Sidney Crosby and the Pittsburgh Penguins are gearing up for an NHL season unlike any other. The dynasty years are a distant memory, and the organization is bracing for an atypical year. On that note, two former teammates of Crosby dropped an ice-cold reminder for the franchise.
Like Bruce Springsteen sang back in 1984, the saying still rings true. Crosby and the Penguins are now sitting back, trying to recapture a little of those glory days. But time slips away, and all that remains are the stories. The 2010s are now just a fond memory in the rearview mirror, while the road ahead looks lonelier and darker for Pittsburgh.
Regardless, the Pens have more than just the ‘boring stories’ Springsteen once sang about. Pittsburgh has three Stanley Cups to show for it—and the countless lives changed along the way. Beyond that, the Black and Yellow still have Sidney Crosby and Evgeni Malkin in their ranks, so the glory days are never too far. All it takes is a look at them to relive them.
That might not stay that way for much longer, though. And that’s the main concern for fans in The Burgh going into the 2025-26 NHL season. On that note, former teammates of Crosby, Mike Rupp and Brian Boyle spoke very sincere words, warning the Penguins to be careful about their captain’s future.
Michael Rupp #17 of the Pittsburgh Penguins skates against the Philadelphia Flyers at the Consol Energy Center on October 7, 2010 in Pittsburgh, Pennsylvania.
Keep an eye on your captain, Pittsburgh
“The one thing that would get [Crosby] to potentially leave, I think it’s just playing out this season. And if Malkin is riding off into the sunset, going to retire, and not be a Penguin,” Stanley Cup champion Mike Rupp said, via NHL Network. “That would break up the core guys, and next summer would be the decision-making time of Crosby potentially leaving. I don’t see anything happening this year.”
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“I think Crosby will go kicking and screaming trying to drag this franchise into relevance and stay in the mix, no matter what. But everyone has a breaking point,” Brian Boyle added. “I assume he wants to stay there, I can’t wrap my head around him leaving, but I know he’s got a desire to win and it’s obvious by how well he plays this late in his career.”
Rupp played with Crosby during the 2009-10 and 2010-11 NHL seasons and won a Stanley Cup with the New Jersey Devils in 2003. Boyle, on the other hand, played the final campaign of his career with Crosby’s Penguins in 2021 and 2022.
In for a miracle?
Believing the Penguins will be anywhere near a playoff spot might be wishful thinking—or downright delusional. However, fans in the City of Bridges could be in for a surprise, or so Boyle thinks.
Sidney Crosby #87 of the Pittsburgh Penguins waits for a faceoff in the second period of a game against the Vegas Golden Knights at T-Mobile Arena on March 07, 2025 in Las Vegas, Nevada.
“In 2017-18 season I was on the New Jersey Devils and a number of guys had career years, but the one guy who had the biggest career year was Taylor Hall. He dragged us in,” Boyle admitted.
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“We had contributions at different times from everybody, we were picked to finish last in the Metro and we got into the playoffs, because of what Hall did. I think Crosby is perfectly capable of that. He just needs all these other guys to have career years and some good goaltending, and he can make it happen.”
