When Connor McDavid inked a two-year, $25 million extension with the Edmonton Oilers just ahead of the 2025-26 season, the message was clear: the clock is ticking. Edmonton has a window - a short one - to deliver a Stanley Cup while the best player in the world is still in town. And while that storyline had cooled a bit thanks to the Oilers’ resurgence this season, a recent theory has stirred the pot once again.
Ryan Whitney of Spittin’ Chiclets floated an intriguing idea: what if Detroit is quietly keeping the door open for McDavid? The theory centers on Red Wings GM Steve Yzerman and his calculated approach to roster building. Whitney speculated that Yzerman might be passing on certain big-name acquisitions - players like Elias Pettersson, Nazem Kadri, and Vincent Trocheck, as well as defensemen like Quinn Hughes and Rasmus Andersson - to preserve cap space and roster flexibility in case McDavid hits the open market in 2028.
It’s a big “what if,” but it’s not entirely out of left field. Yzerman is known for playing the long game, and if McDavid were to consider a move in a couple of years, Detroit - with its rich hockey history, young core, and improving trajectory - could be an attractive destination.
McDavid, now 29, is in the middle of another jaw-dropping season. Through 54 games, he’s already put up 92 points - 33 goals and 59 assists - and he’s making it look routine.
His extension doesn’t kick in until 2026-27, meaning he’s under contract through the 2027-28 season. After that?
All bets are off.
But let’s not get too far ahead of ourselves. Right now, the Oilers are locked in.
They’ve surged to the top of the Pacific Division, and McDavid - alongside Leon Draisaitl - is playing arguably the best hockey of his career. Edmonton looks every bit like a team capable of making a third straight run to the Stanley Cup Final.
The difference this time? They’re aiming to finish the job.
General Manager Stan Bowman knows the stakes. The March 6 trade deadline is looming, and there’s pressure to bolster the roster for a deep playoff push.
The Oilers don’t just want to be contenders - they need to win. Because if they don’t?
The McDavid speculation will only grow louder.
For now, though, the focus in Edmonton is singular: win, and win now. The rest - Detroit rumors, free agency whispers, long-term hypotheticals - can wait.
But if this core doesn’t deliver in the next two seasons, the hockey world will be watching. And teams like the Red Wings might just be waiting in the wings.