Sidney Crosby and his camp had never opened the door, in any way, to a possible trade out of Pittsburgh. But that changed this week, and it’s reopened speculation about the NHL legend’s future with the rebuilding Penguins.
Courtesy of his longtime agent, Pat Brisson, we now have the first, tiny crack of a door that suggests that, perhaps, Crosby could leave Pittsburgh at some point.
“I mean, I’m answering something that … let’s put it this way, it’s always a possibility, you know?” Brisson told Pierre LeBrun of The Athletic and TSN.
That’s different.
Even if it’s a 1% chance, it’s still 1% more than it was before Brisson’s comments. Crosby has always said he’d like to retire with the Pens. He doesn’t want to go anywhere.
If you ask him today, he’d say the same thing. But has Pittsburgh’s fall from playoff contention gone too far?
“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,” Brisson said. “I maintain the same position that I do believe that he should be playing playoff hockey every year. In my opinion.”
The Pens went from a team that barely missed the mark in 2023, to trading Jake Guentzel in 2024. They eventually moved off of other pieces last season like Lars Eller, Marcus Pettersson, Drew O’Connor, Michael Bunting, and Cody Glass.
And rumors are still swirling that Erik Karlsson, Rickard Rakell, and Bryan Rust could be the next ones on the move.
After all, the Penguins are the only team openly rebuilding. In a league where 32 teams are vying for positioning, 31 of them feel like they have a shot at the playoffs. Kyle Dubas and the Pens are the 32nd team.
They’ve seen the writing on the wall. They know it’s time to tear it down.
The one question remains if Crosby is going to stick around for the tear down, or if he’ll accelerate the rebuilding process by accepting a trade for what would be a massive return.
Here’s Crosby’s response to a question at the NHL Player Media Tour in Vegas about his future with the Pens after three bad seasons for the club.
It’s long, but it’s worth a read.
“I mean, I understand it,” Crosby said of the rumors and speculation about his future. “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. I think everybody thinks that the buzzer goes and you lose a game and that sucks, but there’s so much more than that. It’s the (roster) turnover. 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. I don’t think I took it for granted, but I definitely appreciate it that much more now.”
If Crosby were to ever actually get dealt, which, right now on Sept. 10, I’d still put as the far less likely option, the Avalanche would be a possible destination.
Crosby’s friendship and Nova Scotia connection with Nathan MacKinnon has led to years of speculation that Crosby would end his career in Denver. But the recent rise of the Montreal Canadiens has opened the door to an even better fit for him.
The Habs were Crosby’s favorite team growing up. That city — that fan base, celebrate him like he’s one of their own every time he enters that building. It reached a pinnacle of celebrations for him at the 4 Nations Face-Off games in Montreal.
Whether it’s one of these teams, or someone else off the board, it’s still worth following this story in 2025-26. Crosby is starting a two-year extension, carrying the same $8.7 million AAV he’s made since he completed his entry-level contract in 2008. He’s 38 years old, he’s winding down his career.
But he hasn’t shown any signs of slowing down. And if he were to be dealt, it could be one of, if not the biggest trade in NHL history. Up there with the Wayne Gretzky trade.
“He’s been so consistent for 20 years. He had another great year last season. He just keeps going,” Brisson told LeBrun. “The comparison is Tom Brady. We want Sidney to hopefully be in the playoffs every year. We want him to hopefully win another Cup or two. So each year the team that he’s playing for fails to make the playoffs, it creates a lot of speculation.”
