Analyst Says 'Decision-Making Time' Looms for Penguins Legend Sidney Crosby

Analyst Says 'Decision-Making Time' Looms for Penguins Legend Sidney Crosby originally appeared on Athlon Sports.Sidney Crosby has spent his entire NHL career with the Pittsburgh Penguins, winning the Stanley Cup three times and becoming the face of the franchise for two decades and running.With the Penguins having gone three straight seasons without a playoff berth, however, speculation around Crosbys future in Pittsburgh keeps building.Mike Rupp Believes Next Summer Will Be Decision Time for Sidney CrosbyThe question isnt whether Crosby still produces at a high level, but rather how long hell wait for the Penguins to return to relevance.Last September, he signed a two-year, $17.4 million contract that runs through the 2026-27 season.What would it take for Sidney Crosby to leave Pittsburgh?@Rupper17 and @BriBrows22 answer a burning question on the future of the of the Penguins.

@JamisonCoyle | #NHLTonight | #LetsGoPenspic.twitter.com/U5WeX5ruA9 NHL Network (@NHLNetwork) July 28, 2025During a segment on NHL Network, 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," said Rupp, a journeyman player who spent two seasons with the Penguins.

"But I don't see anything happening this year."Rupp clarified that he doesnt expect anything to happen this season regardless of the teams 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 Crosby Exit Is Becoming More LikelyCrosby, 37, has recorded more than 90 points in each of the past three seasons, including 91 (with 33 goals) last year.Pittsburgh Penguins center Sidney Crosby has two years left on his contract.Rob Gray-Imagn ImagesDespite 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 limited.Sportsnet analyst Jason Bukala pointed to the discrepancy between his production and the franchise's lack of winning as the main reason for Crosby to exit Pittsburgh."I would never have thought (about 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 its 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 thats one to keep an eye on."Related: Edited Photo of Sidney Crosby in Maple Leafs Jersey Causes a Stir Among NHL FansRelated: "He's Going To Go Win Somewhere Else": Analyst Predicts Sidney Crosby TradeThis story was originally reported by Athlon Sports on Jul 29, 2025, where it first appeared..

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