Staring down another season with this version of the Pittsburgh Penguins has Sidney Crosby looking back on the good old days.

It also has him navigating questions about his future with a club that&#8217;s missed the playoffs in three straight seasons.
<blockquote>
“I understand it,” <a href="https://www.dailyfaceoff.com/news/pittsbugh-penguins-sidney-crosby-discusses-trade-rumors-avalanche-canadiens">Crosby told Daily Faceoff when asked about the speculation he could leave the only NHL team he&#8217;s ever played for</a>. “It’s not something that you want to discuss. You’d rather be talking about who we’re getting at the [Trade] Deadline or where we’re at as far as are we No. 1, 2 or 3 in the division. But it’s one of those things that’s a hard part about losing. Everybody thinks that losing is, the buzzer goes, you lose the game, and that sucks, but there’s so much more than that. It’s the turnover, it’s the unknown, the uncertainty, the question marks.”
“That’s the stuff that’s tough. And it makes you appreciate all those years that we’re competing and going after that big acquisition every single Trade Deadline. I don’t think I took it for granted, but I definitely appreciate it that much more now.”
</blockquote>
Since winning back-to-back Stanley Cups in 2016 and 2017, the Penguins have advanced out of the first round of the playoffs just once. It was a second-round loss to the Washington Capitals in 2018 and a significant hurdle cleared by Alex Ovechkin on the path to his first Stanley Cup.
The Penguins fell in the first round of the playoffs to the Islanders, Canadiens, Islanders again, and Rangers between 2019 and 2022 and are now out of the contention picture in the Eastern Conference. They narrowly missed the playoffs in 2023 and 2024, but were 11 points shy of Montreal for the second wild-card spot in 2025.
These poor results have come despite excellent numbers from Crosby, who just set an NHL record with his 20th point-per-game season since entering the league. The first-overall pick from the 2005 draft scored 108 goals and 278 points over 244 games over the last three seasons, during which Pittsburgh missed the playoffs for the first time since his rookie campaign.
Now ninth on the NHL&#8217;s all-time scoring list with 1,687 points in 1,352 games, Crosby already owns among the most impressive resumes of anybody ever to play the sport. The Cole Harbour, Nova Scotia native has three Stanley Cups, two Olympic gold medals, along with numerous other international medals and NHL awards to his name.
Though he&#8217;s already a lock for the Hall of Fame, the recently turned 38-year-old has no intention of winding down. The longtime captain of the Penguins is looking to lead an underdog team back into the playoffs.
<blockquote>“It doesn’t change my approach,” Crosby said. “I still go out there trying to win every single game and be the best that I can be. And I think that youth and having that energy around you isn’t a bad thing, either. We’ve got a lot of hungry guys, a lot of competition for spots. So you just try to find different things that you can feed off of and still continue to learn through it.”</blockquote>
Almost one year ago, Crosby inked a two-year extension to stay in Pittsburgh at a wildly team-friendly rate of $8.7 million annually. The deal features a full no-movement clause, so the veteran pivot isn&#8217;t going anywhere unless he wants to be moved.
If the Pens have a solid season in 2025-26 and they aren&#8217;t selling come deadline time, the speculation about Crosby being traded to a contender will go away. That&#8217;s what his agent, Pat Brisson, said to help cool the idea of a franchise icon leaving town, at least.
So, as long as the team is competitive, there&#8217;s no reason to worry. That sounds <a href="https://oilersnation.com/news/connor-mcdavid-confident-edmonton-oilers-right-now-question-long-term-outlook">familiar</a>.
<blockquote>&#8220;I mean, I&#8217;m answering something that&#8230; Let&#8217;s put it this way, it&#8217;s always a possibility, you know?&#8221; <a href="https://www.nytimes.com/athletic/6613059/2025/09/09/sidney-crosby-penguins-canadiens-future/">Brisson told Pierre LeBrun of The Athletic when asked if Crosby would consider a trade</a>. &#8220;It&#8217;s been three years they haven&#8217;t made the playoffs. It all depends on how Sid is going to be and how the team is going to do. I maintain the same position that I do believe that he should be playing playoff hockey every year, in my opinion.&#8221;</blockquote>
The Penguins went 34-36-12 last season despite 33 goals and 91 points from Crosby, and their most notable additions this summer were Anthony Mantha (coming off a season lost to injury) and Matt Dumba (who was scratched in the playoffs by the Stars in favour of AHLer Alex Petrovic). I might be underselling the acquisition of Arturs Silovs, but you get what I mean.
No matter how optimistic anybody might be about a young Pittsburgh team taking a leap forward, it isn&#8217;t something that seems likely. Come late February when the hockey world shifts its focus from the Olympics to the NHL&#8217;s Trade Deadline, there&#8217;s a very good chance we&#8217;ll see Crosby&#8217;s name among candidates to be moved.
Two teams already seem to be established at the front of the line for when this whole thing eventually goes down. The Montreal Canadiens (Crosby&#8217;s favourite team growing up) and the Colorado Avalanche (led by fellow Cole Harbour native and close friend Nathan MacKinnon) are two playoff teams who badly need another top-six centre. The fit makes sense both sentimentally and logically.
And you certainly can&#8217;t leave the Edmonton Oilers out of this hypothetical conversation. If Crosby clicks with Connor McDavid while playing for Team Canada at the Olympics in February, maybe Edmonton rockets to the top of his preferred destinations list.
There are plenty of avenues to speculate about where Crosby could go for a late-career Ray Bourque-style victory lap. It&#8217;s obviously way, way too early to be talking about this sort of thing, but it beats wondering about the future of another generational talent, right?
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Staring down another season with this version of the Pittsburgh Penguins has Sidney Crosby looking back on the good old days.



