Sidney Crosby is heading into his 21st NHL season, and for the first time, his future in Pittsburgh doesn’t feel like a guarantee. The Penguins have now missed the playoffs three years in a row, and questions about what happens next are getting louder.
That conversation picked up again this week, and not from the usual rumor mill. Crosby’s longtime agent put his cards on the table with all the noise around the Penguins essentially being in tank mode.
Is Sidney Crosby Entering His Final Chapter With the Penguins?
Pat Brisson, Crosby’s agent, didn’t dodge the subject by any means.
“We want Sidney to hopefully be in the playoffs every year. We want him to hopefully win another Cup or two,” Brisson told The Athletic. “So each year the team that he’s playing for fails to make the playoffs, it creates a lot of speculation. In reality, he’s not getting any younger.”
If the Penguins are falling short, it hasn’t been because of Sidney Crosby. Last season, he scored 33 goals and added 58 assists for 91 points across 80 games. It was his third straight season above the 90-point mark, proof that age hasn’t dulled his impact.
“We’re here to support him. It’s the beginning of the season here. Let’s see how things are going. Hopefully, they have a great season and the speculation will go away,” Brisson added.
Brisson hammered that point too, saying the constant speculation only exists because Crosby remains elite. “The reason we all talk about this is because he’s such a great player still,” he explained during Crosby’s stop at the NHL Player Media Tour. “He continues to be such a difference maker. Like a Tom Brady, that’s how I look at it.”
Brisson saved the best for last. Speaking on the possibility of Crosby leaving Pittsburgh, he said, “it’s always a possibility, you know?”
Like the NFL legend, Crosby has stretched his prime well beyond what most expected. And like Brady, his presence alone continues to change games.
Of course, the Brady parallel also fuels the obvious question. Brady didn’t finish in New England. He left, won a Super Bowl with Tampa, and showed that even icons sometimes need a change of scenery. Could Crosby walk a similar path?
Montreal Speculation Adds Fire
Fueling that chatter is Crosby’s long-known connection to Montreal. He grew up a Canadiens fan and admitted earlier this year that the ovation he received at the Bell Centre during the 4 Nations Faceoff was something he’ll never forget.
Crosby laughed off the idea that he was dropping hints, but he acknowledged why Canadiens fans continue to dream. “I get it,” he said. “To know a team like that wants you, it’s not the end of the world.”
Like most teams, it’s safe to assume that the Canadiens’ front office would make a serious push if Crosby ever became available. Whether that day ever comes is another matter.
Crosby has always stressed that he wants to finish as a Penguin, but patience is being tested. The franchise is in transition under general manager Kyle Dubas, and the last three years without playoff hockey have only fueled speculation.
“It’s been three years they haven’t made the playoffs. It all depends on how Sid is going to be and how the team is going to do. I maintain the same position that I do believe that he should be playing playoff hockey every year. In my opinion,” Brisson said.
For now, Crosby is locked in. His two-year extension kicks in this season, keeping him under contract through 2026-27 at an $8.7 million cap hit. The deal includes a full no-move clause, meaning any decision would be in his hands.
Speaking at the NHL Player Media Tour, Crosby admitted the hardest part about losing isn’t just the games themselves.
“It’s the unknown, the uncertainty, the question marks – that’s the stuff that’s tough. It makes you appreciate all those years that we were competing and going after the big acquisition every single trade deadline,” Crosby shared.
Still, he hasn’t changed his approach of showing up, competing, and pushing for wins.
