There’s no doubt the Oilers badly want to make the playoffs. This season has been yet another disappointment and it comes at a terrible time as the organization is trying to talk people into shelling out tens of thousands of dollars for luxury seats that exist on three-year contracts.

Is this a product you really want to invest in right now? Would it be if they made the playoffs?

The Oilers fired general manager Peter Chiarelli in January due to a lack of trust that he could clean up the colossal mess he made in the three-and-a-half years he spent in the driver’s seat. Given the moves he made mid-season, like trading for Brandon Manning and Ryan Spooner, letting a desperate Chiarelli go nuts at the trade deadline could have had overwhelming repercussions.

With Keith Gretzky now sitting in the general manager chair, we don’t really know what to expect at the trade deadline. The front office has said they believe in the team making the playoffs (and there’s very likely a big push from ownership in that direction), but Gretzky has also said they won’t sell the farm in order to acquire short-term fixes.

Given how bad the Western Conference is, the Oilers really can go either way at this stage. How should the front office navigate Monday’s trade deadline?

At the time of my writing, the Oilers are eight points back of the Wild for the final wild card spot in the Western Conference. Those eight points aren’t insurmountable, but the Oilers also have to jump over everyone in the West other than the Kings. The team has a very difficult road trip ahead, as they’ll play the Predators, Leafs, and Blue Jackets over the next week.

Still, if you told fans in September the team would be eight points out of the playoff spot, most would have rolled their eyes, but they would acknowledge that’s still within striking distance. Given how important generating excitement is to the organization at this stage, there’s merit to making a playoff push.

I trust Gretzky when he says the Oilers aren’t going to look for rentals this year. That makes sense given there’s a very good chance they miss the playoffs. But if the team can acquire a player (akin to what Toronto got when they acquired Jake Muzzin from L.A.) who can help this year and next, it’s worth looking into.

The team needs scoring help right now and they need it next year and beyond too. A rental wouldn’t be worth the risk at this stage but buying someone who can be a part of the long-term solution does.

There are also a few good reasons for the Oilers to become sellers. Given the parity of the Western Conference, a lot of bad teams being in the mix could turn the market into one that favours the seller. Beyond that, the Oilers have a really, really low chance at climbing back into the playoffs, even if they acquire a good winger or two at the deadline.

I wrote a couple of weeks ago about how the only way out of this mess is patience. The team needs to get out from under bad contracts and they need to acquire high-quality talent while also not further bogging themselves down with more bad contracts. The best way to work out of cap hell is to be patient, unfortunately.

While the Oilers don’t have many worthwhile rental assets beyond Alex Chiasson, a seller’s market could provide them with an opportunity to deal players with term left on their contracts. Kris Russell would be a nice addition for a playoff team, as would Zack Kassian and Kyle Brodziak. While not much would be coming back, Edmonton would be slowly releasing themselves from the chains of cap hell.

The heart says to buy by the head says to sell. How about a little bit of both?

I do believe personally that Gretzky’s top priority at the deadline should be actively looking to shed longer-term contracts while recouping as many draft picks as possible for rental players, but I also empathize with Edmonton’s desire to take advantage of the worst playoff race we’ve seen in years.

An interesting note brought up on Twitter by WheatNOil is the difference in value between draft picks at the deadline than at the draft. One thing, he said, Craig MacTavish did well as GM was acquiring draft picks at their lowest point of value (which is the trade deadline) and then selling them at their highest point of value (which is the draft) for more picks.

While Edmonton won’t get much for any player they potentially move, like Chiasson, Russell, Kassian, Brodziak, or Alex Petrovic, they can stockpile some draft picks now and turn them into more draft picks at the actual draft in June. Stockpiling draft pick capital makes it a lot easier to swallow giving up, say, a second-round pick and a prospect for somebody like Tyler Toffoli, who can help the team right now and next season.