This is a disappointing season for Oilers fans and management. But what can be learned from a season that’s gone so wrong when many thought they’d be competing for a Stanley Cup?

I wasn’t surprised when the Oilers traded Jordan Eberle for Ryan Strome, but that left an incredibly thin right wing unless Leon Draisaitl played the majority of the season alongside Connor McDavid.

The Oilers sold low on Eberle and bet that Drake Caggiula, Anton Slepyshev, and Ryan Strome could replace his scoring. Caggiula and Slepyshev had a few nice goals in the playoffs, but they had 28 points combined last year.

Chiarelli made a bet that either Darnell Nurse or Matt Benning could fill in for Andrej Sekera’s absence. Nurse has assumed more minutes and hasn’t looked out of place, while Benning’s had a rocky campaign. There wasn’t much cover elsewhere on the blueline. Oscar Klefbom’s season hasn’t been as good as last year with injuries holding him back. Kris Russell is a shot-blocking specialist who McLellan trusts, but is limited.

The Oilers have a lot of cap space, even when you account for McDavid’s bonuses. They’re among the lowest spending teams in the league.

The idea was with Eberle traded for Strome and Benoit Pouliot bought out they’d have a ton of room to load up for a Stanley Cup run at the trade deadline. That plan failed. Had this season gone another way, maybe the Oilers add Michael Grabner, Evander Kane, and Mike Green in deadline deals.

I’d rather have Eberle than the majority of the players moved at the deadline. The cost of these deadline acquisitions would have hurt an already shallow prospect pool with draft picks and players headed out, although winning a Stanley Cup makes that matter less.

I get wanting to keep the roster more or less the same. They made the playoffs for the first time in a decade, and management felt confident in a team that was a few goals from the Western Conference Finals. But it’s hard to argue Chiarelli didn’t make the Oilers worse in the off-season.

Chiarelli re-signed Zack Kassian and Kris Russell, signed McDavid and Draisaitl long term, and traded Eberle for Strome. Jussi Jokinen was added on a cheap, one-year deal.

With Sekera injured, Chiarelli should have done more to solidify the defence. He opted to re-sign a third-pairing defenceman for too much money and too many years. There needed to be more done other than bringing back Russell and signing Yohann Auvitu.

The wings were bare unless Draisaitl played right wing. The Oilers don’t have a full-time winger on pace for more than 40 points. Draisaitl is well past that but has split time at centre and wing. Same with RNH recently.

July 2015: Oilers sign Andrej Sekera to a six-year, $5.5M AAV contract.

July 2016: Oilers sign Milan Lucic to a seven-year, $6M AAV contract.

June 2017: Oilers re-sign Kris Russell to a four-year, $4M AAV contract.

The Oilers can’t add another expensive contract in free agency that carries no-trade or no-move protection.

Sekera may not have a working leg by the end of the season. Lucic’s contract is moving into albatross territory. Russell’s deal is too long and too rich for a third-pairing defenceman when the Oilers need to sign Darnell Nurse and still improve their defence.

McDavid is probably going to give you 95-105 points in any given season and crush whatever opposition he faces. He can’t be your entire game plan.

The Oilers outscore and out-shoot teams with McDavid on the ice, but are heavily outscored without. They were about even in terms of shots without McDavid until dipping below lately.

Oilers management needs to bridge the gap between McDavid’s line and the rest of the roster.

The Oilers can’t make the same mistakes they made this season. Whoever is in charge needs to have a better offseason than Peter Chiarelli had last summer. This means acquiring talent without sending a better asset the other way.

It’ll be more difficult. McDavid’s mega-extension kicks in and the Oilers aren’t flush with tradable assets, so they’ll have to get creative if they want to return to the playoffs.