It will be fair to question for a long time whether everyone other than San Jose regrets letting Ivan Demidov fall to Montreal. The Russian winger flashed brilliance, scoring 64 points in his first 84 games. Then, according to his agent, he did the thing that every GM prays their rising star player will do. Ivan Demidov took a discount.
Dan Milstein told the Montreal Gazette that Demidov left money on the table specifically so Montreal would have room for other players.
“If I had it my way, the deal probably would have looked a little different,” Milstein told The Gazette in a phone interview from near his Stuart, Fla., home. “Ivan basically said he wanted the eight-year deal. He wanted it done quickly and wanted to leave room (financially) for Montreal to get even better.
“His exact words were, ‘We’re in a great situation. I feel like we’re going to be winning for many years.’ He wanted to leave money on the table so they can sign other players.”
Demidov signed an eight-year extension worth an average annual value of $9.15 million. It looked like the Habs received an Ivan Demidov discount almost immediately upon signing. In a rising camp environment, this looks even better. It won’t take effect until the 2027-28 season.
The Habs clearly wanted to take advantage of the changing cap environment, handing Demidov an eight-year deal (which won’t be legal after September 15). They also clearly wanted to maximize the up-front bonus structure. The rules governing the bonus structure are also changing. Nearly 80 percent of Demidov’s new deal is signing bonuses.
Montreal Can Take Advantage of Ivan Demidov’s Discount Deal
Demidov, had he waited, likely could have signed for more money and a shorter term, potentially maximizing his overall worth. His contract extension precipitated the game-changing Leo Carlsson offer sheet by two days.
Milstein told the Montreal Gazette that the player knew the landscape was changing, but sought this deal anyway.
“He wanted this deal. He knew there were other, bigger deals coming in the future. He knows he’s going to improve and wanted to be like everyone else on the team.”
It already looks promising in Montreal, but the Canadiens will enter next summer with $39,471,592 in cap space and their entire core locked up. Admittedly, that number will change somewhat once Zack Bolduc signs a new contract.
Presumably, highly touted center prospect Michael Hage will then sign an entry-level deal. It will provide Montreal with the flexibility to swing for the fences.
Additionally, the Canadiens will have the necessary cap space thanks to the Ivan Demidov discount to target premium support pieces that could help them navigate a deep Stanley Cup playoff run.
Next Steps for Montreal
Off the ice, the Canadiens will have looming decisions on their current support pieces. Philip Danault, Josh Anderson, Kirby Dach, Oliver Kapanen, Alex Newhook, Alexandre Carrier and Jayden Struble will hit free agency. The Canadiens’ front office can slow-play Kapanen, Newhook and Struble some. All three are restricted free agents. The Ivan Demidov discount certainly helps.
Danault, Anderson and Dach present a more interesting choice for the Canadiens. The open market in this rising cap environment likely presents the best chance for Danault and Anderson both to land one last big-money contract.
Dach, presumably, looks poised to seek a different opportunity. The Habs didn’t commit to him long-term when given the chance. Plus, a combination of injury issues and roster depth hasn’t always guaranteed him an everyday spot in the lineup.
Montreal broke the playoff drought in 2024-25. Then, in 2025-26, it won two playoff series. The Hurricanes exposed some critical flaws in Montreal last spring.
Still, it seems clearer than ever that Ivan Demidov’s discount contract will help the Canadiens ensure that cap space isn’t a limitation in buying support pieces for their young core.
Montreal Canadiens Winger Ivan Demidov Made Team-First Decision