Speculation is swirling around the future of Sidney Crosby, the Pittsburgh Penguins' captain, with NHL insider Nick Kypreos suggesting he could be on the move after the 2026 Winter Olympics. Kypreos floated the idea of Crosby potentially joining the Montreal Canadiens following the Olympics.

Kypreos made his prediction during a discussion with Justin Bourne and Sam MacKee, stating, "Wait till they get Sid Crosby after the Olympics". While he didn't offer specific reasons for such a trade, he alluded to behind-the-scenes activity within the Penguins organization. Kypreos's cryptic remarks included, "Something's going on in Pitt. Things are going on. Things are going on…".

Several factors are fueling the trade rumors. The Penguins have missed the playoffs for three consecutive seasons, leading to speculation that the team is heading toward a rebuild. With an aging core and an uncertain path to contention, some believe that keeping Crosby in Pittsburgh would be a disservice to his talent. As Kypreos stated, "He's too good right now to just be a babysitter for the next three years... 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 have emerged as a potential destination for Crosby. The Canadiens are a young, developing team that could benefit from Crosby's experience and leadership. Some analysts suggest Crosby could anchor the top line, with Nick Suzuki, the current captain, shifting to the second center position. Other potential landing spots mentioned by fans include the Colorado Avalanche, where he could join his friend Nathan MacKinnon.

Despite the rumors, Crosby's agent, Pat Brisson, has dismissed the speculation as "baseless" and affirmed Crosby's commitment to Pittsburgh. Penguins general manager Kyle Dubas has also indicated that the team is not looking to trade Crosby. However, the rumors persist, especially if the Penguins fail to improve their competitiveness.

If the Penguins were to trade Crosby, they would likely seek a significant return, potentially including a first-round pick, future picks, and young players. Some potential Canadiens assets that could be part of a trade package include goalie Jakub Dobes, defensive prospect David Reinbacher, or center Alex Newhook.

As the 2025-26 season approaches, attention will be focused on the aftermath of the 2026 Winter Olympics. Crosby is expected to represent Team Canada, potentially alongside stars like MacKinnon and Connor Bedard. His performance and experiences at the Olympics could influence his future decision.

While it remains uncertain whether Crosby will be traded, the rumors highlight the complex situation in Pittsburgh. The Penguins face the challenge of balancing their desire to contend with the potential need for a rebuild. Ultimately, the decision rests with Crosby and the Penguins' management, but the speculation is likely to continue as the 2026 Olympics draw closer.