The Montreal Canadiens have a tendency to draft players represented by Dan Milstein and the Gold Star Agency these days, is that a coincidence?
When Kent Hughes and Ivan Demidov met with the media after the Russian wonder signed his 8-year contract extension with the Montreal Canadiens, they fielded a plethora of questions that went far beyond the winger’s contract. The team’s culture, the environment, the strategy for signing players, and Hughes was even asked to describe the nature of the relationship between the organization and agent Dan Milstein.
The question seemed to amused the GM who was, it has to be said, in a great mood: “Ivan thinks it’s because he’s [Milstein] a better salesman than other agents”, said Hughes laughing, before adding: “I’d say that I didn’t know Dan at all before taking this job, I think he’s an agent that’s direct, honest, but the fact that we are drafting his players has nothing to do with who’s the agent. I think it’s more about the Russian market being less open; as a result, there may be players we believe would be scouted more and graded higher if they played in the CHL or the NCAA. I can’t tell you we’ll draft one of his clients every year, but I think he’s a guy that’s direct, honest, and so far, all of our interactions have been good”
Speaking to La Presse’s Guillaume Lefrancois, the Ukrainian American agent reminded the journalist that his first contact with the Canadiens’ GM was at the 2022 draft, when the Canadiens traded Alexander Romanov, whom he represented. He added that it wasn’t the best first interaction.
A lot of water has gone under the bridge since then, though, and the fact that Milstein runs his own combine every year can certainly be a difference-maker. While Nick Bobrov has a Russian passport and Vincent Riendeau is a goalie and a Russia pro scout, the fact that Milstein brings his young clients to North America every year around combine time gives the rest of the organization, including Hughes himself, an opportunity to speak with the youngsters. Before the 2025 draft, that’s where they spoke to Alexander Zharovsky, and before this year’s event, that’s where they spoke to Gleb Pugachyov.
Scouting players and evaluating them on the ice in Russia is one thing, but for the Canadiens, it seems equally important to speak with the prospect and assess the kind of person he is. That much was made obvious when Hughes explained that it was when they spoke to Demidov before the draft that they realized he was a confident and talented player, but he also wanted to be part of something rather than being the thing himself, which indicated that he was hungry for championships rather than greedy and chasing the biggest payday. Turns out they were right.
In the wake of the Leo Carlsson offer sheet, there are a lot of comments online about Demidov having a bad agent because he signed for less money than he could have, but that’s a misconception about the agent’s role. An agent’s job is not to get the player the biggest payday possible; it’s to look after a player’s best interests. If the player says he wants to be rich first and foremost, he will chase the biggest payday, but if a player says he wants to fit in a team’s salary structure and allow the organization flexibility to pursue other players to win as many championships as possible, it’s not just about the money anymore.
By hiring a former agent as a GM, the Canadiens knew what they were doing. Hughes has often said that some of his clients in his past life weren’t after winning money; they were after winning championships. He often mentioned Patrice Bergeron’s willingness to take less money to allow the Boston Bruins to surround him with good players.
On July 1, Hughes gave a lot of credit to his players for buying in and being willing to leave money on the table. Still, the organization must also be given credit for picking players they believed had the character to do so.
As for Milstein, the fact that he’s a player’s agent won’t make the Canadiens draft that player, but when it comes to negotiating a contract, Hughes clearly feels he’s honest in respecting his players’ wishes, even if he feels they are perhaps selling themselves short. At the end of the day, an agent is paid a percentage of the players’ earnings, so when they take less money, he has less money as well. Indirectly, he buys in too.
With Demidov, Alexander Zharovsky, Gleb Pugachyov, and Alexandre Texier all being represented by Milstein, Hughes will have plenty more opportunities to negotiate with Milstein, and he won’t complain about that. If the Canadiens' interest in Kirill Marchenko materializes in a sign-and-trade, Milstein's fingerprints will be all over that deal as well since he's another of his clients.
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