Sidney Crosby Will Be a Montreal Canadien by the Start of the 2026-27 Season

As the 2025-26 NHL season nears, the Sidney Crosby trade speculation has started to ramp up. Crosby's agent Pat Brisson made comments a couple weeks ago where he essentially said anything is possible or even on the table for his client, and even Crosby himself did acknowledge his uncertain future in Pittsburgh at the NHL Media Tour in Las Vegas but did seemingly walk his comments back a bit at a Penguins season ticket holder event.

For years, I firmly believed that Crosby would retire as a Pittsburgh Penguin. But after all the smoke over the last few weeks, I’ve changed my mind.

I now believe Sidney Crosby will be a Montreal Canadien within the next year.

Yes, I’ll admit my bias—I’m a Canadiens fan. But even setting that aside, the situation in Pittsburgh feels like it's only getting worse, and now Crosby himself finally seems to be slowly accepting the fact he is never going to win at a high level in Pittsburgh again, which has led to him floating the idea of leaving. I think Brisson's comments were the first step in softening the ground so fans in Pittsburgh can get used to it. For so long, Crosby and those around him shut the door on the topic. But now, for the first time, it feels like he is starting to warm up to the idea.

There are a few factors at play here. First, this is very likely Evgeni Malkin’s last year with the Penguins. If that’s the case, Crosby would be left as the lone superstar on a roster trending toward the bottom of the standings. I just don’t see him wanting to ride out his final years in that situation.

Second, I think Kyle Dubas wants to finally turn the page and build this team back up. I think he wants the draft capital and young assets in the organization so he can finally start the rebuild process without people getting upset with him by saying he is wasting the final years of Crosby's career.

I think he will almost assuredly work with Crosby on a trade and take slightly less than what Crosby is worth to send him to his preferred landing spot.

Enter the Montreal Canadiens.

Crosby has for a long time talked about how he loves the franchise and city, as he grew up as a fan of the team that drafted his father, Troy, in 1984.

In this scenario, Crosby gets to finish his career with his childhood favorite team, the Canadiens, while Pittsburgh stockpiles picks and prospects to start the inevitable rebuild.

From Montreal’s side, I do think they need to be smart about this. I wouldn’t give up our top young players like Lane Hutson, Ivan Demidov, or Juraj Slafkovsky. Crosby likely only has two or three seasons left, so giving up long-term core pieces doesn’t make sense. But a package of draft picks and top-end prospects like a Michael Hage or David Reinbacher feels more realistic.

Trading players off the roster keeps the Canadiens competitive with Crosby after he leaves while also giving Montreal a great shot at bringing home their 25th Stanley Cup as their young core continues to grow with Crosby helping lead the way.

Of course, all of this could go out the window if Crosby is still on the Penguins after this season and they end up landing Gavin McKenna after this season. Winning that draft lottery would completely change their direction, giving Crosby a reason to stick around and mentor a generational talent like Mario Lemieux did for him in 2005.

Unless that happens, I expect number 87 to end up his career elsewhere, and the bleu, blanc, et rouge just feels right.