The Penguins’ buyout window is open, and with it the opportunity to shape their future

The Penguins off-season has been a long stretch building to this climatic moment. After now months of trying to figure out how to acquire Norris-winning defenseman Erik Karlsson, the Pens have a second buyout window now open, and the ability to shed some money off their salary cap situation to help make it happen.

And yet, a pay-off for accomplishing the goal is not certain. A buyout alone doesn’t clear the necessary room to fit in Karlsson, which has likely been a stumbling block since all the way before the NHL draft in late-June (when rumors of Jeff Petry’s trade availability surprisingly first popped up).

But Petry has not been traded. Karlsson has not been traded. Mikael Granlund has not been traded.

Instead, a high-stakes game of chicken has publicly played out between the San Jose Sharks and the rest of the hockey world. We all know the story by now. Everyone knows the Sharks want to rebuild, and that Karlsson wants out. But his massive $11.5 million annual cap hit will take careful massaging for any suitor to take on.

To make matters worse, San Jose shot themselves in the foot last summer by setting the precedent of taking no return of value when they traded Brent Burns to Carolina. SJ also retained 34% of Burns’ cap hit for a lengthy three seasons. Karlsson’s contract remains even more burdensome at four years and being $3.5 million annually more. Yet, SJ hopes for a return of value to ease to pain of what they will have to retain on Karlsson’s deal.

It’s been a tricky set of obstacles that Pens GM Kyle Dubas has not yet been able to clear this summer. However, this weekend likely will provide one of the truest tests of “it’s now or never” for Dubas, San Jose and Karlsson to figure a series of transactions out.

The road map looks relatively clear, if not having a few questionable steps of various realism or possibility.

Step 1 would be putting Granlund on wavers for a buyout, to be completed this weekend while the window is open for Pittsburgh to do so. After this weekend, no buyouts until next June. It is now or never. The good about buying Granlund out is that it opens up $4.1 million of salary cap space in 2023-24. The bad is that it tacks of $1.83m of penalties for two years in 2025-26 and 2026-27.

Is it worth essentially borrowing from future years’ salary caps to get more space now? Dubas has already said that he doesn’t believe it does. That was also when he might have anticipated being able to clear bad contracts via trade more easily than it turned out.

Step 2 would be clearing Petry’s salary via trade, a problem compounded by Petry’s 15-team no trade clause and the known factor he prefers to stay located relatively central to family in Michigan. Thus, including Petry to San Jose as part of the Karlsson deal seems so simple that it would have happened by now — if only it could. Can the Pens chip in a draft pick with Petry to send him to Chicago or Detroit? In theory, yes. But in practice?

Step 3 is the Karlsson trade itself.

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Pittsburgh is above the salary cap (though Jake Guentzel to LTIR would temporarily solve that issue), so taking Step 1 as outlined above doesn’t necessarily signal that Step 3 is an inevitability. However, if news breaks in the opposite order that Petry has been traded...at that point it would be safe to get the popcorn ready.

Until then, on a sunny summer weekend Penguins nation will be waiting. There’s not much middle ground - either the weekend will pass quietly with no movement, or the franchise is at the precipice of making a series of exciting moves that will add one of the top players of this generation to the final few years of the Sidney Crosby/Evgeni Malkin era.

Usually there’s some sort of middle ground or gray area, but in this situation there is no in between. It’s all or nothing.

For months, there’s been no sense of the timing on when the saga would play out and get a resolution. With the opportunity of a second buyout window, that time is here, and it’s here this weekend. One way or another, the waiting is almost over.