Auston Matthews’ recent four-year, $53 million deal with the Toronto Maple Leafs has sent ripples through the NHL, as he claims the title of the league’s highest-paid player. While the spotlight is on Matthews, an unexpected connection to Pittsburgh Penguins’ veteran Sidney Crosby has been drawn by Dan Kingerski of Pittsburgh Hockey Now.
In a year’s time, Sidney Crosby, currently 36, will enter negotiations for his contract, set to expire after the 2024-25 season, with a $8.7 million average annual value. While he won’t command the NHL’s highest salary, Crosby’s enduring value to the Penguins is undeniable. As Kingerski highlights, lesser players have long out-earned Crosby, whose salary cap hit ranks below numerous others. His willingness to take less to maintain the team’s competitiveness has yielded two Stanley Cup championships.
Related: Matthews’ Evasion of Long-Term Deal with Maple Leafs Calculated
The same can’t be argued of Matthews, whose team hasn’t won anything and he just used his leverage to take the highest per-season earnings in the league and for a lot less term than the team would have liked.

Kingerski argues that Crosby, at 38, could once again be underpaid if he maintains his point-per-game performance. The NHL’s top 20 centers, averaging similar stats, generally earn between $8 to $10 million, but Matthews’ deal has set a new benchmark. That will lead to discussions in Pittsburgh, such as: ‘Should the Penguins reward Crosby for his team-friendly deal?’ Should the team invest heavily in an aging player to keep him a lifer?’ ‘Should there be a reward for loyalty, and if so, how much does Matthews’ massive deal play into the equation?’
The Penguins’ center has displayed loyalty by not seeking the highest salary, enabling the team to remain competitive. The assumption is that he would do so again. But, as Crosby’s contract negotiations approach, the question arises: What will he be worth in the 2025-26 season? Kingerski suggests a continuation of his $8.7 million AAV, offering both value and flexibility to the Penguins. He notes, “Crosby will be 38 when his next contract kicks in, and unless he slows greatly, $8.7 million would again be an underpay and probably less than 10% of the team salary cap.”
Crosby’s Financial Legacy Will Be Different Than Matthews’
While Matthews’ deal marks a milestone in player compensation, Crosby’s legacy underscores the significance of dedication and the impact of a player’s decision on the team’s overall success. If he’s eager to stay with the Penguins and do so at a team-friendly rate, there’s a feeling another trend in the market could be set. “Crosby could have forced the Penguins into a dire cap situation 12 years ago; any team would have paid the best player on the planet full freight,” writes Kingerski. He didn’t do that. Instead, his example was followed by other Pittsburgh Penguins but not by other players and teams.
As negotiations loom, the Penguins and Crosby will navigate the balance between a justifiable salary and the team’s continued competitiveness. It’s not entirely clear how much Matthews weighed both of those factors into his new contract.
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