Discussion continues to swirl around Sidney Crosby’s NHL future speculation as fans and analysts debate where the star center might finish his career. Despite signing a two-year contract extension with the Pittsburgh Penguins in September 2024 worth $17.4 million and featuring a full no-movement clause, rumors about Crosby possibly moving elsewhere are persistent.
The contract carries a $8.7 million average annual value, making a trade or relocation notably challenging, yet speculation remains fueled by Crosby’s iconic status and the changing landscape of the league.
Insights from NHL Insiders on Crosby’s Career Path
Sidney Crosby has been synonymous with the Pittsburgh Penguins since being selected first overall in the 2005 NHL Draft. Now 37 years old, Crosby ranks as one of the most accomplished players in NHL history, accumulating 1,687 career points. The question of where he might conclude his illustrious career has gained traction recently, largely due to comments from notable NHL insiders.
Greg Wyshynski of ESPN, speaking on “The Sheet with Jeff Marek,” suggested that he envisions Crosby finishing his career with the Montreal Canadiens, a team steeped in hockey history and currently on an upward trajectory. Wyshynski stated:
“I’ve long believed that Sidney Crosby will end his career in Montreal.” —Greg Wyshynski, NHL Insider
Wyshynski elaborated that if Crosby were to leave Pittsburgh, joining a team like Montreal could allow him to add to his legacy by contributing to a franchise with a rich heritage and a strong chance to contend for a championship, which the Canadiens have not won since 1993.

Contrasting Views from Within Crosby’s Inner Circle
Despite the buzz generated by Wyshynski, another respected NHL insider, Elliotte Friedman, expressed skepticism about the rumors concerning Crosby’s departure from Pittsburgh. Friedman highlighted that Crosby himself dislikes the speculation and that those close to him also prefer stability.
I know everyone asks about Sidney Crosby; I’ve said people in Crosby’s orbit want him to go; Crosby hates it when this stuff starts; someone said to me if you really want Crosby to leave, don’t talk about it. —Elliotte Friedman, NHL Insider
Friedman’s comments reflect Crosby’s likely desire to remain focused on his on-ice performance rather than engaging with ongoing conjecture about his future, indicating his preference to continue his career with the Penguins.
Crosby’s Legacy and Impact with the Penguins
Throughout his tenure with the Penguins, Crosby has been a six-time NHL All-Star and served as captain in numerous important competitions, including leading Canada during the 4 Nations Face-Off. Under his leadership, Pittsburgh made playoff appearances 16 times from 2007 through 2022 and secured three Stanley Cup championships.
Named captain at just 19 years old, Crosby’s deep connection to the franchise fuels his ambition to achieve another Stanley Cup before retiring. This ongoing pursuit underscores the tension surrounding his future, as he has expressed no public intentions to chase success outside Pittsburgh, despite the allure of joining a storied team like Montreal.
What Lies Ahead for Sidney Crosby and the NHL Landscape
The debate over Sidney Crosby’s NHL future speculation captures more than just trade possibilities; it reflects the complex emotions tied to a player nearing the twilight of his career. Whether Crosby ultimately concludes his playing days with the Penguins or surprises the hockey world by joining the Montreal Canadiens, his impact on the sport remains undeniable.
As the 2025 season approaches, fans and analysts alike will be watching closely to see if Crosby continues to lead Pittsburgh or if the “Great One” embarks on a new chapter in Montreal, aiming to cement a late-career legacy with another historic franchise.
Our Reader’s Queries
Q. How many teeth did Sidney Crosby lose?
A. Sidney Crosby lost two front teeth but still made Penguins fans happy with his goal. He wasn’t available to talk about the amazing one-handed goal that contributed to the Pittsburgh Penguins securing their 11th straight playoff spot.

