For Penguins’ Sidney Crosby, next season might be the hardest one of all

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PITTSBURGH — The reshaping of the Pittsburgh Penguins continued over the weekend. One name after another flooded the Penguins’ prospect pool, something that has needed to happen for so many years.

It’s the dawn of a new era for the Penguins. The focus is on the future, and that’s how it should be.

Through it all, one couldn’t help but think back to Sidney Crosby.

Crosby’s name was prominent over the weekend, of course. Rumors were flying about Crosby’s future, as they have been for several months.

On one level, it’s so disrespectful to Crosby, who has repeatedly stated that his only intention is to finish his career someday with the only team he’s ever known.

On another level, the one Pittsburgh doesn’t really like to acknowledge, things in Pittsburgh must be a little deflating for the captain these days.

Think about it.

Only three of Crosby’s teammates from the glory years remain. Evgeni Malkin is almost certainly about to retire after the upcoming season, meaning Crosby will have to bid adieu to his best friend in the game, his Robin, the guy who dominated the NHL by his side for so long. The other member of the Big Three, Kris Letang, still has three years remaining on his contract, but his play has declined significantly in the past couple of years.

Evgeni Malkin and Sidney Crosby dominated the NHL together for several years side-by-side. (Charles LeClaire / Imagn Images)

Then there’s Bryan Rust, Crosby’s only other teammate from those glorious runs in 2016 and 2017. Rust is one of Crosby’s favorite linemates of all time, a giant in Penguins history. Here’s the problem: Come July 1, Rust loses his no-movement clause power. Kyle Dubas’ phone is ringing consistently as teams line up to make bids for Rust, one of the NHL’s most clutch and versatile players. If you’re Dubas, you can’t afford to worry about Crosby’s feelings. Your job is to build something special for the future, and, of course, you’d like Crosby to be around for the beginning stages of it. Maybe he will be, maybe he won’t. But one way or the other, it’s the future that must be Dubas’ concern. Still, this can’t make Crosby feel any better.

Then, there’s Rickard Rakell. While Rakell wasn’t with Crosby at the height of the Penguins’ power, he’s a darn good NHL player and the two have always enjoyed considerable chemistry. I’d place Rakell in the same boat as Rust. He’s paid very fairly, he’s a very good player and he’s under team control for multiple more seasons. Great.

But he’s also aging. Rakell is 32. Rust is 33. They’re essentially in the same boat. How good will they really be when the Penguins are good again? They’re both quality human beings who would be excellent examples moving forward for younger players, and there is absolutely something to be said for that. Of course, if it’s talented, young players that you crave — and in Dubas’ case, it is — who on this roster, other than Crosby himself, is more equipped to land you such players more than Rakell and Rust?

It’s not like Dubas isn’t aware of this.

Sooner rather than later, Crosby could be without both wingers, not long after losing Jake Guentzel.

All weekend long, there was chatter around the league about Rust receiving heavy interest. I can assure you that, while there’s no indication that Dubas is close to moving him, other teams are indeed heavily interested in Rust. Interest will pick up for Rakell, too. The salary cap is increasing, teams are eager to improve, and Rust and Rakell would both receive more money per season on the open market than they’re currently earning. All of which means they’re in high demand.

Erik Karlsson may get on your nerves, especially if the finer points of playing defense are of interest to you. But I assure you that Crosby likes being his teammate. Karlsson may not dazzle you with his positioning or defensive work, but there has never been a forward who didn’t want to play with him. No one gets forwards the puck quite like Karlsson does.

Don’t be surprised if Karlsson is playing elsewhere when the 2025-26 season begins on Oct. 7. That $10 million cap hit is crippling. The Penguins owe him a $5 million bonus on July 1. Following that time, he’ll become more valuable because other teams won’t owe him said bonus. It only takes one team that’s interested in nabbing him. I believe he will waive his new-movement clause for certain teams. It doesn’t make sense for the Penguins to keep him. It would mark one less talented player for Crosby to skate with.

It’s probably not appropriate to feel sorry for Crosby. He’s lived the life. He’s raised the Cup three times. Including endorsements, he’s earned around $200 million in his career. He’s won an Olympic gold medal twice, and he’ll go for the trifecta in Milan this winter. All things considered, his life is pretty good.

But that doesn’t mean the 2025-26 season will be fun for the greatest player of his generation. I can’t imagine a scenario where it won’t be a torment for the guy who is borderline obsessed with winning. There’s a good chance it will be the fourth straight season that the Penguins miss the playoffs. Dubas isn’t going to do anything gigantic when free agency begins, nor should he. The Penguins weren’t good enough to make the playoffs last season, and on paper, they’ll probably be worse this season.

And so, Crosby, who turns 38 this August, enters next season with the knowledge that his team is very limited. He has the Olympics to focus on, I suppose, but Crosby doesn’t work that way. He’ll worry about Team Canada in February. He would never dismiss his day job, but if a few more teammates go between now and the start of the season, he might feel like a stranger in the locker room.

Crosby’s loyalty should be celebrated this season, and I’m sure it will be. We should probably appreciate his pain tolerance, too. This season, he’ll have to deal with the growing pains of a young team, he will probably have to deal with goaltending that will cost his team even more games than it should, he’ll have to deal with a team that’s not in championship made, and most painful of all, he’ll have to watch Malkin’s farewell tour.

He isn’t going anywhere because he doesn’t wish to. Because he’s the captain. Because he is the Penguins. Anyone who even suggests otherwise doesn’t know him, doesn’t listen to him speak.

Maybe he will stick around long enough to be a part of a Penguins team that is good again. Maybe he’ll sign one more deal, and before it expires, we’ll see Crosby and the Penguins back in the playoffs, making one last charge for a championship. Maybe. What a story it would be.

The best stories deal with some pain before there is glory. Most of Crosby’s career has been a parade of glory, but the pain of the last few years has been real. And the storm is probably going to get worse before the possibility of that wonderful ending presents itself.

What some in the hockey world sadly don’t understand is that, to Crosby, this kind of story is so much more appealing than the idea of playing elsewhere. Maybe it doesn’t seem appealing to you or me. But to him, it is. He’s a little different than the rest of us, and it’s a good thing for the Penguins. His pride in the organization and the city is so deep that I suspect he will stick around long enough to ensure everything is back on track with the Penguins.

It’s going to take a while.

(Top photo: Ethan Miller / Getty Images)

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