How much longer will Sidney Crosby play in the NHL?: Penguins mailbag

New York Times

06-08-2025

Sidney Crosby turns 38 on Thursday, and given the number of excellent questions I received, I decided to write two mailbags for August, both about Crosby.
Part 2 will arrive soon. Here's Part 1.
Away we go.
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? — @runningbeam
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:
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?
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Is Sid's stance on no trade about his one-uniform legacy or does he really believe he can still win here? — @Rizzosarge
Probably both, but he always thinks they can win.
When I sit down with Crosby during training camp, we chat about the team. On the record, off the record, whatever. I just like to get a feel for what he thinks about the current team. He's the ultimate optimist. He always thinks they're going to win and always means it sincerely. I have no doubt he's thinking about the upcoming season and concocting a way for this team to be better than expected.
Will Crosby end up in management, or coaching, or be a team owner someday? — About 40 people
Many of you asked this question in various forms.
Crosby has told me he isn't interested in coaching. That's probably good because great players typically don't make great coaches. There are exceptions, but that's usually how it works.
I could see him being drawn to being a general manager and, let's be honest, if Mario Lemieux and Ron Burkle find a way to reclaim ownership of the Penguins, Crosby would be a natural and qualified investor down the road.
Assuming Sid doesn't have burners do you think he would join social media once he hangs them up? — @YaBoiVaccaro
I don't think he'll ever do that. He's way too smart.
Which Stanley Cup do you think meant the most to Crosby? I think you could make an argument for any of the three in achievement or difficulty. But one has to have the most value to him. — @nathan_lewy
What a great question. The first one is always special because it's your first. The second one was special because I think that's the one that really solidified him as a top-five player, and it helped him and Evgeni Malkin avoid one-hit wonder territory. The third one surely means a lot because of what the Penguins overcame to win that one.
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I'll ask him this at some point next season. I do think he really felt like the 2016 and 2017 Penguins were his team. He was 21 in 2009. He was 28 and 29, respectively, in the final two Cup runs. Maybe that makes some kind of impact for him.
If Sid had been picked by any other team, do you think the love, devotion and culture surrounding him would be the same as Pittsburgh's? Or is our situation unique due the city's previous (and current) affection for its icons – whether they're sports related or not? — @stefdin
I think he would make a profound impact wherever he was, but I do think that Pittsburgh probably was the perfect place for him. Crosby has a lot in common with Mario Lemieux — all-time greats, very well-liked by those who know them, intensely private about their personal lives, very much in love with Pittsburgh.
Lemieux was able to offer Crosby a unique understanding of what life in Pittsburgh would be like, and Pittsburgh already knew how to handle someone with Crosby's desire for privacy. So it was a perfect match.
But I'm sure they'd like him if he was drafted in Anaheim, too.
We all know how much Sid wants to win. We all know he's not going anywhere. What then do you see as his main, realistic goal for the remainder of his time in the league? Wants to be there 'til 'they're good again' like Rusty? Thanks! — @sidearmjones
I think, bare minimum, he needs to be in the postseason again before he walks away. He's played no games in the past three summers, and I assure you it stings him. This upcoming season figures to bring four non-playoff seasons in a row to Pittsburgh. Luckily for Crosby, the middle of this season will bring the Winter Olympics in Milan, which gives Crosby something to get excited about. Perhaps that will be enough to quench his competitive taste this season.
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But yeah, I think he needs to be in the playoffs again. I don't know if he needs another Cup title, though he wouldn't turn that down. He knows his legacy is safe in that regard. I just think he wants to take the ice in Pittsburgh in front of a raucous crowd with that playoff feel in the air again. I think it would mean everything to him.
What's the unhealthiest thing you've ever seen 87 eat? — @letangcult
Nothing that I recall. Though he did tell me once that he enjoys chocolate chip cookies at Subway. Who among us doesn't?
How many Cups does Sid win as the Pens GM after he retires? — @Jeffs_Penguins
I don't know. I just hope he returns calls like Jim Rutherford.
What's Crosby's favorite road city (excluding Montreal)? — @skiab94
I know he enjoys the California swing. In 2009, I asked him what his favorite road arena was. He told me Atlanta. I swear to God.
I asked why.
'The lighting is unreal there,' he said. 'I see the ice better.'
I relayed that story to Matt Cooke, who responded, 'Yeah, he sees things we don't see, so maybe he's onto something.'
I reread your article on Sid for the NHL99 list and was once again struck by the thought that Sid is a better person than he is a player (which is kind of unfathomable). Are there any stories about Sid you have heard since you wrote that article that would add to that narrative? — @GrizzlyAdam930
Oh, all the time.
This June, he showed up every day at the practice facility early in the morning for workouts. You know, four months before the season. At age 37. That's not normal. But he has a drive about him that is very, very different than the rest of us.
With how particular Sid seems about everything, what kind of challenges does that present you as a journalist? In a funny way, not suggesting he would be rude to you or anyone else. — @Franty_N
Well, he's certainly never been rude. He's polite and patient with members of the media, and I assure you we can be an obnoxious group.
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He doesn't present many challenges. Just little quirks. After games, he doesn't like to talk until he has his Penguins ball cap on. So, just don't ask a question until it's on, because if you do, he'll say, 'Oh, just a moment, please. Let me get my hat. Thank you.'
He's a dream to deal with. On rare occasions, he's not in the mood to talk after games. It doesn't happen often. When it does, he'll usually be walking out of the locker room and he may give you the eye contact that conveys, 'Sorry, not tonight.'
That's fine. He seemingly conducts more interviews than any star athlete in the world.
You'll never meet a reporter with a bad word to say about him. He makes our lives much, much easier.
Thanks for all the great questions. Stay tuned for Part 2.