Sidney Crosby has been associated with the Montreal Canadiens for his entire career and that will never change. He grew up a die-hard Habs fan and his admiration for the team, the city and the organization is no secret.
Since the Penguins made their lonely trip to the Bell Center on Saturday night, the debate over whether Crosby could ever suit up for his youth team has reignited.
Those speculations have become rampant at times in recent years given the state of the Penguins, and now that they’ve fallen apart after a strong start to the season — currently on a seven-game losing streak — those conversations are resurfacing.
Some have suggested that Montreal’s recent move to acquire Phillip Danault, spend a second-round pick in 2026 and pick up a $5.5 million cap hit could close the door on any Crosby dreams for the Canadiens. However, analyst Tony Marinaro certainly doesn’t want to rule that out, and with the Pens on the verge of missing the postseason for the fourth straight season, he’s confident Crosby will be traded.
Marinaro said:
“The talk about Crosby, the talk about Crosby, the talk about Crosby. If there’s smoke, there’s fire. I know a gentleman who’s very close to Crosby and his people, and about a year and a half ago he pulled me aside and he said to me, don’t be surprised if Sidney Crosby ends his career with the Montreal Canadiens… The only chance of it becoming a possibility again is if they don’t make the playoffs. So if they’re out If there’s a playoff spot, the trade deadline comes and the teams have gotten better, and they’re on a downward spiral. I bet he’ll get traded.”
Crosby is in the first season of the two-year, $17.4 million extension he signed with the Penguins in 2024. At 38 years old, he remains one of the most productive players in the world, with 35 points (19 goals, 16 assists) in the first 33 games of the 2025-2026 season.
Are the stars aligned for Sidney Crosby to Montreal?
What still stands in the way of Crosby leaving Pittsburgh is not only his loyalty to the Penguins, but also to old teammates Evgeni Malkin and Kris Letang.
That said, circumstances are changing. Despite still playing at a high level, Malkin appears to be close to retirement, while Letang’s play has declined significantly in recent years. Perhaps that will cause one of the most competitive athletes in the world to reconsider his future.
If it ever comes to that, Montreal would undoubtedly be the favorite to land Crosby. The superstar center will have almost complete control over every possible move, meaning the Canadiens would be well-positioned as front-runners if he decides to pursue a Stanley Cup.
Crosby’s preference has always been to ride off into the sunset with the only NHL franchise he’s ever known, but that may not be in the cards, so if he plans to play into his 40s, it’s hard to imagine speculation about his future won’t surface again.
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