Why an unlikely key to resolving the Erik Karlsson trade logjam could be...Drew O’Connor?

As the lingering standoff between all of the Pittsburgh Penguins, Carolina Hurricanes and San Jose Sharks — and Erik Karlsson himself — continues to drag on this summer, a most unlikely contender has emerged as being a key to how and when future events unfold.

This idea and key cog started popping out after reading the latest in The Athletic from Rob Rossi.

As we can all see, it’s been status quo for about a month now and tiring to drone on about (tried not to do so lately, until anything actually happens, if you haven’t been able to tell)

The cliff notes version of what we know is that Karlsson wants out of San Jose. The rebuilding Sharks, likewise, want out from the highest defensive salary cap hit in the league. The Penguins and Hurricanes presumably want Karlsson, but have their own baggage to deal with regarding how to fit his hefty contract. On top of all of that, as the owner of a full no movement clause Karlsson won’t be going to any team he doesn’t want to — but the teams themselves have to figure out the particulars to start the process out.

The complicated dance the Penguins are dancing tend to revolve around Mikael Granlund and Jeff Petry needing to go in order to have the space and cap room to bring Karlsson back in.

A good reason why Karlsson isn’t a Penguin yet and the team has been stuck for a month is that it has been (and will continue to be) extremely difficult to pan these expensive, veteran players under multi-year deals somewhere else for no cap return headed back to Pittsburgh.

Even if a team wanted a $6.25 million, 35-year old defender in Petry, not many have the space to make it work and accommodate that at this stage of the off-season. To further complicate matters, Petry has a partial no-trade clause giving the right block trades to almost half the league. He has used that provision in the past with Montreal to make sure he is located somewhat centrally to his family in Michigan. (Which also presumably eliminated the option of cutting out a middle man and simply flipping him to San Jose).

With the Petry piece of the equation being one area to solve, that makes Granlund 1B. Kyle Dubas has said he prefers not to use buyouts, but he did not outright say he absolutely would avoid using that tool. If Dubas does want to add the most expensive defender in the game, he’s going to need cap space. Buying out Granlund would not come without future penalties, but one thing it accomplishes is opening up $4.1 million in cap space for Pittsburgh in 2023-24. A trade, if possible, would be preferable, but presents the same challenges of finding a willing and able taker to absorb all of Granlund’s $5.0 million cap hit, which might not currently exist.

That is where little old Drew O’Connor comes into the picture. O’Connor, a humble lower-line winger, has filed for salary arbitration. Because of that, once he agrees to a contract the Penguins will be able (if they so choose) to buy out a player making more than $4 million dollars.

This new special buyout window comes with the twist that it only stays open for 48 hours — and begins three days after the O’Connor contract is registered. It’s tricky timing, but very important details. It means that four or five days after the Pens get O’Connor in the fold, they have a chance to remove Granlund via buyout. Such an avenue is more preferable to a Petry buyout that would only clear up $3.25 million in added space for Pittsburgh in 2023-24.

If you’re following along, that means once O’Connor is signed, the clock starts ticking loudly. Luckily the Pens still have some time — O’Connor’s arbitration date isn’t until August 4th. But this is also likely why O’Connor hasn’t signed yet, because when he does that solidifies a firm deadline of when they would be able buyout a player.

To be certain, that deadline does already exist. A team and player must stop negotiating when their hearing starts. The arbiter has 48 hours to issue the salary, which unless it’s $4.5+ million, the team must honor (and this isn’t breaking any news, but it’s not going to be over that amount for O’Connor this year). That means, at the absolute latest, O’Connor will under contract to the Penguins by August 6th, 48 hours after his hearing. Accordingly, the buyout window at latest would start three days later and last for two days until August 10th.

The Pens also have good reason to sign O’Connor close to or before the August 4th hearing, as to not let a neutral party name the salary and risk an award for a little more than they wanted to pay. This speeds up the above timeline by at least two days and means Pittsburgh would have to buy Granlund out between August 7/8, provided and assuming they wanted or were forced to go that route to drop him and help open up some of the room that a big fish like Karlsson will require.

The exciting part to keep an eye towards and what could be an indicator to finally break the Karlsson logjam would be when or if the Pens sign O’Connor any time in the coming days or weeks leading up to August 4th.

There is no reason for Pittsburgh to speed up the process on O’Connor, unless and until of course they are ready to take action. For all we know at this point, if the stalemate continues that action could be deciding not to buyout Granlund and moving on in a different direction from acquiring Karlsson.

So if you’re tracking along, the first domino to fall for acquiring the reigning Norris trophy winner could very well be the timing of when the Penguins agree to a contract with a fourth liner. That goes to show the complexity of the situation that is going to require many moving parts in order to get to the point of being able to make a Karlsson trade possible....If it even is possible at all. Given the current standoff, being unable to find a solution to add Karlsson remains a very real possibility, barring a major trade in the trade market for the corresponding pieces.

To this point, Dubas hasn’t been able to sort the pieces out to make it happen. Astute readers might recall Petry’s name has been floated as available by national media types since before the draft, which makes it no stretch to believe that Dubas has been trying without success for quite a while to get the gears in motion.

Based on the ticking clock with the buyout situation, he only has a limited amount of time for one of the easiest ways to make it happen. It will take the timing of O’Connor’s contract to start up perhaps the last best chance for the Pens to get Karlsson, though at this point there’s good reason for skepticism all these problems actually have workable solutions.