As the 2025-26 NHL season approaches, speculation intensifies regarding the futures of Pittsburgh Penguins legends Sidney Crosby and Evgeni Malkin. With Malkin likely playing his final season, questions arise about Crosby's future. ESPN's Greg Wyshynski suggests that a slow start could lead to Crosby's departure from Pittsburgh mid-season. Despite their storied history, the Penguins' recent struggles—failing to reach the playoffs since 2022—prompt discussions about a potential rebuild.

The core trio of Crosby, Malkin, and Kris Letang complicates matters, as their presence implies a commitment to competing for championships. However, with age and declining performance, the Penguins face a pivotal decision. Teams like the Montreal Canadiens and Colorado Avalanche could be suitable suitors for Crosby should he seek a trade. The looming question remains: how the Penguins will start the upcoming season greatly influences Crosby's trajectory and the franchise's direction.