Sidney Crosby’s next contract may be the easiest tough call in hockey.
The current deal runs through the 2026-27 season, and while that technically leaves one year on the books, almost nobody around the situation believes that will be Crosby’s last season - Crosby included. When he was asked in May at the IIHF World Championships in Switzerland whether retirement could be coming after that year, he brushed it off with a simple, “Not at all,”
The timing feels familiar. Two years ago, Crosby handled his last extension right before training camp, signing a two-year deal on Sept.
16, 2024. This time around, the expectation is similar: a new agreement sometime between now and the middle of September, before the Penguins’ first preseason game on Sept.
- Crosby’s agent, Pat Brisson, said he hadn’t yet discussed the contract with Crosby and was letting his client enjoy the summer, but also noted there’s an understanding they’ll talk before the season gets closer.
The length is the first question. One year or two seems to be the most likely range. Crosby put it plainly himself: “If it makes sense to sign for a couple of years, then we’ll do that,”
The bigger question is the number, and that’s where the landscape has changed around him. Crosby has been at an $8.7 million cap hit since the 2008-09 season, aside from the first three years of his career, when he played on a $3.7 million entry-level maximum.
That $8.7 million figure used to look enormous. In 2008-09, it accounted for 15.4% of a $56.7 million salary cap.
Only Alex Ovechkin’s contract was larger at the time.
Now it looks almost quaint. The NHL’s cap is $104 million, with next season expected to jump to $113 million.
If Crosby stayed at $8.7 million, that would amount to just 7.7% of the cap. By 2026-27, 56 players are projected to carry a higher cap hit than Crosby, including Luke Hughes, Travis Konecny, Noah Dobson, Logan Cooley, Alex Tuch and Pavel Dorofeyev.
Leo Carlsson’s deal in Anaheim will reach $18 million.
That’s not a knock on those players. It’s just the clearest possible reminder that Crosby’s long-running number is now far below the market for a player of his stature.
And yet, there’s a strong case that nothing changes.
Crosby didn’t chase a raise in 2024 when his 12-year contract expired, even though the cap had climbed dramatically and he had every right to ask for more. He has made an estimated $156 million in playing contracts, plus major endorsement and marketing income over more than two decades.
Money has never seemed to be the point. Winning, competing and staying at his best have always been the priorities.
Even when Evgeni Malkin and Erik Karlsson carried bigger cap hits at times, it never became an issue.
There’s also the loyalty factor. Crosby has stayed committed to Pittsburgh even when his own agent was openly questioning whether the Penguins were still the right place for him last year. He could push for a huge number - even something like $18.7 million, which would still leave him behind friend and protege Macklin Celebrini’s $18.8 million cap hit in 2027-28 - but that would be out of character for a player who has spent his career doing things the same way.
Still, the value question is real. For a 40-year-old who is also Sidney Crosby, even a $13 million or $14 million cap hit for 2027-28 would not be out of line.
Auston Matthews and Jack Eichel are both above $13 million on the recent NHL list. Crosby has earned the right to ask for more than he has taken before.
But if history is any guide, he probably won’t.
The most likely outcome remains the familiar one: another deal, probably another $8.7 million cap hit, and another season of Crosby keeping the same financial footprint while extending his career one more year. In this case, the money is almost beside the point. The real news would be the same as ever - Sidney Crosby deciding he’s not done yet.
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