A “be careful what you wish for” scenario emerged late on Tuesday night, as the Edmonton Oilers finally fired Peter Chiarelli as GM.

The following morning, Oilers CEO Bob Nicholson addressed the future, mixing the reassuring (not wanting to blow everything up) with uncomfortable feelings of “same old, same old.” For many who’ve seen this movie before, there’s legitimate concern about sad history repeating itself.

So, what should the Oilers do? Let’s consider the good, the bad, and the Puljujarvi.

First, a quick summary of their cap situation

Thanks to the always-handy Cap Friendly, we know that: the Oilers are basically right up against the ceiling in 2018-19, and are slated to devote about $73M to 15 skaters next season. Yeah, that’s not great.

The most prominent pending free agent is goalie Cam Talbot, who’s almost certain to be gone after the Oilers signed Mikko Koskinen to that baffling extension.

Fresh voices

Keith Gretzky is serving as interim GM, while Ken Hitchcock’s been given very little indication that he’ll be coach beyond next season.

Maybe that’s a good thing. This team needs fresh voices, not situations like the front office being littered with relics from the failed past, like Kevin Lowe and Craig MacTavish.

Nicholson said that the Oilers will take their time when it comes to such future moves, so here’s hoping they get with the program. After years of attempting “heavy” hockey and getting humiliated in trades, how about being forward-thinking, whether that means playing to Connor McDavid‘s speedy strengths, or finding a savvy GM who will sell-high, buy-low, and actually be ahead of the curve for once? Just a thought.

Assessing the good

As The Athletic’s Jonathan Willis aptly mentions, the Oilers do have a lot going for them. Willis mentions:

• McDavid.
• Leon Draisaitl
• Ryan Nugent-Hopkins
• Oscar Klefbom

So, that list includes two stud centers, one nice forward in RNH, and Klefbom, a 25-year-old defenseman who’s been very effective when healthy.

Let’s consider a few other intriguing players who could provide the Oilers with cheap, useful production in the not-too-distant future. If you’re noticing an omission, that’s because a certain Finn is getting his own little section in this piece.

• Kailer Yamamoto, the 22nd pick of the 2017 NHL Draft. A promising, smaller forward, even if he’s struggled at the top level this season.
• Evan Bouchard, the 10th pick of the 2018 NHL Draft, could be a building block defenseman for a team that needs help at that position.

Your mileage will vary on other players, but you could do worse than to start with that mix of proven talent and decent prospects.

Now to what they need to get right, starting with another young player whose future is pivotal for Edmonton, whether he sticks with the Oilers or not:

The Jesse Question

Considering the Oilers’ history of bold moves, it’s tempting to just rubber stamp the word “DON’T” on any talk about trading away Jesse Puljujarvi, the troubled fourth overall pick of the 2016 NHL Draft.

But, as Sean “Down Goes Brown” McIndoe detailed in-depth recently for The Athletic (sub required), sometimes it actually is smart to move a Puljujarvi-type. The key can be filed under “easier said than done,” as it’s all about getting the right trade, if Edmonton chooses to do that.

And, as McIndoe notes, there is some risk in waiting too long.

If your trade bait doesn’t happen to have met expectations, timing is key. Move a guy too soon, and you risk seeing him turn into an Andrew Ladd or Rick Vaive, and you could be left with regrets. But wait too long and he’ll be Andrei Zyuzin or Stanislav Chistov, and you won’t get much of anything in return.

The Oilers have their own painful history when it comes to arguably waiting too long to move on from Nail Yakupov. Could they have gotten more than the weak deal from the St. Louis Blues if they punted sooner?

Look, there are times when I’d trot out advice that should seem obvious, but isn’t. The Oilers have been burned badly not just in trading away skill, but selling low on ice-cold players who were likely to rebound.

Puljujarvi is a little different because it’s difficult to separate his struggles from the Oilers’ own miscues, and to gauge what his ceiling might be. Few can credibly say they know for sure what kind of player he’ll become, but it’s crucial for the Oilers to get this situation right.

Net questions haven’t stopped

It would be irritating but acceptable if the Oilers merely overpaid a bit for Mikko Koskinen, if he was more of a sure thing.

Handing a three-year extension at $4.5M per year gets more reckless when you consider Koskinen’s unsightly combination of unprovenness (just 32 NHL games) and age (he’ll be 31 when the extension kicks in). His .910 save percentage this season doesn’t exactly kick down doors, either, even if Koskinen’s been respectable enough.

That previous paragraph is a procession of bummers, but the Oilers can at least do their best to put themselves in a position to succeed. It’s perfectly plausible that Koskinen could end up a great bet – he’s had his moments, and also goalies are extremely unpredictable – yet Edmonton would be wise to arm themselves with Plans B and on.

Keep an eye on prospects, in the draft and otherwise. Try to identify a free agent bargain, even if you’re unlikely to hit a grand slam like the Islanders managed with Robin Lehner.

Messing up with goalies can sometimes be luck of the draw, but Edmonton should look at, say, the Blues with Jake Allen and realize that contingency plans are crucial.

Shedding dead weight

Let’s be honest: barring a trip to the LTIR, it’s unlikely that the Oilers will get relief from Milan Lucic‘s $6M cap hit anytime soon. (Question: does Lucic have any rashes?)

Keith Gretzky or the Oilers’ next GM should do everything in their power to find creative ways to get rid of any bad contracts other teams might take off their hand, even if it means giving up a little bit of a bribe in return.

Would someone take Kris Russell (31, $4M through 2020-21) or Andrej Sekera (badly injured, $5.5M through 2021-22) off their hands? Maybe a rebuilding team would throw away Brandon Manning‘s $2.25M next season to try to reach the floor?

Sometimes an incumbent GM won’t admit past mistakes, which means bad contracts rot on their rosters for too long. With Chiarelli gone, the Oilers could at least make greater efforts to shake that Etch-a-Sketch. We’ve seen a ton of examples of seemingly untradeable contracts being moved, so it wouldn’t hurt to try.

Bargain hunting

If there’s an area where Chiarelli was passable, it was occasionally targeting some quality, cheap scorers.

To varying degrees, players like Alex Chiasson, Tobias Rieder, and Ty Rattie have served their purpose, at least for stretches. Even if the Oilers alleviate some cap concerns, chances are, they’ll need to be wizards of the bargain bin. On the bright side, McDavid is the sort of guy who should fatten the bank accounts of the Chiassons of the world, so that’s a workable aspect of this team.

One of those “fresh voices” might be especially adept at gauging who might be a diamond in the rough.

Pulling a reverse-Chiarelli

That brings up another point: maybe the Oilers can do to other teams what savvier GMs constantly did to Chia?

By that I mean: a) trading for players who are slumping, but are almost certain to get it together and/or b) determining supposed “lack of character” guys who can help them win.

It’s not just the Oilers who’ve done this with Jordan Eberle and Taylor Hall. The Hurricanes traded Jeff Skinner after a cold shooting season. Dougie Hamilton may once again be an underappreciated asset.

Buying low on a talented player won’t necessarily be easy for the Oilers, considering their cap predicament, so this advice may be more pertinent if they can shed some of the Russells and Mannings. But if the opportunity arises, the Oilers could really start to turn things around.

***

Again, this isn’t the easiest situation. Chiarelli (and others?) really made a mess of this situation after getting the Lottery Ticket on Skates that Connor McDavid is.

Yet, even considering the cavalcade of mistakes this franchise has made, they’re not that far from being a more balanced and competent team.

It might be awkward to ask powerful front office executives to change the way they do business, but winning is worth more than a few ruffled feathers.

—

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.