NHL analyst warns Connor McDavid could leave Oilers to chase Stanley Cup

“These are all the kinds of players that you need to build out a roster that can be successful in the playoffs, and they’re all no longer in Edmonton,” Wyshynski said.

Wyshynski highlighted a deeper issue, saying, “The mismanagement has stretched beyond the last few seasons. Do you realize that only three forwards that the Oilers have drafted since drafting McDavid are still in the National Hockey League?”

That lack of pipeline depth has forced the team into short-term fixes rather than sustainable growth.

The result is a top-heavy lineup that struggles when stars are limited. Both McDavid and Leon Draisaitl played through injuries in the series, exposing the team’s fragile structure. Vasily Podkolzin, Kasperi Kapanen, and Ryan Nugent-Hopkins leveled up their effort, but the team still struggled.

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Defensive breakdowns, especially in the decisive Game 6, further underlined systemic issues.

What this means for Connor McDavid’s future

McDavid remains under contract through 2028, and that timeline gives Edmonton a clear window to contend, but pressure is building quickly.

Elite players in their prime are not expected to wait through prolonged instability. McDavid continues to produce at a historic level, recording 138 points (his 9th 100-point season) and claiming another scoring title this season. However, playoff success remains the defining metric.

Wyshynski mentioned the same saying, “I don’t want to see Connor McDavid retire without winning the Stanley Cup. I don’t want to have those debates when the guy goes into the Hall of Fame.

“But unless this roster stops being, in the words of McDavid, ‘average’ in a hurry, it might have to happen somewhere other than Edmonton.”

The Oilers now face a critical offseason. Management must rebuild depth, stabilize the defense, and support their core stars with a balanced roster. Failure to do so could shift the conversation from speculation to reality.

For now, McDavid stays. But if Edmonton cannot match that ambition, the league’s best player may eventually look elsewhere to chase the Stanley Cup.