One of the quieter moves of Montreal’s rebuild keeps looking better in hindsight: the Tyler Toffoli trade with the Calgary Flames.
At the time, it was never going to be an easy sell. Toffoli had come to the Canadiens ahead of the 2020-21 season and quickly became one of their most dependable scorers. He helped Montreal get to the Stanley Cup Final in 2021, then posted 26 points in 37 games in the 2021-22 season before the team moved him.
Kent Hughes made the deal on February 14, 2022, in one of his first major transactions as Canadiens general manager. Montreal sent Toffoli to Calgary and got Tyler Pitlick, Emil Heineman, a 2022 first-round pick and a 2023 fifth-round pick back in return.
The fit made sense for both sides. Calgary wanted another proven top-six winger for a playoff push, while Montreal was near the bottom of the standings and had already committed to a rebuild. Moving a 29-year-old winger with term left on his deal lined up with where the Canadiens were headed.
Toffoli kept doing what he had always done once he got to Calgary. He produced offensively, helped the Flames reach the second round of the playoffs in 2022 and continued to build his reputation as one of the league’s most reliable goal scorers. After one full season in Calgary, he was traded to the New Jersey Devils in 2022-23, had another productive year there and later landed with the San Jose Sharks.
Across those stops, Toffoli kept scoring in the 25-to-35-goal range while bringing veteran presence and playoff experience. Calgary absolutely got a good player. That still doesn’t automatically make it a loss for Montreal.
The Canadiens were not one Toffoli move away from contending. Holding onto him through a rebuild would not have changed that, and his value was probably as high as it was going to get in early 2022. Hughes saw the moment and acted.
Of the pieces Montreal received, Emil Heineman stood out the most. The Swedish winger developed into an NHL player and fit the profile the Canadiens like: speed, physical play, defensive awareness and enough offense to matter in the middle six. He later became part of another major move, going to Montreal with two first-round picks in the trade that brought Noah Dobson to the Canadiens.
The first-round pick from Calgary turned into Filip Mesar. He never became the impact player plenty of people hoped for and did not grow into a long-term Canadiens piece, but the organization still turned that deal into a first-round selection it would not have had otherwise. Tyler Pitlick gave Montreal short-term depth before moving on, and the fifth-round pick became Yevgeni Volokhin.
That’s how a rebuild works when it’s done well. Teams collect picks, develop prospects and keep turning one asset into the next opportunity. Montreal has done that throughout Hughes’ tenure.
Seen that way, the Toffoli deal was never just about swapping one roster player for another. It gave the Canadiens flexibility, more draft capital and a path to bigger moves later on. One of those assets eventually helped land Dobson, while another added a first-round pick during a key phase of the rebuild.
Now that Montreal is emerging as a legitimate contender with Nick Suzuki, Cole Caufield, Juraj Slafkovsky, Lane Hutson and Dobson leading the way, the Toffoli trade looks even more like a smart piece of long-term management.
It may not have been the loudest move of the rebuild, but it captured the approach that has defined the Canadiens under Hughes: maximize value, stay patient and keep the bigger picture in view.
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Canadiens Risk Chasing The Wrong Upgrade With Kirill Marchenko
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The bigger question is whether Marchenko addresses the right need for Montreal at all. He brings a scorers touch and the kind of game that can help a lineup, but some of the analysis around him points to a broader roster issue for the Canadiens, one that goes beyond adding another skilled winger. If Columbus and Don Waddell decide to move him, the market could get interesting fast, yet Montreals challenge will be resisting the urge to solve one problem while leaving the more important one untouched. [Read more 🡒]