Center Evgeni Malkin and defenseman Kris Letang, Crosby's teammates on all three of his Stanley Cup victories, were at the end of their contracts last season. Free agency loomed. Rare was the team, in hockey or any other sport, that would keep an aging core together that hadn't advanced past the playoffs' opening round in four straight seasons -- let alone find a way to do so under a flat salary cap.
"I was sweatin'," Crosby told ESPN. "You know how it works. The longer it goes, the closer it gets to free agency, the greater the chances are you might want to test it. You're trying to balance being optimistic with being realistic about the fact it was a possible [they'd leave]."
Penguins coach Mike Sullivan led all three players to Stanley Cup wins in 2016 and 2017. He couldn't begin to imagine how Crosby would captain a Pittsburgh team without Malkin and Letang on the roster.
"It would have been hard for him. Those three have been through a lot together," Sullivan said. "They've had their fair amount of successes, but they've also had their disappointments. I think it means a lot to him to continue to try to win; but in particular, to continue to try to win with those guys.
"I can't imagine what it would have been like for Sid to go through. I'm glad we don't have to find out."
Letang, 35, signed a six-year contract extension on July 7 worth $36 million. Five days later, Malkin, 36, signed a four-year, $24.4 million contract. That was right after news leaked that Malkin intended to test free agency, when tense talks with Pittsburgh finally stalled.
Sullivan remembers being optimistic that they'd both return to Pittsburgh -- until hearing about Malkin's negotiations, that is.
"I always believed we'd get it done, up until maybe the last 48 hours before free agency with Geno," he said. "That was the only time that doubt crept into my mind. But in my heart I believed that we'd be able to retain these guys. I know what it means to them."
What did it mean to Crosby?
"Just ... happy," he said. "Relieved. And then immediately thinking, 'OK, we've got an opportunity. These guys are staying. And now we've gotta do something with it.'"
BRYAN RUST IS part of the band, too.
"Yeah, I might be the third backup singer," he said.
Rust, 30, was expected to generate significant interest as an unrestricted free agent. The winger has been a perfect complement to Crosby and Jake Guentzel on the Penguins' top line, and skated well when matched with Malkin, too.
There were times Rust wasn't convinced the core would stay together. He remembers sitting at his locker after losing Game 7 in overtime to the New York Rangers last May and being unable to shake that dread.
"I was like, 'Oh s--- ... is this my last chance with this team?'" he said. "Because of how the business works, and because the cap is the way it is."
Turns out, Rust was the first member to stay with the band, signing a six-year contract extension on May 21 worth $30.75 million. He didn't test the waters to see what other riches were out there from NHL contenders. He feels the free agents who stayed with the Penguins made out fine financially, with Pittsburgh understanding they weren't going to take steep discounts to stay.
"Everyone has to do what's best for them and the business, but [also] as a team and as individuals," he said. "Those guys want to win. They want to be here. I'm no different. That point was made clear, but we weren't going to lose out individually."
Letang was another player many expected could test the market. Despite entering his 17th NHL season, his effectiveness as a defenseman hasn't waned. He played 78 games last season and posted 68 points, with an average time on ice per game of 25:47. Letang finished seventh in the Norris Trophy race, the fourth straight season he received votes.
He would have elevated the blue line of many contenders. There was also talk of him joining his former agent, Kent Hughes, in Montreal, where Hughes is now the Canadiens' general manager.
Letang was never sure if he would end up staying with the Penguins. "Otherwise I would have been signed the summer before. Would have been easier, right?" he said with a laugh.
His conversations with Crosby hinted at that uncertainty.
"Sid is probably my closest friend. We talked about the entire summer and the entire year," Letang said. "We weren't sure if it was going to happen. So we're glad it's behind us and we can look forward."
OF THE PENGUINS' holy trinity, Crosby and Letang don't have many doubters about their continued excellence at their advancing age.
Malkin is a different story.
The former Hart Trophy and Conn Smythe Award winner had major knee surgery before last season, as his right ACL was repaired for a second time. While his point production remained strong -- he posted 42 points in 41 games, including 20 goals -- it appeared he had lost a step. The Pittsburgh Post-Gazette noted that Malkin's rush attempts had trailed off significantly, as he generated 0.57 per 60 minutes two seasons before his 2021 knee surgery compared to just 0.22 rush attempts on average last season.
"On numerous instances, Malkin's skating looked like what you'd expect from a 35-year-old less than a year removed from his second significant knee injury," wrote the Gazette's Mike DeFabo.
