This season, there will undoubtedly be another run for the Stanley Cup on the Canadian prairies. As the 2025–26 NHL season gears up, the Edmonton Oilers find themselves in a familiar position. Once again, they came right up to the window of greatness, looked in, but couldn’t grab the gold. For the second offseason in a row, the sting of another heartbreaking Stanley Cup Final loss is still fresh.
It’s not a question of whether the Oilers are good enough. That much is clear. The real question is whether they can finally finish the job.
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Connor McDavid remains the best player on the planet, and Leon Draisaitl—still under contract for multiple seasons—continues to be his unstoppable counterpart. But if last season taught us anything, it’s that superstar talent alone isn’t enough. The Oilers need every part of their roster to deliver when it matters most.
Three Storylines that Could Make or Break the Oilers’ Season
Here are three storylines that could make or break their season.
Storyline One – McDavid and Draisaitl: Can This Duo Finally Deliver a Cup?
This dynamic pair has carried Edmonton to back-to-back Stanley Cup Final appearances, and their numbers remain jaw-dropping. In 2024-25, Draisaitl scored 52 goals and posted 106 points. Both he and McDavid tied with 33 playoff points, leading the charge as Edmonton pushed to the Final for the second straight year.
McDavid, now entering the final season of his eight-year, $100 million contract, still hasn’t lifted the Cup. There are talks of an extension soon. Rumours are swirling that he might sign a short-term extension—or even test free agency—if the Oilers don’t prove they can win. Draisaitl is locked in for several more seasons, but their shared legacy will ultimately be defined by one thing: bringing a Stanley Cup back to Edmonton.
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They’ve done everything except win the last game of the year. The 2025–26 season may be their best—and perhaps last—chance to do it together.
Storyline Two – Goaltending: Will Skinner Be Steady Enough?
Stuart Skinner has delivered some of his best hockey during Edmonton’s recent playoff runs, but inconsistency under pressure remains a concern. While he’s capable of brilliant stretches, there have been moments when his game wavered at the worst possible time.
Analysts such as Ray Ferraro have openly questioned whether the Oilers can make another run with the same goaltending setup. Behind the scenes, whispers of trade talks involving Skinner—or the pursuit of another starting goalie—have grown louder.
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The thing about the playoffs is pretty simple—at some point, you need your goalie to flat-out steal a game—one night where he slams the door, no matter what’s happening in front of him. If Skinner can hit that level when it counts, the Oilers take a huge step toward finally breaking through. If he can’t, general manager Stan Bowman might have to make a move—and fast—before the trade deadline rolls around.
Storyline Three – Secondary Scoring: Who Fills Kane’s Spot?
Evander Kane’s time in Edmonton ended on June 25, 2025, when the Oilers dealt him to his hometown Vancouver Canucks for a fourth-round pick. The trade freed up some badly needed cap space, but it also left a big hole in the lineup.
Kane wasn’t just a goal scorer—he brought muscle, edge, and that playoff experience you can’t fake. Without him, someone else will have to step up. It could be a third-liner, a bottom-six grinder, or even a defenceman who can jump into the rush. In the playoffs, it’s often those greasy rebound goals or unexpected blasts from the blue line that turn a series. Edmonton’s going to need more of those this year.
In the postseason, momentum often turns on the so-called “dirty” goals—rebounds, deflections, and scrappy plays in the blue paint. Without players willing and able to do that job consistently, the Oilers risk leaning too heavily on their superstars.
For the Oilers, This Season Feels Like Now or Never
Over the past two years, the Oilers have experienced the full spectrum—franchise-defining highs, gut-wrenching lows, and two straight Stanley Cup Final appearances. Management has assembled a roster featuring elite top-end talent, greater depth than in years past, and newfound salary-cap flexibility. However, all of it has to come together simultaneously.
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McDavid’s contract situation hovers like a storm cloud, Draisaitl remains the emotional and physical backbone of the team, and the goaltending decision could determine whether Edmonton finally crosses the finish line. The loss of Kane means others will have to play bigger roles—and sooner rather than later. For fans in Edmonton, the “win-now” window has never felt more urgent. This is not about building for the future or laying groundwork. This is about seizing the present moment, while two of the game’s greatest players are still at their peak.
They’ve come within one win of hockey’s ultimate prize twice in a row. Now the task is simple in theory but brutal in execution: win that elusive fourth game in Round 4. The 2025–26 season offers one more chance for all the puzzle pieces to fall into place—no symbolism, no moral victories—just the Stanley Cup returning to Oil Country.
[Note: I’d like to thank Brent Bradford (PhD) for his help co-authoring this post. His profile can be found at www.linkedin.com/in/brent-bradford-phd-3a10022a9]
