It starts with a single image that ignites a thousand debates: Sidney Crosby, iconic number 87, his intense gaze fixed forward, and right beside him—the bold, red-and-white logo of the Montreal Canadiens. For a split second, it feels real. For a split second, the world of hockey holds its breath. Is this just wishful thinking, a fan-made fantasy, or the first hint of a seismic shift that could shake the very foundations of the NHL?

Nobody saw the rumor coming. One day, Crosby is the undisputed captain of the Pittsburgh Penguins, a living legend whose name is synonymous with loyalty and generational greatness. The next, whispers swirl around Montreal—Crosby’s childhood team, the franchise that shaped his earliest dreams, the city where every street corner seems to carry the echo of his French-Canadian heritage. Suddenly, the impossible feels possible, and the question is everywhere: Could Sidney Crosby, at 38, really finish his career in a Canadiens jersey?

It’s a scenario that seems ripped from the wildest corners of sports fiction. Yet, as the season unfolds and the Canadiens search for a superstar center to anchor their future, Crosby’s name keeps resurfacing. Not just in fan forums or speculative tweets, but in the analysis of respected insiders. Chris Johnston, one of the most trusted voices in hockey journalism, doesn’t just mention Crosby—he urges Montreal to “go all-in” if the chance ever arises. The suggestion is more than clickbait. It’s a challenge to the very identity of the Canadiens, a dare to risk everything for a once-in-a-generation talent.

But what would it actually take? Crosby’s contract is not the obstacle some imagine. At $8.7 million per year, he remains one of the most valuable players in the league, especially considering his remarkable 91-point performance last season. The Canadiens have the cap space, the assets, and—if they are bold enough—the willingness to pay the price. Two first-round picks, a top prospect, maybe more. It’s a king’s ransom, but for a king, perhaps the only way.

Yet, beneath the surface, the story is far more complicated. The Penguins, riding the wave of a strong start, have no intention of moving their captain. Crosby himself has given no indication he wants out. The trade, if it ever happens, would require a perfect storm—Pittsburgh sliding into a rebuild, Crosby opening his mind to a new chapter, and Montreal’s management willing to gamble the club’s future for a shot at hockey immortality.

And then there’s the emotional angle, the one that statistics and salary caps can’t measure. Crosby’s connection to Quebec, his childhood memories of the Canadiens, the possibility of finishing his career where it all began. It’s a narrative that tugs at the heartstrings of fans and players alike, a dream that refuses to die even as reality intrudes.

So what’s really going on behind the scenes? Are the Canadiens quietly preparing the greatest coup in recent hockey history? Or is this just another rumor destined to fade away? The answers are elusive, and the stakes could not be higher. As the season progresses and the Penguins’ fortunes shift, one thing is certain: the Sidney Crosby file will keep sparking debate, fueling hope, and tempting Montreal to chase the impossible.

Photo credit: All Montreal Hockey / NHL

The name Sidney Crosby keeps coming up when discussing the Montreal Canadiens’ needs at center, and with good reason.

Several analysts believe the Canadiens should “give everything” to try to lure the captain of the Pittsburgh Penguins in a trade, if he were ever to become available.

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.