NHL analyst points out one major factor that could stop Sidney Crosby from pulling a Tom Brady

Sidney Crosby will be starting his 21st NHL season on October 7. He has remained loyal to the Pittsburgh Penguins, even though the team has missed three straight playoffs. Now, what's more interesting is that he has hit the 90-point mark in each of those three seasons.

Considering his impressive production at the age of 38, Crosby could've won a championship on the right roster. The same was discussed by NHL insider Josh Yohe in Thursday's column for The Athletic. He compared Crosby’s career to Tom Brady’s later years.

"43-year-old Brady would have the occasional off game ... (unlike) 30-year-old Brady," Yohe wrote. "Yet he was still among the best, even at that age, ... (winning) another championship even after so many had written him off. Is it inconceivable to imagine Crosby doing something similar?"

Tom Brady won his seventh Vince Lombardi Trophy after signing with the Tampa Bay Buccaneers in 2020. Yohe wondered if Crosby could do something similar in the NHL. However, Yohe pointed out one major difference.

Crosby is still playing for the Penguins, a team now in a rebuild. Brady joined a strong Buccaneers team to win. Crosby is staying loyal to a team that needs time to improve.

"Oh, it won’t happen this season," Yohe wrote. "Or the one after ... Crosby is playing for a rebuilding team, something Brady never had to do."

That could make it harder for Crosby to win again.

Sidney Crosby could have another shot if Penguins rebuild fast

Josh Yohe believes Sidney Crosby can achieve more if the rebuild happens fast and Penguins general manager Kyle Dubas makes smart moves.

In the 2025 NHL draft, they made 13 selections, the most of any team. Additionally, they have more picks for the coming years. If the team improves quickly, Crosby could have another shot at the Stanley Cup.

"He’s (Crosby) hopeful Dubas pushes the right buttons, this rebuild happens faster," Yohe wrote. "And a new era of Penguins arrives in the playoff ... The clock is surely ticking, but it ticks a little more slowly for him, and maybe it won’t be dark for a while. He isn’t like the others, after all."

Crosby has already signed a two-year extension starting in the 2025–26 season. In March, he broke Gretzky’s record for most points-per-game seasons (20 such). But without a better roster, that chance may not come. And that’s something which could stop Crosby from repeating what Brady did.