Sidney Crosby begins his 21st NHL season on October 7, continuing his commitment to the Pittsburgh Penguins despite the team missing the playoffs for three consecutive years. Remarkably, Crosby has recorded at least 90 points in each of those disappointing seasons, highlighting his individual excellence amid team struggles. The ongoing conversation around Crosby’s NHL career comparison to Tom Brady has gained traction, especially as both athletes continue performing at high levels late into their careers.

NHL insider Josh Yohe recently discussed Crosby’s situation in a column for The Athletic, drawing parallels between Crosby and Tom Brady’s longevity and success in their respective sports. While Brady remained a top competitor into his 40s and even won another championship with Tampa Bay, Yohe suggested that such a feat might be more complicated for Crosby due to significant contextual differences.

Tom Brady famously secured his seventh Super Bowl title in 2020 after joining a strong Tampa Bay Buccaneers roster. In contrast, Crosby remains with a Pittsburgh Penguins team currently undergoing a rebuild, which makes a deep playoff run less likely in the short term.

The Impact of Pittsburgh’s Rebuild on Crosby’s Championship Ambitions

Josh Yohe emphasizes that Crosby’s loyalty to the Penguins comes with challenges that Brady did not face late in his career. While Brady moved to a competitive team primed for success, Crosby is rebuilding with a roster that is still developing. This fundamental difference limits Crosby’s immediate opportunities to capture another Stanley Cup.

“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.” —Josh Yohe, NHL insider

This ongoing rebuilding phase means that Crosby’s chances of winning another championship largely depend on the speed and success of the Penguins’ turnaround. Despite the challenges, Crosby’s consistent production and resilience have maintained hope around his potential to compete at a high level for a few more years.

Possibility of a Future Stanley Cup with a Swift Penguins Rebuild

Yohe points out that the Penguins’ moves in recent drafts could accelerate their return to playoff contention. Notably, Pittsburgh made 13 selections during the 2025 NHL draft, the most of any team that year, positioning them with valuable assets to improve the roster over time.

Crosby has already committed to the Penguins beyond the current rebuilding period, having signed a two-year contract extension starting with the 2025–26 season. His individual achievements remain significant, including breaking Wayne Gretzky’s record for most seasons with a high points-per-game average. However, team improvement will be essential to translate Crosby’s elite play into another championship opportunity.

“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.” —Josh Yohe, NHL insider

General manager Kyle Dubas’s ability to accelerate the rebuild will be critical to Crosby’s legacy. If Pittsburgh can quickly assemble a competitive lineup, Crosby may still have a shot at another Stanley Cup run despite the team’s current challenges.

Ultimately, the Sidney Crosby NHL career comparison to Tom Brady highlights not only the greatness of both athletes but also the contrasting contexts of their teams late in their careers. While Brady capitalized on joining a championship-ready squad, Crosby’s future success hinges on the Penguins’ capacity to navigate a complex rebuilding process. Fans and analysts will continue to watch closely as the franchise works to match Crosby’s enduring excellence with the team success he still seeks.