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Tyler Toffoli, Montreal Canadiens (Photo by Curtis Comeau/Icon Sportswire via Getty Images)

Montreal Canadiens’ 5 Best Free Agent Signings Since 2000

Originally posted on The Hockey Writers
By William Bourget | Last updated Mar 3, 2025 3:45 PM ET

Since the turn of the century, the Montreal Canadiens have made some significant moves in the free-agent market, often adding crucial pieces to their roster. From game-changers who helped push the team deep into the playoffs to players who brought leadership and stability, these five signings stand out as some of the best decisions made by the Habs’ front office in recent memory. Each player not only made an immediate impact but also left a lasting mark on the team’s culture and legacy. Let’s take a look at the Canadiens’ five best free-agent signings since 2000.

5 – The Alexander Radulov Experiment

The Alexander Radulov signing in 2016 was one of the most impactful and polarizing free agent moves in recent memory. After years of inconsistency and bouncing between the NHL and Kontinental Hockey League, Radulov returned to the NHL with something to prove. The Habs took a chance on him, bringing him in on a one-year, $5.75 million deal, and it paid off.

Radulov immediately became a dynamic offensive force for Montreal, showcasing his impressive skill set and playmaking ability. Paired with captain Max Pacioretty and center Phillip Danault, Radulov quickly formed one of the most productive lines on the team. He finished the 2016-17 season with 18 goals and 36 assists for 54 points in just 76 games, good for second on the team in scoring behind only Pacioretty. His creativity and vision with the puck made him a constant threat on the ice, and his willingness to mix it up physically also added an edge to the Canadiens’ attack. Radulov unfortunately left the following season to join the Dallas Stars.

4 – A Solid Blue Line Addition

The Roman Hamrlik signing in 2007 was another shrewd move that strengthened the team’s blue line at a critical time. Coming off a successful tenure with the Tampa Bay Lightning and the Edmonton Oilers, Hamrlik was an established veteran defenseman with a reputation for being a steady, two-way presence. The Canadiens, looking to bolster their defense corps, signed him to a four-year, $22 million deal, a significant commitment at the time and one that would prove to be a valuable addition in both the short and long term.

Hamrlik’s role with the Canadiens went beyond just his on-ice play (he had 22 goals and 97 assists for 119 points in 312 games with the franchise.) His influence on the development of younger players, particularly goalies Carey Price and Jaroslav Halák, as well as his mentorship of young defenseman P.K. Subban, was vital in the team’s overall growth during his tenure.

3 – A Sharpshooter

The Tyler Toffoli signing in 2020 was a masterstroke by the team’s front office, and it paid off almost immediately. On Oct. 12, Toffoli agreed to a four-year, $17 million contract, a deal that seemed like a low-risk, high-reward situation for a team coming off a disappointing early exit from the 2020 playoffs. Little did they know, Toffoli would not only meet expectations but would exceed them in a big way.

Toffoli had a strong reputation as a proven goal-scorer, and it didn’t take long for him to show why. In his first season with the Canadiens (2020-21), he hit the ground running, posting an impressive 28 goals and 16 assists in 52 games. Ultimately, Toffoli’s contributions during his two seasons with the Canadiens solidified him as one of the best free-agent signings in recent memory. He not only filled an immediate need for scoring but also provided valuable leadership and experience to a team going through a rebuild with an eye on returning to contention.

2 – A Scorer and Playoff Hero

The Michael Cammalleri signing in 2009 was a move aimed at adding scoring punch to a team that needed more offensive firepower. Cammalleri, coming off a strong stint with the Calgary Flames, was known for his quick release and goal-scoring ability.

In his first season (2009-10), Cammalleri delivered, putting up 26 goals and 24 assists in the regular season. His real impact, however, came in the playoffs, where he was a major force in Montreal’s unexpected run to the Eastern Conference Finals. Cammalleri scored 13 goals in 19 games that postseason, including a memorable series against the Washington Capitals in the first round where he was instrumental in the Canadiens’ stunning upset.

1 – The Signing of a Future Captain

The Brian Gionta signing in 2009 was a bold move to add leadership, speed, and scoring to their roster. Coming off a successful stint with the New Jersey Devils, Gionta was brought in to be a top-six forward and a key contributor to Montreal’s offense. In his first season, Gionta quickly became a fan favorite with his relentless work ethic, speed, and goal-scoring ability. He posted 28 goals and 18 assists for 46 points in 2009-10 and was a driving force behind the Canadiens’ surprise Eastern Conference Finals run that year.

While Gionta’s numbers tapered off in subsequent years, his value went beyond stats. He served as captain from 2010 to 2014, providing a steady, reliable presence both on and off the ice. His leadership and clutch scoring made him one of the most important signings of the decade for Montreal, despite the eventual decline in his production.

Each signing not only filled an immediate gap but also brought leadership, stability, and clutch performances when it mattered most. While not all of these deals were flawless in the long run, these players made significant impacts during their tenures and are still remembered fondly by fans for their contributions to the team’s success.