Fri. Sep 5th, 2025

Hypothetical: Could Sidney Crosby Join the Canadiens?

Among the numerous questions submitted for this mailbag, one stood out as particularly intriguing.

The way Jon phrased his question is excellent. Given that Sidney Crosby is currently a highly discussed topic in Montreal, it seems appropriate to begin this mailbag here, with the understanding that this is purely speculative.

I am offering only my perspective, without any new information and relying on numerous assumptions.

As far as is publicly known, Crosby desires to remain a Pittsburgh Penguin for his entire career, and there`s no indication that this wish has changed.

I suspect very few people know his true feelings about potentially moving to Montreal, should his situation change. There`s been considerable speculation that the soon-to-be 38-year-old might welcome such an opportunity. This speculation is largely based on his known history: growing up a Canadiens supporter, his father Troy being a former draft pick of the team, the notion that he`d be drawn to the Canadiens` developing team and promising young core, and his well-documented affection for playing at the Bell Centre throughout his two decades in the NHL.

Even if these personal factors hold significant weight for Crosby, they might not be compelling enough for him to leave Pittsburgh and choose Montreal over other potential destinations.

My appreciation for Jon`s question stemmed partly from it starting by considering those `other places`. Without evaluating the broader market, it would be impossible to determine what the Canadiens would truly need to offer to acquire him.

Predicting the required package remains challenging, however, as a significant assumption in this hypothetical exercise is where else Crosby might be willing to play.

By Rupert Caldwell

Rupert Caldwell is a veteran journalist from Newcastle who has traveled to every corner of England covering regional sporting events. Known for his distinctive voice and ability to uncover the human stories behind athletic achievements, Rupert specializes in boxing, athletics, and motorsport.

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