Penguins' Sidney Crosby addresses future ahead of 2023-24 NHL season

Pittsburgh Penguins superstar captain Sidney Crosby isn't yet riding off into the sunset of retirement but also realizes he's in the closing stretch of his Hall of Fame career. 

"I think when you stop having fun, it's probably time," Crosby recently told Emily Kaplan of ESPN about when he will retire. "So, I'm still having fun, and there's different challenges, different motivations. When that spark isn't there, that fire isn't burning, then it's probably time to put 'em away."

As shown by ESPN stats, Crosby led the Penguins with 60 assists and 93 points for the 2022-23 season that featured the end of the franchise's incredible 16-year playoff streak. The three-time Stanley Cup champion turned 36 years old in August and has two seasons remaining on his contract, and he indicated in May 2022 that he wanted at that time to "for sure" play for at least three more campaigns. 

Pittsburgh's "big three" of Crosby, center Evgeni Malkin and defenseman Kris Letang aren't going anywhere anytime soon even though ownership blew up the front office this past spring and ultimately hired Kyle Dubas as the club's new general manager and president of hockey operations. Acquiring three-time Norris Trophy defenseman Erik Karlsson in August likely helped further ease Crosby's mind as it pertains to Fenway Sports Group doing everything possible to pursue one last championship before the franchise's inevitable rebuild commences. 

A reflective Crosby revealed how he wants to be remembered once he calls time on his career. 

"Just that I competed hard, that I was a good teammate, dependable every night, someone that didn't take it for granted," he said. "And I think you want to be known as a winner. Someone that, when stakes were high, you showed up and were at your best."

The Athletic's Rob Rossi noted for a piece published on Oct. 3 that Crosby will "want the Penguins to avoid any ideas about rebuilding" before he puts pen to paper on an extension. Rossi added that "all have stressed they expect a smooth negotiation process as soon as allowed" next summer, but one wonders if the situation could change if the Penguins crash and burn for the second consecutive season.