Ken Holland is not taking any days off. The Oilers GM has been making moves with pending free agents, both big and small, and not just pushing it down the line like the Oilers might have in years past. He’s given the Oilers a certain degree of cost certainty heading into the trade deadline and that’s very important.
I’ve said countless times that the only way Ken Holland would spend significant assets at the upcoming trade deadline would be if the player is under contract or team control for next season. Well, the fact that he’s already taken care of Darnell Nurse and Zack Kassian makes it much easier to go and add a player that could carry a cap hit between $2.5-$4.5 million for next season. Even signing a player like @Joakim Nygard to a cheap, one-year deal helps. It’s just one less question mark on this roster.
As we head into the summer, it would have been very difficult to go out and add an impact forward if you weren’t sure what @Darnell Nurse’s next contract would look like. For that reason, I applaud Ken Holland and his ability to work quickly and prioritize these negotiations.
Still, there are a few things that could really change what kind of player Ken Holland could add to this lineup. 
The most important question is, what kind of contract will pending RFA @Ethan Bear get? He’s enjoying a breakout season and while I think there’s no doubt that the organization loves the player and he enjoys being an Oiler, I don’t know if it’s a lock that Bear gets signed to a long-term deal.
In my opinion, a two or three-year deal for Bear would likely carry a cap-hit around $2.5-3 million while a longer-term deal, I’m talking six or more years, would likely push $4.25-4.75 million per season. That might seem like an insignificant gap when it comes to locking up a top-four defenseman for the foreseeable future but when you’re an organization that is operating close to the salary cap, every sliver of cap space counts, which brings me to the next big question facing Holland this summer: which contracts can he offload?
There are three contracts that Holland should be trying to move out this summer. The first is @Kris Russell. The ageing defenseman is a more than capable NHL defender, but he makes far too much money. It’s imperative that Holland rids himself of that $4 million cap hit without retaining anything. That might seem like a tall order, but last June the @San Jose Sharks traded 32-year-old defenseman @Justin Braun, and the final year of his $3.8 million cap hit, to the @Philadelphia Flyers in exchange for both a second and a third-round pick. 
I’m not going to argue that Russell is a better defenseman than Braun but if Doug Wilson could offload that entire deal and get two valuable picks for him, then Holland should be able to find a team that will value Russell for a season, even if they only get a sixth-round pick back for him. His no-trade clause might make things tougher, but on July 1st it goes from a ten-team no-trade list to a 15 team list. It’s do-able.
Look at how much @Andy Greene just got as well. He’s a shutdown defenseman making $5 million and the Islanders coughed up a second-round pick and a decent prospect for just a few months of him.
There’s also @Alex Chiasson, who I like as a bottom-six winger but not at his current $2.1 million price tag. He brings value on the powerplay, but the Oilers have James Neal who is just as good at parking himself in front of the net. Finally, I would look at finding a team to give Jujhar Khaira a fresh start. He’s scheduled to make $1.2 million but is really a player that you could replace with Patrick Russell for $700k. His contract is easy to move as well.
Assuming the salary cap ceiling stays flat at $81.5 million (it should certainly go up a little bit though) and the Oilers find a way to move all three of those contracts, they would have roughly $19 million in cap space to spend on six or seven forwards (depending on how you view Tyler Benson), three defensemen (this includes getting deals done for Bear and Benning who are both RFA’s), and a backup goaltender.
If I’m allowed to go really into my ‘armchair GM’ role for a second, imagine that the Oilers sign @Josh Archibald, @Riley Sheahan, and another depth forward for a combined $3.0 million. They could probably get their 13th and 14th forwards (pick two of @Sam Gagner, @Gaetan Haas, or @Patrick Russell) for $1.5 million.  I’ll also assume that Benning’s next cap hit will be $2 million and a backup goaltender will cost $2.5 million. I might be under-valuing some of those pieces, but I’m trying to look at this as a ‘best case scenario’.
That means they’d have $10.5 million to get two more forwards and sign Ethan Bear. The difference between giving Bear a long term deal worth $4.5 or a short term deal worth $2.5 makes a big difference. They could also wait and see just how much the cap goes up before deciding on what to do with Bear.
Things are going to be very tight this summer which makes it even better that Holland won’t have the dark clouds of tough negotiations with either Darnell Nurse or @Zack Kassian looming over him as he heads into the trade deadline. In fact, I wouldn’t mind it at all if Holland took it a step further and continued signing more pending free agents in the next few weeks. If he can get new deals done for Josh Archibald and Riley Sheahan in the next week, then it will only help him navigate through his next six months as Oilers GM.
Cost certainty is a very good thing and I love that Ken Holland has put an emphasis on working quickly.