Sidney Crosby’s contract, the Penguins’ rebuild and Kyle Dubas’ next move

The dogs days of summer are on the horizon, so I figured I’d sneak in the July mailbag a little early before everyone — and potentially myself — is checked out from hockey for a bit.

Lots of great questions this month. So many, in fact, that I’m going with a two-part mailbag. Thank you for the great questions, as always.

CHICAGO, ILLINOIS - FEBRUARY 15: Sidney Crosby #87 of the Pittsburgh Penguins skates with the puck against the Chicago Blackhawks during the first period at the United Center on February 15, 2024 in Chicago, Illinois. (Photo by Michael Reaves/Getty Images)

By Josh Yohe

I think it’s a matter of interpretation, Chuck.

On one hand, it’s easy to say that the Penguins are never really rebuilding while Crosby is on their roster. There is wisdom in this. Even Kyle Dubas essentially said that he knows he’ll never have a top-five pick so long as Crosby is on this roster. He won’t let them get that bad.

That said, I’d argue that the Penguins’ rebuild has already begin. It’s just not the “be a bottom-feeder, get a couple of Hall of Famers in the draft and then win the Cup” method that the Penguins have mastered historically.

They did trade Jake Guentzel. They didn’t make any big signings on July 1. They are stockpiling draft picks. Their prospect field is improving. Dubas, in fact, even said last month that he’s eager for Crosby, Evgeni Malkin and Kris Letang to show the way to a new wave of Penguins.

The rebuild has begun. It just doesn’t feel like a rebuild, so we aren’t calling it that.

My guess is that Crosby’s next contract will be for three years. I don’t know that with absolute certainty, but that’s what I’ve heard. If that’s the case, Crosby would be under contract through the 2027-28 season. At that point, he will be 40 and would have played 23 seasons for the Penguins, having spent almost 23 of his 40 years wearing the Penguins’ logo, and 21 of those 40 years as Penguins’ captain.

Will that be the end of the road for Sid? I don’t know. If he’s still playing at a high level, if he’s still enjoying hockey and if he still has his health, I could see him playing into his 40s. It’s certainly in play. But I could also see him walking away from the game at that point.

What more does he have to prove? What more is there to accomplish? I’m sure he’d love to hit 700 goals and 2,000 points. Those numbers are not unrealistic, especially the 700 goals. But he’s won the Cup three times. He’s won Olympic gold twice. He’s one of the five best players of all time. His legacy is safer than safe. He’s got a nine-figure bank account.

So, I suspect he’ll stop going when he doesn’t enjoy it anymore.

It will be a sad day in Pittsburgh when No. 87 hangs up the skates. He’s been here for so long and has been so consistently brilliant that it’s hard to imagine walking into PPG Paints Arena and not seeing him. Enjoy him while he’s still performing. There will never be another quite like him.

I believe Lambert is a forest ranger, so I don’t suspect Sid will take that route.

He has so much money that he has houses in many different places, including Pittsburgh, Nova Scotia and Montana. He bought his parents a place in Florida. He loves vacationing in Europe. I suspect he’ll live all over the place.

But I have no doubt Crosby will remain something of a fixture in Pittsburgh. He loves it here. I also think he’ll be involved in hockey in some capacity, perhaps with the Penguins. He has the money to invest in ownership if he wants. He told me once that he’d never have interest in being a coach, but perhaps would love to be a general manager, like his hero, Steve Yzerman. We shall see.

Probably, but I have to save a few of them for the book someday. Ha. (There aren’t any damning stories … he’s pretty much as you’d expect.)

I’m sure Dubas will make another signing or two, perhaps looking for a bargain. But I wouldn’t expect anything major. The Penguins are strapped by all of the no-movement clauses on their payroll, they don’t have much wiggle room under the cap and there aren’t exactly many impactful players out there.

I think he was a good hire. Most encouraging, to me, was Dubas going out of his way to mention that Quinn won’t be afraid to challenge Sullivan. This is important. I think Sullivan is a great coach and a good human being. But I don’t think surrounding him with yes men on the coaching staff is a good idea.

There are no particular stories. I found him to be somewhat surly and uncooperative to the point that I asked some people in the organization about him. They told me that he made it very clear from Day 1 that he wasn’t interested in being in Pittsburgh.

Remember Zbynek Michalek? I always liked him and thought he was the kind of defensive presence the Penguins needed. I was wrong.

I thought Brandon Sutter would be better in Pittsburgh than he was. He wasn’t awful, but something was lacking.

As for a prospect? Tough to say. I never thought Derrick Pouliout was any good from the very beginning. Beau Bennett always looked a step slow.

I guess I’d have to go with Daniel Sprong. I remember Mike Lange being blown away at Sprong’s first training camp, predicting a mega-career for him. I could see why. What a talent.

You get to see Crosby play every night. There should be plenty of gratitude in that.

Sure, fans want to see teams win. I get it. But still. I remember, in 2003, knowing that the Penguins stunk but still being excited to watch Mario play every night (he was always hurt, but you get the point).

Also, while I don’t think the Penguins will be very good this season, stranger things have happened.

I’m only 44. Watch it, pal.

And sure, but only when I was a little kid. Look up 1986. All three teams were horrible. But watching a young Mario and a young Barry Bonds wasn’t all bad.

We all freeze in this industry. They always hand us the microphone when Sullivan is talking after home games. It still makes you feel a little weird. On occasion, I’ve forgetting what I was going to ask. So if you hear me ask something really lame and cliched, that’s probably what has just happened.

Probably, and let’s not undersell this. I’ve had enough RC Cola in that building to last a lifetime and Coke > Pepsi by a mile in my opinion.

I would never bungee jump or sky dive for any amount of money — well, it would have to be many, many millions — so scuba diving would be the way for me. And I’m a big window seat guy. I don’t like flying. It makes me intolerably nervous. But getting to see outside the plane always makes me feel better, and gives me the opportunity to take cool photos.

This morning, before it was noon, I had cleaned cat litter, made breakfast, vacuumed, taken the trash and recycling outside, done dishes and laundry.

Josh of 2019 would have been miffed by this and would have either slept in or played video games.

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