Sidney Crosbys Old Penguins Deal Looks Different After Agents Admission

As NHL salaries soar, Sidney Crosby's long-term deal raises questions about potential earnings and the lasting impact of past health concerns on his negotiations.

Sidney Crosby’s famous $8.7 million cap hit has long looked like the kind of number that only works for a player willing to take less. But according to his agent, Pat Brisson, that’s not really how the 2012 deal came together.

Brisson said the Penguins captain’s contract was shaped as much by Crosby’s injury history and uncertainty about how long he’d keep playing as by any desire to land on a neat figure. Crosby had missed almost a full year after a concussion, returned, and played 20 games. His next contract, Brisson explained, was not insurable and required an exclusion to his head.

“We were talking about a five-year deal, probably $11 million a year. And then we pushed.

He’s 26. Doing five years, he’s gonna be 31 (at the end).

And then we said, why don’t we do eight years? We had agreed to do nine years at 11 a year.

(So), nine years, he was going to be 35, and we said, are you going to play past 35 years old, the way you play the game? And Sidney was like, ‘I’m going to do my best, but there might be a time when I might not be able to.'”

Brisson said the number that became attached to Crosby was more a product of the negotiation than the goal from the start.

“Sidney’s a physical player, he grinds it every night, and he had that concussion. So, we decided to add three years to the (12-year) deal and lower the AAV. Then we started playing with the numbers; we’re at 9.1, 9.2, and then 8.7 came about again, and we end up doing 8.7 times 12.”

That history matters now because the NHL’s salary ceiling keeps climbing. Macklin Celebrini’s new deal carries an $18.8 million cap hit for the next five years, and Leo Carlsson briefly sat atop the league’s pay scale after the Philadelphia Flyers put an $18 million offer sheet in front of the Anaheim Ducks before Anaheim matched it.

Crosby, meanwhile, suddenly looks cheap by comparison.

Brisson suggested that could change. “Now, the last negotiation, two years at $8.7 million, he didn’t care much.

He kept it that way,” Brisson reported. “His next deal, he may do an extension next summer.

He may sign a one-year deal for $12 (million). I don’t know.”

The gap between Crosby’s actual earnings and what he might have made under a different path is sizable. PuckPedia.com’s historical salary calculations show that Crosby’s first contract, a five-year deal signed at age 20, was worth just over 15% of the cap and fit the market at the time. The 12-year extension that followed kept the same $8.7 million AAV, and at the start of that contract it represented 13.5% of the salary cap.

By the time that deal ended in 2025, Crosby was down to about 10% of the Penguins’ cap. Over the life of the contract, he earned $104.4 million.

But if Crosby had taken the shorter route Brisson described - eight years at $11 million - he would have been eligible for free agency again after 2020-21. That version of the 2012 deal would have paid him $88 million instead of $69.6 million over the same span.

From there, the math only keeps climbing. In 2020, the top AAVs in the league were Connor McDavid at $12.5 million and Auston Matthews at $11.6 million. Under that cap landscape, Crosby could have landed another deal in 2020-21, and the article projects at least a five-year, $55 million contract starting in 2021 and running through June 30, 2026.

Put together, those hypothetical contracts would have totaled $143 million. Crosby’s actual earnings over the last 13 years came to $113.1 million, leaving a difference of about $29.9 million.

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