Crosby's Extension Talks with Penguins Expected Before Season

Sidney Crosby is believed to be in discussions with the Pittsburgh Penguins about a contract extension, and those talks are said to be expected before the 2026-27 NHL season, per reports. Crosby’s agent, Pat Brisson, told The Athletic’s Josh Yohe that an extension is expected to be discussed in the offseason. The development may offer more insight into the future of the Pittsburgh Penguins captain.

Crosby is entering the final year of his current two-year contract, which carries an $8.7 million AAV and expires after the 2026-27 season. The last year of a two-year, $17.4 million extension Crosby signed in September 2024 carries an $8.7 million cap hit for each of the next four seasons, through 2026-27. The big thing about the 2024 agreement is that it kept Crosby with the franchise and with the same $8.7 million cap hit that was attached to his previous long-term deal. Pittsburgh Penguins president of hockey operations and general manager Kyle Dubas called Crosby’s decision a personal sacrifice to help the organization remain competitive.

A new deal would keep one of the most important players in Pittsburgh Penguins history under contract past the 2026-27 season. Crosby has spent his entire NHL career with Pittsburgh, winning three Stanley Cups with the club. It’s also notable timing, because Crosby previously indicated in May that his plans beyond 2026-27 weren’t settled. His philosophy, he said, was to look at his situation year by year.

Trade Speculation and Montreal Connection Resurfaces

It wasn’t that long ago when Crosby trade talks were dominating the hockey rumours columns, but he shut that down by signing a two-year extension and reiterated his commitment to the organization. Now, two years later, he is due for another extension, and the same conversation has returned. The link between Crosby and the Canadiens comes from them being his favourite team growing up, his junior days with the Rimouski Oceanic, and being the closest team to his home in Nova Scotia. On top of all that, the fit would be great: they need a second-line centre and are looking to contend.

Over the past few days, a clip from The Sid Seixeiro Show has been circulating with Seixeiro stating, “I’ll believe it when I see it,” when it came to a Crosby extension. He built off of the idea of Crosby going to the Canadiens and suggested Michael Hage and a first-round draft pick as a trade offer.

This all came just days after The Athletic’s Josh Yohe wrote about Crosby and his future, where he stated that he expects extension talks to pick up at the end of the summer, before the season starts. The idea of a new deal being a one- or two-year deal makes perfect sense. Crosby’s last deal was signed in the middle of September, which would make sense for this time around, too. As of now, all signs point to Crosby finishing his career with the Penguins.

Context Around the Penguins' Recent Moves

The Penguins returned to the Stanley Cup Playoffs in 2025-26, after missing the postseason for three straight years. Evgeni Malkin signed a one-year extension through 2026-27, and Tommy Novak signed a longer deal starting in 2027-28. Crosby’s next contract has not been publicly confirmed for any specific term, salary, or signing date.

Hellebuyck's Status and Other NHL Notes

In other NHL news, Connor Hellebuyck is staying with the Winnipeg Jets so far this offseason. Jets captain Adam Lowry spoke with Murat Ates of The Athletic, saying, “...Until something happens, he's a Jet, he's a good friend, and we're excited to get him back.” The Buffalo Sabres are the team many think will land Hellebuyck if he is dealt. Hellebuyck has a no-move clause for the 2026-27 season, which gets reduced down to a 21-team no-trade list next offseason.

Additionally, the Canadiens have a strong defensive group led by Lane Hutson, Mike Matheson, Noah Dobson, and Kaiden Guhle. Arber Xhekaj does not have a contract and has been in trade talks as a restricted free agent. Adam Engstrom, Jayden Struble, and David Reinbacher remain in the conversation for bottom-pair minutes. Apron Basu noted that Engstrom has been dangled as a trade chip and the Canadiens are trying to use him or another defenseman to upgrade their forward group.