‘Whenever he’s ready’: Oilers’ GM Stan Bowman ready to work on Connor McDavid’s timeline for extension talks

When a generational player like Connor McDavid enters the final two years of his contract, the hockey world begins to buzz. The anxiety is natural. The speculation inevitable. For the Edmonton Oilers, though, the situation is being handled with remarkable calm and clarity — led by their new General Manager, Stan Bowman, who has made it clear that he’s prepared to operate on McDavid’s terms. There’s no rush. No pressure. No looming clock, at least not publicly. Bowman, who took the reins as GM following the team’s organizational shakeup this past offseason, has quickly learned one of the most important principles of his new job: with Connor McDavid, everything moves when he’s ready.

In a recent interview following Edmonton’s dramatic Stanley Cup Final appearance, Bowman was asked about potential extension talks with McDavid, who is eligible to sign a new contract beginning July 1, 2025. His response was direct but respectful: “Whenever he’s ready,” Bowman said. “Connor has earned the right to dictate his own timeline. We’ll be ready when he is.”

It was a simple phrase, but it carried enormous weight.

Bowman’s deference to McDavid’s process isn’t just good PR — it’s smart, player-centric leadership. The Oilers’ captain has spent the last nine years as the face of the franchise, leading the team through turbulent rebuilds, narrow playoff heartbreaks, and now, deep playoff runs that have put Edmonton back on the NHL’s center stage. His 2024–25 season was another masterpiece: 123 points in the regular season, 28 more in the postseason, and a level of playmaking and drive that once again left his peers and opponents shaking their heads in disbelief.

McDavid’s current eight-year, $100 million contract, signed in 2017, has been a bargain in hindsight. The deal carries a cap hit of $12.5 million — once the league’s highest, but now surpassed by several newer contracts. While the cap landscape has evolved, so has McDavid’s influence. He’s no longer just a phenom; he’s a foundational figure in modern hockey, and arguably its greatest active player.

And yet, despite the enormous leverage he holds, McDavid has never wielded it recklessly. He’s never flirted with public ultimatums. Never issued veiled trade demands. Never hinted at dissatisfaction, even when the Oilers failed to surround him with the depth or stability he deserved early in his career. He’s handled everything — from the weight of expectations to the demands of superstardom in a hockey-mad market — with poise and professionalism.

That’s why Bowman’s approach matters. It acknowledges who McDavid is, not just as a player, but as a person. There’s no scenario in which the Oilers force McDavid into a premature decision, or leak details to pressure him into talks. Bowman has made that clear internally, and externally. And according to team sources, the relationship between McDavid and the front office has never been stronger.

Much of that is due to the culture shift implemented over the past 18 months. Following the departure of Ken Holland and the surprising midseason firing of Jay Woodcroft in 2024, Edmonton’s brass pivoted toward a new leadership group, one more collaborative, more transparent, and more adaptive to modern player dynamics. Bowman’s hire was initially controversial, given his previous tenure in Chicago and the baggage attached to his exit, but within Edmonton, he has so far handled his second act with focus and humility. He knows his most important job isn’t managing the entire team — it’s making sure Connor McDavid wants to stay.

The importance of that goal cannot be overstated. McDavid is eligible to sign an extension as of next summer, and while there’s no sign he’s unhappy in Edmonton, there’s also no guarantee he’ll rush into a new deal. That’s not how he operates. McDavid is meticulous, thoughtful, and deeply invested in the success of the franchise. But he’s also 28. He’s entering the back half of his prime. And if the Oilers are going to remain legitimate contenders, he wants to see a long-term vision that matches his championship aspirations.

What that means, functionally, is that Bowman and the rest of the Oilers’ front office must deliver on multiple fronts: roster construction, development pipeline, organizational alignment, and cap efficiency. The recent extension of Leon Draisaitl was a massive step in that direction. Locking in McDavid’s closest on-ice ally to an eight-year deal showed not just loyalty, but a commitment to the core that has brought Edmonton to the brink of glory. The two superstars have spent nearly a decade together. Their chemistry is historic. Their bond is personal. It’s not lost on anyone that Draisaitl’s early extension was also a sign to McDavid — we want you here, with him, for the long haul.

Still, McDavid’s decision will be about more than just friendships. It will be about sustainability. The Oilers’ window is open now, but keeping it open requires precision. Key players like Evan Bouchard, Dylan Holloway, and Stuart Skinner are due for new contracts within the next 24 months. Veterans like Zach Hyman, Ryan Nugent-Hopkins, and Darnell Nurse are aging, with various cap implications. And younger depth — the kind required to win playoff wars — must continue to be developed or acquired affordably. In short, Bowman needs to do something few general managers have done successfully in the cap era: win now, while preparing for later.

That balancing act will undoubtedly influence McDavid’s outlook. If he signs an extension in 2025, it will likely be another long-term deal — eight years at what could be the highest AAV in league history. Some estimates already place the potential value north of $14 million per year, depending on the salary cap’s continued rise. That kind of commitment is generational. It also comes with the implicit question: Will the Oilers keep building a Cup-caliber team around me, every year?

So far, Bowman has responded to that challenge with pragmatism. He restructured the front office, adding voices from outside the organization and enhancing analytics and scouting departments. He’s worked closely with head coach Kris Knoblauch to establish a more consistent development pipeline from Bakersfield to Edmonton. And perhaps most importantly, he’s prioritized internal dialogue with the team’s core players — including McDavid — rather than shutting them out of decisions.

“Connor has earned a voice in the room,” Bowman said last month. “That doesn’t mean we’re turning the keys over, but it means we respect the investment he’s made in this franchise. We value his perspective. He’s not just a player — he’s a partner.”

That partnership model isn’t just lip service. Sources close to the team say McDavid was consulted before the Draisaitl deal was finalized, and was kept in the loop on trade deadline strategies, locker room dynamics, and coaching adjustments throughout the playoff run. He’s not micromanaging — that’s not his style. But he is informed. And he wants to be.

Still, McDavid’s focus right now isn’t on contracts. It’s on recovery. It’s on reflection. After coming so close to lifting the Stanley Cup, only to fall short in Game 7, there’s an emotional wound that takes time to heal. Friends and family say the loss hit him hard — not because he played poorly (he didn’t), but because he knows how rare these chances are. The NHL is unforgiving. Great teams don’t always win. Windows close fast.

That heartbreak, however, may also be a motivator. Those close to McDavid believe the 2025 loss — while painful — has only deepened his hunger. There’s no sense he’s looking elsewhere. No hint he wants out. In fact, some believe the loss may accelerate his desire to commit long-term, not as a reward, but as a recommitment to finishing what he started.

For now, though, Bowman and the Oilers will wait. Quietly, respectfully. There may be informal conversations. A few early frameworks laid out. But until McDavid is ready — until he’s had the offseason to reset, to reflect, to plan — there will be no pressure.

In many ways, this dynamic mirrors how McDavid has always operated. On his own timeline. With his own standards. Never swayed by the noise around him. And now, with a front office that finally understands and embraces that, the Oilers may be closer than ever to securing their captain for the long haul.

Whatever happens, whenever it happens, it will be done the right way. Because McDavid has earned that. And Bowman, to his credit, seems to know that every move from here on out begins with one core principle: trust.

So while Oilers fans may count down the days to July 1, 2025, anxiously refreshing news feeds and scanning every quote, the message from inside is simple.

Whenever he’s ready.