Sidney Crosby faces a very difficult decision with the Pittsburgh Penguins: whether to stay with the team that brought him glory despite currently not being a contender, or to think about a surprising trade in pursuit of one last Stanley Cup.

According to a report by Chris Johnston, all signs point to Crosby leaving Pittsburgh next season. “I’m still of the mind that it’s more likely than not he doesn’t finish in Pittsburgh. He’s not there today or the trade would already have happened. Ultimately, the decision rests with one man and we know who that is. We know why Sidney Crosby is a Pittsburgh Penguin today. Because he wants to be. But the minute that changes, he will no longer be a Penguin.”

The Penguins have missed the playoffs in the last three seasons, which could be pushing Crosby to ponder a change of team. He might not want to waste the final years of his career watching stars like Connor McDavid and Nathan MacKinnon try to dethrone the Florida Panthers. All of them have real chances of winning the trophy.

Is Sidney Crosby a free agent?

Sidney Crosby is not a free agent. He is currently under contract with the Pittsburgh Penguins through the end of the 2026–27 NHL season, after signing a two-year extension. The deal includes a full no-movement clause, which means any potential trade would require his approval.

While he remains under contract, speculation about his future continues due to the Penguins’ recent struggles and failure to reach the playoffs. If the team doesn’t show signs of progress, questions will likely intensify about whether Crosby might consider a trade before the end of his deal to chase one more Stanley Cup elsewhere.

In fact, Greg Wyshynski is on the same page as Chris Johnston. Next season could bring a historic trade involving Crosby. “If the Penguins get off to the start that we assume they’re going to get off to, I think he moves on before the end of the season. That’s my prediction.”