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Sidney Crosby-to-Canadiens Speculation Grows Because of ESPN Insider

Originally posted on Athlon Sports | By Antonio Losada | Last updated Jul 9, 2025 8:12 AM ET

Pittsburgh Penguins captain Sidney Crosby's trade speculation is heating up again, and this time, rumors point toward a move to the Montreal Canadiens.

NHL insider Greg Wyshynski appeared on "The Sheet with Jeff Marek" on Monday and said that, in his eyes, if Crosby ever leaves Pittsburgh, it's the Canadiens who remain as the team to watch.

“I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski said. “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."

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

Crosby led the Penguins with 91 points in 80 games last season and remains under contract through the 2026-27 season.

The superstar center signed a two-year, $17.4 million extension on Sept. 16, but with the Penguins' playoff drought reaching three years, speculation has grown over a potential trade before his contract and career are over.

Fellow insider Nick Kypreos also weighed in on Crosby's future at the start of free agency, saying on Sportsnet 590 that Crosby’s exit could come after the 2026 Winter Olympics.

“(Crosby) is too good right now to just be a babysitter for the next three years,” Kypreos said. “This guy can play peak (hockey)."

While no deal is imminent, Kypreos believes Crosby’s level still deserves playing for a contender, and he pointed toward Montreal as his final destination.

“Wait till they get Sid Crosby after the Olympics,” Kypreos said. "I'm liking the odds a little better than I did maybe a few weeks ago."

This article first appeared on Athlon Sports and was syndicated with permission.

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