Connor McDavid’s contract status has clearly become the NHL’s biggest storyline heading into the 2025–26 season. Fans and media are hanging on every word McDavid says and reading into the things he doesn’t say. NHL insider Elliotte Friedman says the hockey world is right to be on edge.
On the latest 32 Thoughts Podcast, Friedman admitted he was “surprised” McDavid hadn’t signed an extension with the Edmonton Oilers by now, and that uncertainty is fueling league-wide speculation.
“I think guessing what he’s going to do here is a loser’s game,” Friedman said. “The amount of people who really know what McDavid is considering is very small. But what his words and actions have done is get other teams asking: is this real? Could Connor McDavid actually be an unrestricted free agent next July 1st?”
According to Friedman, rival clubs are already evaluating whether they should leave cap room untouched — just in case McDavid actually hits the open market. “If you believe you have a chance at him, you can’t do anything that prevents you from getting him if this occurs 10 months from now,” Friedman explained.
No one knows if McDavid will actually leave the Oilers. And, even if he does, no one knows what will attract him to a different organization. If winning is the only option, that leaves out 90% of NHL rosters.
Friedman drew a parallel to Christopher Walken’s famous “more cowbell” sketch, suggesting McDavid’s “only prescription” is now a Stanley Cup. After two straight Final losses, Friedman says McDavid’s obsession with winning has hit another level.
“He was always fanatical about winning. Now, he’s in another stratosphere,” Friedman said. “The only prescription is a Stanley Cup. I think he sees it as: he’s got to go to another level, and the team has to go to another level. And he’s not going to allow himself to be in a situation where he doesn’t think that’s possible.”
Part of McDavid’s hesitation, Friedman suggested, may come from questions about Edmonton’s long-term competitiveness. The Oilers moved on from promising young pieces like Dylan Holloway and Philip Broberg in order to acquire depth and have cap flexibility, but that may have left holes on the roster that McDavid now sees and wonders if that’s a long-term problem.
“He’s basically put the Oilers on notice,” Friedman said. “This is about staying power. It’s a really good team, but does it have three-to-five-year staying power? That’s what McDavid wants to be convinced of.”
It was suggested that there isn’t much the Oilers can do in the next few months to prove it, but one thing that will help is if Matt Savoie or Isaac Howard turns out to be an impact player.
Interestingly, Friedman believes McDavid would actually take less money to stay in Edmonton — provided he is convinced of the team’s commitment to winning. This isn’t about dollars and cents, something that McDavid admitted on Thursday when he spoke with TSN’s Ryan Rishaug. It’s not his priority to make the most money. After all, he’s so good, the money will always be on the table. Right now, it’s about winning and giving himself a shot to finally win.
“I don’t think he’s going to take a number that makes it impossible to build a championship team around him,” Friedman noted. “In fact, if he hit the market, my bet is he’d actually get more elsewhere than he would in Edmonton.”
Ultimately, Friedman circled back to the heart of McDavid’s hesitation: the pain of losing back-to-back Cup Finals. His motivation heading into the 2025-26 will be off the charts. That’s why he mentioned scoring 50 or 60 goals and that having done it before shouldn’t be a one-off.
The rest of the league should be ready for McDavid to come out of the gates blazing. “If Edmonton starts badly, that’s where you risk it,” Friedman said. “The noise can affect a team when things aren’t going well. And I’ve heard he wasn’t particularly happy in that room after Game 6.”
“When someone asks me what this is about, it’s those two losses in a row,” Friedman emphasized. “He can’t stand it. It makes him crazy. It’s scary for the rest of the league because it means he’s pushing himself to an even higher level. But in the short term, it’s also very intriguing for the rest of the league — because there’s a real question now about his future.”
For now, McDavid has stressed he’s not in a rush. Time is on his side, and he’s looking for a sign that he can feel comfortable in whatever decision he makes. This isn’t about looking outside the Oilers organization or feeling like there’s a better fit elsewhere. This is all about winning and for how many years he’ll give himself the chance to keep winning. It eats at him that he hasn’t yet. Money and everything else come a distant second.
The Oilers begin the season on October 9th against Calgary, and if no extension is in place by then, the circus will only grow.
As Friedman put it, “He’s already said this year is what matters. The question is whether Edmonton can convince him that the next three-to-five years matter too.”
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