Demidov & Agent Differ On Why He 'Left Money On The Table' In Signing His Extension

Ivan Demidov signed an eight-year extension for a $9.15 million AAV with the Montreal Canadiens on the first day he was eligible, back on July 1. Just two days later, Leo Carlsson signed a breakthrough $18 million AAV offer sheet with the Philadelphia Flyers that changed NHL salaries forever.

Did he jump the gun? Is his agent Dan Milstein happy about it? 

Milstein spoke to Herb Zurkowsky of the Montreal Gazette this weekend, explaining that it didn't quite go down the way he would have liked. 

If I had it my way, the deal probably would have looked a little different.

But he admitted that the young Russian was in a hurry to get something done, and was happy to take less to help out the Habs. 

NHL agent Dan Milstein on Ivan Demidov signing a team-friendly contract with the Habs:

“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 (Montreal) can sign other players.” pic.twitter.com/aImfkR9pNT

— /r/Habs (@HabsOnReddit) September 6, 2026

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.

The Canadiens still have $9.7 million in cap space at the moment, and although GM Kent Hughes has spoken of another big splash he was hoping to make, there were no notable additions this summer. 

Players the Habs could acquire thanks to Demidov:

But that cap space will certainly come in handy when an opportunity does come along. The biggest splash would be Dylan Larkin, whose trade request with the Detroit Red Wings remains in place. But Montreal does not seem to be on his trade list at this time, despite a local insider pleading the Habs' case. 

“Dylan Larkin, if you’re ready to be traded, Montreal will be ready to welcome you as a city and as a hockey team,” said TVA Sports' Renaud Lavoie recently. “You just have to put your name forward, and it could be settled extremely quickly.”

Kirill Marchenko, Demidov's good friend, is perhaps a more realistic target, and has been strongly linked to Montreal this summer, and there's still "a good chance" of something happening there. There'd be plenty of room for his team-friendly $3.85M cap hit this season if they're able to convince the Columbus Blue Jackets to swing a deal. 

Demidov is 'grateful & gracious' with his deal, wanting to help the Habs

Meanwhile, Demidov will happily "get by" on $9.15M a year for the next eight seasons, whether his agent likes it or not. But Milstein realizes the player was aware that bigger deals are coming down the pike eventually. He can be an unrestricted free agent in 2035 at the age of 29.

“My client, at the age of 28 or 29, will be able to sign whatever deal’s available at the time,” Milstein said. “That will probably be four or five times bigger than what it is today. For the time being, Ivan is extremely happy. He’s grateful and gracious. They came to him after only 84 (career) games. There are no regrets.

“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.”

Demidov registered 19 goals and 62 points in an electrifying rookie season, finishing as runnerup in Calder Trophy voting and making the first All-Rookie team.