NHL Insider Predicts Sidney Crosby Trade After 2026 Olympics
NHL insider Nick Kypreos believes Sidney Crosby's time with the Pittsburgh Penguins may come to an end next season.
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The Penguins, who have missed the postseason for three consecutive seasons, should be headed toward a rebuild.
That doesn't seem to be the front office's mindset as the franchise has made clear that Pittsburgh won't entertain trades for Sidney Crosby or any of their other core veterans, trying instead to contend while they remain active.
Appearing on Sportsnet 590 The Fan with fellow analysts Justin Bourne and Sam MacKee on Thursday, Kypreos suggested the Penguins could trade their 37-year-old longtime captain after the Milano Cortina 2026 Winter Olympics.
Kypreos went as far as predicting Crosby's landing spot.
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'Wait till they get Sid Crosby after the Olympics,' Kypreos said, referring to the Montreal Canadiens. "I'm liking the odds a little better than I did maybe a few weeks ago."
Kypreos pointed to the Penguins' declining trajectory — three consecutive regular seasons in which their point total has decreased — and aging core, including Evgeni Malkin turning 39 at the end of July and entering what may be his final season.
'(Crosby) is too good right now to just be a babysitter for the next three years,' Kypreos said. 'This guy can play peak (hockey)."
"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.'
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Team Canada and Pittsburgh Penguins forward Sydney Crosby before the 4 Nations Face-Off championship game against the United States on Feb. 20, 2025.Winslow Townson-Imagn Images
Kypreos, however, didn't provide direct evidence of any trade talks between the Penguins and any franchise, let alone the Canadiens, but made cryptic comments about Pittsburgh's internal situation.
'I don't know what's going on in Pitt, but something's going on in Pitt," Kypreos said. "Things are going on, things are going on …'
In case an agreement for a trade is reached with one of the other 31 NHL franchises, it's fair to assume the Penguins would demand multiple assets in return for Crosby, most likely at least one first-round pick and other future picks and young players.
Related: Penguins GM Breaks Silence on Sidney Crosby Trade Rumors
Related: Penguins GM Highlights 'Major Focus' for Evgeni Malkin Amid Uncertain Future
This story was originally reported by Athlon Sports on Jul 4, 2025, where it first appeared.
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