The first order of business is to address their coaching situation, but after that, general manager Stan Bowman has to turn his attention to their roster.

It is undoubtedly the most important offseason of the Connor McDavid-era, and to make it a success, they need to make some significant additions to their roster, and in order to do that, they must create additional cap space.

So my second defining question: how can they create additional cap space?

There are two very obvious candidates: Darnell Nurse and Tristan Jarry, but each one comes with a very unique set of roadblocks.

Let’s start with Nurse, whose $9.25 million cap hit is going to be very tough to get off the books.

I can’t see a contending team touching it, but maybe the Oilers could find an up and coming team with a lot of cap space that would be willing to bring him in as a minute-eating veteran who could ease some pressure on their young players.

Think of teams like the San Jose Sharks, Chicago Blackhawks, or maybe even the Ottawa Senators. I am curious if teams like Buffalo or Detroit would have interest as well, considering the Sabres were trying to make their blue line bigger at the deadline and the Red Wings are reportedly in the market to add a veteran to their back end.

If you could get one of those teams interested, the Oilers would almost certainly need to hope that they are willing to just take Nurse’s contract for nothing because if the Oilers find themselves in a situation where they have to pay a premium asset in the deal, then they have a totally different problem on their hands, which I’ll get to in a moment.

The final hurdle here is that Nurse still has a full no-movement clause, and it doesn’t change to a modified no-trade clause until next summer. Even if the Oilers find a team that’s willing to engage, there’s no guarantee that Nurse will agree to leave.

With all that said, I do think that there is a very realistic chance that they trade Nurse this summer. It’s not a guarantee, but I think it’s close to 50/50.

David Pagnotta told me the other day on Oilersnation Everyday that the Oilers tried to move him to Toronto at the trade deadline, so clearly there is an appetite from Bowman to make this happen.

Jarry, on the other hand, does have a 12-team no-trade clause, but considering how rough his half-season in an Oilers jersey was, I think there’s a pretty good chance that he would be open to waiving it to go to another team. Finding a taker for Jarry will be just as difficult as moving on from Nurse.

Why would a team agree to take on a $5.375 million backup goaltender when there are plenty of cheaper and potentially better options on the market? This is one where the Oilers will either have to attach a solid asset or take back a similarly bad contract in the process.

If the Oilers really need to attach a first-round pick or a high-end prospect like an Isaac Howard in order to get out of one or both of these contracts, then that creates a totally different issue considering they really don’t have a lot in their system.

The free agent class this year is incredibly weak. If Alex Tuch doesn’t make it to market, which the expectation is that he will re-sign in Buffalo, then there are basically no true impact players available.

That means if the Oilers do clear up a bunch of cap space, they’ll need to find their upgrades on the trade market.

Well, here’s the problem: they don’t have a lot of assets and if they use the few pieces that they have to dump off bad contracts, then what are they going to have left to use on trades

It’s quite the paradox. If they have to spend assets to free up money, then they won’t have any assets to use to properly spend the money… so if that’s the case, then what is the point of spending assets to free up the money?

I think the most likely outcome here is that the Oilers do one or two ‘Lucic for Neal’ type swaps where they attach a later pick, or possibly retain some money, and move out a player like Nurse, Jarry, or potentially even Trent Frederic for another player on a similarly bad contract.

They might save a little money in these deals, but the main goal would be to just simply bring in a fresh face who could play a role that they need better than these current players are.

If they don’t move out any dead money, then Bowman isn’t totally screwed. They do currently have $16.8 million in cap space, and even after they sign some pieces, they should still have some wiggle room.

Let’s say they bring back a handful of their current free agents, and I’ll take a guess on their cap hits for the sake of this exercise.

Let’s put Connor Ingram at $2.75 million, Connor Murphy at $4 million, Jason Dickinson at $2.5 million, Kasperi Kapanen at $2.5 million, Spencer Stasney at $1 million, and Colton Dach for $850,000.

Again, these are just rough numbers.

I’m also going to assume they find a new home for Mattias Janmark and have Howard on their roster next season. With all that being done, the Oilers would have right around $4 million in cap space with 12 forwards, 7 defensemen, and two goalies on the roster.

So even if they only offloaded Janmark, they should have enough money to sign a middle-six forward.

If they want to swing higher, they’re going to have to find a way to get some money off the books, or they’ll have to cut back on some of their pending free agents.

Finding a way to be more cost-effective is a must for this Oilers front office as they head into an offseason that could drastically change the direction of the franchise.

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