Pittsburgh Penguins center Sidney Crosby. Charles LeClaire-Imagn Images

Insider on Canadiens' playoff chances: 'Wait until after the Olympics when the Habs get Sidney Crosby'

Originally posted on Dose.ca | Last updated Jul 4, 2025 11:11 PM ET

Sidney Crosby has been, and for a long time will be, linked with the Canadiens.

People dream of seeing the Penguins captain in the metropolis, and a very reputable tipster in Nick Kypreos believes it will happen … in 2026, after the Olympics.

On Sportsnet 590, one of the hosts asked his colleagues: “Will the Canadiens make the playoffs, true or false?” Both colleagues said yes, especially after Kent Hughes’ recent acquisitions. Kypreos followed up with “wait until after the Olympics, when the Habs get Sidney Crosby.

A well-connected tipster wouldn’t be at all surprised to see him traded to the Canadiens. https://t.co/Uo5n7QlwvM

– TVA Sports (@TVASports) July 4, 2025

Well, maybe it’s more of a wish or a joke than inside information he got, but it’s good to know that even Toronto informants, working in a market outside Montreal link Sid to the Habs.

By many accounts, Montreal is the most likely club to acquire him.

The Olympics in Italy will take place in February 2026 (6 to 22), just a few days before the trade deadline. It would therefore be logical/probable, especially considering that the Penguins are likely to be at the bottom of the overall standings and, consequently, will be sellers, to see Crosby traded.

However, such trades, especially for a legend, are rarely made in the middle of the season. But who knows? Maybe, after a great Olympic tournament for Captain Canada and a gold medal, Hughes will finally decide to pull the trigger.

Imagine this forward line-up in the second half of the 2025-2026 season:

Slafkovsky-Suzuki-Caufield

Demidov-Crosby-Dach

Bolduc-Newhook-Laine

Gallagher-Evans-Anderson

Easily a forward on a championship team.

This article first appeared on Dose.ca and was syndicated with permission.

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