The No. 1 pick of the 2005 NHL Draft has spent his entire NHL career with the Penguins, winning the Stanley Cup three times (2009, 2016, 2017). 

Crosby, forward Evgeni Malkin and defenseman Kris Letang are the longest-tenured trio of teammates in North American major professional sports, and they are entering their 21st — and perhaps final — season together. Malkin, 40, signed a one-year, $5.5 million contract on May 26. Letang, 39, is signed through 2027-28 on a six-year, $36.6 million contract ($6.1 million AAV). 

“I think it forms a certain bond, whether it’s with your teammates or with the team itself or the fan base,” Crosby said. “There’s something with that connection that it feels a little bit stronger, especially when you’ve gone through, like, challenging times, whether it’s tough losses or, in some guys’ cases, injuries. I think that’s what makes winning so special, and there’s a lot of things you’ve got to overcome, but I think that part of it is very unique to that.”

Crosby won four best-on-best tournaments — the 2010 Vancouver Olympics, 2014 Sochi Olympics, World Cup of Hockey 2016 and the 4 Nations Face-Off (2025) — before settling for silver at the Olympics this past February in Milan.

He wore the “C” and had six points (two goals, four assists) in four games for Team Canada before missing the last two games with a lower-body injury, including a 2-1 overtime loss to Team USA in the gold medal game.

The next World Cup of Hockey will be played in Prague, Calgary and Edmonton in Feburary 2028. Crosby will be 41. Is that a goal?

“Yeah,” Crosby said. “I feel really good, and I want to keep playing, like I said, as long as I can. Yeah, I think that Olympics was an amazing experience overall. It still stings the way that it finished, you know? Like, that’s difficult. But at the same time, it was incredible to have the opportunity to play with all those guys and to see the way we played and just the chemistry that the team had. That was pretty unique. And I think having the 4 Nations leading up to that probably was a part of that too.

“But I think that experience definitely motivates me to want to be part of it again, so in that way, I think it was definitely helpful.”