As the transition game is a key to Sullivan's system, that impacted Malkin's effectiveness at even strength. Sullivan called Malkin's 5-on-5 game "sporadic" last season, but said last week that he hasn't made many adjustments to Malkin's usage based on that decline.
"Nothing's really changed in how we use him," Sullivan said. "He's still a dynamic offensive talent who has the ability to single-handedly take over a game. There aren't a lot of those guys around the league."
One change Sullivan made last season that could stick for 2022-23: Moving Rust to play with Malkin. Sullivan said Malkin's best games came with Rust on his wing, thanks to the latter's ability to forecheck and his defensive awareness. Crosby and Guentzel have spent time this preseason with winger Rickard Rakell, who isn't a "band member" per se but who signed a six-year, $30 million contract to stay in Pittsburgh before free agency this summer.
Rust was happy to see Malkin back. Much like with Letang, Rust couldn't fathom how the Penguins could improve their impact on the ice without sacrificing something off the ice if they let the duo walk.
"Someone else could come in here, but why disrupt this chemistry in the face of getting more of the same, when we know we have a team that can do something?" he said. "[Without Malkin and Letang], there would have been a lot of conversations floating around about not having them in this room. Thank god those aren't happening."
Letang said the feeling was mutual about Rust and Malkin.
"If you lose Geno, if you lose Rusty, can you actually replace them? Are you getting better by not having them? I don't think so."
Does Letang believe there's another Stanley Cup in this group?
"That's what I want. For sure."
MIKE SULLIVAN MIGHT not skate with Crosby, Malkin and Letang during games, but he's a member of the band, too. The contract extensions weren't exclusive to the players: Sullivan, who has coached the Penguins since the 2015-16 season, signed a three-year deal that pays him into 2026-27.
"We've been through a lot together. This hasn't been all apple pie and ice cream. We've had hard conversations over the years," Sullivan said of his core. "I couldn't be more humbled to continue to get to coach these guys. I just think the world of them. It's hard to keep a team together in sports. That's what I think is so great about this circumstance."
The Fenway Group, the Penguins' new owners, didn't balk at approving new contracts for Letang and Malkin. Neither did general manager Ron Hextall, who sought to build around the veteran stars as they play out the rest of their years in Pittsburgh.
"In a perfect world, Geno retires a Penguin. And I think Tanger's the same," Hextall said before free agency. "These two are generational players. They don't come along very often."
Rust believes the Penguins' recent playoff performances made Hextall's call easier.
"There's such a fine line in the playoffs between winning and losing. There are some years when you get in when you can just tell," he said. "You're getting dominated and you're like, 'OK, maybe we need to make some changes.' But you could see not just last year, but the year before, that those were series we could have and should have won. Management saw that too."
On paper, they were opening-round failures: a six-game loss to the New York Islanders after the COVID-shortened 56-game season in 2020-21, and a seven-game loss to the Rangers last postseason. Yet both series had mitigating circumstances.
Against the Rangers, nothing went right for the Penguins. DeSmith was injured during a brilliant Game 1 performance, leaving the game in double overtime with a core muscle issue that put him out for the series. Jarry was out with an injury until Game 7, when he replaced the struggling Louis Domingue only to lose in overtime. Defenseman Brian Dumoulin and Rakell were both lost after Game 1, too.
Pittsburgh had a 3-1 series lead when a Jacob Trouba hit injured Crosby in Game 5, turning the series on its ear: The Rangers scored three goals in 2:42 to take the lead for good, and rallied with three straight wins to take the series.
"We had a good team. It didn't go our way. We played some of our best hockey in the playoffs and we didn't manage to win those series," Letang said. "We had the team to make a run for it, but we didn't get the bounces we needed. To take a run at it again was the right thing to do."
That hunger thrives as part of the Penguins' culture. Defenseman Jeff Petry, whom they acquired from Montreal, felt it immediately when he arrived for training camp.
"What those guys have together is special," he said. "They've obviously been to the top. The thing I noticed is that's not enough. They want to do it again."
That's why the band is back together: To make another push toward a fourth Stanley Cup in the Sidney Crosby era. They know there will be skepticism. Some will see this as a nostalgia play from a team that refuses to turn the page on past glory. Some will note that Father Time is undefeated and that the Penguins' core has a combined age of 106 years old -- the window to contend must close at some point.
But Sullivan and his players make the following counterargument: Gaze upon the past two postseasons and tell us that window isn't still agape. Tell us that this band doesn't have another chart-topper in it.
"When you look at those two series -- and both of those opponents went to the conference finals -- we felt good about our team," Sullivan said. "Our core players were a big part of it. They're providing evidence that there's still elite play in them.
"We recognize that we're getting older. But we're not old. There's a difference."