When Ken Holland was hired back in May, it was clear that his sights were set on the future. He inherited a difficult mess to clean up left by his predecessor, with a flawed roster, bad contracts, very little much wiggle room, and a disgruntled, frustrated fanbase.

While the goal for the Oilers this season was to make the playoffs, it wasn’t an expectation. Nobody would have deemed Ken Holland a failure if the team missed the playoffs in 2020 after just one year of his leadership. The plan was that this was going to be a retooling process that took some time.

But, thanks to a better-than-expected start, things have changed. The Oilers have sat at the top of the Pacific Division for virtually the entire first two months of the season. Things and working and the playoffs are seemingly within reach.

Given how much parity there is in the league, the majority of NHL teams head into the season with the objective of making the playoffs. That said, for a lot of these teams, it isn’t determined how realistic that goal is until a few months of the season has unfolded.

Think back to September. How many teams were in full-on tank mode, with absolutely zero designs of making the playoffs? Detroit, Ottawa, and Los Angeles. Otherwise, we have a handful of serious contenders who, barring disaster, you could pencil into a playoff spot, and over a dozen middle-of-the-pack teams that could go either way.

The Oilers were one of those middle-of-the-pack teams. The goal was to make the playoffs but the big-picture was the top priority. There was a lot of skill on the roster but also a lot of question marks that made it difficult to gauge how successful the team would be. Now Ken Holland has to decide which goal is the true priority right now. Is it about making the playoffs and going on a run this year or is it about the long-term retool of the organization?

That brings us to this week’s What Would You Do Wednesday SATURDAY EDITION question. If you were Ken Holland, would you be prepared to go all-in on this season? Is this team close enough to not just making the playoffs, but going on a deep run to make it worth it? How important is success in 2020 to the Oilers?

One thing I’ve learned about the NHL in recent years is how random the league is. There’s a wild amount of parity that makes it nearly impossible to pick year by year who will actually be good. I mean, look at Tampa Bay and Calgary. The best teams in the East and the West last year respectively aren’t in playoff positions this year. The Golden Knights went to the Stanley Cup Final as an expansion team. The Senators were one win away from the Final and became bottom feeders the following season.

When you have lightning in a bottle as it seems the Oilers do right now, you really have to consider going all-in. You don’t know if it’ll still be there next year. You don’t know if Mikko Koskinen will be good again. You don’t know if McDavid and Draisaitl will be able to dominate like this again. You don’t know if Oscar Klefbom will be healthy again.

If Holland stands still this year, the Oilers might be good enough to make the playoffs. The Pacific Division is a crap-shoot, as first and sixth are separated by seven points right now. The team has played well and maybe they can keep it going all year. But if the team does end up missing out, it would be gut-wrenching. Not just for the fans who crave meaningful hockey, but for the players on the team. McDavid and Draisaitl are pouring it all out there this year. I think their work warrants an investment.

Acquiring Taylor Hall would give the Oilers an elite second-punch behind their top line. Acquiring J.G. Pageau would give them another very good two-way centre to build an excellent third line around. Acquiring Chris Kreider or Tyler Toffoli or Andrew Shaw or Boone Jenner or Mikael Grandlund or any number of players who could become available would go a long way in taking this team to the next level.

What say you, Nation? Is the goal this year to make the playoffs? If so, should Holland go all-in? Is the team good enough to ride into the playoffs as it is now? Or could it be turned into a legitimate contender with some major additions? 

Discover Jasper this Winter

With the landscape sparkling and the fireplaces at their coziest, there’s no better time to experience Jasper than in winter. Dust off your skis and snowboards and gather some friends as Marmot Basin is opening this Friday, November 8th. Check out the Escape Card for half price lift passes all season long! Whether you prefer a calm and cozy night next to a fireplace or yearn to see the mountainous backcountry without breaking a hip, you’ll find a winter activity that’s right up your alley.