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Could Sidney Crosby really leave Penguins? Insider's pitch fuels Montreal Canadiens speculation

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Sidney Crosby ’s name is once again at the center of NHL conversations, and this time, the speculation is impossible to ignore. The 38-year-old Pittsburgh Penguins captain remains one of hockey’s most respected figures, but with the team struggling and his contract running through 2027, fans and insiders are wondering if Crosby’s story in Pittsburgh might take an unexpected turn. Could the next chapter for the NHL superstar be with the Montreal Canadiens ?

NHL insider drops bombshell on Sidney Crosby’s future and potential Canadiens move

TSN insider Darren Dreger added fuel to the rumor fire on the Flamesnation show Barn Burner, suggesting a “win-win” scenario could emerge if Crosby and the Penguins part ways. “As much as Sid loves the romantic idea of staying with the same organization the entire year, there’s something noteworthy and sweet about giving something back to that organization on your way out. Why can’t it be a win-win?” Dreger said.


While Crosby is known for loyalty and legacy, Dreger notes the veteran’s consideration for both sides. With Montreal’s young talent and admiration for Crosby, Dreger believes the Canadiens “would do whatever is possible” to bring him in. He also added that general manager Kyle Dubas is weighing Pittsburgh’s rebuilding needs, making discussions around Crosby timely and relevant.

Trade speculation isn’t new, but it intensified after Amazon Prime’s FACEOFF: Inside the NHL highlighted his agent, Pat Brisson, dodging trade questions. Brisson revealed that multiple teams have inquired about Crosby’s availability, acknowledging that being outside the playoff picture “must be hard to see the light at the end of the tunnel.” Crosby himself admitted the rumors linger in tough times: “When you’re losing and not sure where things are going to end up and you hear all the rumors, there’s obviously thoughts that run through your head.” Yet, he emphasized his loyalty, adding, “You take so much pride in being part of the team and the organization. The people there have been so great to me – that’s difficult to just walk away from.”

Why Montreal could be the perfect fit?

If Crosby ever leaves Pittsburgh, Montreal appears to be the most natural destination. A lifelong Canadiens fan, Crosby received a warm welcome at the Bell Centre during the 4 Nations Face-Off earlier this year, reminding fans of that enduring connection. Insiders suggest the Canadiens’ young core and promising future could appeal to Crosby if the Penguins fully rebuild.

Although GM Kyle Dubas calls trade rumors “a distraction,” sources note that a significant team overhaul could test the relationship. Both sides remain focused on returning to contention, yet the image of Crosby donning a Canadiens sweater continues to spark imagination across the hockey world.

Also Read: NHL Trade Rumors: Sidney Crosby reportedly on one team’s radar as they plan to do whatever it takes to acquire him
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