Canadiens insider not ruling out Sidney Crosby eventually coming to Montreal

Sidney Crosby will begin his 21st season as a member of the Pittsburgh Penguins tomorrow night.

Everything remains the same for the superstar center, though what's different is that for the first time in his illustrious career, there is more conversation about his future with the team rather than the Penguins' chances of competing for a Stanley Cup.

The topic that is Crosby potentially asking for a trade has quieted down in recent weeks, particularly thanks to comments about his love for Pittsburgh and desire to stay. 

However, given the current state of the Penguins, we know these rumors are bound to pop up again, and Sportsnet's Eric Engels is still of the belief that the Montreal Canadiens will be his number one destination if it ever reaches that point. Here was what he said during the latest episode of the "Spittin' Chiclets" podcast. 

"I'm a believer that Sidney Crosby could end up in Montreal. I believe the Canadiens would love to make it happen. And I believe that anybody else that's in the race for Sidney Crosby can't necessarily give up as much as the Canadiens would to take care of Pittsburgh. But two things need to happen. One, the Canadiens need to be good, and two, the Penguins need to be really bad. So we'll see where that goes," Engels said.

Sid to Montreal!?@EricEngels still believes there is a chance where Sidney Crosby ends up in Montreal. pic.twitter.com/cdyUDsFtbj

— Spittin' Chiclets (@spittinchiclets) October 6, 2025

The 38-year-old Crosby is about to begin the first season on the two-year, $17.4 million extension he inked with the Penguins prior to the 2024-25 campaign. 

Pittsburgh remains the likely ending

While the Montreal Canadiens make a lot of sense and would be one of, if not Sidney Crosby's preferred landing spot, his real preference is to help turn things around in Pittsburgh.

The Penguins have obviously missed the playoffs in three consecutive seasons, but a group of young talent that includes the likes of Harrison Brunicke, Ben Kindel, Ville Koivunen, and Rutger McGroarty is pushing its way onto the big club, potentially a sign of better days to come.

It could be another difficult year in the Steel City, but a top-five pick in a loaded 2026 draft class could further propel the Penguins back into contention, and Sidney Crosby wants nothing more than to lead them through it. 

For now, Crosby's focus is on the new-look Pens season opener, which goes down on Tuesday night in New York against the rival Rangers.