Montreal Canadiens

Hosts Debate Blockbuster One-for-One Crosby Trade Pitch with Canadiens

Learn about the Crosby trade pitch to Montreal debate. Can Sidney Crosby elevate the Canadiens, or is a budding star too valuable?

by
NHL Trade Talk
September 10, 2025

The hosts of TSN’s OverDrive stirred up a trade talk storm this week by debating a hypothetical one-for-one trade: Montreal Canadiens prospect Ivan Demidov for Pittsburgh Penguins captain Sidney Crosby. Not everyone was in total agreement, each host making different points for why the Penguins or Canadiens should or shouldn’t do the deal.

The #OverDrive guys discuss whether a hypothetical Crosby for Demidov deal would be worth it for the Canadiens.@OverDrive1050 pic.twitter.com/ZIaP1ZQ1v8
— TSN (@TSN_Sports) September 10, 2025

Bryan Hayes posed the question on air, asking if his co-hosts would move the 19-year-old Demidov for the 38-year-old Crosby. Jeff O’Neill didn’t hesitate, saying “of course,” arguing that two years of Crosby’s elite play would be worth it for any team. Jamie McLennan, however, wasn’t convinced. While he praised Crosby as a “Mount Rushmore player,” McLennan questioned whether adding Crosby would truly make the Canadiens contenders within his remaining window of peak performance.

The debate quickly spilled onto social media, where fans overwhelmingly pushed back against the idea.

Fan Reaction to the Crosby for Demidov Trade Question

“You are trading for Crosby to play with Demidov. There’s no way that’s the trade you make in the current situation Montreal is in,” one fan wrote. Another pointed out bluntly, “Trading Demidov, only 19 lmaooo… future superstar.” One Canadiens fan added, “Do not trade Demidov under any circumstances.”

Another fan added that these hosts who were thinking the Canadiens would even consider this don’t know the team very well. They wrote, “They don’t trade core pieces or players they’ve drafted top 10, certainly not for two years of anybody. They’ve talked about not sacrificing the long term for anything short-term since Gorton got there.”

Other insiders have suggested that the Canadiens would love to get their hands on Crosby, who mentioned during an interview with Pierre LeBrun on Tuesday that he was a Canadiens fan growing up. If true, how much are the Habs willing to sacrifice, assuming Crosby would ever tell the Penguins he’s ready to move on?

Should the Canadiens trade Demidov for Crosby straight up?

Canadiens Want Crosby, But Not That Badly

O’Neill even suggested the Penguins would ask for Lane Hutson. He clearly thinks that highly of Crosby. But, the consensus among the fanbase was that while Crosby remains one of the greatest players in NHL history, Montreal isn’t in a win-now position that justifies moving a cornerstone prospect like Demidov.

If they were a season or two ahead in their development and the Canadiens knew for certain what Demidov was, it might be a different story.

As one fan summed it up: “They aren’t ever going to give up a big asset for Sid, period.”

Next: Jack Hughes Hints Leaving Devils to Join Brother Quinn and Canucks