting up decent numbers with the team.

It was a bit of a shock when the Habs drafted the talented goaltender instead of other equally talented players such as Anze Kopitar or T.J. Oshie who were drafted 11th and 24th respectively. But the Canadiens obviously knew what they were doing because Price turned out to be one of the best goalies in the NHL.

So far in his ten-year career, Price has won the Vezina Trophy, Ted Lindsay Award, William M. Jennings Trophy, and the Hart Memorial Trophy. He is also currently ranked third among all goaltenders in franchise history with 270 wins – only 19 wins away from tying Patrick Roy for second place and 44 wins away from tying Jacques Plante for the all-time franchise record.

8 Worst: Chris Chelios For Denis Savard

via nhl.com

In June 1990, the Montreal Canadiens traded Chris Chelios and a 2nd-round draft pick to the Chicago Blackhawks for Denis Savard.

While Savard averaged well over a point a game during his time with Chicago with 1,013 points, along with a +85 plus/minus rating, in 736 regular season games, this center’s performance with Montreal wasn’t as great as expected. He spent three seasons with the Canadiens from 1990 to 1993 and recorded 179 points, along with a +6 rating in 210 games.

The point-producing defenseman Chelios had an exceptional seven-year career with Montreal and was equally as successful with Chicago, having produced 487 points and a +120 rating in 664 games with the Blackhawks. He also served as their team captain. While he did win one James Norris Memorial Trophy during his time with Montreal, he was awarded two more during his time with Chicago.

There’s no doubt that the Habs should have kept Chelios for a lot longer than they did.

7 Best: A Steal Of A trade For Ken Dryden

via nhl.com

Ken Dryden was drafted 14th-overall in the third round of the 1964 NHL Amateur Draft by the Boston Bruins. Shortly after that, Dryden’s rights were traded to the Montreal Canadiens along with Alex Campbell in exchange for Guy Allen and Paul Reid. Considering that neither Allen nor Reid ever made it to the NHL, and Dryden is one of the best goalies of all-time, there’s no doubt that this could be the greatest trade in the history of the Habs.

Dryden spent his entire eight-year NHL career with the Canadiens between the 1970-71 and 1978-79 seasons. He produced 258 wins (including 46 shutouts), 57 losses and 74 ties, along with a 2.24 goals against average. He also appeared in 112 playoff games and earned 80 wins. He helped the Canadiens win six Stanley Cups in 1971, 1973, 1976, 1977, 1978 and 1979. He was also awarded five Vezina Trophies, one Conn Smythe Trophy, and one Calder Memorial Trophy.

He was inducted into the Hockey Hall of Fame in 1983 and then on January 29, 2007, the Montreal Canadiens retired his number 29 jersey.

6 Worst: Trading Pierre Turgeon

via habseyesontheprize.com

Pierre Turgeon played a total of 104 regular season games with the Montreal Canadiens between the 1994-95 and 1996-97 seasons and averaged over a point a game with 127 points, along with a +35 plus/minus rating. Then on October 29, 1996 came the trade that made very little sense. The Canadiens traded Turgeon, along with Craig Conroy and Rory Fitzpatrick, to the St. Louis Blues for Shayne Corson, Murray Baron and a 5th-round draft pick.

The Canadiens didn’t receive much in the trade. Corson was known to drop the gloves and defend his teammates, but wasn’t overly impressive on the score sheet with 136 points and a -15 plus/minus rating in 242 regular season games with the Habs from 1996 to 2000. As for Baron, he played one season with them and tallied just 6 points in 60 games, along with a very disappointing -16 plus/minus rating and racked up 107 penalty minutes.

It was clear that St. Louis won this trade, with Turgeon again averaging over a point a game during his five seasons with them from 1996 to 2001.

5 Best: Giving “The Rocket” A Tryout

via huffingtonpost.ca

With many players going to fight in the war, along with the fact that the Montreal Canadiens were struggling to win games, they decided to give Maurice Richard a tryout in 1942. He earned a spot with the team and spent his entire eighteen-year NHL career with them from 1942 to 1960 and also served time as their team captain.

During that time, he racked up 965 points (544 goals, 421 assists) and 1,285 penalty minutes in 978 regular season games. He also appeared in 132 playoff games and earned 126 points. He helped the Canadiens win eight Stanley Cups in 1944, 1946, 1953, 1956, 1957, 1958, 1959 and 1960. He was also awarded the Hart Memorial Trophy in 1947.

He became the first ever player in NHL history to score 50 goals in a single season and what’s even more amazing is the fact that he did it in exactly 50 games. He also became the first ever player to reach 500 regular season goals.

