Sidney Crosby has doubled as the face of the Penguins franchise and the face of the league since 2005-06. He’s someone we’ll always associate with Pittsburgh more than anywhere else, and when his playing days are over, expect him to be involved with the Penguins in some capacity.
He’s an NHL legend who will see himself inducted into every single Hall of Fame that’s hockey-related, and it’s a guarantee that the Penguins will either retire his number or take it out of circulation.
Crosby is to the Penguins what Joe Greene was to the Steelers, and Roberto Clemente was to the Pirates. He’s won three Cups during his time in the Steel City, and while there’s always a chance he can snag a fourth Cup at some point, his time in the league is running out, and he’s been on a bad hockey team lately.
Pittsburgh Penguins should retool in the 2025 offseason, unless…
I’m 100 percent for seeing this team retool and try to make another playoff run, but right now, I’m not sold on general manager Kyle Dubas going that route. So, if Dubas is ready for the prospects to take over, maybe Sidney Crosby will seek to end his career with a current contender.
It’s something Elliotte Friedman discussed on his 32 Thoughts Podcast. The guilty team? The Colorado Avalanche. The (supposedly) guilty player? Nathan MacKinnon. Now, MacKinnon has not approached and tried to recruit Crosby, but it didn’t stop Friedman from speculating.
So, if MacKinnon managed to recruit Crosby, and Crosby forced the Penguins hand via a trade at some point this summer, then yeah, Dubas needs to rebuild and not retool. Heck, while they’re at it, move the other aging players and start fresh, especially with a few top prospects who may be ready to make the jump.
A rebuild is the preferred route for the Penguins if Crosby wanted out
Yeah, I get it. Rebuilds are painful, and that would be especially true for a Penguins fanbase that just watched the best days of its franchise between the 2008-09 and 2020-21 seasons. Still, it wouldn’t surprise me if a rebuild like this would be as painful as those we’ve seen from teams like the San Jose Sharks or the Chicago Blackhawks.
One reason is that players like Sidney Crosby, Bryan Rust, and Rickard Rakell still hold enough value to warrant strong returns, and I wouldn’t sleep on Evgeni Malkin, Erik Karlsson, or Kris Letang to bring in value, either. No, the Pens wouldn’t trade them all in one offseason, but by the 2026 trade deadline, all would probably be gone if Crosby left in the summer.
But considering the returns, with draft picks, high-end prospects, and even young, NHL-ready talent, you’d see a few seasons’ worth of pain. But you also wouldn’t see some long, drawn-out playoff drought that teams like the Buffalo Sabres and Detroit Red Wings have been facing.
Still, do I see any of the above happening? No. My projection is that Crosby stays and finishes his career in Pittsburgh. Yet it’s worth speculating.