Ken Holland held his season-ending media availability yesterday and now, it really feels like the offseason. The regular season was fun, the playoffs sucked, and now it’s time to turn the page and shift our focus to how this team can improve in the next few months.
Holland’s availability didn’t leave me feeling too inspired. The Oilers will need to eventually get aggressive if they want to turn themselves into Stanley Cup contenders and this summer is a great opportunity to do that. It didn’t sound like Holland felt that same sense of urgency.
Before they get can start bringing in outside talent to fill this roster, there are some big questions that they need answers to. Here are the biggest ones:

1 – WHO WILL GET BOUGHT OUT?

Ken Holland made it sound like a buyout is pretty certain. The two obvious candidates are @James Neal and @Mikko Koskinen. The cost of buying out either of them is pretty appetizing.
James Neal has two more years left on a deal that carries a cap hit of $5.75 million. If they were to buy him out, his cap-hit would drop to $1.9 million but it would stay on the books for four years. So they would save $3.83 million for two years and then have a $1.9 million penalty for two years after that.
Koskinen has one more year at $4.5 million. If they bought him out, that would go to two more years at $1.5 million. So they would save $3 million for one year and then one year of a penalty.
I don’t love the idea of buying players out because having dead cap space on the books is far from ideal, but you can’t ignore the fact that buying out one of Neal or Koskinen makes a lot of sense.
I don’t think either will be back next season, but I also don’t think that they’re both going to be bought out. The Oilers will need to get creative to move out one of the contracts. If they can get each of these deals off the books and only one of them is through a buy-out, there’s a chance they clear up an extra $7 million.
That could make a huge difference. That amount of money could get you a scoring top-six winger and then still have some extra money left over.
As it sits right now, they have $22.16 million to spend with 17 players already under contract. They have enough money to do some damage as it sits right now and if they move out some money, then Holland can get extremely aggressive this summer.

2 – WHAT’S THE DEAL WITH KLEFBOM?

It’s far from a guarantee that @Oscar Klefbom ever plays hockey again but there’s a chance he could return. Holland didn’t say much about Klefbom at his press conference but if Klefbom can return at some point next season, then it probably means they aren’t bringing back Tyson Barrie.
If Klefbom is going to miss another season, then the Oilers will need to seriously consider getting in on the free-agent defenseman market. I still don’t think they’ll bring back Barrie, they might want to go get a left-shot to round out their top-four, but the bottom line is that the Klefbom situation will really decide how Holland builds his defense this offseason.

3 – HOW WILL THE EXPANSION DRAFT BE HANDLED?

The expansion draft is another interesting wrinkle. I don’t think Klefbom will be protected because I don’t think Seattle will want a player who might not be healthy. 
The Oilers could either protect four forwards and four defensemen or seven forwards and three defensemen. I’m not sure which route they’ll go, but if they leave Klefbom unprotected, then there is a chance that the Oilers walk away from the Seattle expansion draft without losing a good young player.
If they can create a scenario where there isn’t an obvious candidate for the Kraken to take, maybe a conversation could be had about Seattle taking a bad contract for a small asset. That could be how the Oilers create even more cap space this offseason.

4 – WILL THE NUGE BE BACK?

Here is my very simple take on this: the Oilers need to add more talent to their top-nine, not take away talent. Nugent-Hopkins had a down year but he’s still a damn good top-six forward, he’s still a good penalty killer, and he’s a part of this team’s leadership core. The Oilers should bring him back. 
They shouldn’t overpay him, but they shouldn’t let him walk over $250k or something silly like that. These two sides should find a way to make a deal work.
If he’s back, then the Oilers only need to add one more top-six winger. If they let Nugent-Hopkins go, then they’ll need to add two top-six wingers. I’d rather keep the guy I’m comfortable with and then go add another big piece rather than have two newcomers. I think even if they keep Nugent-Hopkins, they could realistically add two more top-nine wingers. They need to load up this forward group and they have the money to do it.

5 – HOW ATTACHED ARE THEY TO THE FIRST-ROUND PICK?

Ken Holland didn’t make it sound like he wants to move one of the team’s top prospects for immediate help. I get that to an extent because players like Dylan Holloway and Philip Broberg are close to being able to help the NHL team. Especially Holloway, who realistically might be in the Oilers lineup at some point next season.
I understand not wanting to move a top prospect, but then Holland needs to be serious about trading one of their next two first-round picks. Their pick this year will be fairly early in the draft and will hold some serious value. If they can get a young, cost-controlled top-six winger with that pick and a lower-level prospect, they absolutely need to pull the trigger on a move like that.
With a lot of teams right up against the cap and some facing roster problems in regards to the expansion draft, Ken Holland is in a spot to get very aggressive and take advantage of teams that are in trouble. There will be forwards and goaltenders on the market that normally wouldn’t be.
On Wednesday, he didn’t sound like a GM that was overly interested in getting aggressive this summer, but I am saying that he absolutely needs to be. Holland should be spending money and assets this summer to make the 2021-22 Oilers roster as strong as possible. No excuses. He needs to make this team a Stanley Cup contender.