On October 6, 1960, the Canadiens retired Richard’s number 9 jersey. He was then inducted into the Hockey Hall of Fame in 1961. And since 1999, the NHL has been awarding the Maurice Richard Trophy to the league’s top goal scorer for each season. There’s no doubt that giving “The Rocket” a tryout was one of the best decisions in Canadiens’ history.

4 Worst: The Game That Led To Patrick Roy’s Departure

via habs4life.ca

On December 2, 1995, the Montreal Canadiens were facing the Detroit Red Wings and Patrick Roy was in the net for the Habs. While most coaches would have pulled their goaltender after letting in three or four goals, then-coach Mario Tremblay left Roy in the net for an embarrassing 9 goals. Humiliated and fed up, Roy informed then-president of the Canadiens, Ronald Corey, that he had played his last game with the team. The Canadiens ended up losing that game 11-1. Four days later, Patrick Roy and Mike Keane were traded to the Colorado Avalanche for Jocelyn Thibault, Andrei Kovalenko and Martin Rucinsky.

Considering that Roy had won the Stanley Cup twice with the Habs, as well as having received three Vezina Trophies, four William M. Jennings Trophies, and two Conn Smythe Trophies, the Canadiens should have received a lot more in return for the extraordinary goaltender. Not to mention the fact that he won two more Stanley Cups with the Avalanche.

This awful trade could have all been avoided had they not humiliated him in front of their home crowd during that awful blowout game against the Red Wings.

3 Best: How They Got Jean Beliveau

via zimbio.com

Jean Beliveau had signed a contract with the Montreal Canadiens that indicated if he ever turned professional, he could only play for them. So while he was having an amazing career in the Quebec Senior Hockey League, the Canadiens decided to buy the entire league in 1953 and turn it professional, making him a full time member of the Habs.

That move certainly paid off, since Beliveau spent his entire 20-year NHL career with the Canadiens before retiring in 1971 and averaged well over a point a game with 1,219 points in 1,125 regular season games. In fact, he’s ranked second among all Habs players in franchise history in points. He helped Montreal win ten Stanley Cups, along with being awarded two Hart Memorial Trophies, one Art Ross Trophy, and one Conn Smythe Trophy.

The Canadiens retired his number 4 jersey on October 9, 1971 and then he was inducted into the Hockey Hall of Fame in 1972.

2 Worst: Ryan McDonagh For Scott Gomez

via gohabsgo.com

In June 2009, the Montreal Canadiens traded Chris Higgins, Ryan McDonagh, Doug Janik and Pavel Valentenko to the New York Rangers in exchange for Scott Gomez, Tom Pyatt and Michael Busto.

In addition to acquiring Gomez, they also took on his very expensive contract which had five years remaining on it and over $30 million left owed to him. For that kind of money, he should have produced a lot more than 108 points in 196 games, along with a disappointing -23 plus/minus rating. And after playing just three seasons with the Habs, they bought out the remainder of his contract.

McDonagh, on the other hand, is having a fantastic career with the Rangers with 212 points and an incredible +134 plus/minus rating in 467 games. This defenseman just finished playing his seventh season with them and is currently their team captain.

There’s no doubt that this ranks as the one of the worst trades in Canadiens’ history.

1 Best: The Trade That Landed Guy Lafleur

via thestar.com

In May 1970, the Montreal Canadiens traded Ernie Hicke and a 1st-round draft pick in 1970 to the California Golden Seals for Francois Lacombe, some cash, and a 1st-round draft pick in 1971.

While the 1970-71 season was a terrible one for the Golden Seals, it looked as though the Los Angeles Kings were going to claim the last spot in the standings which also meant the first overall draft choice in 1971. Montreal had California’s 1st-round pick and they wanted to make sure they would get Guy Lafleur, so they made a very gutsy move when the Canadiens traded Ralph Backstrom to Los Angeles in hopes of raising their standings. The plan was flawless and the Golden Seals finished in last place, ensuring that the Canadiens drafted Lafleur 1st-overall at the 1971 NHL Amateur Draft.

Lafleur spent fourteen seasons with the Canadiens and averaged well over a point a game with 1,246 points and an incredible +477 plus/minus rating in 961 regular season games. In fact, he holds the record for the most points recorded in franchise history. He also won five Stanley Cups with the Habs, along with three Art Ross Trophies, three Ted Lindsay Awards, two Hart Memorial Trophies, and one Conn Smythe Trophy.

The Canadiens retired his number 10 jersey on February 16, 1985, and he was then inducted into the Hockey Hall of Fame in 1988.

More in NHL