Revisiting the Canadiens’ Tyler Toffoli Trade

The Montreal Canadiens have made several important trades during their rebuild, but one that often flies under the radar is the Tyler Toffoli deal with the Calgary Flames. At the time, moving a proven goal scorer was never going to be a popular decision, but it perfectly reflected where the Canadiens were as an organization.

Trading a Fan Favorite

Toffoli arrived in Montreal ahead of the 2020-21 season and immediately became one of the team’s most reliable offensive players. After helping the Canadiens reach the Stanley Cup Final in 2021, he followed it up with 26 points in 37 games during the 2021-22 season before being dealt.

On February 14, 2022, Kent Hughes completed one of his first major trades as Canadiens general manager, sending Toffoli to the Calgary Flames. In return, Montreal received Tyler Pitlick, Emil Heineman, a 2022 first-round pick and a 2023 fifth-round pick.

At the time, Calgary was looking to make a run and wanted another proven top-six winger for a deep playoff run. The Canadiens, meanwhile, were sitting near the bottom of the standings and had officially entered a rebuild. Trading a 29-year-old winger with term remaining on his contract was a logical move, especially considering the return.

Toffoli Continued to Produce

Toffoli remained exactly the player Calgary expected after the trade. He produced offensively, helped the Flames reach the second round of the playoffs in 2022, and continued to establish himself as one of the league’s most dependable goal scorers. After one full season in Calgary, in 2022-23, he was eventually traded to the New Jersey Devils, where he enjoyed another productive campaign before later joining the San Jose Sharks.

Throughout those stops, Toffoli consistently scored between 25 and 35 goals while providing veteran leadership and playoff experience. There is no question Calgary received a very good player. Still, that doesn’t necessarily mean Montreal lost the trade.

The Canadiens were never one Toffoli away from competing for a Stanley Cup. Keeping him through a rebuild would have made little sense, and his value was unlikely to get much higher than it was in early 2022. Hughes recognized the opportunity and capitalized on it.

The Return

The most intriguing piece acquired by Montreal was Emil Heineman. The Swedish winger steadily developed into an NHL player, bringing exactly the type of game the Canadiens value. His speed, physicality, defensive awareness and ability to contribute offensively made him a useful middle-six option during his short time in Montreal.

Eventually, however, Heineman became part of another significant transaction. The Canadiens included him alongside two first-round picks in the blockbuster trade that brought Noah Dobson to Montreal, making him an important asset in landing one of the organization’s cornerstone defensemen.

The first-round selection acquired from Calgary became Filip Mesar. While Mesar never developed into the impact player many had hoped for and ultimately did not become a long-term piece of the Canadiens’ future, the organization still added a talented prospect with a valuable first-round selection that otherwise would not have existed. Meanwhile, Tyler Pitlick provided short-term depth before moving on, and the fifth-round pick was used to draft Yevgeni Volokhin.

Even though not every asset became a star, that’s often how successful rebuilding teams operate. They collect draft picks, develop prospects, and continue turning assets into bigger opportunities down the road. That’s exactly what Montreal has done throughout Hughes’ tenure.

Looking back, the Toffoli trade wasn’t just about replacing one player with another. It was about creating flexibility, accumulating assets and setting the foundation for future moves. The Canadiens transformed an aging scorer into multiple assets, one of which eventually helped facilitate the acquisition of Dobson, while also giving themselves another first-round selection during an important stage of the rebuild.

Today, with Montreal emerging as a legitimate contender led by players like Nick Suzuki, Cole Caufield, Juraj Slafkovsky, Lane Hutson and Dobson, the decision to move Toffoli looks like another example of strong long-term asset management.

It wasn’t the flashiest trade of the rebuild, nor did it generate the same headlines as some of Hughes’ later blockbuster deals. But it perfectly illustrated the philosophy that has guided the Canadiens over the past several years: maximize value, stay patient and always keep the bigger picture in mind.