Oilers offseason outlook: Biggest questions, needs, free agent targets

So close, yet so far. For the past two years, the Edmonton Oilers have made the playoffs and made some noise when they got there. Each time, they fell convincingly to the eventual Stanley Cup champions.

Ideally, you’d take lessons from those losses and bolster your roster to better handle best-on-best matchups. Considering their 2023 offseason outlook, the Oilers might just be lucky if they can maintain what they had.

The Oilers will need to be agile during this offseason, making modest investments in free agency and ideally trading someone like Kailer Yamamoto.

With a rising star defenceman in Evan Bouchard to re-sign and a goalie situation that needs mending, expect a challenging summer for Oilers GM Ken Holland.

Oilers’ 2023 free-agent outlook and salary cap situation

Notable UFAs: Oscar Klefbom, 29 (may retire due to injuries); Nick Bjugstad, 30; Mattias Janmark, 30; Devin Shore, 28; Mike Smith, 41 (retirement also likely), Ryan Murray, 29.

Notable RFAs: Evan Bouchard, 23; Klim Kostin, 24 (arbitration eligible); Ryan McLeod, 23 (arbitration eligible)

Projected salary cap space: A misleading $5.07M. The Athletic named the Oilers’ salary cap situation the worst in the NHL.

The projected salary cap space estimate is with the Oilers covering 18 of 23 roster spots. Even if you pencil in some entry-level/bargain-bin talent in a spot or two, it’s clear things are going to be tight for Edmonton.

At least the bright side is quite bright: while there could be some belt-tightening this summer, the Oilers aren’t expected to lose any essential pieces from their hyped-up squad that caught fire down the stretch of 2022-23.

Unless, of course, they mess things up with Bouchard.

Oilers’ biggest offseason needs in 2023

Don’t mess around: sign Bouchard

The Athletic’s Daniel Nugent-Bowman recently noted two things about Bouchard that could raise the eyebrows (and pulses) of Oilers fans.

First, Nugent-Bowman believed that Holland nudged at the possibility of a one-year deal that could carry around a $3-million price tag. (For whatever it’s worth, Evolving Hockey’s great contract projection tool priced a one-year Bouchard deal at about $3.98 million.) While that contract would serve as a steal for the Oilers, it seems short-sighted.

The second Nugent-Bowman comment was scarier: he believed the Oilers wouldn’t be able to match a significant offer sheet if one was tendered. Now, sure, the NHL is full of cowardly GMs who bank on chummy friendships to land future gigs and create musical chairs of retreads … but all it takes is one bold team to upset the apple cart.

NHL teams covet right-handed defencemen, and Bouchard is a young one who can bring serious offence to the table. One measure of market value priced him as high as $8.7 million, while Evolving Hockey’s most common projection for his next contract is a six-year deal with a $5.36-million cap hit. While that would present obvious immediate challenges for the Oilers, it could be the sort of contract that makes people wonder what an agent was thinking.

Ideally, the Oilers would try to hammer out a few years to get value out of Bouchard before the league truly catches on to his significant potential. If someone else realizes what he already brings to the table (and his potential to climb the ranks), then they might be willing to try to nab a rising star.

A one-year deal feels like it would open the door for future trouble, but one way or another, Edmonton just needs to get things done with Bouchard.

Clear up salary-cap space

Speaking of one way or another: the Oilers need to clear up some money.

The dream might be to trade Jack Campbell, citing the Kings wiggling out of Cal Petersen’s deal as an example of a team bribing someone to relieve them of a problematic contract. When you wake up to the reality that Campbell’s $5 million is even harder to move because his contract runs through 2026-27, it would be a tough sell even to a long-haul rebuilding team. Creating space that way is at least worth a try, and buyout talk isn’t that outrageous.

This screen grab from CapFriendly’s buyout calculator isn’t pretty, but almost $3.5 million in up-front savings might just be appealing for the win-now Oilers. Granted, it would be an expensive punt for Holland.

Most realistically, the Oilers will probably try to trade or buy out someone like Yamamoto.

The fear is that a bad Holland habit re-emerges in all of this: woefully misjudging the value of supporting-cast members (some Red Wings fans might call this Abdelkadering).

Theoretically, the Oilers might get some assets in trades for Yamamoto ($3.1-million cap hit for next season) and/or Cody Ceci ($3.25-million AAV for the next two seasons). Management may instead decide to part ways with superior supporting options in Warren Foegele ($2.75 million next season) or Brett Kulak ($2.75 million for three more seasons). Such misjudgements would sting extra if a quality depth player gets scuttled out because the Oilers pay Kostin too much money.

Ultimately, those decisions are quite granular, though. The main fear might be that in trying to keep nice-but-not-vital players, they may hurt their chances of retaining Bouchard. Further down the line, you don’t want to forget that Leon Draisaitl’s bargain $8.5-million cap hit only lasts for two more seasons (expiring after 2025-26).

Figure something out with Campbell

As stated above, there’s the outside chance you either trade or buy out Campbell after a disastrous season. Chances are, you’re not shaking him loose this early, though.

So the Oilers need to pour some resources into helping him (and Stuart Skinner) better succeed. Maybe that means putting money into a quality sports psychologist. Perhaps you could dig deep into your system, asking if there are ways to accentuate positives and hide weaknesses. There could be value in even taking him aside and emphasizing that he’ll get a clean slate.

Realistically, the Oilers’ best chances to improve revolve around improving from within. A bounce-back year from Campbell and continued progress from Skinner could raise Edmonton’s ceiling in 2023-24.

Seek out a forward like Connor Brown

There are all sorts of rumblings that there may be a match between pending free agent forward Connor Brown and the Oilers. They even have the chum factor: Connor McDavid and Brown were linemates at the junior level.

Crucially, Brown figures to be cheap, yet still has something to prove at age 29.

At their most efficient, the Oilers should attract free agents to make short-term investments in their careers by hoping that playing with Draisaitl or McDavid for a cheap year could help them set up big gains in the future. It may not be easy for Edmonton to eventually say goodbye to those bargains, but it’s a lot more affordable to master the bargain bin than pay full price for diamonds that other, brighter teams unearthed.

Maybe pump the brakes on nostalgia?

When people asked Holland why he traded for Duncan Keith in 2021 (in a deal where Edmonton gave up assets, rather than getting bribed to take that contract off Chicago’s hands), Holland might as well have bellowed out “harumph.”

Predictably, Keith performed at his most recent level, resembling an aging player whose locker room leadership may have been overstated.

It’s not overwhelmingly promising, then, to hear that the Oilers are eyeballing Jonathan Toews.

Now, sure, Toews might alleviate some of his current issues if the Oilers used him as a famous fourth-liner instead of being exposed higher up Chicago’s lineup in recent years. But there’s no denying how Toews’ play has plummeted, and how his health is far from certain.

That nostalgia can be a dangerous drug for coaches, too. Underlying metrics might argue that Ryan Suter and Patrick Kane shouldn’t get the same heightened roles anymore, but a veteran coach may still elevate them too much, reasoning that they’re “safe” choices.

This isn’t to say that a dirt-cheap, big-name veteran couldn’t work; someone like Corey Perry could make sense, particularly since he’s embraced a more supplementary role.

It’s just that with the Oilers — and Holland even before he joined the organization — you always have to wonder. For every shrewd move such as adding Mattias Ekholm, there are enough Keith/Zack Kassian-type decisions that create obstacles for that dream team that elevates McDavid rather than holding him back.

Is Holland still a Hall of Fame-level GM? Masterfully handling the Oilers’ 2023 offseason would show he still “has it.”