Insider Offers Real Reason Behind Connor McDavid’s Team-Friendly Extension

The ups and downs of the Edmonton Oilers this season have once again started to raise questions about the future of Connor McDavid.

If the Oilers don’t win or reach a Stanley Cup Final in the next two years, will he ask out before the final year of his deal? Could that process be expedited if Edmonton flames out early in 2025–26? That chatter is starting to swirl around the hockey world, and everyone will be keeping a close eye on how the Oilers fare down the stretch.

---

Nobody will truly know what’s going to happen until we see how the next few months—and more likely the next year—unfold. However, Sportsnet insider Nick Kypreos believes the real reason McDavid signed such a team-friendly extension to stay in Edmonton goes beyond simply helping the team win. While Kypreos believes that was certainly part of it, he feels the main motivation was to show that if—or when—he leaves, no one can say he didn’t give it every last chance to win as an Oiler.

Kypreos said:

“Never got a raise, like, go find me a superstar that, I know he could have, but like he chose not to for a number of reasons. Not like that, not in their prime, not in their prime with a small window of you claiming that you are far and away the best player on the planet. My point is that he did it for a number of reasons, but the biggest reason of all is when I leave, no one can accuse me of not giving it every last chance to win here,”   

The 29-year-old McDavid’s two-year, $25 million extension signed with the Oilers in October begins next season (2026-27), and will expire following the 2027-28 campaign. 

His mention of “when I leave” feels like the most important part of it, though if Edmonton finds a way to get over the hump and win a Cup this year or next, that “when” becomes irrelevant.

All of this is to say there is immense pressure not just on McDavid, but especially on the Oilers to maximize this short window where the best player in the world is in his prime—and not even among the top five highest-paid players over the duration of his next deal.

McDavid is in year 11 in Edmonton; 11 years with one team is an eternity in sports. He truly has done everything he can to win as an Oiler, and while he still has a great opportunity to follow through on that—especially in such a weak Pacific Division—if it doesn’t happen, it will be hard to fault him should he ultimately decide to chase it elsewhere.

Next: Insider Asks the Difficult Question: What Has Happened to John Tavares?