No team is under more pressure to win in 2026-27 than the Edmonton Oilers, because the future of their captain and the world’s best player could very well be riding on it.
It’s well known that Connor McDavid’s short-term contract extension to stay in Edmonton gave the Oilers a window to win while allowing him to reconsider all of his options again in a few years’ time.
If he doesn’t win a Stanley Cup in Edmonton during that time, many believe McDavid will leave to pursue a championship elsewhere. TSN analyst Jeff O’Neill recently went as far as to say that there’s a 0% chance the superstar center stays in Oil Country beyond his current deal.
“I think it’s zero. I think he told them I’ve got two years here and if we don’t win a Cup, I’m gonna go do it somewhere else. When your assistant captain says, you know, like, look around here, we’ve got two years to make this thing happen, I think that means something. And I’m not trying to cause a controversy. I think he told them I’m going to sign a two-year extension, I’m gonna chop that off the cap for you guys to try to do some work. That’s the window he gave them,”
The 29-year-old McDavid is, of course, about to enter the first year of the two-year, $25 million contract extension he signed with the Oilers in October 2025. He won the Art Ross Trophy in 2025-26 with 138 points (48 goals, 90 assists) in 82 games played.
All of this ultimately depends on how Edmonton fares this season and potentially next as well. The Oilers and their fans have known this from the moment that extension was signed, and it’s now crunch time to see whether they can get the job done or watch the McDavid slip away without winning the ultimate prize.
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