Tim Benz: Sidney Crosby, FSG have the right answer on his future — but were they asked the right question?

Pittsburgh Penguins fans haven’t been able to find many positives over the past week. However, one news item surrounding team icon Sidney Crosby was reassuring.

Both Crosby and the team seem unified in a desire to see the 35-year-old captain play out his remaining years in Pittsburgh.

At least that’s how co-head of Fenway Sports Management Dave Beeston framed it Friday.

“It’s very important that Sidney Crosby never plays a game in another uniform other than the Pittsburgh Penguins,” Beeston said.

Crosby echoed that tone during locker cleanout on Saturday.

“I’d love to,” Crosby responded when asked if he would want to stay a Penguin his entire career. “That’s been the case since Day 1. I feel really fortunate to have been drafted here, and I have great memories. I’ve got to play with two teammates (Evgeni Malkin and Kris Letang) for a really long time. So I’d love that to be the case.”

That’s encouraging to hear. It’s also easy to say. From both sides. I would’ve been stunned if either side had hinted at any other potential outcome.

Asking someone from Fenway Sports Group if they’d like to keep Crosby his whole career and asking Crosby if he’d like to stay here in Pittsburgh his whole career is like asking me if I’d like a $1 billion.

Yes. Yes, I would.

The harder question to ask me is how I would propose making that happen.

Similarly, the harder questions to ask FSG and Crosby are what sort of agreement it would take to make that happen and when both sides would like to make that decision. Furthermore, how much longer does Crosby want to play?

No one asked those questions.

Maybe no one wanted to hear the answers.

But Crosby, for the first time, did address the mortality of his career on locker cleanout day a year ago, after a similarly frustrating end to a season.

“Three for sure,” Crosby replied when asked in May 2022 how many more years he’d like to play. “And then we’ll see after that. I don’t want to get too far ahead of myself. But three, definitely.”

That window of time — which is now two years — aligned with the amount of time remaining on his contract. Crosby is locked in with the Penguins through the end of 2025 at $8.7 million per season. Theoretically, the team could extend his contract at the end of next season.

But for how long? Malkin is signed through 2026. Letang is locked up through 2028. Those issues were unknown the last time Crosby spoke about this. Does Crosby’s timeline have to be aligned with either — or both — of those players? Is $8.7 million per year still the magic (cap) number as it has been since 2008-09? Malkin and Letang are each making just over $6 million during the rest of their deals. How will the total money be spread out on a “35-plus” contract?

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Is Crosby willing to be part of a long-term rebuild? Is he OK with staying after the likes of Malkin, Letang, Jake Guentzel and Bryan Rust are gone? What if Mike Sullivan is soon no longer his coach? Does he still want to do business with FSG as much as he clearly was willing to do with Ron Burkle and Mario Lemieux?

Or, we can forget all those specifics and hypotheticals and just ask the question, “Is 20 years of NHL hockey a nice round number, and do you want to be done at 37 after 2024-25?”

Based on the beating he has absorbed and the accomplishments he has racked up, I wouldn’t blame Crosby one bit if the answer to that question was, “Yes.”

Does No. 87 still have All-Star potential into his 40s? That appears thoroughly plausible.

In fact, that was probably the more difficult question to ask Crosby. Not “do you want to remain a Penguin for the rest of your career?” But “how much longer do you see your career lasting?”

Because an honest answer to that second question from Crosby could dictate the confidence and sincerity of the response from FSG.

Look, I get it. Tom Brady retired as a Tampa Bay Buccaneer. Peyton Manning wound up in Denver. Wayne Gretzky ended up playing more seasons away from Edmonton (11) than he did with the Oilers (9). Babe Ruth’s last team was the Boston Braves. LeBron James is on his fourth franchise. Shaquille O’Neal played in six cities.

If Sidney Crosby does put on another jersey at some point in his career, the sports world will keep turning. I’m sure at some point, each of those sports legends felt they’d be a one-team, one-city icon like Lemieux got to be here in Pittsburgh. I bet they all had a quote similar to Crosby’s from Saturday. And I bet their original ownership groups all said something similar to what FSG did Friday about Crosby.

I sure hope those ideas are eventually spoken into reality here in Pittsburgh with Crosby. If you made me bet, I’m leaning toward believing that will be the end result.

But as comforting as the words spoken by both sides last weekend may have been, they are still a long way off from assuring that it will happen.