The Montreal Canadiens are the most storied and successful franchise in NHL history. With 24 Stanley Cups, their legacy spans decades of dominance and excellence. However, the last quarter of a century has been a different story. Over the past 25 years, Montreal has struggled to maintain the same level of success that defined them in the 20th century.
Since 2000, the Canadiens rank 22nd in the NHL in wins, a statistic that includes the Utah Hockey Club, the Seattle Kraken, and the Vegas Golden Knights, franchises that have only been around for a fraction of that time. While it hasn’t been easy to be a Canadiens fan during this period, some bright spots and key moves have helped shape the franchise’s future. Here’s a look at the five best moves Canadiens management has made over the last 25 years.
5 – The Sean Monahan Trade and Sell
We still don’t know what these first-round picks will look like, but getting at least two first-round picks for nothing is a heist. On August 18, 2022, general manager Kent Hughes made one of his best moves by acquiring Sean Monahan and a 2025 1st-round pick for future considerations.
The Calgary Flames needed to clear cap space and dumped an injury-prone and ineffective Monahan on Montreal. The 1st-round pick acquired by the Bleu-Blanc-Rouge will likely land between 13 and 20. Not even two years later, Hughes sent Monahan to the Winnipeg Jets for another 1st-round pick and a conditional third in 2027. With that 1st-round pick acquired by Winnipeg, the Habs moved up in the draft and picked the promising Michael Hage. In less than two seasons in Montreal, Monahan brought the team two first and a conditional third. During that stretch, the Ontario native gave his career a second life, recording 52 points in 74 games.
4 – Turning Craig Rivet Into a Future Captain
In February 2007, former general manager Bob Gainey sent Craig Rivet and a 5th-round pick to the San Jose Sharks for Josh Gorges and a 1st-round pick. While Rivet was successful in San Jose, no one knew at that time that Montreal was acquiring their future captain.
With that 1st-round pick, the Canadiens drafted Max Pacioretty. The American native played 628 games in Montreal, scoring over 200 goals and was named the 29th captain in the franchise’s rich history. Gorges played eight seasons in Montreal before being traded for a second-round pick to the Buffalo Sabres. He became a dependable defensive defenceman over the years while Pacioretty developed into a regular 30-goal scorer for the Habs.
3 – Trading a Captain for a Future Captain
While Pacioretty came to Montreal following a great move by Gainey, he also left the city on a deal that benefited Quebec’s only NHL franchise. In September 2018, former general manager Marc Bergevin traded Pacioretty to the Vegas Golden Knights for Tomas Tatar, promising prospect Nick Suzuki and a 2019 2nd-round pick.
Pacioretty had success in Vegas, scoring 97 goals in 224 games, but Montreal ended with a very solid return. First, Tatar offered respectable services to the Canadiens. Forming a line with Phillip Danault and Brendan Gallagher for a bit less than three seasons, the Slovak forward recorded 149 points in 198 games before being moved to the New Jersey Devils.
However, the key piece of that trade was Nick Suzuki, who became the youngest captain in franchise history in 2022. The 25-year-old forward has been solid for Montreal, leading the team in points over the last four seasons, while being great at both ends of the ice. With the 2nd-round pick, Les Glorieux drafted defenceman Jayden Strubble, who is slowly developing into a good depth piece.
2 – Alexei Kovalev to Montreal
Montreal took advantage of the New York Rangers in March 2004. The Habs traded for Russian star Alexei Kovalev and only gave up Jozef Balej and a 2004 2nd-round pick. Balej played only 13 games in New York, while that 2nd-round pick became Bruce Graham, who never played a single game in the NHL.
Kovalev played 314 games in Montreal, tallying 264 points. He had an immediate and profound impact on the Canadiens, bringing a level of skill and creativity to a team that had been lacking offensive firepower for years. His vision and ability to make plays out of nothing quickly made him the centrepiece of the Habs’ attack. Kovalev became one of the most exciting players to watch during his time in Montreal, with his dazzling moves and ability to score from almost any spot on the ice.
1 – A Perfect Way to Sell
It’s never exciting to be a seller at the trade deadline. However, in 2016, Bergevin found a way to make it interesting. The former Canadiens general manager traded veterans Dale Weise and Tomáš Fleischmann to the Chicago Blackhawks for Phillip Danault and a 2018 2nd-round pick.
While the two veteran forwards gave Montreal solid depth production, it never translated to Chicago. Both played less than 20 games with the Blackhawks before leaving. On the other hand, Danault became a fan favourite, and played at home for six seasons, establishing himself as a solid shutdown center. He recorded 194 points with the team before signing with the Los Angeles Kings as a free agent. With the 2nd-round pick, Montreal drafted Jacob Olofsson, who has yet to play in North America.
Since 2000, the Canadiens have made several impactful trades that have helped shape their roster, bringing in key players to strengthen both their defence and overall team dynamics. While the team has faced challenges and a lack of sustained success over the last 25 years, these moves offer hope for the future, with the current roster showing promise and potential for growth. The future looks brighter as the Canadiens continue to rebuild and evolve, positioning themselves for greater success in the coming years.
