Ten Seasons, No Stanley Cup: Is It Finally Time for Connor McDavid to Leave Edmonton Oilers and Chase Glory Elsewhere?

Ten years. That’s how long Connor McDavid has dedicated himself to the Edmonton Oilers. A decade defined by breathtaking speed, game-breaking talent, and unmatched offensive brilliance—but not the one thing that defines hockey immortality: a Stanley Cup.

Now, with another season in the books and Edmonton once again falling short, the question that looms larger than ever is this: is it time for McDavid to move on?

It’s a question that feels almost blasphemous to some Oilers fans, who’ve watched McDavid transform their franchise into a perennial contender after years of futility. It’s also one that makes perfect sense to those outside the fanbase, observers and analysts who understand the relentless tick of the career clock, the finite number of chances even generational talents get at winning it all.

For McDavid, loyalty has never been in question. Drafted first overall in 2015, he became the face of not just a franchise, but of the entire league. His commitment has always been resolute. He signed an eight-year extension in 2017—at a time when the Oilers still looked promising, fresh off a second-round playoff appearance and boasting a strong young core.

Since then, though, the results have been maddeningly inconsistent. Sure, there have been thrilling playoff runs and moments of brilliance. But for all the flashes of what could be, the Oilers have never broken through. Not to the Cup Final. Not even to consistent contention. And for every magical McDavid rush or jaw-dropping stat line, there’s been a season-ending handshake line, heads hung low, potential unfulfilled.

It begs the question—how much longer can one of the greatest players of this generation wait?

McDavid will turn 29 during the 2026 postseason. That isn’t old by NHL standards, but it’s approaching the back half of his prime. He has just two years left on his contract. The Oilers still have time, but not much. Each playoff exit without a Cup brings them closer to a franchise-altering decision.

And McDavid—reserved, professional, eternally team-first—will eventually have to make one of his own.

This isn’t a column about blame. The Oilers have tried. They’ve made bold moves, signed and traded for veteran depth, hired and fired coaches, built around McDavid and Leon Draisaitl with varying degrees of success. They reached the Western Conference Final in 2022. They made it to the Stanley Cup Final in 2024-25, only to fall short in heartbreaking fashion. But it’s that loss that may have finally brought this debate to a head.

What more can McDavid do?

In this year’s playoffs alone, he led all scorers. He created offense out of nothing, carried Edmonton through moments when the depth disappeared, and was, once again, the best player on the planet. And yet, it wasn’t enough. It rarely has been.

There’s a parallel here that’s hard to ignore: LeBron James during his first stint in Cleveland. A hometown savior, carrying flawed teams deep into the postseason, his individual brilliance constantly undermined by a lack of consistent help or system support. Eventually, James left—not because he wanted to betray the franchise, but because he couldn’t afford to waste any more time waiting for the stars to align.

For McDavid, the idea of a “decision” looms in the not-so-distant future. Would he ever demand a trade? It’s hard to picture. But what happens if next season ends just like this one? Or the one after that? Does he re-sign in 2026 without knowing if his Cup dream will ever be realized in northern Alberta?

Some will argue he must stay. That great players don’t abandon the teams they were drafted by. That if McDavid wins, it should be as an Oiler, for a fanbase that’s supported him through every twist and turn. After all, Edmonton is hockey-mad, steeped in tradition, and McDavid has already etched his name beside Gretzky and Messier in franchise lore.

But what if he doesn’t win here?

The NHL is a league of parity. Even the greatest players can finish their careers without ever lifting the Cup. Marcel Dionne never did. Neither did Gilbert Perreault. And while McDavid has already carved out a legacy, his resume—no matter how decorated—won’t feel complete without that ring.

There are those who say chasing a title somewhere else is selfish. That loyalty matters. But ask Joe Thornton if he regrets not leaving San Jose earlier in his career. Ask Jarome Iginla if he wonders what might have been. Or, conversely, ask Ray Bourque if his late-career move to Colorado and eventual Cup win didn’t mean everything.

The truth is, the NHL world would understand if McDavid decided to look elsewhere in 2026. He’s given everything to Edmonton. He’s performed at an absurdly high level year after year, dragging his team forward with generational brilliance. He’s never complained. Never publicly criticized management. Never threatened to leave. That kind of patience and professionalism earns him the right to eventually explore another chapter—if he chooses to.

Of course, the Oilers still have time to convince him to stay. Maybe they finally get over the hump next season. Maybe they double down, surround him with the depth and stability required to win. Maybe the Finals loss fuels them, not breaks them.

But it’s clear that time is now a factor. The countdown has started, even if nobody in the Oilers’ front office wants to say it out loud. Two years left. Two chances to give McDavid what he deserves: not just another strong season or impressive stats, but a legitimate shot at winning it all.

The fans feel it, too. There’s a quiet desperation in the way they cheer, a knowledge that their window with McDavid and Draisaitl is rapidly narrowing. The Oilers are good—very good—but good isn’t enough when you’ve got greatness on your roster and no banners to show for it.

Some will scoff at this conversation, dismiss it as premature or reactionary. They’ll point to other superstars who waited it out and were rewarded—Alex Ovechkin, for instance, won his first Cup in Year 13. They’ll say McDavid isn’t wired to give up or demand change. And maybe they’re right.

But professional sports are ruthless. They’re about moments, opportunities, windows. They don’t wait for loyalty to pay off. And Connor McDavid—this quiet, explosive, generational marvel—has waited long enough.

If Edmonton can’t win it all in the next two years, if they fall short yet again, then the most pressing question in hockey won’t just be whether McDavid should leave.

It’ll be: how did it come to this?

Because no one, absolutely no one, deserves to win more than Connor McDavid.

And eventually, he might have to go find that win somewhere else.