The dust has settled on the Oilers’ infuriating four-game loss to the Chicago Blackhawks. While there’s surely still a very sour taste in everyone’s mouths, we can take a step back and ask — what does it all mean?

I think Dave Tippett summarized it perfectly with this succinct quote after Game 4…

“In the regular season, we overachieved a little bit. It feels like in this play-in series, we underachieved.”

As maddening as it is that the Oilers came out and flat out laid an egg against a team that sold at the trade deadline and had no business being anywhere near the playoffs, it doesn’t erase everything that preceded it. A four-game sample size after a four-month layoff due to a global pandemic isn’t a situation where you want to be making too many sweeping conclusions.

I mean, yeah, there are things to draw from the loss to Chicago, even if it was a wonky, unprecedented situation. The goaltending leaves a lot to be desired, the team lacks the high-quality depth to produce at even strength, and there are simply too many instances of prolonged stretches of uninspired, disinterested play.

But it’s important to look at the big picture. If I had told you at this time last year that the Oilers finished the season with the fifth-highest points percentage in the Western Conference, you’d have been thrilled. After back-to-back miserable seasons in 2017-18 and 2018-19, we wanted to see the Oilers take a step in the right direction. And that’s exactly what happened.

The Oilers’ retool was never going to happen overnight. There was a huge mess left for Ken Holland to clean up and it was always going to take time to deal with it. Back in February of 2019, shortly after Peter Chiarelli was fired, I wrote that patience was required to turn the Oilers from a disappointment into a contender

Unfortunately, the only way through this mess is patience. The Oilers have two major issues to fix due to the Chiarelli era. They’re deep in salary cap hell and they lack high-quality depth. You can’t quickly work out of salary cap hell, and, if you’re in salary cap hell, you can’t just go on a shopping spree to acquire quality depth.

Chiarelli made a lot of mistakes during his time here, obviously. I think the biggest issue, though, was haste to make changes. He came in and quickly spent the open salary cap room he had on free agents and dealt away high-quality assets to fill holes. Had he taken the time to allow the young team to figure itself out, things could have gone a lot differently.

Through Holland’s first year at the helm, he’s mostly taken a conservative, long-term-oriented approach.

He didn’t make any big splashes in free agency last summer, instead opting to sign players like Josh Archibald, Riley Sheahan, Gaetan Haas, and Joakim Nygard to one-year deals to add some depth to the roster and fix a glaring need on the penalty kill.

Holland also showed patience in finding a good trade for Milan Lucic rather than rushing into an ugly buyout that would have had massive long-term salary cap ramifications. Again, he was also patient with the disgruntled Jesse Puljujarvi, hanging on and letting him rebuild himself in Finland rather than dealing the talented young forward away for nothing.

The one time he deviated from this plan was buying at the trade deadline, but the team had warranted such an investment with their strong play during the regular season. It didn’t work out, unfortunately, as Mike Green opted out, Tyler Ennis got injured, and Andreas Athanasiou couldn’t find his footing. But, at the very least, the Oilers still have their first-round draft pick.

A lot of Edmonton’s improvement this year came internally, which is an encouraging sign. While we can’t entirely credit Holland for the strong play of rookies Kailer Yamamoto, Ethan Bear, and Caleb Jones, we can praise his decision to hire the stabilizing presence of Dave Tippett, a coach known for his ability to develop young talent.

Tippett and his staff did great work with the Oilers’ roster this year. He managed to do the impossible and split up the dynamic duo of Connor McDavid and Leon Draisaitl in order to create two scoring threats. He also made the team play a much stronger defensive game. Perhaps most importantly, he completely flipped Edmonton’s poor special teams into elite ones.

Mar 5, 2020; Chicago, Illinois, USA; Edmonton Oilers head coach Dave Tippett directs his team against the Chicago Blackhawks during the third period at United Center. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports

So, all told, even with the sour conclusion, the 2019-20 season was a positive one. What now?

Let’s circle back to that quote from Tippett.

While the Oilers underachieved in the playoffs, we also need to accept that they overachieved a little during the regular season. They finished in the bottom third in the league in even-strength shot and goal differential, which generally isn’t an indicator of a contending team. They also benefitted from playing in the Pacific Division, which featured three of the five worst teams in the league. As great as it is to have elite special teams, that can’t be the driving factor behind your success.

If you watched the Golden Knights and the Avalanche play their seeding-round game on Saturday night, you saw the cream of the crop in the West. Two strong, deep teams with loads of skill who push the pace. The Oilers aren’t there yet.

If the Oilers go into 2020-21 with the exact same roster as the one they have right now, they’re more than likely not going to finish fifth in the West and 12th in the league again. There are a few things in the way of the Oilers bridging the gap from where they’re at as a playoff bubble team to a Stanley Cup contender.

One of those things, as we saw in the playoffs, is goaltending. Mikko Koskinen has proved that he can be a good half a goaltending tandem, but he isn’t an ace goalie who can play 60 games. Holland needs to find an upgrade on Mike Smith to complete a high-quality goaltending tandem.

And then there’s a couple of holes up front. Connor McDavid needs a good two-way winger who can keep up with him in the offensive zone while also helping the line out defensively. The Oilers also need a third-line centre between the one-two McDavid-Draisaitl punch and the fourth line of Riley Sheahan or Jujhar Khaira.

The challenge will be finding the cap space to make these upgrades. The Oilers have about $71 million allocated to their 2020-21 roster with Ethan Bear and Andreas Athanasiou in need or new deals. Finding a taker for Kris Russell’s $4,000,000 hit would be huge and moving on from Adam Larsson’s $4,166,667 tag could possible with Evan Bouchard knocking at the door. The flat cap will make life difficult on general managers this summer, so Holland will have to be creative.

I’m willing to give the Oilers a mulligan on that play-in series loss because, ultimately, their showing this season was a big step in the right direction. But this is just the beginning. There’s a lot of work to be done in order to build on this positive step and turn the team into a legitimate contender. Holland can’t afford to be stagnant this fall.