Ken Holland has found himself in a tricky situation halfway through his first season at the helm of the Edmonton Oilers.

His big-picture plan is to retool the organization, through the draft. There’s a core here of Connor McDavid, Leon Draisaitl, Oscar Klefbom, and others along with a nice prospect pool in the minors. But there’s still a ways to go, and the most prudent way to add talent is through drafting and developing.

But there’s also a team and a fanbase desperate for playoff hockey. There’s a building that isn’t being sold out on a nightly basis because fans aren’t interested in paying top dollar to see a team that isn’t winning. There are also two superstars in McDavid and Draisaitl doing everything they can to drag this team to the playoffs.

The Oilers are on the bubble. Their hot start has come to an end and a cold stretch in December has the team right on the cusp of the playoffs. It’s pretty much a coin flip at this point. That, of course, is if Holland doesn’t do anything before the deadline. If he makes a big addition or two, the likelihood of the team making the playoffs obviously becomes a lot higher.

So, what do you do now? Do you stick with the original plan and think about the big picture? Or do you lean into what’s right in front of you and try to make the playoffs?

According to Elliotte Friedman, Holland is wary of trading draft picks away to improve the roster right now… 

The Oilers are wary of trading picks. There’s no guarantee all work out, but, the more lottery tickets you have, the better. They didn’t have a second- or third-rounder in 2015; their 2016 first-rounder is estranged from the organization; didn’t have a second-rounder in 2017; nothing in round three-to-five in 2018; and six picks last year. That’s one of the reasons they passed on Taylor Hall — not wanting to give up two more high selections.

Friedman went on to make another Oilers-related point, this time in regards to McDavid and Draisaitl’s frustration…

You can see the frustration on Leon Draisaitl and Connor McDavid as the rest of the Pacific catches the Oilers. St. Louis players in particular noticed in-game how upset Draisaitl was by missed chances in a 2-1 loss to the Blues on Dec. 17. They thought it really affected him.

So there are a couple of things going on here.

First, we have Friedman suggesting that Holland is skeptical of giving up draft picks, which isn’t all that surprising, given the fact we know his priority here is building the Oilers up for long-term success. When Peter Chiarelli came in, he was trigger happy, dealing away everything in his sight in order to fill what he viewed as primary needs for the organization. That won’t happen with Holland.

Second, we have the classic McDavid and Draisaitl are frustrated analysis. I mean, there’s no doubt that they are. They’re first and second in the league in points and they’re dragging the team on their backs to the best of their ability and they might not have anything to show for it at the end of the year. No, this isn’t McDavid and Draisaitl want out of Edmonton but there is merit to them being frustrated with potentially missing the playoffs for the third year in a row.

That’s what makes this situation so challenging. Holland’s plan of worrying about the future is the right one for the Oilers. I wrote last February that, as awful as it sounds, the best course of action is for the Oilers to be patient in order to be successful.

If the next general manager comes in and tries to remedy the Oilers with a quick fix, things will only get worse. Buyouts will worsen the cap situation long-term. Trading prospects and draft picks for short-term solutions will continue to hemorrhage the organization of depth. Being active in free agency will sink the Oilers deeper into cap hell.

The only solution is patience. It’ll take time, but they have to get it right this time.

That hasn’t changed. After 2020-21, the Oilers have a much neater salary cap situation that’ll afford them flexibility in free agency. They’ll also likely have a handful of internally-developed, young talent establishing itself on the roster. If they’re patient, they can continue to stock the farm this year and continue working towards a very deep farm system, something we haven’t seen since, well, I don’t even know.

But is being patient that easy? Can you tell McDavid and Draisaitl to be patient? Can you ask them to drag this roster all season to a position in which they’re in playoff contention at the trade deadline and then stand pat, hoping they can do a few more months of heavy lifting? That’s a big ask.

I can understand why Holland doesn’t want to deal draft picks away at this stage, but hopefully, he can find some kind of middle-ground, because standing pat and giving McDavid and Draisaitl nothing to work with down the stretch isn’t ideal.