Sidney Crosby's Future With Penguins Suddenly Uncertain

For many years now, even as the team struggles to make a return to the Stanley Cup Playoffs, there has always been an assumption that Sidney Crosby would never leave the Pittsburgh Penguins. Recent comments from Crosby and his agent, Pat Brisson, however, have raised some eyebrows, putting the veteran’s future with the Penguins into question.

Brisson said that Crosby leaving the Penguins “is always a possibility.” That quote is a stunner because it never felt like a “possibility” until Brisson said it.

Sidney Crosby to the Habs?👀 pic.twitter.com/h6zjujqjeV
— TSN (@TSN_Sports) September 9, 2025

Penguins fans may want to see Crosby in black and gold forever, but Brisson wants to see his client competing for the Stanley Cup each and every season.

“I maintain the same position that I do believe that he should be playing playoff hockey every year,” Brisson said to Pierre LeBrun of the Athletic. “In my opinion.”

Crosby was also asked about his future in Pittsburgh, and he didn’t give a straight answer one way or the other.

“I mean, I understand it,” Crosby said. “It’s not something you want to discuss. You’d rather be talking about who we’re getting at the (trade) deadline or, you know, where we’re at as far as, are we one or two or three in the division? But you know, it’s one of those things. That’s the hard part about losing.”

Tom Wilson and Sidney Crosb — Apr 17, 2025; Pittsburgh, Pennsylvania, USA; Washington Capitals right wing Tom Wilson (43) and Pittsburgh Penguins center Sidney Crosby (87) share a laugh during the first period at PPG Paints Arena. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

Crosby has always been a fierce competitor and wants nothing more than to win and compete for the Stanley Cup. The Penguins won’t be a Cup contender again for at least a few more seasons.

At 38, does Crosby have a few more seasons left? Likely, but can he afford to waste one, two or even three more before he can compete it Pittsburgh again?

Both Crosby and his agent had a chance to outright deny any visions of leaving Pittsburgh and squashing any trade speculation once and for all, and they didn’t.

Crosby could have said he’s content with his past success and is focused on helping the Penguins rebuild back into true contenders. Instead, he talked about roster turnover and uncertainty.

Brisson could have said his client has no interest in ever leaving the place he’s called home for two decades. Instead, he said he wants to see Crosby win another “Cup or two.”

All of sudden, it’s not clear if Crosby will be a Penguin for life. It still might be the likely outcome, but Crosby has earned the right to determine his future for himself.

If Crosby wants to finish his career with the Penguins, even if it means no more playoffs, that’s his choice and Pittsburgh will support that decision. If he wants to join a contender and get his final cracks at the Cup, he deserves that opportunity.

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