It’s not going to be long before one of the best eras in the history of the Pittsburgh Penguins comes to an inevitable close, given the fact that both Sidney Crosby and Evgeni Malkin are in their late 30s and will have to eventually hang up the skates at some point.
In the meantime, both players are under contract for at least one more season; the prevailing belief is that Malkin, who agreed to a one-year extension earlier in the offseason, is heading into his final NHL campaign.
Meanwhile, Crosby is entering the final season of the two-year extension that he agreed to in September 2024 with his usual $8.7 million salary cap hit, a tremendous discount and arguably the best bargain in the NHL today.
Crosby has openly dismissed thoughts of retiring any time soon, and for Penguins fans wondering when he could potentially sign a new contract, top Insider Josh Yohe has the latest update.
Pittsburgh Penguins Captain Sidney Crosby Could Soon Sign Another Extension, Per A Report From Top Insider
According to Penguins Insider Josh Yohe, Crosby is likely to have a new extension in place by the time Pittsburgh drops the puck on the 2026-27 NHL season, which will be his 22nd.
“Crosby made it clear in May that he’s willing to work with the Penguins on his salary and contract term before his current deal expires. He indicated that he would like to play for a few more seasons, health permitting. When the puck drops for opening night Sept. 30 in Philadelphia, Crosby will begin his 22nd season with the Penguins, the longest any athlete has played for a Pittsburgh professional sports team. There’s a real chance Crosby will have a new deal before that day.”
He continued:
“The 39-year-old Crosby has never been one to push for as much money as he could get. These aren’t expected to be negotiations in the traditional sense — president of hockey operations/general manager Kyle Dubas is fully aware that Crosby is a living legend and is happy to have him in Pittsburgh for as long as possible. When the time comes, Crosby and Brisson will name their price and term, and the Penguins are likely to accept the demand.”
It was another highly productive year for Crosby in 2025-26, as he scored 29 goals with 45 assists while also helping the Penguins return to the Stanley Cup Playoffs for the first time since 2022.
The first-ballot Hall of Famer, who has helped Pittsburgh win the Stanley Cup three times, has scored 654 goals with 1,107 assists in 1,420 career games, all with the Penguins.
Sidney Crosby Dismissed Thoughts Of Retiring
In May, not long after he and the Penguins were eliminated in the opening round of the postseason, Crosby said, “not at all” when asked if 2026-27 could potentially be his final NHL season.
He also noted that he has plans on taking his upcoming contracts on a year to year basis.
“I said year to year because of where the team is at,” he said. “It just makes sense, whether it’s our cap, who we have coming in and out, just to have that flexibility. It’s important.”
Top Penguins Insider Reveals Sidney Crosby’s Future Plans