Sidney Crosby Trade Scenario Sends Him to Canadiens for Monster Package

Sidney Crosby remains the face of the Pittsburgh Penguins, but that hasn’t stopped fans and analysts from dreaming about an alternate future. 

On Monday, Sportsnet’s Eric Engels addressed the idea of Crosby joining the Montreal Canadiens, calling it speculative and grounded more in fantasy than fact.

"All I’m presenting here is opinion, with no new information to go on and endless assumptions to make," Engels wrote. "As far as anyone knows, Crosby wants to be a Pittsburgh Penguin for life, and there are no indications that’s changed."

Still, Engels explored the scenario at the request of a fan and made a compelling case for the trade happening at some point in the future.

Engels noted that while Crosby has never expressed a desire to depart, the Canadiens could make a strong case if the situation ever changed.

Crosby, a native of Nova Scotia and longtime admirer of the Bell Centre, grew up as a Canadiens fan. 

"There’s been a lot of speculation the soon-to-be 38-year-old would jump at (the) opportunity (of playing in Montreal)," Engels wrote. "But it’s all been driven by perception: by Crosby growing up a Canadiens fan, by father Troy being a former draft pick of the franchise, by the idea he’d be compelled by the team’s rise and its promising core, and by Crosby making his love for playing at the Bell Centre well known throughout his 20 years in the NHL."

Montreal, more realistically and in a potential effort to acquire Crosby, has the assets to interest Pittsburgh.

“The Canadiens are flush with high-value picks and quality prospects,” Engels said. “They could outbid teams like Colorado and Los Angeles, who lack the same draft capital.”

 

Engels proposed a theoretical package including first-round picks in 2025 and 2026, a second-rounder, and NHL-ready prospects like Logan Mailloux and Oliver Kapanen—all while taking on Crosby’s full $8.7 million cap hit.

"(The Canadiens) have the 16th and 17th picks in this year’s draft and can part with either one (or both) in a package to acquire Crosby," Engels wrote. "They could also package one with a lottery-protected first in 2026, and they could even dip into one of their second-round picks—they have two in each of the next two drafts—as a potential sweetener. 

"And they can throw in any combination of two prospects not named Demidov, Reinbacher, Fowler, or Hage to complete the deal while taking on Crosby’s full cap hit."

Engels, however, cautioned that Crosby has shown no signs of being interested in a move. The 37-year-old recently signed an extension through 2027 and holds a full no-movement clause.

“I know how speculation works,” Crosby said in January. “I don’t think it’s something I’m going to discuss every time someone speculates something.”