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The Contract Conundrum: Sidney Crosby and the Penguins

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Tick, tick, tick … Hockey, like all sports, thrives on numbers. Goals, assists, points, power-play percentages, advanced statistics, salary cap figures, player ages—these metrics define the essence of the game. With that in mind, here are several numbers that demand our attention:

  • 43 — The number of days since Sidney Crosby could have signed a new contract with the Pittsburgh Penguins, a deal that both the team desires and Crosby has consistently indicated he wants as well.
  • 36 — The approximate number of days remaining until training camp commences in Cranberry. If Crosby has yet to sign by then, prepare for a barrage of contract-related questions. And if he remains unsigned when the season kicks off? The Penguins will already have played games in Toronto and Montreal, where Crosby can expect even more scrutiny.
  • 321 — The number of days until July 1, 2025, when Crosby is set to become an unrestricted free agent.

I’ve stated this before, and I’ll reiterate: I firmly believe Crosby will ink a contract with the Penguins before the training camp opens. It would genuinely surprise me if that doesn’t come to fruition. However, as time passes, the situation becomes increasingly perplexing.

What’s the Hold-Up?

For Penguins president and general manager Kyle Dubas, there’s no reason to negotiate hard. Sure, it would serve the Penguins well if Crosby were to take a hometown discount, and maybe he will, considering he’s done so for nearly two decades. But Dubas isn’t in a position to play hardball with Crosby. This is more than just another exceptional player or aging superstar—this is the face of a franchise known for its showbiz flair and star power. He has been the face of the NHL for the majority of his career. He is one of the five greatest players in hockey history and remains among the elite in the sport even in 2024.

Showing someone like Crosby the door or offering him a lowball contract is simply not an option. Dubas understands this well. If Crosby wishes to continue playing at an annual rate of $8.7 million, that’s perfectly acceptable. If he wants to play for an even lower figure to assist the team, fantastic. If he seeks a raise, so be it—he has undeniably earned that and more.

From Crosby’s perspective, the situation is equally baffling. He has publicly stated his desire to play exclusively for the Penguins. Even the mere suggestion of him donning another team’s jersey elicits a look of disbelief. I had a conversation with Crosby the night Kris Letang signed his six-year contract in Montreal two summers ago. He expressed, “I hope we can play another six years together.”

Having known Crosby for 15 years, I trust his sincerity. Letang is under contract for another four years, while Evgeni Malkin is signed for two more. These are not just teammates with whom Crosby has triumphed in the Stanley Cup three times; they are his closest friends on the team.

The State of the Penguins

The State of the Penguins

Given the current condition of the Penguins, one could understand if Crosby wished to finish his career in the limelight. There is a prevailing sense of decline surrounding the franchise. While they might exceed expectations this season, reach the playoffs, and perhaps even pull off a few upsets, the trajectory of the franchise is concerning. The glory days of the Penguins ruling the hockey world seem like a distant memory. They now compete in relative obscurity, with a handful of all-time greats merely finishing their careers as younger, hungrier, and deeper teams vie for the championship that Crosby once dominated.

If Crosby were to consider leaving, it wouldn’t be without consequence. Some fans might feel betrayed, while others would remind him of his efforts to keep Letang and Malkin on the roster, suggesting he should mirror that loyalty. While that perspective is reasonable, it’s crucial to recognize that Crosby doesn’t owe Pittsburgh or the Penguins anything. He embodies excellence both on and off the ice. He has the freedom to make his own choices.

However, based on my observations—and those of many others—Crosby genuinely wants to remain in Pittsburgh. I don’t get the impression that he is even contemplating a departure.

If Dubas had it his way, I suspect he would consider trading Malkin and Letang if it meant aiding the team’s rebuild. They command substantial salaries, are in decline, and could yield a significant return. But Crosby is a different story. He remains an elite player, and there is a compelling case to be made that he is the greatest captain in hockey history. Don’t just take my word for it; listen to how his teammates and peers speak of him.

Under no circumstances should the Penguins risk losing Crosby. For the integrity of the on-ice product, the franchise’s brand, and every conceivable aspect of the organization, ensuring that No. 87 remains in Pittsburgh until his number is retired is an absolute priority.

What Comes Next?

What Comes Next?

So, why isn’t this being prioritized? What’s causing the delay? While Dubas and Crosby’s agent, Pat Brisson, are undoubtedly busy, it’s summer. Hockey personnel typically enjoy vacations during this season. Still, they aren’t so occupied that they can’t address this crucial matter. Crosby will always be Brisson’s most significant client and Dubas’ most essential player. Crosby was already skating in Cranberry back in July, so it’s not as if he has been absent. Regardless of other issues occupying the Penguins and Brisson, the relationship between Crosby and the Penguins is always paramount. So why does it feel like something is amiss?

This situation isn’t just detrimental to ticket sales; it also impacts corporate sponsorships. The absence of buzz surrounding the Penguins is palpable and only grows louder with each passing day that Crosby remains unsigned. He is the heartbeat of the franchise, a stabilizing force for the organization. He keeps coach Mike Sullivan’s squad respectable, even as the team grapples with its transformation. Hockey enthusiasts in Pittsburgh still anticipate the arrival of autumn, knowing that the NHL season is on the horizon. Even if their beloved team is no longer a contender, they still have the privilege of watching Crosby play every night, and there’s something inherently special about that.

Will Crosby sign a new deal before the middle of September when training camp kicks off? I believe he will. However, if Crosby arrives in Cranberry in September without a new contract, the Penguins will find themselves in a whirlwind of attention—just not the kind they desire.

(Photo: Steph Chambers / Getty Images)

The Contract Conundrum: Sidney Crosby and the Penguins

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