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Edmonton Oilers’ Connor McDavid and Leon Draisaitl (Perry Nelson-Imagn Images)

McDavid’s Future Is Oilers’ Biggest Gamble Since Gretzky

Originally posted on The Hockey Writers | By The Old Prof | Last updated Oct 1, 2025 1:40 PM ET

Connor McDavid isn’t just a player on an expiring contract. He’s the best hockey player on the planet, the face of the Edmonton Oilers, and maybe the most gifted skater we’ve ever seen. So when whispers start about whether he’ll re-sign, short-term or long-term, it’s not just about the Oilers. It’s about the entire NHL.

McDavid’s contract is the biggest story in hockey, and in the video below, Frank Seravalli doesn’t shy away from it. He joins Kyper and Bourne to break down how Kirill Kaprizov’s deal impacts the talks in Edmonton, and what happens if McDavid stays unsigned past the season opener on Oct. 8.

That’s why every angle—how long he signs for, whether he signs at all, or if the Oilers should ever think of trading him—feels like it carries the weight of a franchise. The truth is, Edmonton is staring at the highest-stakes gamble it’s faced since the Wayne Gretzky trade.

If McDavid Signs a Short-Term Deal, It Will Be a Big Statement

Most NHL stars chase security: eight-year deals, life-changing money, guaranteed stability. McDavid could have all that in a heartbeat. However, some insiders believe he might opt for a shorter contract—perhaps two or three years.

Why? Not because he needs more money (he doesn’t), but because it gives him flexibility. It allows him to see if the Oilers can continue building a Stanley Cup contender around him. It also forces management to stay aggressive. Short deals are a message: “I’m here, but only as long as you hold up your end of the bargain.” For Edmonton and Oilers’ fans, that’s thrilling and terrifying at the same time.

What If McDavid Doesn’t Sign Soon?

Here’s where things get interesting. If McDavid doesn’t sign an extension before the season starts, nothing really changes—at least not right away. As Seravalli notes, one random date in October isn’t more important than one in February or June.

But what it does mean is uncertainty. Every game, every media scrum, every Oilers losing streak will come with the same question: “Is McDavid staying?” That noise can take a toll on a team. It can also define a season, but in which way, who knows?

NHL Trade Deadline Fantasy

Fans love to throw around trade deadline scenarios. What if the Dallas Stars offered Jason Robertson and Roope Hintz, Nick Kypreos asked? What if the New York Rangers came calling with a boatload of picks and prospects?

Seravalli didn’t blink: you don’t trade McDavid. Not if you’re in Edmonton. Not if you’ve built your entire franchise identity around him. Instead, the Oilers would rather ride it out, chase a Stanley Cup, and take their chances than flip the best player in hockey for a package that will never measure up.

It’s a gamble, yes—but it’s the right one. Because the moment you move McDavid, you’re not the Oilers anymore. You’re just another rebuilding team.

The NHL Players’ Union vs. the Player

Another wrinkle: the NHL Players’ Association (NHLPA). Kaprizov’s recent contract set a new salary bar, and union voices would love to see McDavid push it even higher. It’s good for every player when the game’s top player makes record-breaking money.

But does McDavid care about being the highest-paid? Probably not. Like Sidney Crosby before him, he’s wired differently. Winning matters more to McDavid than being the highest-paid player. He might even leave money on the table if it means Edmonton can build the kind of roster that gives him another shot at a Stanley Cup.

Pittsburgh Penguins’ Sidney Crosby gets off a backhand pass with Edmonton Oilers’ Connor McDavid defending (THE CANADIAN PRESS/ AP/Gene J. Puskar)

That kind of decision wouldn’t make agents or the union happy—but it would fit who McDavid is. It would make him even more of a hero in Edmonton with the Oilers’ fans.

Edmonton’s Big Gamble with McDavid

So, what does all this mean? It means the Oilers are living with risk, day in and day out. If McDavid re-signs, they’re golden. If he doesn’t, they’re playing chicken with the hockey gods, hoping a deep playoff run convinces him to stay.

It’s not an easy spot to be in, but maybe it’s the only spot they can be in because you don’t push McDavid out the door. You trust him. You try to win with him, and you hope that winning is enough to make him believe Edmonton is still the right place for him.

This isn’t just about numbers on a contract. It’s about legacy, identity, and the future of an entire franchise. The Oilers know it. McDavid knows it. And every hockey fan should know it too: the next move in this story could reshape the NHL.