While there’s already been lots of talk about the potential for a star-studded 2027 free-agent class, there hasn’t been much chatter surrounding Sidney Crosby and his situation with the Pittsburgh Penguins.
Like Quinn Hughes, Nikita Kucherov, Jason Robertson, and many more, Crosby will be playing on the final year of his current deal in 2026-27, and on Tuesday at the NHL/NHLPA Player Media Tour, he was asked about his future beyond next season.
“Pat (Brisson)’s talking to Kyle (Dubas). It’s just a little bit more difficult at my age as far as trying to project where you’re gonna be. … I’d like to continue playing for a number of years. It’s just I don’t know what that number is. I guess your mind and body tell you that eventually. Right now I feel pretty good, though,”
The 39-year-old Crosby, as mentioned, is poised to enter the second and final year of the two-year, $17.4 million contract extension he signed with the Penguins in September 2024. He once again produced at over a point-per-game rate in 2025-26, tallying 74 points (29 goals, 45 assists) in just 68 games played.

Similar to Tom Brady, LeBron James, and Lionel Messi in their respective sports, Crosby is the kind of athlete who has managed to defy Father Time thus far, and it would come as no surprise to see him continue doing so for years to come given his work ethic and love for the game.
There’s no doubt that Crosby’s next contract is trickier to figure out than most because of his age. However, in the end, it seems most likely that it will be another one- or two-year extension where he earns his patented $8.7 million per season in Pittsburgh.
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