'Decision-Making Time' Looms for Sidney Crosby as Penguins Spiral

During a segment on NHL Network, former player and analyst Mike Rupp said Crosby could be nearing a pivotal moment in the last stage of his career.

"I think next summer would be that decision-making time, and potentially, Sidney Crosby may be leaving," Rupp said. "But I don't see anything happening this year."

Rupp clarified that he doesn’t expect anything to happen this season, regardless of the team’s performance. But he identified one key factor that could change everything once the 2025-26 season is over.

"The one thing that would get him to potentially leave, I think, is just playing out this season and, if getting (Evgeni) Malkin riding off into the sunset, if (Malkin) is going to retire and not be a Penguin (after next season), that would break up the core guys," Rupp said.

Other Analysts Suggest A Sidney Crosby Exit Is Becoming More Likely

Crosby, 37, has recorded more than 90 points in each of the past three seasons, including 91 (and 33 goals) last year.

Despite Crosby's consistency as he approaches age 40, the Penguins have failed to build a competitive roster around him, and it's fair to assume Crosby's chances at another title in Pittsburgh are rather limited.

Sportnet's analyst Jason Bukala pointed to that discrepancy between the player's production and the franchise's lack of winning as the main reason for Crosby to exit Pittsburgh.

"I would never have thought [a Crosby trade], even going back a couple years ago," Bukala said. "Crosby is still an elite talent, and Pittsburgh is not going to be very good for a long time," Bukala said. "I guess it’s going to be a while (before they contend). He is going to age out of that roster (and) go win somewhere else, is what I think. And I think that’s one to keep an eye on."