New Angle Emerges on Canadiens Trade Talk Around Sidney Crosby

The possibility of Sidney Crosby leaving the Pittsburgh Penguins, long considered unthinkable, has taken on a new turn this past week — one that involves the Montreal Canadiens. While nothing is imminent, recent developments suggest the Canadiens could be among the few teams positioned to make a blockbuster trade if Crosby ever seeks a new home.

He’s yet to say publicly that a fresh start is what he wants, but his agent is teasing the idea, and Crosby has been a bit more vocal in the teases that other teams have some appeal for him.

At 38, Crosby remains one of the NHL’s most elite players, but his future in Pittsburgh has been the subject of speculation, particularly as the organization navigates a rebuild and a potential ownership transition. In an interesting new twist, at the recent NHL/NHLPA media tour in Las Vegas, Arpon Basu of The Athletic reports that Crosby did not deny trade possibilities — leaving the door open for discussion without signaling an intent to leave.

Enter Montreal.

The Canadiens’ prospect pool is among the league’s deepest, featuring top-five picks Ivan Demidov and David Reinbacher, first-rounder Filip Mešár, and several other young players developing quickly. For Penguins general manager Kyle Dubas, this is like a candy bar where he can try to pick from some of the best young talent the NHL has to offer. What he’ll want in any Crosby trade is a combination of draft picks and NHL-ready talent to fast-track Pittsburgh’s rebuild.

The Canadiens will only give up so much, and a number of players will be non-starters in trade conversations, but the Canadiens still have great options to choose from.

Montreal, meanwhile, needs to upgrade at the No. 2 center position. Acquiring Crosby would not only be one of the better upgrades available in the league, but he would immediately come in and improve their chances to compete in the playoffs. And, the Canadiens wouldn’t just be a team that has a chance to win this season with Crosby. They’d be competitive for the rest of his contract and any extension he chooses to sign after this contract ends.

Few teams have the combination of young assets and willingness to overpay for a player of Crosby’s stature, making the Canadiens a uniquely viable partner.

The Timing of a Crosby Trade to the Canadiens Is Key

Of course, timing and fit are critical. Montreal must balance its own roster-building needs with the potential for a blockbuster trade, ensuring core prospects like Demidov remain protected while still assembling a package that satisfies Pittsburgh. Crosby himself would likely want to join a team where he could compete immediately, and he isn’t going to a team that’s giving away its best assets to acquire him.

For now, this remains a theoretical scenario. But the alignment of Crosby’s possible departure, Montreal’s rising roster, and Pittsburgh’s rebuild could create one of the NHL’s most intriguing trade possibilities as the 2025-26 season rolls along.

Strangely, these trade rumors are picking up steam. And, while no one is confirming anything, where there is smoke, there is often fire.

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