Pittsburgh Penguins player competes against Montreal Canadiens during NHL game
(Photo by David Kirouac/Icon Sportswire)

HIGHLIGHTS

  • Crosby directly addressed Montreal trade speculation for first time this season
  • ESPN’s Greg Wyshynski believes Canadiens are top destination if Crosby leaves Pittsburgh
  • Read below for Crosby’s comments plus potential trade timeline

Sidney Crosby knows Montreal wants him. And honestly? He gets it.

The Pittsburgh Penguins captain addressed the never-ending trade speculation linking him to the Canadiens on Monday, keeping things real but still playing it cool about his future.

Speaking with the Athletic’s Pierre LeBrun, Crosby didn’t shut the door completely.

“Trust me, growing up a Montreal fan and being from not too far from there, I understand how passionate they are,” Crosby said. “Whether it’s those experiences or guys that I’ve played with that have played there, or playing there in the playoffs or 4 Nations — all these different things — I get it.”

Crosby grew up in Nova Scotia idolizing the Habs. He’s never been shy about it. Pittsburgh has now missed the playoffs three years running, while Montreal made an unexpected playoff appearance last season. The Crosby to Montreal rumors aren’t going anywhere.

ESPN’s Greg Wyshynski threw gasoline on the fire during an appearance on “The Sheet with Jeff Marek” this summer. His take was blunt: if Crosby ever leaves Pittsburgh, it’s Montreal or nowhere.

“I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski said. “If he’s gonna go anywhere and he’s gonna try to do something spectacular, being part of the legacy and lineage of the Montreal Canadiens, being part of a team that’s got upward trajectory and have a good chance, maybe win a late career championship with a team that hasn’t won since 1993.”

The timing is everything here. Multiple NHL insiders, including Nick Kypreos, have pointed to the 2026 Olympics as a potential turning point. Crosby’s signed through 2026-27 at his signature $8.7 million cap hit. In today’s NHL market, that’s a massive steal.

“I don’t think he’s going anywhere for a while, but all bets are off after the Olympic Games.”

— Nick Kypreos

Crosby’s agent Pat Brisson isn’t shutting down the talk, either. When Pierre LeBrun asked if a trade could happen, Brisson left the door wide open.

“I mean, I’m answering something that… let’s put it this way, it’s always a possibility, you know?” Brisson said. “It’s been three years they haven’t made the playoffs. It all depends on how Sid is going to be and how the team is going to do. I maintain the same position that I do believe that he should be playing playoff hockey every year.”

The agent even dropped a Tom Brady comparison.

“The comparison is Tom Brady. We want Sidney to hopefully be in the playoffs every year. We want him to hopefully win another Cup or two.”

Remember what Brady did? Left New England after 20 years and won another Super Bowl in Tampa. That’s not lost on anyone.

What would it cost Montreal? Mathias Brunet reported the Canadiens would likely offer their two first-round picks from 2025 (16th and 17th overall). Eric Engels suggested a package including multiple firsts, prospects Logan Mailloux and Oliver Kapanen, plus a second-rounder.

That’s a massive haul. But for a team that hasn’t won since 1993 and just clawed back into the playoffs? You make that trade every time.

Crosby put up 91 points in 80 games last year. He’s still elite. The Penguins are rebuilding, whether they want to admit it or not. Meanwhile, Montreal’s young core is on the rise with Cole Caufield and Nick Suzuki becoming stars.

Could you imagine Cosby and McDavid both changing teams in the same year? Unlikely, but we can dream.