Edmonton Oilers

Exploring the Edmonton Oilers two-year Stanley Cup window

The Edmonton Oilers don’t have a first-round pick in this year’s NHL Draft or next year’s either, but more than any team in hockey, they’re on the clock. Connor McDavid’s extension will kick in next season, guaranteeing the Oilers at least two more seasons with the best player on Earth as the captain.

In the summer of 2028–29, McDavid will become a UFA at age 32, and it’s not guaranteed he’ll be signing in Edmonton again. Thus, Edmonton has two more confirmed seasons to take serious runs at the team’s sixth Stanley Cup Championship. After a disappointing first-round loss to the Anaheim Ducks, let’s take stock of the Oilers’ two year window and assess what position they’re in.

Positives to the Oilers roster

Of course, that assessment begins with Connor McDavid and Leon Draisaitl. Still two of the league’s absolute premier talents, neither #97 nor #29 had top-level years. However, McDavid won his sixth Art Ross and Draisaitl finished three points shy of 100 due to injury. He then led the team in playoff points with 10 in six games. A Norris Trophy level season from Evan Bouchard doesn’t hurt the long-term outlook either. Very few teams can claim they have such a high level 1–2 punch at centre as well as surefire #1 franchise defenceman, but Edmonton certainly can. With McDavid, Draisaitl, and Bouchard all in the picture, the very top of the Oilers lineup is never in question.

The team is lucky enough to have top-end players past #97, #29, and #2 though. Although none of them are getting any younger, the ageless wonders of Mattias Ekholm, Zach Hyman, and Ryan Nugent-Hopkins still play vital roles in the lineup. Hyman can still play on McDavid’s wing, and is still an effective net-front man on the power play. Nugent-Hopkins is a similar power play producer. Although his 5v5 game took a step back this season, he’s still an effective player. Ekholm is the steady hand that controls Bouchard’s occasional defensive miscues, and still munches 20 minutes a night like it’s nothing.

One important aspect the Oilers have begun to see building in their lineup is something they’ve been chasing for a long time: production and growth from the youth. The Vasily Podkolzin trade is holding up as Stan Bowman’s savviest move with Edmonton. He blossomed into a 19-goal man this year playing alongside Draisaitl. Moreover, he was arguably the Oilers’ best winger in their six playoff games. Even better, Edmonton has him signed for three more years at an AAV of $2.95M.

Matthew Savoie finally emerged as a top line player and began to build some solid chemistry with McDavid. On the defensive end, Ty Emberson has been the ideal third pairing RD. You almost never hear his name, and for a bottom pairing defenceman, calm and quiet is the name of the game. Josh Samanski, Quinn Hutson, and Isaac Howard all also showed flashes of being able to contribute sooner rather than later.

The Oilers have lots of positives despite the two-year window, but there’s still questions to be answered.

A Number of big decisions loom

For a team with “Cup or Bust” aspirations like Edmonton, an opening round loss, and more specifically the kind of loss they suffered to Anaheim does raise a number of questions. In the coaching department, will back-to-back trips to the Finals be enough for Kris Knoblauch to keep his job? He was out-coached against the Ducks. He also showed many signs of the same stubbornness that got him into trouble against the Florida Panthers. The team was sitting back too much with a lead and trying to nurse home tight games rather than continuing to press with offensive chances. Assistant coaches Mark Stuart and Paul McFarland’s jobs may also be in question, especially Stuart, who’s atrocious penalty kill almost lost Edmonton the series single-handed.

Despite only two years on the job, GM Stan Bowman’s job could also be in jeopardy. He’s made some good moves, with the aforementioned Podkolzin trade, along with this year’s trade deadline pickups of Connor Murphy, Colton Dach, and Jason Dickinson. However, he’s got some big misses on his resume. He was GM during the Dylan Holloway-Philip Broberg offer sheet saga, but he didn’t handle the Oilers not matching either player. He did, however, sign Trent Frederic to an eight-year deal with a $3.85M AAV, and traded for Tristan Jarry. The jury is still out on his other big move: the acquisition and signing of Jake Walman to a seven-year, $49M contract. Walman had a tough go with injuries and lineup mixing. However, he was good in the immediate aftermath of the trade, so I’m more positive on the outlook for that.

The biggest roster moves for Edmonton will likely involve two players. Jarry, and Darnell Nurse. Jarry at $5.375M for two more years just isn’t a contract the Oilers can afford to have on the books. The same goes for Nurse and his $9.25M AAV. Rumours swirled about a potential Nurse trade last summer. Although he has a no-move clause, speculation has only grown that Edmonton might move off the 31-year-old to shed some salary. Nurse’s no-move clause moves to a 10-team no-trade list next season. Maybe he’d accept a trade now, knowing he can still control where he ends up.

Oilers President and CEO Jeff Jackson shouldn’t feel comfortable either. He was the main decision maker during the Holloway-Broberg saga. It was also his signings of Jeff Skinner and Viktor Arvidsson that ultimately left Edmonton with too little room to counter the Blues’ offers. Sure, that 2025 team made the Final too, but they played one less game and didn’t truly look equal to Florida. It’s possible Oilers owner Darryl Katz opts to clear out management and install a new leader for this crucial two-year stretch.

No more mistakes allowed

With the Oilers in this two-year window, there can be no more major mistakes when it comes to roster building. Any Jarry-like sideways moves or straight up bad decisions could be the end for any dreams of serious contention in the McDavid-Draisaitl era. Not every move has to be perfect, but every move from now on does need to work at a minimum.

Ironically enough, it’s possible an early exit could be a blessing in disguise for Edmonton. Their flaws were laid bare against the Ducks, and no team has played more hockey over the last three seasons than the Oilers. Maybe the loss to Anaheim shows the braintrust what kind of hard decisions need to be made roster-wise. This also allowing those staying with the team to have a full summer of rest and recovery to heal nagging injuries, rather than toughing it out into June for a third straight year.

Still, Edmonton has two years at a minimum to win with McDavid. After that, who knows. A Cup win in this window could guarantee he re-ups come 2028. Failure to capture a championship could see him look elsewhere in search of a title. Whatever happens, the Oilers are on the clock, and everyone is watching.

Photo by Melissa Tamez/Icon Sportswire

Alex Stewart

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