Sidney Crosby’s name swirling around in Montreal trade rumors is nothing new, but this time, the speculation has reached a fever pitch—and for good reason.

When the legendary Penguins captain recently spoke with Pierre LeBrun, he didn’t exactly slam the door on leaving Pittsburgh, sending Habs fans and hockey insiders into a frenzy of theories and wishful thinking.

Crosby’s candid remarks about the Canadiens’ passionate fanbase and his subtle hints about the possibility of a move north have reignited dreams that once seemed impossible.

But what would it actually take to bring No. 87 to Montreal? TSN’s OverDrive recently threw gasoline on the fire, shocking listeners with a blockbuster trade proposal that has everyone talking.

Is the idea of swapping a rising star for a hockey icon pure madness, or is there more strategy behind the suggestion than meets the eye? With key figures weighing in, and Crosby himself keeping the door open just a crack, the situation feels more unpredictable than ever.

As rumors swirl and pressure mounts, the Canadiens’ front office faces a dilemma that could reshape the franchise’s future. What will Kent Hughes do next—and who might be sacrificed to make the impossible happen?

The answers are tantalizingly close, but nothing is certain yet.

Mar 15, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins center Sidney Crosby (87) moves the puck against the New Jersey Devils during the first period at PPG Paints Arena. Mandatory Credit: Charles LeClaire-Imagn Images

Photo credit: Charles LeClaire-Imagn Images

Rumors and speculation linking Sidney Crosby to the Montreal Canadiens have been raging for quite some time and don’t seem to be stopping anytime soon.

The player himself recently reignited the chatter in an interview with Pierre LeBrun for “The Athletic”, where he didn’t shut the door on leaving Pittsburgh.

He even openly addressed the speculation that could bring him to Canada in the near future:

“Canadiens fans are so intense and I understand why that leads to speculation.

Hearing those rumors, when you’re losing, doesn’t make things easier.

But at the same time, knowing that a club like that wants you, it’s not the end of the world. It could be worse.”

– Sidney Crosby

Adding to his comments, Renaud Lavoie also mentioned on BPM Sports that No. 87 noticed all Canadiens players are currently training in Brossard even though camp hasn’t officially started yet.

That fact seems to have made quite an impression on “Sid.”

What would the price be for Sidney Crosby with the Montreal Canadiens?

From what can be gathered, it seems less a question of IF and more a matter of WHEN in this case.

On that note, teams will need to be ready for all scenarios if they want to acquire No. 87.

In a segment on TSN’s OverDrive, the three hosts asked themselves what the price would be for Montreal.

Jeff O’Neill didn’t hold back, throwing out a bold one-for-one trade proposal:

“Sidney Crosby for Ivan Demidov, I’m doing that all day if it’s just one for one.

Of course!”

– Jeff O’Neill

Excuse me?

Trading a 19-year-old for a veteran – as great as he may be – who is 38 years old is pretty ridiculous given the Canadiens’ current situation.

Let’s be honest: the Habs won’t be Cup contenders for the next 2-3 years, and losing Demidov, who will be entering his prime at that point, would only set them back.

Yes, the Canadiens will need to give up something to land Crosby, but I don’t think it will be Demidov – or even Lane Hutson, another name brought up during that segment.

Kent Hughes will need to get creative, because someone from the current roster (to clear cap space) would have to go in order to make room for the great Sidney Crosby.

Now the only question is: who will it be?