Edmonton’s window to win a Stanley Cup might be slamming shut on Connor McDavid’s legacy.

After losing the last two Stanley Cup finals, the Oilers got eliminated by Anaheim in this year’s first round and looked “mediocre” all season, to quote McDavid. (Not exactly what a leader says, no matter how frustrated.)

What will McDavid do?

If McDavid never wins a Stanley Cup, it stains his status as a top-five player of all time. Any claim thereof will be statistically-based and have lots of detractors.

You’ve got to win. The current occupants of those spots all did: Mario Lemieux, Bobby Orr, Wayne Gretzky, Sidney Crosby and Gordie Howe.

If McDavid has to leave Edmonton to win, that’s a different kind of stain.

A star should win where he starts. Ray Bourque’s finagled Cup with Colorado at career’s end has a stench about it. Bourque failed in Boston, then rented himself out.

It’s not like McDavid is blameless in Edmonton going without a Cup during his tenure.

The last three times the Oilers got eliminated, McDavid went pointless in that game.

But McDavid was playoff MVP in 2024 and has 156 points in 102 postseason contests.

Edmonton coach Kris Knoblauch said McDavid played with a fracture in his foot/ankle during this year’s playoffs. That sounds both limiting and convenient.

Edmonton has bigger issues than McDavid occasionally being held off the scoresheet.

Like goaltending. This parish was unsurprised when Tristan Jarry didn’t solve that problem.

McDavid, 29, signed a two-year bridge extension this past October. That deal has a reasonable salary-cap hit of $12.5 million, giving the Oilers a bit of financial flexibility to further build around McDavid.

But not as much room as Crosby has given the Penguins with his cap hit of $8.7 million.

Guess it depends on how bad you want to win.

McDavid likely has an exit strategy.

If Edmonton goes flat again next season, perhaps he leaves the Oilers as early as next year’s NHL trade deadline.

McDavid has had a checkered career.

There’s no doubting his quality: He’s got six scoring titles and three regular-season MVPs.

McDavid certainly passes the eye test: He’s the best ever when it comes to executing at blurry speed. That’s his superpower.

But he isn’t the face of hockey. That’s still Crosby and Alex Ovechkin, even at 38 and 40, respectively.

Part of that is playing in Edmonton. (At least Crosby and Ovechkin had the time zone working in their favor.)

Part of that is having had charisma bypass surgery. (McDavid is a sourpuss.)

Part of that is not winning.

After the Penguins were eliminated, some dopey hockey blogger went on X and posted all of the team’s playoff failures since 2018 and said that “Sidney Crosby is running out of time.”

Crosby has three Stanley Cups and six international gold medals.

McDavid is the one running out of time.