What's next for Connor McDavid? Four scenarios for Oilers superstar

“Winning would be at the top of the list,” said McDavid, who will be an unrestricted free agent after the 2025-26 season. Then he added, “If I feel that there’s a good window to win here over and over again, then signing is no problem.”

That’s not “I’m staying.” It’s cautious. Vague. Calculated. Especially when the 28-year-old superstar added, “I’m not in a rush to make any decision. So I don't think that there needs to be any timeline.”

Sportsnet’s Elliotte Friedman insists it’s a lock McDavid stays in Edmonton. But until McDavid signs a deal, anything is on the table.

Here are four possible timelines for how this could play out:

1. Signs this offseason

This would be the cleanest scenario. Get the deal done and silence the noise. But McDavid’s tone makes it clear: A July 1 signing isn’t coming. “I’m not in a rush,” he said, and it sounded genuine.

Still, if he and the Oilers map out a clear long-term plan, and if he feels confident the team can win “over and over again,” as he put it, an extension later in the offseason is still possible. Even if it's a four-year deal, similar to what Toronto center Auston Matthews did with his last contract. Then McDavid would get more on his next contract, as the cap goes up.

Last season, Edmonton star Leon Draisaitl signed his own extension on Sept. 3. So, Edmonton clearly isn’t afraid of letting things marinate. The question is: Does McDavid want to stay in Edmonton for the long haul?

2. Signs during the season

This is the trickiest path. NHL stars rarely sign massive extensions midseason, especially not ones with McDavid-level stakes. It’s a distraction, and the spotlight would only get hotter with each game.

That said, there’s a slim chance McDavid will decide to end the speculation during a high point, maybe after a strong first half or an early clinch of a playoff spot for the Oilers. If Edmonton comes out flying and looks like a contender again, he might feel more confident about the long-term outlook.

However, as of now, this feels more like a “break glass in case of clarity” scenario rather than a plan.

3. Re-signs with the Oilers next offseason

Waiting until July 1, 2026, would turn up the heat and speculation.

Still, McDavid could take the year to evaluate everything: the team’s direction, his health and whether the Oilers still feel like home. He’s loyal, and if Edmonton keeps contending, he may take the decision down to the wire.

But the longer this drags out, the more noise and suitors it invites.

4. Tests free agency

This is the Oilers' worst-case scenario and Toronto’s dream.

If McDavid hits the open market, there’s a chance he doesn’t come back. 

Teams will line up, but Toronto will lead the pack. As a native of the greater Toronto area, it’s home for McDavid. It’s a hockey-mad market. And if the Maple Leafs are still in the mix, the story writes itself: McDavid comes back to Ontario to chase a title with Matthews to end the longest Stanley Cup drought in NHL history.

Unlikely? Maybe. Impossible? Not if winning takes priority over loyalty.