It’s nothing new at this point, fans in the Steel City have grown used to, but this time around it might not be a drill. Sidney Crosby could actually set for new horizons in the NHL. With the Pittsburgh Penguins languishing at the bottom of the league, the three-time Stanley Cup champion could be eyeing the exit door. And if that’s the case, an insider believes there is one clear candidate.
Fans in Pittsburgh and in the NHL might be witnessing the end of an era. While Crosby has made his allegiance to the Penguins clear, the buzz continues to grow around a potential departure. It would make sense for Crosby to explore his options, even if he has no true desire to leave the team and the city where he played his entire career.
At the moment, it seems almost impossible Crosby will walk away before the 2025-26 NHL season. His longtime teammate, Evgeni Malkin, will play his final year in Pittsburgh, and Crosby will most surely want to be by his side when he steps away from the City of Bridges. What happens afterwards, that’s a mystery.
According to insider Greg Wyshynski, there is an obvious answer if Crosby ever leaves the Penguins. And it’s the Montreal Canadiens. “I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski said in dialogue with Jeff Marek on The Sheet.
Sidney Crosby #87 of Team Canada warms up prior to a game against Team USA in the 4 Nations Face-Off game at the Bell Centre on February 15, 2025 in Montreal, Quebec, Canada.
Makes sense
“If he’s gonna go anywhere and he’s gonna try to do something spectacular, being part of the legacy and lineage of the Montreal Canadiens,” Wyshysnki added. “Being part of a team that’s got upward trajectory and have a good chance, maybe a late career championship. With a team that hasn’t won since 1993. A team he clearly has a lot of affinity for. I always assumed if it wasn’t Pittsburgh, it would be Montreal.”
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In addition to the Canadiens being Crosby’s childhood club, the Habs have now assembled a solid young core that is well ahead of schedule in its development. Montreal was one of the biggest surprises of the past NHL season, reaching the Stanley Cup Playoffs and putting up a fight against the Presidents’ Trophy-winning Washington Capitals.
The new wave
Ultimately, Ovechkin and company proved too much for the young Habs, but the season was already considered a success long before they even clinched a postseason berth. The message to the league was clear: beware of what’s brewing in Montreal.
If Crosby joins the fun in Festival City, the NHL could be in serious trouble. Canada’s Stanley Cup drought—dating back to 1993—might finally be that much closer to ending.
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At this stage, it’s all just speculation. Crosby is under contract in Pittsburgh for two more years, with the deal set to begin this coming season. It includes a no-movement clause, but it’s evident that if either side were to seek a change, it would more likely be Crosby requesting a trade rather than the other way around.
