Sidney Crosby to Montreal Canadiens? NHL insider hints at shocking post-Olympics move amid Penguins rebuild

Could the face of the Pittsburgh Penguins be skating toward a new home in 2026? NHL insider Nick Kypreos believes it's more than just a rumor. During a recent appearance on Sportsnet 590 The Fan, Kypreos floated a bombshell idea—Sidney Crosby, the long-time Penguins captain and one of the league’s all-time greats, could be heading to the Montreal Canadiens after the 2026 Winter Olympics.

Sidney Crosby trade rumors heat up as NHL insider hints at move to rising Canadiens

“Wait till they get Sid Crosby after the Olympics,” Kypreos teased, leaving hosts Justin Bourne and Sam McKee visibly stunned. When challenged to elaborate, Kypreos didn’t back down: “I'm liking the odds a little better than I did maybe a few weeks ago. Something's going on in Pitt. Things are going on. Things are going on…”Though Kypreos didn’t dive into specifics, he pointed to what many believe is an impending rebuild in Pittsburgh.

The Penguins have missed the playoffs for two consecutive seasons, signaling the possible end of an era. With aging stars and no clear path to contention, speculation is growing that the team may be heading toward a teardown.

“He's too good right now to just be a babysitter for the next three years,” Kypreos emphasized. “It will be such a disservice to the history of our game if we watch him stay in Pittsburgh the next three or four years.”

The Montreal Canadiens, valued at over $3 billion, are an ideal landing spot for Crosby, should the Penguins part ways with their longtime leader. The Habs are a young team on the rise and could greatly benefit from Crosby’s experience and leadership. Analysts already envision Crosby anchoring the top line, with captain Nick Suzuki sliding into the second center spot, while Kirby Dach and Alex Newhook could shift down or to the wings.Also Read: NHL Predictions: 3-time All-Star Ryan Suter likely to retire as market interest fades in offseasonThough it remains a hypothetical scenario, Kypreos’ comments have sparked serious intrigue across the hockey world. As the NHL edges closer to the 2026 Olympics, all eyes will be on Pittsburgh—and whether Crosby’s final chapters might be written in a different jersey.