The hosts of TSN’s OverDrive recently debated a hypothetical trade that would send Pittsburgh Penguins captain Sidney Crosby to the Montreal Canadiens in exchange for 19-year-old prospect Ivan Demidov. This discussion followed comments made by Crosby that he was a fan of the Canadiens growing up, and during an interview with Pierre LeBrun, he admitted it was nice knowing a team like that wants you.
“And I get it why that would come up and that sort of thing (speculation). It doesn’t make it any easier when you’re losing to hear those things. But at the same time, to know that a team like that wants you, it’s not the end of the world. It could be worse (he smiled). Yeah, I think that’s just part of it.”
source – ‘Sidney Crosby on Penguins future, Canadiens speculation, more: ‘That’s the hard part about losing’ – Pierre LeBrun – The Athletic – 09-09-2025
There has been no imminent trade chatter linking Crosby to the Canadiens. Let’s get that out of the way. However, if Crosby ever decides it’s time to move on from the Penguins, it sounds like the Canadiens would be high on his list. But what does a trade look like?
Fans Say No To Demidov For Crosby
Bryan Hayes raised the question on air, asking whether the co-hosts would move Demidov for Crosby. Jeff O’Neill didn’t hesitate, saying “of course,” arguing that even two years of Crosby’s elite-level play makes that deal worth it for the Canadiens. He was alone in that thinking.
Jamie McLennan disagreed. While praising Crosby as a “Mount Rushmore player,” he questioned whether Montreal is truly close enough to contending for the deal to make sense in the short term. He argued that while no one knows what Demidov is yet, he’s got too much potential to sacrifice him for an aging Crosby on his way out of the NHL.
If the Canadiens were further along in their window to compete, things might be different. As it stands, Demidov is too high a price to pay.
If Demidov is out, that likely rules out any consideration the Habs would move Lane Hutson, who O’Neill suggested the Penguins might ask for.
Related: Crosby to Canadiens, Kaprizov Ignores McDavid & More NHL Rumors
Fans largely rejected the idea on social media. Many argued that Demidov, a projected future superstar, is untouchable. One wrote, “Do not trade Demidov under any circumstances.” Another argued that trading away young prospects, regardless of how much they’d like to acquire Crosby, is not how GM Kent Hughes operates.
So What Would a Blockbuster Crosby Trade Look Like?
It’s important to note that Crosby controls the action here. If things ever get to a point where he tells Kyle Dubas he’s ready to move on, he’ll be able to pick where he goes, and the Penguins will be left to get the best possible return they can. Crosby is a superstar, but the return will be underwhelming compared to expectations.
Dubas’ job will be to get what he can, giving the Penguins pieces to work with going forward. Without Crosby in the fold, a roster player coming back is not a necessity. That means picks and prospects will be of the highest value to the rebuilding Penguins.
Meanwhile, the Canadiens aren’t likely to give up anything that can help them in the next two or three seasons. If they acquire Crosby, that means they think they’re close. He potentially puts them over the top. Thus, moving a player like Demidov Hutson, Cole Caufield, Nick Suzuki, or Jaraj Slafkovsky is probably a non-starter.
One might ask why the Penguins would do this? If none of those players are on the table, what would be the reason behind moving Crosby if the return is so lackluster? First, there are good players in the system that the Penguins could probably use. Second, the draft picks the Canadiens would give up could be worth it to the Penguins in the long run. They have all their first-rounders in the next three seasons, four seconds in the next three years, three thirds, and four fourths. Expect multiple picks to go back to Pittsburgh in any deal.
Also, expect the Canadiens to send salary to the Penguins to make the financial math work. The Habs will have some $20 million at the cap to spend on a deadline player, but Crosby has another season at $8.7 million on his contract and the Penguins won’t retain salary unless something big comes their way.
It’s not ideal, but then again, neither is having to trade Crosby at all.
