Pittsburgh Penguins captain Sidney Crosby could be playing for another team next season following the 2026 Olympic Games, according to NHL insider Nick Kypreos.
During an appearance on Sportsnet 590 The Fan, Kypreos floated the idea that Sidney Crosby could join the Montreal Canadiens next season. The Habs, currently valued at $3.1 billion, according to a report by CNBC, could land the future Hall of Famer as the Penguins enter a full-on rebuild.
The conversation between Justin Bourne and Kypreos hovered around the Canadiens’ playoff chances next season. In particular, Kypreos hyped the Habs’ playoff chances by floating this idea:
“Wait till they get Sid Crosby after the Olympics.”
The comment stunned Bourne and co-host Sam McKee. McKee dared Kypreos to double down on his comment, prompting Kypreos to state:
“I'm liking the odds a little better than I did maybe a few weeks ago. Something's going on in Pitt. Things are going on. Things are going on...”
While Kypreos didn’t elaborate on the precise nature of what exactly is “going on,” he alluded to the fact that the Penguins are going through a roster churn. That churn could lead to a full-on rebuild.
Kypreos underscored how much Sidney Crosby’s talent would be wasted if he played in Pittsburgh during the team’s rebuild. Kypreos doubled down:
“He's too good right now to just be a babysitter for the next three years. This guy can play peak. It will be such a disservice to the history of our game, if we watch him stay in Pittsburgh. The next three or four years.”
The Penguins have now missed the playoffs two seasons in a row and look to have embraced a teardown of their current roster. Meanwhile, the Canadiens are a team on the rise and could use a superstar like Sidney Crosby to take them to the next level.
Where Sidney Crosby would fit into Canadiens’ depth chart

Justin Bourne commented on where Sidney Crosby would fit into the Canadiens’ depth chart. He declared Crosby as the team’s new number-one center.
Under that assumption, Crosby’s presence would slide the Canadiens’ current center core down a notch.
Daily Faceoff shows captain Nick Suzuki as the Habs’ top-line center. Suzuki is followed by Kirby Dach, Alex Newhook, and Jake Evans. Crosby’s addition could mean dropping Suzuki to the 2C role with Dach and Newhook hitting the bottom six. Jake Evans would then have to move to the wing.
Alternatively, one of the Canadien’s current crop of centers could move to a position on the wing to accommodate Crosby.
Determining where Sidney Crosby could fit into the Canadiens’ lineup is purely hypothetical at this point. Nevertheless, Montreal has a clear need to upgrade its center depth. Crosby would do that as the Habs look to compete with the Toronto Maple Leafs and Florida Panthers in the Atlantic Division.
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