The unthinkable may no longer be impossible: Sidney Crosby’s future with the Pittsburgh Penguins is being questioned more seriously than ever. After two decades of wearing the black and gold, the franchise legend is now at a point where timelines between player and team no longer appear aligned, sparking speculation about a potential split.
Growing frustration in Pittsburgh
For years, Crosby has been the face of the Penguins, delivering three Stanley Cups and countless unforgettable moments. Yet, recent reports suggest the 38-year-old captain’s patience may be running thin with the organization’s direction.
“I never thought a Crosby trade was imaginable. Now, I’m not so sure. If Brisson is indeed speaking for his client, then there is reason to believe that Crosby’s frustration with the current state of the Penguins is at a boiling point,” The Athletic’s Josh Yohe revealed.
The Penguins’ aging core and inconsistent performances stand in stark contrast to Sidney Crosby’s competitive fire and desire to contend for another championship before his career ends. The possibility of the captain even considering life outside of Pittsburgh has NHL executives and fans on high alert.
Canadiens emerge as a potential landing spot
If Crosby ever decides to move on, one franchise appears to be closely monitoring the situation — the Montreal Canadiens. Known as Crosby’s boyhood team, Montreal represents both sentiment and opportunity.
Insider Elliotte Friedman recently highlighted this possibility on the 32 Thoughts Podcast: “[Canadiens’] Jeff Gorton and Kent Hughes are they sitting there and saying ‘we’re not doing anything with X player because we think it may prevent us from doing a Crosby deal.’”
Unlike Pittsburgh, Montreal boasts a young roster entering its prime years. Adding Sidney Crosby would not only fulfill his childhood dream but also inject the Canadiens with the leadership and playoff experience they sorely lacked in last year’s first-round exit to the Washington Capitals.
Balancing loyalty with legacy
Despite speculation, Crosby remains loyal to the Penguins and has no interest in harming the organization that gave him everything. A move before or during the 2025–26 season appears unlikely, as Crosby reportedly wants to play alongside Evgeni Malkin during the Russian star’s final year in Pittsburgh.
At the same time, the looming 2026 Winter Olympics could influence Crosby’s decision-making, as stability and focus are paramount in his preparation. Still, the long-term dilemma remains: stay with a franchise whose window appears to be closing, or chase one last Stanley Cup elsewhere.
As the situation develops, one thing is clear — Sidney Crosby’s decision, whenever it comes, will reshape not only his legacy but also the landscape of the NHL.