We now know Sidney Croby's plans for 2027 and beyond

According to a report from Pittsburgh Penguins insider Josh Yohe, Sidney Crosby is expected to sign a contract extension with the team before the puck drops on the 2026-27 regular season.

Crosby has just one year left on his current contract and he's expected to sign a one or two year extension at a "team-friendly" discounted rate.

From Yohe:

Crosby's career to date has been defined by championships, records and individual brilliance, but one of the more remarkable aspects of his time with the Penguins has been his willingness to structure his contracts in a way that gives the team room to build around him.

Crosby entered the NHL in 2005 on a three-year entry-level contract worth $2.55 million. After quickly establishing himself as one of hockey's biggest stars, he signed a five-year, $43.5 million extension in 2007. The $8.7 million annual cap hit was enormous at the time, but Crosby was already arguably the face of the league.

The real evidence of Crosby's team-first approach came with his next contract. In 2012, he signed a 12-year, $104.4 million extension that again carried an $8.7 million annual cap hit. On the surface, that number looked enormous, but the structure was extremely favorable to Pittsburgh. Crosby was scheduled to earn $12 million annually in each of the first three seasons before his actual salary gradually declined, eventually reaching just $3 million in each of the final three years.

That structure mattered. Rather than maximizing his average annual value, Crosby and his camp deliberately kept his cap hit at $8.7 million, even as his actual earnings in the early years were substantially higher. The result gave Penguins management additional flexibility to retain or acquire talent around him. It was a particularly important decision for a franchise trying to remain competitive alongside Evgeni Malkin and Kris Letang.

Then came perhaps the clearest example of Crosby's financial sacrifice. In September 2024, at 37 years old, he signed a two-year, $17.4 million extension. His $8.7 million cap hit remained exactly the same as it had been since 2008-09, despite the salary cap having risen considerably and Crosby still producing at an elite level.

Crosby could almost certainly have commanded more money on the open market, particularly given his production and status as one of the greatest players in NHL history. Instead, he chose to remain in Pittsburgh and again provide the Penguins with valuable cap flexibility. NHL.com specifically described the deal as a "personal sacrifice" designed to give Pittsburgh a better chance to surround him with talent.

That sacrifice has become even more meaningful as Crosby has aged. Pittsburgh's challenge is no longer simply building around one superstar; it is maintaining enough depth to support an aging core. During the 2025-26 season, the Penguins' non-star depth finally showed improvement, helping Pittsburgh return to the playoffs after three straight seasons outside the postseason.

Crosby's contracts therefore tell a story beyond dollars and cents. He has earned superstar money, but he has repeatedly resisted squeezing every possible dollar out of the Penguins. For a player who has already won three Stanley Cups and virtually every individual honor imaginable, his willingness to leave money on the table may ultimately become one of the most important parts of his Pittsburgh legacy.