Many National Hockey League observers assume that Pittsburgh Penguins captain Sidney Crosby will sign his contract extension this week. After all, the notoriously superstitious No. 87 has his 37th birthday coming up on Aug. 7 (8/7).

During this week’s “Madden Monday” podcast, Mark Madden of 105.9 The X and TribLive says that is exactly what he expects to happen.

But what if Crosby doesn’t ink an extension on Wednesday? Keep in mind, a lot of people thought Crosby would just sign on July 1, the first day of free agency.

“If he doesn’t, I think we can start wondering,” Madden said.

To reiterate, Madden stressed that he anticipates Crosby will sign a contract extension with the Pens in the near future. Per NHL rules, with just one-year remaining on his current deal, Crosby is now allowed to work out an extension with his current club.

If Crosby doesn’t, Madden says the Penguins might have to consider trading the team legend.

“If he’s not signed, this is something that drags on all year. It’s gonna drive him crazy, so he will sign the contract, just to avoid that,” Madden predicted. “Honestly, if he doesn’t sign the contract, they should trade him this year.”

That sounds dire, but think about it.

If Crosby doesn’t sign an extension this offseason, what would convince him to sign during what is expected to be another mediocre campaign for the Penguins? And if Crosby becomes a free agent, it’s doubtful the Penguins would be able to win a war for his services on the open market next summer.

So trading him with a full year left on his contract would have to be something that’s considered by Penguins management.

• DeMarvin Leal using versatility to take on larger role on Steelers defense • Leta Lindley storms back to win U.S. Senior Women’s Open at Fox Chapel • Steelers camp report: 6-day stretch ends with emphasis on short-yardage, goal-line situations

Madden, though, isn’t expecting things to come to that cataclysmic point.

“If he doesn’t sign the contract and they start the season with him being a pending free agent, it just makes the season a mess from the beginning of training camp,” Madden said. “I don’t want to see ‘Madden says trade Crosby.’ Because I’m not. I’m just saying that if Sid creates these heightened circumstances we’re discussing, well, that would be an extreme time. It might call for an extreme measure. But I do not see it coming to that.”

Crosby was 100% on board with the team extending the contracts of longtime teammates Evgeni Malkin and Kris Letang. Now, those two are on the books for a total of $12.2 million this year and next. Letang’s $6.1 million hit remains until the end of the 2027-28 season.

If Crosby were to be the one to jump ship first after the organization went to the extent of extending the contracts of his two longtime friends and teammates in the summer of 2022, that will likely rub the fanbase the wrong way.

“If Sid is so attached to those guys, even when the team is struggling in no small part because they did pick nostalgia, that would be something bad about him. But I don’t think that’s the case,” Madden said about the notion of Crosby perhaps wanting out of Pittsburgh.

Also, the prospect of Malkin and Letang actually playing out their contracts in Pittsburgh doesn’t appear to be a lock.

“I’ve been told (Malkin) won’t be back after this year — that he’ll go to Russia and forgo the last year of his deal,” Madden said. “How does that impact Sid? Does Sid know? I bet he does. And I heard there were discussions about trying to get Letang to Montreal at Letang’s request, but nothing came of that. So I don’t know where this is headed.”

Madden and I also talked about the Pirates’ painful losses to Arizona this weekend, Oneil Cruz’s ups and downs, Steelers training camp, Liverpool’s trip to South Carolina and Aerosmith canceling the rest of their tour.

Copyright ©2025— Trib Total Media, LLC (TribLIVE.com)