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NHL Insider Predicts Sidney Crosby Trade After 2026 Olympics

Originally posted on Athlon Sports | By Antonio Losada | Last updated Jul 4, 2025 9:22 AM ET

NHL insider Nick Kypreos believes Sidney Crosby’s time with the Pittsburgh Penguins may come to an end next season.

The Penguins, who have missed the postseason for three consecutive seasons, should be headed toward a rebuild.

That, however, 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 longtime captain after the Milano Cortina 2026 Winter Olympics.

“[Sidney Crosby] is too good right now to just be a babysitter for the next three years.”@RealKyper, @jtbourne & @SamAMcKee discuss Crosby’s future in Pittsburgh with a game of ‘True or False.’ #LetsGoPens

https://t.co/hryjtDbDU6 pic.twitter.com/RG5IfGFNsZ
— Sportsnet 590 The FAN (@FAN590) July 3, 2025

Kypreos went as far as predicting Crosby's landing spot.

“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 they have steadily decreased their points percentage — 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.”

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.

This article first appeared on Athlon Sports and was syndicated with permission.

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