The Montreal Canadiens acquiring Sidney Crosby has been a pipe dream ever since he was set to become an unrestricted free agent for the first time. Canadiens fans have held a belief that the former Canadiens fan would want to wear the iconic sweater at least once before he retires. However, Crosby remained committed to the Pittsburgh Penguins and showed no interest in Montreal.
Now that the Penguins are struggling and look primed to head toward a rebuild, it leaves people wondering if Crosby will want to finish out his career as a non-contender. One player can remain committed to a team throughout his entire career, but once the front office decides to rebuild then there's no shame in wanting to chase the Stanley Cup one final time.
We've seen it recently with a rival in the Boston Bruins, as Brad Marchand moved to the Florida Panthers. Crosby could follow in the footsteps of his fellow Nova Scotian and people believe the Canadiens are a perfect fit with their need to add at center. For the right price, a Crosby acquistion would be a great full-circle moment. However, it has to be for something reasonable considering he might not have many seasons left.
Denis Gauthier dropped a shocking take on Friday when he went on The Sick Podcast and suggested that a one-for-one trade for Cole Caufield might be the trade to make. It'd be quite the scene to see Crosby in Montreal, but giving away the rest of Caufield's career for it would be malpractice after how well Kent Hughes has been doing as general manager.
🚨New episode🚨@DGauthierRDS joins @TonyMarinaro to discuss:
— The Sick Podcast with Tony Marinaro (@thesickpodcasts) May 30, 2025
🔵Blockbuster trade for Crosby?
🔵#GoHabsGo path to playoffs next season
🔵And much more
Full pod👇
Watch: https://t.co/aSNZStPLxr
Listen: https://t.co/OQBeYfxZMD#thesickpodcast pic.twitter.com/5abgAQvS1o
Hughes' rebuild will be the one that every other rebuild is measured against for the next 20 years. If the Canadiens continue on their path to contention, Hughes will be a hero in Montreal as he transformed a listless roster into one of the most promising young cores in the league. Caufield is a big part of that future, and trading him for Crosby is just a way of accelerating a rebuild that doesn't need to be accelerated.
Caufield has found a home on the right wing of the first line with Nick Suzuki and Juraj Slafkovsky. Acquiring Crosby to fill the hole at No. 2 center is promising, but sacrificing one-third of that first line to do it is just taking one step forward and two steps back.
The argument is that Ivan Demidov would then move up to the first line, but then who plays second line with Crosby? The Canadiens have plenty of moves they can make this offseason, but trading Caufield would be the last thing I'd do.