Connor McDavid is entering the final season of his contract with the Edmonton Oilers, and there is still no clarity on his long term future. With each passing day, the best hockey player in the world gets one step closer to becoming a free agent, and every other team in the NHL is taking notice.

McDavid has one year remaining on an eight-year deal that carries an AAV of $12.5 million. July 1 came and went without McDavid signing an extension with the Oilers, and the two sides still have yet to reach an agreement.

On the latest episode of the “32 Thoughts” podcast, Sportsnet insider Elliotte Friedman said he was “surprised” there wasn’t already an extension in place. Apparently, the rest of the NHL feels the same way, because the other 31 teams are starting to evaluate their chances of making the biggest free agent splash in league history.

“I think the biggest thing his words have done — or his actions have done — is they have other teams asking, ‘Is this real? Is there really a chance that Connor McDavid is going to be an unrestricted free agent next July 1?'” Friedman said.

McDavid’s next contract will almost certainly make him the highest paid player in NHL history, so most teams would probably have to clear some cap space in order to sign him, if it gets that far. Would teams be willing to make moves in the 2025-26 season that set them up to land McDavid next summer?

“If you believe you have a chance at him, or you want to have a chance at him, you have to make sure your decks are cleared,” Friedman said.

In an interview with TSN’s Ryan Rishaug earlier this week, McDavid was asked about his confidence level in the Oilers’ ability to win the Stanley Cup. The Edmonton captain said he has plenty of faith in the team, but he remained non-committal when it came to his long term plans.

“My confidence in this team this year has never been higher. That’s what I can say about that,” he said. “Listen, does anyone have a crystal ball and know what two years, three years, four years, five or whatever [will look like]? Nobody has a crystal ball. Nobody knows what that’s going to look like. The belief is not the issue — not that there is an issue.”

The words “this year” seem to be doing a lot of work there. What about down the line? Does McDavid think the Oilers front office is capable of surrounding him with the talent necessary to win hockey’s ultimate prize? After two straight Stanley Cup Final losses, McDavid has become obsessed with winning his first championship.

“Connor McDavid, I’ve been told by several people in the aftermath of that second defeat, has become even more fanatical about winning,” Friedman said. “All he cared about was winning before. Now, he’s in another stratosphere about it.”

Edmonton’s missteps

It would be hard to blame McDavid for losing faith in management after their moves last summer. Edmonton turned down the opportunity to match perfectly reasonable offer sheets on up-and-coming players Dylan Holloway and Philip Broberg, allowing them to become St. Louis Blues.

Holloway, 23, was second on the team in goals (26) and third in points (63). Broberg flashed some top-four potential on the blue line while contributing 29 points on the offensive end.

With Holloway and Broberg gone, Edmonton brought in veteran forwards Jeff Skinner and Viktor Arvidsson, two moves that fell flat. Neither player provided much in the way of reliable depth scoring, and Skinner was a healthy scratch for most of the playoffs.

Perhaps the most glaring problem the Oilers have faced over the last couple of years has been their inability to stop the puck with any consistency, especially when it matters most. In 2024-25, Edmonton chose to roll with the tandem of Stuart Skinner and Calvin Pickard. Those two were anywhere from pedestrian to below average in the regular season, and they didn’t get any better in the playoffs. Skinner and Pickard combined to allow 5.36 goals above average while posting a .882 save percentage, per Natural Stat Trick.

With players like McDavid, Leon Draisaitl and Evan Bouchard at the top of the lineup, Edmonton can outrun its depth and goaltending concerns in the regular season — and even for most of the postseason. However, when the Oilers have faced the impressive depth of the Florida Panthers, they’ve come up short both times.

McDavid’s decision

This conversation could all be moot in a matter of hours, days or weeks. McDavid could sign an extension with the Oilers and remain the cornerstone piece of that franchise for years to come. After all, Edmonton has reached the Final in back-to-back years, and it’s been a few plays away from a different result each time. Many teams would love to swap places with the Oilers.

That being said, the more these negotiations drag out, the more it seems like McDavid is making the team prove that it has a real long term vision for Stanley Cup contention. If the Oilers can’t fix the same issues that have plagued them throughout McDavid’s career, there will be 31 teams itching to make their pitch next July.