
For over two decades, Sidney Crosby has been the face of the Pittsburgh Penguins franchise, and in that time, the team have won three Stanley Cups and have consistently competed year in, year out throughout the regular season.
Throughout that time, the team have had Evgeni Malkin and Kris Letang leading the charge with Crosby, but now, with all approaching the age of 40, with the core trio likely to call it quits in the NHL sooner, rather than later. However, a surprise 2025/26 that saw them bounce back into the post-season may have changed that timeline, and now, we have the latest on 87’s future, with Crosby not looking to retire after this season.
Sidney Crosby Likely to Sign a new Deal in Pittsburgh

GettySidney Crosby of the Pittsburgh Penguins.
Heading into 2025/26, there was a chance that the two-year extension Crosby signed would be his last in the NHL, but last season he was once again stellar, posting 29 goals and 74 points in 68 games played despite being 38-years-old throughout the season.
Clearly, with an elite level IQ and health on his side once again (for the most part), Crosby remains one of the best players in the National Hockey League, and with the future arriving in Pittsburgh, No. 87 is clearly excited. As a result, he wants to be around to help lead this young group, and as a result, he’s likely to sign a new deal according to Josh Yohe of The Athletic, who provided the latest on Crosby’s NHL future.
“The smart money would be on Crosby signing a new deal sometime between now and the middle of September. That’s how it went before; that’s the timeline Crosby is comfortable with, and a new contract seems inevitable,” Yohe writes.
“How many years will it be? Likely one or two.”
Can Sidney Crosby Lead the Penguins Back to the Playoffs?
Last season, many expected the Penguins to be one of the worst teams in the NHL, but with the emergence of players like Ben Kindel and Yegor Chinakhov alongside veterans Rickard Rakell and Bryan Rust, this team was competitive enough to return to the Stanley Cup Playoffs.
Now, Crosby and the entire core are another year older, but that means their young group will be too, and with solid off-season additions in Andrei Kuzmenko and Trevor van Riemsdyk, this is a team that’s shaping up as a genuine threat once again, even with Crosby closing in on 40-years-old.
Ultimately, it makes sense for Crosby to sign another deal in Pittsburgh, as he’s clearly still one of the fittest players in the NHL to go along with an elite hockey IQ that will never go away, and given all that he’s done for the Penguins over his career, the team will keep bringing him back as long as he wants to play, and now, it appears he’ll play until at least 42-years-old.
Insider Reveals the Latest on Sidney Crosby’s Penguins Future