Love them or hate them, there is no denying that the Montreal Canadiens have the most storied history out of all teams in the NHL. Since their arrival as an Original Six team, the Canadiens have won an astonishing 24 Stanley Cups and no team is even close to catching that number. From the 1940s to the 1970s, no NHL team came close to ever stopping them and they formed a handful of dynasties in the process.
With all of this said, this article will look at the eight best offseason moves by this franchise and the seven worst. Most of the decisions made for this article were either based off the success each player had in their Stanley Cup chases or the failed expectations that these moves made. It is fair to say that the Canadiens have made some of the greatest moves in the entire NHL’s history, but also some of the worst.
With that, here are the eight best moves made by the Canadiens and the seven worst.
15 Best: Vincent Damphousse Trade
When the Montreal Canadiens acquired Vincent Damphousse from the Edmonton Oilers in the 1992 NHL offseason, their fans were absolutely ecstatic. Damphousse had developed into a perennial scorer at that time and averaged over a point per game each season. When he arrived in his hometown of Montreal, Damphousse’s success only continued.
This was a spectacular move by the Canadiens because, although they lost fan favorite Shayne Corson in the process, Damphousse was a star in Montreal. Damphousse hit the 90 point mark three times during his stint in Montreal and also won the Stanley Cup in the 1993 Stanley Cup Playoffs. Without Damphousse, the Canadiens may not have reached that success.
14 Worst: Alexander Semin Signing
At one point in time, Alexander Semin was one of the best pure snipers in the NHL and was a core member of the Washington Capitals. Yet, by the time the Canadiens signed him during the 2015 offseason, he was showing signs that he was dropping in skill as a player. The season before he only had 19 points with the Hurricanes.
When he signed the contract with the Canadiens, many fans were happy with it because it was a low risk contract with a very small salary. However, Semin’s production with the Canadiens was absolutely abysmal and he only managed to score one goal in fifteen games. Shortly after this, he was cut by the Canadiens and now is playing in the KHL.
13 Best: Max Pacioretty Extension
Max Pacioretty has become a very solid piece of the Montreal Canadiens over the past few seasons and rightfully deserves to be their captain. During the 2012 offseason, the Canadiens made a very smart move and gave him a six year, $27 million contract extension, which is a remarkably low salary for a player of his skill today.
Although Pacioretty has faced some criticism as a leader for the Canadiens, there is no denying that this contract was a genius move by the Canadiens’ management. Pacioretty has become the best scorer on the Canadiens and besides Carey Price, is the main reason why the Canadiens have had a lot of success over the past few years.
12 Worst: Alexei Emelin Extension
Alexei Emelin was a very important piece of the Montreal Canadiens for a handful of seasons because of his strong defensive and physical play. During the 2014 offseason, the Canadiens rewarded Emelin for his style of play by giving him a four year, $16.4 million contract extension. This was a very steep price for a player of his caliber.
After receiving the contract, Emelin was not necessarily bad, but he clearly was not playing at the level of someone who should be making that sum of money. Emelin never again reached his career high of 17 points and quite honestly, even if he had, it still would not be justifiable enough for him to be making over four million dollars per season.
11 Best: Drafting Carey Price
The 2005 Entry Draft is one of the best of all time and the Canadiens were extremely smart for drafting Carey Price 5th overall. It is pretty shocking that Price ended up not being a top 2 pick in this draft, but nonetheless, the Canadiens are fortunate for this occurrence. Since being drafted, Price has become the best goaltender in the entire league.
Although Price has yet to lead the Canadiens to a Stanley Cup, it seems very likely that he one day will. The main issue for this is the fact that the Canadiens have not put a good enough team in front of him. The Canadiens need a top line center to help Price because with one, it is clear that he would be able to carry this team to glory.
10 Worst: Sergei Samsonov Signing
Sergei Samsonov was a superstar during his tenure with the Boston Bruins, but injuries eventually plagued him and hurt his production. Yet, before signing with the Canadiens, he was still a very productive top line winger and after being traded, helped the Oilers make the Stanley Cup Finals. With this, the Canadiens signed him to a two year, $7.05 million contract.
Samsonov sadly could never find his game in Montreal and put up his worst season ever in the NHL. In Montreal, Samsonov only put up 26 points in 63 games, which is far lower than any other season he played for. He eventually was put on waivers and then traded to the Chicago Blackhawks. He was even worse in Chicago and only put up 4 assists in 23 games.
9 Best: Carey Price Extension
This offseason, the Canadiens locked up their franchise goalie, Carey Price, to an eight year contract with a cap hit of $10.5 million. Although this is a very steep price, Price’s stellar play has earned him the right to have this massive contract. As previously stated, he is the main reason why the Canadiens are contenders each season.
There is no doubt that the Canadiens will run into some cap problems after this signing, but it will all be worth it if they manage to win their first Stanley Cup in the 21st Century. This contract was more about making the Canadiens still a contender because if they lost Price to free agency, they would have had to rebuild again.
