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Penguins Insider Josh Yohe Projects Sidney Crosby's Retirement Plans


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Julien Trekker
August 6, 2025  (10:02)
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Pittsburgh Penguins captain Sidney Crosby in action.
Photo credit: Jess Starr / Hockey Writers

Pittsburgh Penguins insider Josh Yohe projected Sidney Crosby's retirement plans in a recent paper published on The Athletic.

While there's been no shortage of speculation about Crosby's future in Pittsburgh, most of the discussion tends to revolve around potential trades rather than his eventual retirement.
As Crosby turns 38 tomorrow, August 7th, and enters the second-to-last year of his current contract, discussions surrounding his retirement will surely keep going.

Sidney Crosby's Retirement Timeline Could Shape the Penguins' Future for Years to Come

In a Q & A, the insider was asked how much longer the Pens' captain is expected to play, and if he'd be interested in chasing a few milestones before hanging up the skates.
He replied by listing some variables that'll come into play when decision time comes, but still suggested Crosby could retire after the 2028-29 season.
Check it out:
Best guess at how many more years Sid plays before retiring? Is passing Jagr for #2 all time and/or 2000 points important milestones for him personally if you had to guess?

I don't think those numbers are terribly important to him. I'm sure he'd love to reach them, but I don't think it's what drives him.

How much longer he decides to play depends on many variables:

How is his health? (Avoiding concussions is very important to him)

What is his level of play?

Are the Penguins showing signs of improvement?

To me, those will be the big questions next summer, when only one year will be remaining on his deal.

I could see him retiring after the 2026-27 season if any of the above three questions don't have the desired answer.

But because we're having fun here, if I had to guess, I'll predict that Crosby's final NHL season will be the 2028-29 campaign. Just a guess, though. If he goes out by winning the Cup 20 years after his first one, well, wouldn't that be just about right?
Crosby's decision will have a big impact on the team's short-term future, but also the long term. If he leaves the team, he won't be able to help develop the young prospects or inspire the next generation of players in Pittsburgh.
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Penguins Insider Josh Yohe Projects Sidney Crosby's Retirement Plans

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