Sidney Crosby and the Pittsburgh Penguins are in uncharted territory.
For 16 straight years, making the playoffs and competing for a Stanley Cup was pretty much a given in the Steel City. Led by the core trio of Crosby, Evgeni Malkin, and Kris Letang, it never mattered what else was going on around them.
But now that those three legends are in their late thirties, things have changed. The Penguins have missed the postseason three years in a row, and they don’t appear to be going in the right direction.
General manager Kyle Dubas is rebuilding, and it’s sparked mass speculation about Crosby’s future with the team as he seeks a return to the playoffs before all is said and done.
The captain has always firmly reiterated his desire to spend his whole career as a Penguin, though he doesn’t like to talk about it all that much. On Tuesday, we got to hear from Crosby, who spoke at the NHL Player Media Tour, and TSN insider Pierre LeBrun shared some of his comments on all of the speculation in an article for The Athletic.
“I mean, I understand it. It’s not something you want to discuss. You’d rather be talking about who we’re getting at the 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,” Crosby said.
“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,” Crosby added.
Sidney Crosby on his Penguins future, on speculation (Montreal?) about it and more: ‘That’s the hard part about losing’
My latest for @TheAthletic from the NHL Player Media Tour in Las Vegas ⤵️ https://t.co/RP5u8qNUW8— Pierre LeBrun (@PierreVLeBrun) September 9, 2025
The 38-year-old remains one of the league’s best players, having just racked up another 91 points (33 goals, 58 assists) in 80 games played last season.
Crosby still has so much left in him
While the Pittsburgh Penguins are in a state of transition, don’t count out the possibility of Sidney Crosby still being at the forefront when they return to contention.
The next year or two might not be pretty in Pittsburgh, but based on what we’ve seen from Crosby, he could keep playing at an elite level for years to come.
Perhaps a few more high draft picks (Gavin McKenna?), along with other top prospects that Crosby mentioned himself, will jolt the Penguins into a turnaround sooner rather than later.
If they do, there’s no better player or captain to lead the charge than Sidney Crosby. Many hockey fans want to see him chase a Stanley Cup elsewhere, though it would be pretty cool to see him stick it out and get back to the postseason in Pittsburgh after years of struggle.
