Sidney Crosby’s future with Penguins could shift after teammate’s retirement decision

For nearly two decades, Sidney Crosby has been the face of the Pittsburgh Penguins, the pillar of stability through championship runs, roster changes, and front-office upheaval. But as the franchise faces the twilight of an era, Crosby’s own future may not be as fixed as it once seemed.

Longtime teammate Evgeni Malkin, whose looming retirement could trigger significant repercussions. According to insider reports, Crosby’s desire to finish his career in Pittsburgh may hinge entirely on whether Malkin chooses to play beyond the 2025–26 season.

“If Geno’s there for one more year… then all bets are off as far as where Sid’s going to end up,” said ESPN’s Greg Wyshynski during a recent appearance on The Jeff Marek Show. The implication is clear: the retirement of one Penguins legend could lead to the departure of another.

Malkin’s last ride?

Malkin, who turns 39 this July, is entering the final year of his contract. While he hasn’t officially announced his retirement, all signs point to a potential farewell tour. In February, he reaffirmed his commitment to the organization in a conversation with The Athletic: “When I retire, it’s here. This is my only team.”

Evgeni Malkin #71 of the Pittsburgh Penguins skates against the New Jersey Devils at Prudential Center on April 11, 2025 in Newark, New Jersey. (Photo by Bruce Bennett/Getty Images)

The Penguins’ front office, led by general manager Kyle Dubas, has not yet made any formal decisions about Malkin’s future. “We’ll meet at the Olympic break this year and see where Geno’s at,” Dubas said. The implication is that any contract decision will be postponed until deep into the 2025–26 season, leaving Crosby and the organization in a holding pattern.

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Crosby, who signed a two-year, $17.4 million extension in 2024, is under contract through 2027. But if Malkin departs and Pittsburgh leans further into a rebuild, Crosby’s loyalty may be tested like never before.

Crosby’s loyalty

Crosby has long embodied the values of consistency and loyalty, rarely engaging in speculation about leaving Pittsburgh. However, Wyshynski’s comments suggest that even Crosby may be contemplating alternatives. “I’ve heard from many people that know him… he’s there as long as Geno’s there,” the ESPN analyst stated.

That sentiment has sparked renewed speculation about a possible end-of-career move, with Montreal again surfacing as a potential destination. “I’ve long believed that Sidney Crosby will end his career in Montreal,” Wyshynski added. The Canadiens, Crosby’s childhood favorite team, have often been linked to the Nova Scotia native in the realm of fantasy trades and legacy plays.

An era in flux

The Penguins have missed the playoffs for three straight seasons, and while a full teardown hasn’t officially begun, the writing may already be on the wall. Rebuilding around young talent could mean saying goodbye to the aging core that brought three Stanley Cups to the city.

Crosby, who posted 91 points in 80 games last season, remains productive, but may not want to spend his final years on a non-contender. If Malkin walks away next summer, the Penguins could be forced to confront a painful truth: their golden era is truly over.