After years of being on the precipice, the Edmonton Oilers are once again staring down a season with Stanley Cup aspirations. But as any fan knows, that hope comes with a healthy dose of anxiety. Another deep playoff run that ended without a parade means the pressure is on, and the team’s strategic priorities for the upcoming season are under a microscope. It’s a high-stakes game of chess for second-year general manager (GM) Stan Bowman, and every move will be scrutinized. Let’s break down the biggest challenges facing the Oilers as they look to finally get over the hump.
The McDavid Question: Short-Term Pain for Long-Term Gain?
This is the big one, the question that looms over everything. What will Connor McDavid’s next contract look like? The whispers out of the Team Canada orientation camp are deafening: a shorter-term deal is on the table. We’re talking maybe 4-5 years, at a king’s ransom of around $16-17.5 million average annual value (AAV). While the Oilers would love to lock him up for the full eight years, like they did with Leon Draisaitl’s new $14 million AAV benchmark, a shorter deal gives McDavid a chance to capitalize on a skyrocketing salary cap down the road, potentially earning upwards of $20 million annually.
For the organization, it’s a gamble. A longer deal would provide cost certainty and be an absolute steal as the cap inflates. A shorter deal, however, means they have to be all-in, every single year. It’s a constant, high-pressure championship window. The timing of the announcement, expected after the Team Canada camp and before training camp begins, is crucial. It’ll set the tone for the entire season. The relationship is strong, and McDavid isn’t going anywhere, but the structure of this deal will define the next chapter of the Oilers’ dynasty window.
The Crease Conundrum: Is “Good Enough” Actually Good Enough?
Goaltending. The perennial Achilles’ heel of the Oilers. Last season, the Stuart Skinner and Calvin Pickard tandem was a rollercoaster, especially in the playoffs. Skinner’s .889 save percentage in the postseason, and the number of times he was pulled, is a stat that keeps fans up at night. The team’s decision to stick with this duo, and use the money they could’ve spent on a higher-priced goalie on a different roster player, is a bold bet.
The front office is hoping that a “league average goalie” is all they need, someone who can post a .905-.910 save percentage. But is that realistic? And more importantly, is it enough to win a Stanley Cup? If the tandem of Skinner and Pickard struggles early in the season, you can bet a trade for an upgrade will be top of mind for Bowman. This team’s success hinges on stability in net, and they’re rolling the dice that they have it.
Youth Movement: Who’s Stepping Up?
The Oilers are desperate for some fresh blood to make a real impact. With the departures of prospects like Philip Broberg and Dylan Holloway last offseason, the pressure is squarely on the shoulders of players like Matthew Savoie and Isaac Howard. The hope is that at least one of them can graduate from prospect status to a bonafide top-six forward. We’re not talking about Calder Trophy numbers here, but a solid 15 goals and 40 points would be a huge boost.
The coaching staff, led by Kris Knoblauch, will have to decide on the best development path. Do you throw them into the deep end with McDavid or Draisaitl and hope they swim? Or do you give them a more sheltered role in the bottom six to build confidence? The lack of long-term development has been an issue for the Oilers, and the success of this season may very well depend on whether one of these kids can finally break through.
Power Play Problems: The Need for New Wrinkles
It sounds crazy to say, but the Oilers’ vaunted power play, a unit with generational talents like McDavid and Draisaitl, regressed last season. They went from 5th in the league to 11th, and the drop was noticeable. The “Zach Hyman factor,” or lack thereof, played a big role, with fewer net-front goals. But more than that, defences have figured out the Oilers’ tactics. They’re pre-scouting the drop pass entry and McDavid’s puck-holding style, leading to wasted time and fewer shots on goal.
The team needs to introduce “new looks” and “new wrinkles” to their power play. This could mean a change in personnel, maybe swapping out a player like Ryan Nugent-Hopkins for a different handedness to create a new one-timer threat. The power play has been a crutch for this team when their 5-on-5 game has been inconsistent, and getting it back to a top-10 unit is essential for a deep playoff run.
Cap Crunch and Bad Contracts: Navigating the Financial Minefield
Bowman’s first priority was to shed some of the team’s albatross contracts, and he’s made some progress by trading away Evander Kane and Viktor Arvidsson. But the Oilers are still strapped against the cap, and some of the remaining contracts are a serious issue. The biggest elephant in the room is Darnell Nurse’s eight-year, $9.25 million AAV deal, which many in the league consider the worst contract in the NHL. With a full no-movement clause until 2027, moving him is nearly impossible. The reality is, the team needs an upgrade on their top-four defence, but Nurse’s contract makes it a logistical nightmare.
Then there’s the Trent Frederic contract, a new deal that has people scratching their heads. An eight-year term at $3.85 million AAV for a bottom-six player with injury concerns and a full no-movement clause for the first four years is a big swing. Add in Adam Henrique’s final year at a $3 million AAV—a contract that’s overpaying for his production at this stage of his career—and you have a cap situation that severely limits the team’s ability to improve. The Oilers will need to be creative and possibly make more cap-clearing moves to give themselves any flexibility at all.
Final Thoughts: The Ultimate Goal
The Oilers have all the pieces to be a contender, but they’ve been unable to get over the hump, losing to the eventual Stanley Cup champion in four consecutive playoff runs. The path to a championship is paved with challenges, from McDavid’s contract to a questionable goaltending situation, and the need for young players to step up. They also need to avoid their notorious slow starts and stay healthy after a season of significant injuries to key players.
For this core—McDavid, Draisaitl, Bouchard, Nugent-Hopkins, Hyman, and Nurse—this may be their best chance. The window is wide open, but it won’t be forever. The pressure is immense, and every decision, big or small, will determine whether this team can finally bring a Stanley Cup back to Edmonton.
Created with the aid of Gemini AI