Sidney Crosby has handed Dan Muse and the Penguins a delicate contract question as Pittsburgh weighs how long to extend its captain.

Crosby, now 39, acknowledged that age has made the next deal harder to map out. He wants to keep playing, but projecting exactly how many seasons remain isn't nearly as simple anymore.

That uncertainty puts Pittsburgh in an unusual position. Crosby's desire to remain a Penguin is clear, yet neither side can simply pick a long term without considering how quickly circumstances can change.

His current contract carries an $8.7 million cap hit and runs through the 2026-27 season. No extension is listed beyond that deal.

The production still gives Crosby plenty of leverage. He recorded 29 goals and 74 points across 68 regular-season games last season, remaining Pittsburgh's offensive engine deep into his career.

"It's just a little bit more difficult at my age trying to project … I'd like to continue playing for a number of years, but I just don't know what that number is."

And that's what makes this negotiation different. The Penguins aren't deciding whether Crosby can still drive their top six. They're trying to determine how long they can confidently plan around him.

Crosby leaves Pittsburgh without an easy contract term

Crosby has indicated there's no fixed deadline for getting something signed. That takes some pressure off the front office, but it also leaves a major piece of Pittsburgh's future unresolved.

Kyle Dubas remains the executive responsible for navigating the talks, while Muse prepares for another season with Crosby sitting at the center of Pittsburgh's lineup.

Crosby also produced 5 points in 6 playoff games last season. The Penguins know the captain can still handle meaningful minutes when the schedule tightens.

The harder question is what Crosby will want after another full season of wear. A multi-year extension offers security, while a shorter agreement would give both sides more flexibility.

For Crosby, that flexibility may matter more now than it did earlier in his career. He's openly admitted that judging his body and future from one year to the next has become part of the equation.

Pittsburgh's problem is that Crosby remains too important to treat this like a routine veteran negotiation. His contract affects roster planning, cap allocation and the direction Dubas can take around him.

There's no sign of a breakup. The tension comes from something far simpler: Crosby wants more hockey, but nobody can put an exact number on how much more.

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