Sidney Crosby trade rumors intensify as analysts warn Penguins’ inaction could force iconic move

Sidney Crosby’s future with the Pittsburgh Penguins is drawing growing scrutiny amid concerns about the team’s performance and direction. While Crosby remains a top player at age 37, NHL insiders are increasingly suggesting that a trade could be on the horizon if the Penguins fail to make significant strides this season. The upcoming 2026 Winter Olympics may prove pivotal in shaping that decision.

On the July 1 episode of the Real Kyper & Bourne podcast, analysts Nick Kypreos and Elliotte Friedman both highlighted the possibility of Crosby being moved, though they disagreed slightly on timing. Kypreos expressed strong confidence that a trade is coming if the team falters, while Friedman emphasized Crosby’s routine-oriented personality, suggesting any move would be carefully considered.

Crosby’s legacy as a lifelong Penguin and multiple Stanley Cup champion adds complexity to the situation. Yet with the team outside the playoffs last year and limited offseason reinforcements, fans and management alike may soon face tough choices about the future of their iconic captain.

Winter Olympics could mark a turning point

Both analysts pointed to the upcoming 2026 Winter Olympics as a natural breaking point — emotionally, competitively, and contractually — for Crosby and the Penguins. If Pittsburgh remains outside the playoff picture by the Olympic break, the notion of trading No. 87 could become less speculative and more strategic.

Crosby continues to perform at an elite level. Yet, following a playoff miss in 2024 and minimal roster upgrades this summer, a rebuild seems increasingly plausible. For Crosby, the desire to compete for another Stanley Cup may eventually outweigh his historic loyalty.

Legacy in question or last shot at glory?

The idea of Crosby wearing a jersey other than Pittsburgh’s black and gold is still difficult for many fans to process. But if the Penguins don’t take a major leap early in the season, it may become the only viable path for both the player and the franchise.

Friedman’s remarks about Crosby’s structured nature suggest any move would be carefully weighed — not rushed or forced by media narratives.For now, the ball is in Pittsburgh’s court. But the clock may already be ticking.