8 Worst: Drafting Jarred Tinordi
In the 2010 NHL Entry Draft, the Montreal Canadiens selected Jarred Tinordi and at the time, it made a lot of sense. Tinordi is a very big defenseman and was praised for his strong defensive style of play. Yet, Tinordi simply could never find a way to crack into the Canadiens’ lineup and as a result, ended up being a complete bust for the club.
Tinordi never made it through a full season with the Canadiens and consistently was sent back down to the AHL. They eventually gave up on him and sent him to the Arizona Coyotes, but even there, he still could not get a permanent job. He has not played an NHL game since the 2015-16 season and it appears he will not again for quite some time.
7 Best: Acquiring Ken Dryden
Believe it or not, Ken Dryden was actually drafted by the Boston Bruins in the 1964 NHL Amateur Draft before he ended up being traded to the Montreal Canadiens shortly after. The Canadiens ended up getting their franchise goalie from their biggest rivals, who they always seemed to beat. What a win for Montreal.
Dryden ended up being one of their greatest goalies in history as soon as he made it to the NHL. He led the Canadiens to a Stanley Cup in 1971 during his rookie season and never looked back from there. Dryden would end up winning five more Stanley Cups with the Canadiens, so needless to say, acquiring him did wonders for this franchise.
6 Worst: Chris Chelios Trade
During the 1990 offseason, the Montreal Canadiens shockingly traded their number one defenseman, Chris Chelios, to the Chicago Blackhawks for Denis Savard. At first, this seemed a bit of a gamble, but also fine because Savard was a franchise player himself. Yet, Savard’s play dropped immensely as soon as he came to Montreal.
While Savard dropped, Chelios continued to blossom into an even better superstar in Chicago. He would end up becoming an offensive juggernaut and managed to win two Norris Trophies as the league’s best defenseman. With that, Savard would only end up playing three lackluster seasons in Montreal, so it is clear who won this trade.
5 Best: Tryout for Maurice Richard
During the 1942 offseason, the Canadiens gave Maurice Richard a tryout opportunity to play with the big club and that is by far one of the greatest decisions they have made in their history. Although he spent a lot of his first season injured, he became a pure sniper and the best natural goal scorer in the league.
Richard became a legend for the Canadiens and today even has an award named after him for the NHL’s leading scorer each season. Richard ended his career with a whopping 544 goals in 978 games, which is a remarkable feat. Without this tryout, the Canadiens may never have won the eight Stanley Cups they did with Richard.
4 Worst: Scott Gomez Trade
During the 2009 offseason, the Montreal Canadiens made a surprising trade by acquiring Scott Gomez from the New York Rangers. Everyone knew that the Canadiens were on the search for a number one center so it made sense, but the price they paid to acquire him was absolutely too big. The Canadiens gave up Ryan McDonagh and we all know how spectacular of a player he is today.
This trade would not have been a total bust if Gomez ended up being the superstar he was on the other teams he played for. Yet, Gomez could never find his game in Montreal and ultimately became a depth forward for the club. This will forever go down as an atrocious trade because today, McDonagh is an elite defenseman and the Canadiens could have used him now.
3 Best: Drafting Patrick Roy
The Canadiens struck gold when they drafted Patrick Roy 51st overall in the 1984 NHL Entry Draft because he ultimately became their franchise. Roy shocked the world and became the best goaltender in the league shortly after his debut. Roy would end up winning two Stanley Cups with the Canadiens before being shipped out to Colorado.
Although Roy’s career in Montreal was cut short in a wrong manner, the Canadiens understand how important he was to the franchise. Not many second round picks end up turning into franchise goaltenders so the Canadiens should always look back at this part of their history with a lot of gratitude and happy memories.
2 Worst: P.K. Subban Trade
When the Montreal Canadiens traded P.K. Subban in the 2016 offseason, it was an absolute surprise to everyone. Although he had been in many trade rumors that summer, it just did not seem likely that he would end wearing a different jersey than the Habs. Yet, that summer marked the biggest change in the history of the franchise.
The Canadiens sent Subban to the Predators for elite defenseman Shea Weber, but this ultimately is an atrocious trade. Weber is a spectacular player, but he is far older than Subban and Subban is right in the prime of his career. Also, Weber has a horrible contract that will make him a member of the Canadiens until his forties, which will hurt their salary cap later on. All Canadiens fans cringed when they also saw Subban lead the Predators to the Stanley Cup Finals this year.
1 Best: Drafting Guy Lafleur
The Montreal Canadiens got extremely lucky when they acquired the first overall pick of the 1971 NHL Entry Draft from the California Golden Seals. The Canadiens made the deal the year before knowing that the Golden Seals would struggle and that they would have a greater chance of either drafting Lafleur or Marcel Dionne.
The Canadiens elected to go with Lafleur and that ended up doing wonders for their franchise. Lafleur became one of the greatest players in their history and a fantastic leader for the club. Lafleur is the all-time leading scorer of the Habs, won countless individuals awards, and most importantly, five Stanley Cups.