PITTSBURGH — Perhaps those speculating, as irritating as it might be every single time it happens, are relying on simple math.

The Penguins missed the playoffs when Sidney Crosby was a rookie in 2005-06 before advancing to the postseason 16 consecutive times. They've missed the past three. This upcoming season doesn't look good. Perhaps 2026-27, too.

Does anyone expect a five-year hiatus from high-stakes hockey to sit well with one of the greatest winners the sport has ever seen?

Look, I'm not trying to sound alarm bells like Paul Bissonnette, Kevin Weekes or — this past weekend — Georges Laraque. I actually hate the idea of Crosby playing somewhere else and bristle every time it comes up.

But we should have an honest conversation about urgency, timing and what's realistic to expect here. Here's how that starts in my head:

— Immediately, I'd love to see the Penguins keep Bryan Rust and Rickard Rakell, trade Erik Karlsson and Tristan Jarry and reconstitute themselves as quickly as possible. If not for 2025-26, definitely the following year.

— It feels like I'm in the minority there.

— As far as the plan Penguins president of hockey operations Kyle Dubas has been rolling out, the distance to the finish line seems to be growing, the same for the size and scope of whatever you want to call what they're doing.

Caught in the middle of this, of course, is Crosby, who I genuinely believe doesn't want to leave Pittsburgh. He loves it here. He long ago became one of us. And he absolutely grasps the significance of being a one-sweater player.

But he's also not stupid, nor has Crosby ever been forced to go an extended period of time without competing for something — and typically, winning.

It could be a strange, new frontier for the Penguins captain, and the longer this goes, the more I wonder whether Crosby will ultimately be forced to make a choice: He can stay in Pittsburgh or return to the postseason. But not both.

Some of that was fueled by the draft haul amassed by Dubas and vice president of player personnel Wes Clark. They made 13 picks, didn't mortgage anything to slide into the top-five and largely stuck to junior kids who will take three or four years to develop.

There's nothing wrong with that. But it doesn't help the 2025-26 team.

We also learned Dubas had myriad conversations about players on his NHL roster — as he absolutely should. I learned long ago, never stop another person from being stupid. But just because nobody wanted to overpay for Rust or Rakell now, it doesn't stop them from doing so in the future.

What if that happens?

What if Dubas, clearly focused on doing this in a thorough way that preps the Penguins to compete for longer, finds a deal he likes? It would mean another winger gone for Sid, maybe two, and a longer road back to competitiveness.

Crosby isn't required to ride it out, in my opinion.

Regardless of what a handful of former NHL players seemingly love to gossip about, the how-much-will-Crosby-tolerate question does have at least some merit in my mind.

Mike Babcock has described Crosby as a "serial winner." Nobody should begrudge Crosby for needing or wanting that in his life.

Especially after losing Marc-Andre Fleury as a teammate, soon Evgeni Malkin as well and who ultimately knows what happens with Kris Letang. Again, I'm not saying it's likely or even possible. Just that I wouldn't begrudge Crosby for wanting to win after all his best friends have moved on.

As far as the draft, I actually liked a decent amount of what the Penguins did. Benjamin Kindel, Bill Zonnon and Will Horcoff might've appeared as reaches to some, but let's try to have some perspective here.

Teams have their own scouting staffs and draft boards, the same as other sports. There's also more variance baked into NHL draft evaluations due to ranking junior kids against college players, North Americans versus international players, etc.

The Penguins clearly prioritized production, upside and predictability. But one trait that didn't seem to excite them as much was proximity to the NHL. Dubas, Clark and others seem willing to wait.

What I can't help but worry about is whether the same applies for Crosby, as well as how the start of free agency on Tuesday might further change the calculus.

It's why I'd like to see the Penguins take a specific approach — and one that I don't think is asking too much:

— Try to trade Karlsson and Jarry and admit failure and buy out Ryan Graves.

— Pursue players via trade who are being misused by other teams, similar to what the Capitals did with Pierre-Luc Dubois. With roughly $20 million in available cap space, the Penguins can attempt a small gamble or two.

— Patch a few more holes via free agency: Matt Grzelcyk returning, adding a bottom-six scoring threat and potentially acquiring a cheaper veteran to start until Sergei Murashov or Joel Blomqvist earned a legitimate look.

— Don't trade Rust or Rakell and instead take a peek at how the team might look under new head coach Dan Muse. That includes a few stylistic changes, as well as my pie-in-the-sky hope of the Penguins adding some shred of physicality.

Hey, it's asking a lot, I understand.

But if those moves — none that would meaningfully sacrifice the future, mind you — can't resuscitate the Penguins, I'd feel better about taking as long as necessary and in the process making it easier for Crosby to decide if he wanted to pursue competitive hockey elsewhere.

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