Everything you are about to read should be prefaced with the fact nothing appears imminent, and that is just fine for the Montreal Canadiens.
Sidney Crosby had many opportunities to put this whole thing to bed at the NHL/NHLPA player media tour in Las Vegas on Tuesday, to say he has no interest in being traded and intends to finish his career in a Pittsburgh Penguins uniform.
But he did not do that. And neither did his longtime agent.
Crosby didn’t exactly announce he would welcome a trade, but he didn’t deny it either. And thus, the possibility of Crosby one day doing the unthinkable and leaving Pittsburgh suddenly became a little more real.
Meanwhile, in the Montreal suburbs on Thursday morning, the start of Canadiens rookie camp featured two top-5 NHL draft picks in Ivan Demidov and David Reinbacher and another first-round pick in Filip Mešár, while yet another first-rounder, Michael Hage, was in Ann Arbor preparing for his sophomore season at the University of Michigan. There were also three second-round picks, four third-round picks, and so on, several of whom have shown very real potential to play in the NHL very soon, while others are still promising wild cards.
As a whole, this prospect group represents the fruits of a rebuild process that the Canadiens embarked on four years ago — a process that the Penguins are currently just beginning, and one that Crosby could greatly facilitate.
If he were to one day decide to leave the Penguins, it would be difficult to find a better trade partner than the Canadiens, because they already have what Penguins general manager Kyle Dubas would likely be seeking: a complex, lucrative haul of promising young players and draft picks.
And in the Canadiens, Dubas would find an incredibly willing trade partner.
All summer, the Canadiens have heard about how they lack a No. 2 center, about how it is not only the biggest hole in their lineup this season but potentially in their entire rebuild. Crosby would be the ultimate prize here, and whenever the Jeff Gorton and Kent Hughes administration has been faced with the chance to acquire an established player who can fill an organizational hole, they have displayed a willingness to overpay to get the deal across the finish line.
This, of course, is far different from the Kirby Dach or Alex Newhook trades, or even the Noah Dobson and Zachary Bolduc trades from this summer. Crosby is 38 yet so exceptional, so legendary and so culturally significant to what the Canadiens are trying to build that there is little doubt they would show that same willingness to do whatever it takes. To a certain extent.
Certain core pieces would likely be untouchable, both because they are so crucial to what the Canadiens are building and because they are equally crucial to Crosby’s desire to win wherever he hypothetically goes next. Demidov, for instance, would be an obvious draw for the Penguins — but also for Crosby, who would almost assuredly be playing with him on the same line. Accepting a trade to a team that’s significantly weakened by the acquisition cost would be counterproductive.
For other potential Crosby suitors, while they would likely need to send one or more current roster players just to make the money work, they have very little to help the Penguins’ future. (And those roster players heading back would only prevent Pittsburgh’s ability to bottom out this season and potentially draft Gavin McKenna.) The Colorado Avalanche, led by Crosby’s buddy Nathan MacKinnon, have the NHL’s worst prospect pipeline, according to our Corey Pronman, and the Tampa Bay Lightning aren’t much better in 28th. The New York Rangers and Crosby’s old coach Mike Sullivan? They’re 24th.
In fact, just about every contending team that would give Crosby a chance to win soon finds themselves in the bottom third of that pipeline ranking. But that’s the natural circle of life in the NHL, just as all the teams in the top third of that ranking missed the playoffs last season.
Every team but one.
The Montreal Canadiens.
Crosby constantly talks about his desire to win, and he did so again this week in Las Vegas. But he is also extremely loyal to the Penguins, though it should be noted that the organization is amid a potential sale process, and Crosby has no ties to that seemingly imminent ownership group — just as he has no real ties to the current ownership group, or to new coach Dan Muse. And even Dubas has only been there two years.
But still, if Crosby wants to do right by the Penguins and the city of Pittsburgh – which he surely does – he can help the Penguins fast-track their rebuild by facilitating a trade to a team that helps his old one win too. And it seems clear the Canadiens are just about the only team that would meet both criteria.
The part about Crosby’s ability to win in Montreal is surely more debatable. No doubt he would have a better chance in Colorado or Tampa Bay or perhaps even Toronto, Dallas or — could you imagine — Florida. But the Canadiens were the youngest team to reach the playoffs in decades, they are clearly on an upswing and Crosby grew up a Canadiens fan, as he loves to remind people.
Now, that is all from the Penguins and Crosby’s perspective.
From the Canadiens’ perspective, while their cupboard is still stocked with prospects, some draft picks and even young roster players, they have a finite amount of trade resources at their disposal. Logan Mailloux is in St. Louis, and they packaged the 16th and 17th picks in the 2025 draft with Emil Heineman to get Dobson from the New York Islanders. There are limits to what they can do, and if they use any of their remaining resources to make another trade while waiting for Crosby to make up his mind, they might just jeopardize their ability to pull off a massive one like this.
And make no mistake, this is the trade the Canadiens would want to make more than any other.
Is it wise to bet on a long shot — to wait and hope that Crosby requests a trade, to wait and hope that he puts the Canadiens on his list of desired teams, to wait and hope that they can satisfy the Penguins’ needs in any such deal?
Simply, yes. Yes, it is worth it.
But that is only simple for now.
Let’s say, as a thought exercise, the Islanders get off to a terrible start this season and the Penguins, thanks to Crosby and their core of veterans, manage to tread water through mid-November. And let’s say at that point, Islanders GM Mathieu Darche decides it’s time to add another core piece in the McKenna draft and build for the future, so he puts Bo Horvat on the trade market. Do the Canadiens go hard after Horvat, knowing the pieces required to make that trade would essentially pull them out of the running for Crosby?
Or let’s say it’s the Bruins who make a similar call and put Pavel Zacha on the market. Do you pull the trigger on someone who would clearly help this team for the next two seasons at a very low salary cap cost but would also eat up some of those trade assets, thereby jeopardizing a hypothetical Crosby trade?
That’s not quite as simple.
Then again, it could be the Penguins who find themselves in that situation in mid-November, and instead of Darche or Bruins GM Don Sweeney making those calls, it could be Crosby deciding enough is enough and it’s time to move on. Which would be the perfect scenario for the Canadiens.
They have the assets to help the Penguins in the future. They have an ascending team to satisfy Crosby’s desire to win now. They have a building where he has always loved playing. They are the team he cheered for growing up.
It would just make sense. It just requires a decision from Crosby.
It’s a decision worth waiting for. The only question for the Canadiens is how long is too long?
(Photo: Vitor Munhoz / NHLI via Getty Images)