NHL insider Nick Kypreos has raised the possibility that Sidney Crosby‘s long tenure with the Pittsburgh Penguins could end following the 2026 Winter Olympics in Milano Cortina. With the Penguins having missed the playoffs for three straight seasons amid a downward trend, the speculation about a Sidney Crosby trade rumors after Olympics has gained momentum.
Penguins’ Ongoing Struggles and Aging Core Fuel Trade Speculation
The Pittsburgh Penguins have struggled to return to postseason competition, signaling that a rebuild may be necessary. However, the team’s leadership has resisted trading Crosby or other veteran core players, prioritizing contention while their key talents are still active. Despite this, Kypreos suggested on Sportsnet 590 The FAN, during a discussion with analysts Justin Bourne and Sam MacKee, that the Penguins might consider trading Crosby after the 2026 games.
Kypreos specifically predicted that Crosby could be traded to the Montreal Canadiens, indicating an increased likelihood recently compared to several weeks ago. He attributed this outlook to the Penguins’ declining point percentages over three consecutive seasons and an aging roster, including Evgeni Malkin turning 39 and potentially facing his final playing season.
Kypreos Emphasizes Crosby’s Value and Potential Future Impact
According to Kypreos, Crosby remains far too talented to serve merely as a placeholder for rebuilding purposes. He stated,
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(Crosby) is too good right now to just be a babysitter for the next three years,
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and emphasized Crosby’s capability to perform at his peak level.
He expressed concern over Crosby possibly staying in Pittsburgh without meaningful team success, adding,
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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.
”
Uncertainty Surrounds Penguins’ Internal Direction Amid Trade Talk
While Kypreos did not reveal concrete details of trade discussions, he hinted at internal turmoil within the Penguins organization, stating,
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I don’t know what’s going on in Pitt, but something’s going on in Pitt,
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and
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Things are going on, things are going on…
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This suggests uncertainty regarding the team’s strategy moving forward.
If a Sidney Crosby trade rumor materializes into a formal deal, it is expected that the Penguins would seek substantial returns, likely including first-round draft picks and promising young players, to match Crosby’s elite status and the impact he brings to any franchise.
Penguins’ Future Hinges on Decisions About Veterans and Rebuilding
The situation with Crosby and other veterans like Malkin reflects a critical juncture for the Penguins. With the franchise’s direction unclear and post-Olympics trade possibilities looming, Pittsburgh faces a complex balance between honoring franchise legends and rebuilding for sustained competitiveness. Fans and analysts alike will be watching closely as the 2026 Winter Olympics approach, anticipating possible major changes in the NHL landscape.