Since the turn of the century, the Montreal Canadiens have made a number of bold moves in the pursuit of building a championship-calibre roster. While some signings have paid off in spades, others have quickly turned into costly mistakes. Whether due to underperformance, injuries, or simply poor fits, certain free-agent acquisitions have left Habs fans shaking their heads in disbelief. In this article, we’ll take a closer look at Montreal’s five worst free agent signings since 2000.
5 – The Mike Hoffman Experience
In the summer of 2021, Marc Bergevin signed forward Mike Hoffman to a three-year, $13.5 million contract. The team was looking for a consistent goal-scoring winger to bolster their offense, and Hoffman, a proven sniper with a lethal shot, seemed like an ideal fit. Coming off a strong stint with the St. Louis Blues, where he scored 17 goals in 52 games during the pandemic-shortened season, Hoffman appeared to be the missing piece for a Habs squad that had made a deep playoff run in 2021.
However, the reality of Hoffman’s tenure in Montreal has not lived up to the hype. While he has remained a steady contributor in terms of goal-scoring, with 15 goals in his first season and 14 in his second, the overall impact on the team has been underwhelming. His defensive play has often been a liability and his inconsistency on both ends of the ice has drawn criticism.
4 – Lots of Money for an Enforcer
The Canadiens’ decision to sign Georges Laraque to a three-year, $4.5 million contract in 2008 came at a time when the team was looking to add more physicality and toughness to a roster that had been known for its speed and skill. However, Laraque’s time in Montreal turned out to be a disappointment. Despite his tough reputation, he rarely made a meaningful impact on the ice. Over the course of his three-year contract, Laraque only registered a goal and four assists in 61 games. His role as an enforcer wasn’t as impactful as the Canadiens had hoped, and his limited offensive production didn’t justify his $1.5 million annual cap hit.
3 – Too Much for a Veteran
After the Canadiens signed Daniel Brière to a two-year, $8 million contract in 2013, hopes were high that the veteran forward could provide a spark for a team that had just finished first in the Atlantic Division. Brière, known for his playoff heroics with the Buffalo Sabres and Philadelphia Flyers, was expected to offer scoring depth and leadership to a squad aiming for a Stanley Cup. However, his time in Montreal quickly turned disappointing.
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At 35 years old, Brière’s decline was evident, and the offensive contribution the Canadiens anticipated never materialized. In his two seasons with the team, he managed just 13 goals and 25 points in 69 games—far below the expected output for a player earning $4 million per year. Brière was then traded in the summer of 2014 to the Colorado Avalanche for PA Parenteau and a fifth-round pick.
2 – A Russian Disappointment
The Canadiens’ signing of Sergei Samsonov to a two-year, $7.05 million contract in 2006 was meant to add a talented, speedy forward to an offense that needed a boost. Samsonov was a 1997 first-round pick and a player with a strong track record of offensive production but the deal quickly became one of the more disappointing free-agent signings in Montreal’s recent history. While Samsonov’s individual talent was undeniable, his time in Montreal was marked by inconsistency and an inability to find the chemistry needed to thrive in the Canadiens’ system. The Russian forward only recorded 16 points in 63 games before being dealt to the Chicago Blackhawks in 2007.
1 – The Awful Karl Alzner Experience
In 2017, Bergevin made a significant move to replace longtime staple Andrei Markov on the blue line by signing defenceman Karl Alzner to a five-year, $23.125-million contract. The Habs were looking for a reliable, veteran presence to anchor their defense after Markov’s departure, and Alzner, who had built a reputation as a steady, shutdown defenseman with the Washington Capitals, appeared to be a strong fit for the role.

However, Alzner’s tenure in Montreal turned out to be a disappointment. Despite the high hopes surrounding his signing, he struggled to live up to his hefty contract. He was no longer the shutdown defenseman he had been in Washington, and his inability to adapt to the speed of the game in Montreal was evident. In his first season with the Canadiens (2017-18), Alzner posted a modest 12 points in 82 games, but his defensive play wasn’t as reliable as anticipated. His slow skating and inability to keep up with faster forwards quickly became an issue. By the 2018-19 season, Alzner found himself demoted to the American Hockey League, spending a significant amount of time with the Laval Rocket, a testament to how far his game had fallen from the level expected of him when the contract was signed.
In conclusion, the Canadiens have made several high-profile free-agent signings since the turn of the century, but not all of them have panned out as expected. From the disappointing contracts of veterans like Brière and Laraque to the struggles of Alzner and Hoffman, the Habs’ attempts to add pieces to the roster through free agency have often fallen short of expectations. Whether due to underperformance, injuries, or poor fit with the team’s needs, these signings highlight the risks of relying too heavily on established players without fully considering how they will mesh with the team’s evolving system and direction.
