After finishing as Stanley Cup runners-up for two consecutive seasons, the Edmonton Oilers remain among the favorites to hoist the fabled chalice in 2026.
But it’s not too difficult to surmise why the third time may not be the charm for Connor McDavid, Leon Draisaitl, Evan Bouchard and the rest of the team.
Believe it or not, a world exists where the Oilers aren’t even expected to make it to the Western Conference Finals. In a Tuesday column for Daily Faceoff, Matt Larkin lists Edmonton among the five NHL teams that he feels “got noticeably weaker” during the offseason.
“(T)his team simply isn’t as good as last year’s. You’re lying to yourself if you believe otherwise,” Larkin warned. “That doesn’t mean Edmonton’s pursuit of a third straight Cup Final appearance is doomed. Any team with McDavid, Draisaitl and Bouchard will contend. But a shallower team makes the task taller – and makes Edmonton far more vulnerable if any of the big three gets banged up.”
Analysts Sour on Oilers’ Stanley Cup Chances Due to Goaltending Concerns
But of course, it isn’t really any concerns with the team’s depth that riles up the naysayers. It’s the situation in net that has people like Gary Pearson of Sportsbook Review looking to hitch their wagon to a different horse.
“I backed the Oilers to win the Cup in the last two seasons,” Pearson lamented. “What do they say about fool me twice? I’m not willing to learn what they say about being fooled three times. Unless, of course, they finally sign an elite and consistent netminder.”
Or, more likely, trade for one, which isn’t the easiest transaction to make under the best of circumstances. It certainly doesn’t help to have a front office undergoing a transition period.
In the summer of 2024, after the Oilers lost to the Florida Panthers in the first of their back-to-back matchups in the Stanley Cup Finals, the team had a mutual parting of the ways with general manager Ken Holland. It had reportedly been agreed upon months prior, but was not made official until after the playoffs concluded.
It was about a month later that Stan Bowman was introduced as the team’s new GM, and he immediately had several important items on his to-do list, not the least of which was pending free agency for its three top players, as well as the RFA status of Dylan Holloway and Philip Broberg. For a team that had just advanced to the finals, and had both of its goaltenders under contract, addressing that position was not a high priority.
But perhaps it should have been. Because a year later, the Oilers have yet to address the goaltending situation, which most NHL insiders believe is what ultimately holds the team back from reaching the top.
And at least one insider suggests the chaos from last summer may have led to Edmonton missing out on a golden opportunity to make a major goaltending move.
Pierre McGuire Suggests Edmonton Missed Opportunity to Acquire Jeremy Swayman
Appearing Monday on Jeff Marek’s Daily Faceoff podcast “The Sheet,” NHL analyst Pierre McGuire revisited the contentious contract standoff between the Boston Bruins and goaltender Jeremy Swayman last summer. The dispute dragged on until just days before the regular season, when Swayman signed an eight-year, $66 million deal. The tension ran deep enough that, with Swayman holding out for all of training camp, McGuire suggested a serious trade offer from Edmonton might have pried him loose and made him an Oiler.
“Did they miss out on Swayman?” McGuire pondered. “The only reason I bring it up is … I was living in Boston then. It was volatile beyond belief with what was going on with the goaltending situation there. And I just wonder if they didn’t miss out on the potential of hitting a home run with Boston to solidify their goaltending position.”
McGuire stressed that the Jacobs family, which owns the Bruins through Delaware North, the company that was by the late Jeremy Jacobs Sr., “don’t like long protracted contract negotiations.” Marek agreed, noting how the situation involving Joe Thornton had worked out.
“When things go south, the Boston Bruins don’t hesitate to pull the trigger on big deals,” Marek acknowledged.
It’s unclear what Edmonton would have needed to give up to make such a deal work, but a tandem of Swayman and Stuart Skinner would have been a formidable one.
NHL Analyst Says Oilers Whiffed on ‘Home Run’ Trade for Star Goalie