The Pittsburgh Penguins' years of dominating the NHL seem to be all but over. Their core is all over the age of 35, and as cliché as it sounds, hockey is a young man's game. Sidney Crosby, however, has aged like fine wine and does not seem to be slowing down anytime soon. It does not look like Crosby wants to end his career missing the playoffs every season, and with his ties to the Montreal Canadiens, could he finish out his illustrious career in Montreal?
Crosby has long shown his affinity for the Canadiens, as he has mentioned previously, they were his favourite team growing up. That might have something to do with his dad, Troy Crosby, being a former 12th-round draft pick of the Canadiens in 1984. His fandom of the Canadiens has raised the question of whether he might one day finish his career in Montreal. Those talks have increased now, with the Penguins potentially starting a rebuild.
“I grew up a Montreal Canadiens fan and to have an ovation like that was pretty special.”—Sidney Crosby
— Eric Engels (@EricEngels) February 13, 2025
General manager Kyle Dubas has said he is open to listening to offers for nearly every player on the roster, and speculation about Sidney Crosby potentially coming to Montreal has intensified. It is no secret that the Canadiens are on the hunt for a legitimate number two centre, and Crosby, even at 37 years old, would more than fit that role. A one/two punch of Nick Suzuki and Crosby would potentially be the best centre duo in the entire NHL.
Kyle Dubas said he would be active in trade talks. And from what I hear, this is very much the case today.
— Josh Yohe (@JoshYohe_PGH) July 3, 2025
Crosby has not shown any signs of slowing down as he finished this past season with 33 goals and 91 points. Crosby was arguably the Penguins' only bright spot on a team that finished below .500 and missed the playoffs. He is coming off three straight seasons of scoring 90-plus points, and broke Wayne Gretzky's record for most seasons averaging at least a point per game with 20. In recent seasons, Crosby has had to carry the team to keep their playoff hopes alive. In Montreal, he would not have to be the driving force, but instead the missing piece that could make the Canadiens Stanley Cup favourites.
However, if this deal were to happen, it would not transpire this offseason. The reports are that Crosby still wants to see how the start of the season goes with the Penguins before he makes his decision. If a deal were to happen, it would likely be closer to the trade deadline or next offseason. That could benefit the Canadiens because Crosby only has two years left on his deal. The assets required to acquire Crosby will only decrease as he ages and the years remaining on his contract diminish.
ESPN’s Greg Wyshynski today on The Sheet with Jeff Marek:
— /r/Habs (@HabsOnReddit) July 8, 2025
“I’ve long believed that Sidney Crosby will end his career in Montreal.”
“If he’s gonna go anywhere & he’s gonna try to do something spectacular, being part of the legacy & lineage of the Montreal Canadiens. Being part… pic.twitter.com/g9wUfX0oG7
Crosby is already an all-time great and has nothing left to prove. He has won everything possible. He sits ninth all-time in NHL points (1687), and his numbers could be even higher if he did not miss time in his prime due to injury. He has three Stanley Cups, winning the Conn Smyth in two of those. It will be tough to convince him to leave the team he has played for his entire career. He has earned the right to retire in Pittsburgh. However, he is still one of the most competitive players in the league, and there may be no more fitting end to his legendary career than playing for the team he grew up cheering for and helping them win their first Stanley Cup since 1993.