It also has him navigating questions about his future with a club that's missed the playoffs in three straight seasons.
<blockquote>
“I understand it,” <a href="https://www.dailyfaceoff.com/news/pittsbugh-penguins-sidney-crosby-discusses-trade-rumors-avalanche-canadiens">Crosby told Daily Faceoff when asked about the speculation he could leave the only NHL team he's ever played for</a>. “It’s not something that you want to discuss. You’d rather be talking about who we’re getting at the [Trade] Deadline or where we’re at as far as are we No. 1, 2 or 3 in the division. But it’s one of those things that’s a hard part about losing. Everybody thinks that losing is, the buzzer goes, you lose the game, and that sucks, but there’s so much more than that. It’s the turnover, it’s the unknown, the uncertainty, the question marks.”
“That’s the stuff that’s tough. And it makes you appreciate all those years that we’re competing and going after that big acquisition every single Trade Deadline. I don’t think I took it for granted, but I definitely appreciate it that much more now.”
</blockquote>
Since winning back-to-back Stanley Cups in 2016 and 2017, the Penguins have advanced out of the first round of the playoffs just once. It was a second-round loss to the Washington Capitals in 2018 and a significant hurdle cleared by Alex Ovechkin on the path to his first Stanley Cup.

The Penguins fell in the first round of the playoffs to the Islanders, Canadiens, Islanders again, and Rangers between 2019 and 2022 and are now out of the contention picture in the Eastern Conference. They narrowly missed the playoffs in 2023 and 2024, but were 11 points shy of Montreal for the second wild-card spot in 2025.

These poor results have come despite excellent numbers from Crosby, who just set an NHL record with his 20th point-per-game season since entering the league. The first-overall pick from the 2005 draft scored 108 goals and 278 points over 244 games over the last three seasons, during which Pittsburgh missed the playoffs for the first time since his rookie campaign.

Now ninth on the NHL's all-time scoring list with 1,687 points in 1,352 games, Crosby already owns among the most impressive resumes of anybody ever to play the sport. The Cole Harbour, Nova Scotia native has three Stanley Cups, two Olympic gold medals, along with numerous other international medals and NHL awards to his name.

Though he's already a lock for the Hall of Fame, the recently turned 38-year-old has no intention of winding down. The longtime captain of the Penguins is looking to lead an underdog team back into the playoffs.
<blockquote>“It doesn’t change my approach,” Crosby said. “I still go out there trying to win every single game and be the best that I can be. And I think that youth and having that energy around you isn’t a bad thing, either. We’ve got a lot of hungry guys, a lot of competition for spots. So you just try to find different things that you can feed off of and still continue to learn through it.”</blockquote>
Almost one year ago, Crosby inked a two-year extension to stay in Pittsburgh at a wildly team-friendly rate of $8.7 million annually. The deal features a full no-movement clause, so the veteran pivot isn't going anywhere unless he wants to be moved.

If the Pens have a solid season in 2025-26 and they aren't selling come deadline time, the speculation about Crosby being traded to a contender will go away. That's what his agent, Pat Brisson, said to help cool the idea of a franchise icon leaving town, at least.

So, as long as the team is competitive, there's no reason to worry. That sounds <a href="https://oilersnation.com/news/connor-mcdavid-confident-edmonton-oilers-right-now-question-long-term-outlook">familiar</a>.
<blockquote>"I mean, I'm answering something that... Let's put it this way, it's always a possibility, you know?" <a href="https://www.nytimes.com/athletic/6613059/2025/09/09/sidney-crosby-penguins-canadiens-future/">Brisson told Pierre LeBrun of The Athletic when asked if Crosby would consider a trade</a>. "It's been three years they haven't made the playoffs. It all depends on how Sid is going to be and how the team is going to do. I maintain the same position that I do believe that he should be playing playoff hockey every year, in my opinion."</blockquote>
The Penguins went 34-36-12 last season despite 33 goals and 91 points from Crosby, and their most notable additions this summer were Anthony Mantha (coming off a season lost to injury) and Matt Dumba (who was scratched in the playoffs by the Stars in favour of AHLer Alex Petrovic). I might be underselling the acquisition of Arturs Silovs, but you get what I mean.

No matter how optimistic anybody might be about a young Pittsburgh team taking a leap forward, it isn't something that seems likely. Come late February when the hockey world shifts its focus from the Olympics to the NHL's Trade Deadline, there's a very good chance we'll see Crosby's name among candidates to be moved.

Two teams already seem to be established at the front of the line for when this whole thing eventually goes down. The Montreal Canadiens (Crosby's favourite team growing up) and the Colorado Avalanche (led by fellow Cole Harbour native and close friend Nathan MacKinnon) are two playoff teams who badly need another top-six centre. The fit makes sense both sentimentally and logically.

And you certainly can't leave the Edmonton Oilers out of this hypothetical conversation. If Crosby clicks with Connor McDavid while playing for Team Canada at the Olympics in February, maybe Edmonton rockets to the top of his preferred destinations list.

There are plenty of avenues to speculate about where Crosby could go for a late-career Ray Bourque-style victory lap. It's obviously way, way too early to be talking about this sort of thing, but it beats wondering about the future of another generational talent, right?
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Poor outlook for Penguins has Sidney Crosby’s future with club back in question

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