It’s been well-documented that Kyle Dubas is having to walk a managerial tight rope with conflicting interests in mind these days. The Penguins want and need to incorporate younger players and are long overdue to get better prospects in their system that hopefully one day will make NHL impacts. A team needs to stock up on draft picks in order to accomplish that.

However, the elephant in the room is that the Sidney Crosby era isn’t over yet. In fact, by all indications the Crosby era is officially about to be extended with the reports trickling out that Pittsburgh and their long-time captain are closing in on announcing a contract extension that will kick in for 2025-26. It wouldn’t be shocking if it’s a two or three year deal, either that should see Crosby playing in Pittsburgh through 2027 or 2028.

“It’s hard to put a timeframe on [when the Pens get back to contention”, Dubas said earlier this summer. “But this is not a strip-it-down-to-the-studs situation here.”

The Pens are left with something less than a fire sale or effort to get intentionally bad before trying to build back up, but far from a team in a position to go anywhere in the present.

Unlike last summer, when the team was active in free agent signings, the avenue to keep piling on long-term contracts to the mix doesn’t make sense any longer either.

“What we’re not going to do is get into the free agent quick fixes like some of the longer-range things that we’ve seen [July 1].” Dubas said. “If we had been in a situation where we had been a playoff team and close to being a contender, we would do that. But I think the appetite here is to try to get the team back into contention for the great players who have been here for so long of a time.”

Get back into contention with the aging core, but not spend on costly free agents. It’s no secret that most of Pittsburgh’s acquisitions are either bounce-back candidates or players with some flaws in their profile these days. That’s not going to cut it in terms of being a solid strategy towards improvement.

Which brings the fascinating question of just how bold are we talking here? How much are the Pens even able to “try and win” at this point?

Does that mean using Marcus Pettersson (himself on an expiring contract that the team may or may not be in position to commit to long-term) as trade bait to help snag a Patrik Laine or Nikolaj Ehlers? Or look to get a youngster like Arthur Kaliyev or Rutger McGroarty. Is taking a flyer on a free agent like Ondrej Kase or Filip Zadina enough to move the needle? Maybe the best bet is to acquire a player who isn’t even in the rumor mill?

All options look to have low odds for realism, and they become lower still when factoring in that the Penguins aren’t flush with cap space and it would make little sense to flip the younger assets they’ve been working hard to acquire to prop up chasing that playoff spot that’s eluded them over the past two years.

How Dubas balances all of that will be interesting. It was well-reported that the Penguins were attempting to sign Vladimir Tarasenko, though he chose to go with Detroit’s two-year offer instead. Tarasenko at 32-years old isn’t the 40-goal scorer he once was, but still would have given Pittsburgh a missing piece of a productive and legitimate top-six winger. That might have been the best case scenario, but now the team will have to pivot to something else being as Tarasenko chose a different option.

In many ways, the answer to this question about how to balance trying to surround Crosby with talent while also strengthening the future will dominate the Pens’ off-season. It arguably has been their top issue since trading away Jake Guentzel earlier this year. Crosby extending his time in Pittsburgh is great for the organization, but it will force Dubas and the managerial strategy to be different and unique from most situations when a team looks to rebuild.