Sidney Crosby joined the NHL in 2005 as the first overall pick for the Pittsburgh Penguins, and since then, he’s really been the heart and soul of the team. Crosby has had quite the career, winning three Stanley Cups in 2009, 2016, and 2017, along with several MVP awards and consistently top-notch performance. He’s really made his mark in Penguins history and in the hockey world overall. After a tough 2024-25 season where he scored 33 goals and tallied 91 points in 80 games, it feels like the finish line is right around the corner.

That campaign wrapped up on a pretty disappointing note: for the third year in a row, Pittsburgh didn’t make it to the playoffs. With talk of a possible rebuild in the air, some are questioning whether this could be Crosby’s last chapter in Pittsburgh, or if he’s thinking about chasing one more chance at glory somewhere else.

Veteran voice John Shannon has been pretty clear about his stance: “I do not see it, period,” he recently shared on the Sekeres & Price podcast, as per NHL Rumor Report on X. He’s not buying into the idea of a mid-season trade and thinks Crosby will stick it out in Pittsburgh for the duration of his contract. Frank Seravalli is backing that up, saying, “I think ‘eventually’ might be the key word there. I could see it. I think it’s still a real long shot. Mostly because I think we’re taking Sidney Crosby — I think you have to take him at his own word. He wants to be a Pittsburgh Penguin. He wants to finish his career in Pittsburgh.”

David Pagnotta is on the same page, saying, “Pittsburgh, yeah they’re selling everybody, almost, no Crosby’s not getting traded; they’re willing to sell, but it’s a high price.” But some other well-informed individuals have a different take on things.

Greg Wyshynski, chatting about Crosby’s future on The Sheet with Jeff Marek, shared, “I’ve long believed he will end his career in Montreal.” He’s asserting that if Pittsburgh keeps having a tough time, Crosby might look for a new challenge, especially Montreal, which he loved as a kid, makes sense given the story. Jason Bukala takes it a bit further, saying, “He is going to age out of that roster (and) go win somewhere else, is what I think. And I think that’s one to keep an eye on.”

Chris Johnston has a more careful perspective, saying, “I’m still of the mind it’s more likely than not he doesn’t finish in Pittsburgh; but obviously he’s not there today or the trade would already have happened.” This split really brings things to life: Crosby’s future feels less like a done deal and more like a turning point.

Is he going to stay the iconic figure of a dwindling Pittsburgh team, or is he off to pursue another Cup somewhere else? We’ll just have to wait and see what time and the season bring us. Right now, everyone in the hockey world is on edge, waiting to see what happens next with Crosby at this pivotal moment. But if you think about it positively, there’s a situation that could allow Sidney to keep playing in Pittsburgh.

Sidney Crosby’s Penguins future tied with another player

With a cap charge of $8,700,000 each season, Sidney Crosby is signed to a two-year, $17,400,000 deal to play for the Pittsburgh Penguins. His contract wraps up at the end of the 2026-27 season, which means Crosby will be a pretty appealing unrestricted free agent. Even with getting older and a team that’s going through some changes, Crosby is still playing at an incredible level, keeping up his amazing point-per-game streak. His long-term commitment to Pittsburgh really depends on one key thing—forward Evgeni Malkin. What’s the reason for that?

So, sports journalist Greg Wyshynski shared some insights, saying, “I’ve heard too many people that kind of know him and know that situation that tell me that’s he’s there as long as Geno’s there; if Geno’s there for one more year, then all bets are off as far as where Sid ends up.” They’ve been partners for almost twenty years now, winning three Stanley Cups together and forming a really strong bond.

Malkin once shared in a straightforward interview that Crosby is his favorite. He talked about their great teamwork on the ice and expressed his genuine admiration for Crosby’s hard work and talent, stating, “I can say a lot about Crosby because we are together at practices, I see him in the locker room, I see how he works very hard, how he is dedicated to hockey. And all of his victories, all of his awards came to him through the sweat and very hard work. He is very talented, but the way he works on himself — I don’t think I have seen anyone who lives hockey like he does.”

Absolutely, just like Crosby, Makin is really woven into the history of the Penguins. This season, the hockey star racked up 50 points, with 16 goals and 34 assists over 68 games. He’s got quite the record, sitting second in franchise history for games played with 1,213, and he’s also third in goals at 514, assists with 832, and total points at 1,346. With Malkin’s contract set to expire in 2025–26 and no word on a renewal, the upcoming NHL season is shaping up to be a pivotal moment for both legends. If Malkin decides to leave, Crosby might look for one final chance at success somewhere else.