Willis: The Edmonton Oilers are rapidly approaching their “all-in” moment

The NHL is often, and to its detriment, an imprudent league. Short-term, rather than long-term, thinking tends to dominate.

My favourite example of this trend in recent years came from Toronto, where then-general manager Dave Nonis was asked about the long-term ramifications of signing David Clarkson to a seven-year, buyout-proof contract taking up 8.2 percent (the modern equivalent of $6.74 million) of the Maple Leafs’ cap space.

“I’m not worried about (years) six or seven right now,” said Nonis, in true damn-the-torpedoes fashion. “I’m worried about one. And Year 1, I know we’re going to have a very good player. I believe that he’s got a lot of good years left in him.”

It’s a fun quote in a lot of ways, not least because Clarkson scored a grand total of five goals in his first season with the Leafs. What I’ve always enjoyed about it is its honesty. Few NHL managers are willing to so openly state their indifference to the future.

Generally, when an NHL manager makes a dodgy long-term bet, he finds reasons to justify it, as Peter Chiarelli did after signing Milan Lucic.

“He’s 28, he (has) very limited injuries, if anything,” Chiarelli said then. “And yes, the way he plays, it’s a little more difficult to play that into your 30s. I’ve seen him grow physically and mentally as a young man, I know what care he takes of his body, I know what his wife — she’s very into nutrition, as Milan has become into nutrition. He was always one of the best-conditioned athletes on the Bruins, so that stuff mitigates the risks.

“But there’s risks, yeah, there’s risks.”

Compared to the overwhelming mass of data that says power forwards and underwhelming skaters tend to age poorly, the “I know this guy, he takes care of his body and hasn’t had a pile of injuries” argument is thin gruel. It was a signing made with a focus on the present, and the decision to load the signing bonuses heavy in Years 5-7 of the contract made it clear that Chiarelli either hadn’t given much thought to or didn’t care what happened down the line.

There are countless similar examples of short-term thinking burning NHL teams. Yet there are times where a reasonable actor might weigh the options and heavily focus on the present. This is rarely true for rebuilding or mediocre teams, but for the best clubs it can make sense.

Take Calgary Flames GM Brad Treliving. This summer the Flames — coming off a 50-win season and the second-best goal differential in the NHL — faced the loss of their two best forwards, Johnny Gaudreau and Matthew Tkachuk. It was potentially a crippling blow to a legitimate contender, and there was an argument for Calgary to take a step back and retool, despite the fact that the average age of their remaining top-six forwards/top-four defencemen next year will be 28.

Instead, Treliving sacrificed prudence for a series of moves aimed at maintaining Calgary as a contender:

Those actions will certainly help the Flames next season. They’ll just as surely hurt the team down the road. That’s imprudent, but not necessarily unreasonable; for a team that can win right now, there’s a good argument to maximize the present. The question is whether the Flames lost so much of what made them formidable in Gaudreau and Tkachuk that these efforts are in vain, and there’s no certain answer to that. Treliving is betting on “no.”

Alberta’s other NHL team has taken a different path for most of Ken Holland’s time in the chair. That longtime executive has mostly aimed for prudence.

As a deadline buyer, the Oilers have been miserly. They’ve refused to part with first-round picks. When dealing second-rounders, they’ve targeted players they hoped would be long-term fits (Andreas Athanasiou, Brett Kulak). The only pure rentals of interest to Edmonton these last three years were bargain-bin pickups (Mike Green, Tyler Ennis, Dmitry Kulikov, Derick Brassard).

Even in free agency, where the Oilers have been active, they’ve mostly avoided big splashes. Darnell Nurse — irreplaceable on the team’s top pair and hitting the market at a time defenders were getting paid — is the only true exception. Zach Hyman, Ryan Nugent-Hopkins, Evander Kane, Tyson Barrie, Cody Ceci and Jack Campbell all signed carefully measured contracts, and all were inked with an eye to at least the medium term. In each of the latter cases, at least two of cap hit, term or signing bonuses were carefully limited.

Holland has at times defended his moderate approach. In 2021, he stirred fan anger with his comments following the trade deadline.

“I don’t think that you can be all-in every year,” Holland said. “I think you pick and choose.”

The anger is easy to understand. The Oilers are blessed with Connor McDavid and Leon Draisaitl, certainly the best one-two punch at centre in the NHL since the early days of Sidney Crosby and Evgeni Malkin. A team with those two players in their respective primes should be a contender, period.

“Should be” and “is” aren’t the same thing, of course. In 2019-20, the Oilers finished minus-16 in five-on-five situations. They improved to minus-one in 2020-21 and finally in 2021-22 hit the lofty plateau of plus-eight.

Add it all together and in that three-season span, Edmonton was the 18th-best five-on-five team in the NHL, with a total of minus-nine. The two teams with Cup rings in those three years ranked first (Colorado, plus-135) and second (Tampa Bay, plus-88) over that same period. When Joe Sakic or Julien BriseBois mortgages the future to try for a title, it’s done from a very different position than the one Holland has been in during his run with the Oilers.

Edmonton has had the superstars to go on a run, but it hasn’t had the team around them. Forcing things at the deadline wouldn’t change that, not enough. Holland’s restraint has been justified.

So what, then? Sit back and make modest improvements in the hope that something changes before Draisaitl hits free agency in 2025 and McDavid does in 2026? No, because something changed at midseason last year, though it took time to appreciate how significant the shift was.

In fact, a lot of things changed. Kane was signed as a free agent. Kulak was acquired at the deadline. Most importantly, Jay Woodcroft replaced Dave Tippett as head coach.

When Tippett was fired, the Oilers had played 44 games. They were minus-12 at five-on-five and scarcely better by other metrics, with a 50 percent shot share and 51 percent expected goals percentage. Over their next 38 games under Woodcroft, they went plus-20 with a 53 percent shot and expected goal share.

Then came the playoffs. It took seven games to dispatch the Kings, but at five-on-five the series wasn’t close: Edmonton took 52 percent of the shots, 57 percent of the expected goals and outscored Los Angeles 16-12. The underlying numbers were less pretty against Calgary (largely due to how good the Flames were when trailing) but again Edmonton had a four-goal margin at five-on-five in the 4-1 series victory.

The Oilers then got cut apart by the Colorado buzz-saw in the third round. The scores probably would have been more respectable if bits hadn’t kept falling off Draisaitl and Nurse during play, but even healthy they weren’t at the Avs’ level.

That last failure isn’t enough to undo what came before. The NHL’s deadliest power play team now looks like it could be a legitimate contender at five-on-five. This is the first time during Holland’s tenure that there’s reason to believe aggressive action could put the team over the top.

That’s reason for urgency, even if it isn’t the one normally heard. There has long been a sense in Edmonton that if the Oilers want to keep their fantastic McDavid/Draisaitl duo together, some winning needs to happen before they hit free agency. There is a clock on success.

That clock has been ticking, ever louder, since those contracts were signed. It’s good pressure to have. It’s also been wise to tune it out until the team around those players was ready. That might be now, though a cautious GM might wait until there’s longer proof of five-on-five success before committing.

Either way, the Oilers are rapidly approaching the moment where it will actually be time for imprudent moves, for sacrificing prospects or first-round picks in the right deal, for pushing the chips to the centre of the table.

They might be there already. There’s typically a flurry of moves in the early fall, right before the season begins. If Holland judges the time is right, it could and should be a busy window for Edmonton.

(Photo of Leon Draisaitl and Connor McDavid: Ed Mulholland / USA Today)