Crosby, 38 years old, recorded 91 points in 80 games last season - a high-level performance for a veteran his age. His current contract at $8.7M per year remains reasonable for what he brings, which makes the idea of a trade even more tempting for the Habs.
But turning the dream into reality looks difficult. The Penguins show no desire to move their captain, unless he is the one who asks to leave.
Moreover, to acquire Crosby, the Canadiens would undoubtedly have to sacrifice at least two 2025 first-round picks and add a high-end prospect - a price many consider extremely high.
Analysis of the possibility of bringing Sidney Crosby to Montreal
The Habs have the necessary cap space to absorb Crosby's salary - though they would still need to free up some room for the playoffs. In return, the asking price would be massive: two first-round picks, a strong prospect, and possibly more.
Several voices around the NHL nevertheless believe that if Pittsburgh enters a rebuild, the situation could change.
"The Sidney Crosby trade conjecture has quieted down, given how well the start of the season has gone for the Pittsburgh Penguins, but that's the player I think Montreal should go all-in for if the Canadiens ever get a chance to land him.
There's absolutely no guarantee Crosby opens his mind to the possibility, but he'd be an ideal fit. The Habs also have the assets needed to make a trade work if the opportunity ever comes their way." - Chris Johnston
Even if the idea seems crazy to many hockey fans, there is a sometimes overlooked angle: Crosby's attachment to his French-Canadian roots - the Canadiens represent a childhood memory, an adult dream. If the stars align, Montreal could offer an ideal context for an incredible end to his career.
It remains to be seen what the Canadiens' management will do: will they really risk the club's future to try to attract a 38-year-old player? However, let's be honest, this is not "just a normal 38-year-old player".
This file promises to spark discussion, especially if the Penguins start playing worse.