People love to talk about where NHL star Sidney Crosby is going to end up.
August undoubtedly brings the end of the free-agency craze, but regardless of what time of the year it is or what contract a player has, speculation is always abound. Crosby signed a two-year contract with the Pittsburgh Penguins back in September of 2024. It’s worth $17.4 million and has an AAV of $8.7 million and includes a full no-movement clause.
And still, people love to speculate if he’s going somewhere for some reason.
NHL Insider Chimes in on Crosby’s Future
Crosby has spent most of his life playing for the Penguins. The 37-year-old center was drafted at No. 1 by Pittsburgh in 2005, and his since been named among the greatest NHL players of all time en route to tallying 1,687 points so far.
According to Yahoo Sports, NHL insider Greg Wyshynski is responsible for the recent spike in the rumor mill surrounding the Pittsburgh captain no longer being a Penguin. Wyshynski said that there’s reason to believe Crosby could one day be a Canadien.
ESPN’s Greg Wyshynski today on The Sheet with Jeff Marek:
“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
— /r/Habs (@HabsOnReddit) July 8, 2025
“I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski said on Monday’s “The Sheet with Jeff Marek“. “If he’s gonna go anywhere and he’s gonna try to do something spectacular, (that’s) being part of the legacy and lineage of the Montreal Canadiens, being part of a team that’s got upward trajectory and have a good chance, maybe (win) a late career championship with a team that hasn’t won since 1993.
I always assumed if it wasn’t Pittsburgh, it would be Montreal.”
However, a different NHL insider disagrees.
Elliotte Freedman reacted to the rumor on Wednesday evening, saying Crosby himself doesn’t even want to talk about a future surrounding a Pittsburgh departure.
Elliotte Friedman: 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 – 32 Thoughts Podcast
— NHL Rumour Report (@NHLRumourReport) July 10, 2025
While with the Penguins, Crosby has been a six-time All-Star Game participant and was most recently he was named the captain of Canada’s 4 Nations Face-Off. The Pittsburgh Penguins have additionally qualified for the Stanley Cup Playoffs a whopping 16 times with Sidney Crosby on the team, specifically from 2007 to 2022.
He has hoisted the Stanley Cup three times as captain of the Penguins (which he was named by the time he was only 19 years old), and clearly yearns to do so at least one more time while with Pittsburgh, and not the Canadiens.
