Oilers Destined to Repeat Heartbreak Until They Address Biggest Issues

The Edmonton Oilers are kind of like the Myth of Sisyphus. Sisyphus was cursed to push a boulder up the hill for all eternity as punishment for their hubris and cheating death. Today, we use it to describe a task that is unending and repetitive.

The Oilers are in an unending and repetitive task, cursed to continue this futile pursuit of a Stanley Cup. Following another defeat by the Florida Panthers, Edmonton is the league's runner-up for a second straight year. Like Sisyphus pushing the boulder up the hill, the Oilers are destined to keep pushing toward the Stanley Cup Finals, but they will never reach the summit until they truly address their most significant issues. They failed to correct the same issues after falling short in 2024.

It starts and ends with defense. The Oilers were woefully outbattled in the Finals by the Panthers. Florida hounded Edmonton's puck carriers; they were nasty along the boards and in front of the net and were relentless on every shift. The Oilers couldn't match that intensity, and even when they had periods or bursts of strong possession or chance creation, it would quickly give way to the Panthers and their response.

Edmonton's response to having its defense pushed around in the 2024 Finals was to add puck-movers and unproven stay-at-home defenders. They gave up a significant haul for Jake Walman, a top-4 defenseman who excels on the rush and on the power-play unit. They acquired Ty Emberson, a right-shot blue liner who has 106 NHL games under his belt. They signed former power-play specialist John Klingberg as well.

The problem is that Emberson is the only player who was truly tough to play against. Walman possesses a nasty streak and was unafraid to mix it up, but when it came to his stick positioning and ability to win body position, he woefully underperformed. The same can be said for Klingberg, who was virtually a non-factor during the Finals. Emberson didn't play in the final two rounds.

That's continued to put all of the onus and responsibility on Evan Bouchard, Mattias Ekholm, and Darnell Nurse. Bouchard is an offensive juggernaut, evidenced by his 23 points this most recent playoff run. When it comes to 5-on-5 defense, he's average. When it comes to penalty killing, he's below average. Ekholm is in the twilight of his prime, and while he's an offensive chance suppressor, it's not enough to counteract the chances allowed by the rest of their defense.

It's also about goaltending. Stuart Skinner was miserable in the 2025 Stanley Cup Playoffs, and backup Calvin Pickard played his worst postseason contests in the final round. The organization has to comprehend the lesson learned in back-to-back seasons: their goaltending isn't good enough.

And then there's offensive depth. Sure, the Oilers deserve credit for attempting to solve this. They added players like Viktor Arvidsson, Trent Frederic, Max Jones, Kasperi Kapanen and Jeff Skinner in the hopes that they would provide the ideal mix of speed, tenacity, and physicality that could match up with the Panthers. That was a collective failure.

The team's two superstars, Connor McDavid and Leon Draisaitl, will take the blame for another loss. Is it all on them? Absolutely not. McDavid and Draisaitl finished tied for the lead in postseason scoring. Both recorded 33 points. This is the fourth year in a row that McDavid has reached or exceeded 20 points in the playoffs and the third time he's reached or exceeded 30 points. This was Draisaitl's third 30-point postseason in the past four years as well. There's no argument to make that their superstars aren't doing enough.

The Oilers have an option to truly make changes in the offseason. It was easy to see that Edmonton didn't do enough before the 2024-2025 season began. It's why I predicted that they would lose in the Stanley Cup Finals again this year. They need to round out their roster at multiple positions, which is a Herculean task. It can be done, however. If they don't, the Oilers will continue their ill-fated run in 2026. The NHL's Sisyphus will push that boulder up the hill, only to plummet all the way back down just before reaching the top.