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Oilers Goalie Shakeup Coming? Jason Gregor Makes Bold Trade Deadline Guarantee


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Daniel Lucente
August 21, 2025  (1:41 PM)
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Edmonton Oilers' Calvin Pickard and Stuart Skinner have a chat
Photo credit: Sportsnet

NHL insider Jason Gregor made a bold guarantee on the DFO Rundown, stating that it's inevitable that either Stuart Skinner or Calvin Pickard will be gone next year.

Goaltending has been the shared ailment thus far in the Connor McDavid era with the Edmonton Oilers. With one of the league's elite offenses, the Oilers continue to look for a solid number one goaltender, and that absence continues to haunt them.
The past two seasons have ended on a disappointing whim with Edmonton falling short by a hair in the Stanley Cup Final to the Florida Panthers.
Why? Florida possessed Sergei Bobrovsky, an otherworldly, consistent presence in net, and the Oilers are beset by inconsistency and subpar play from their stable of goalies.
This season has unfolded very similarly. The combination of Stuart Skinner and Calvin Pickard has still not demonstrated that they can perform when it matters.

Both Oilers Goalies had Save Percentages Under .900 in the Playoffs

With both goaltenders posting sub-.900 save percentages in the playoffs, the verdict is already in: you don't win titles with poor goaltending.
As Edmonton is attempting to begin the 2025-26 season with Skinner and Pickard, not many believe this combination makes sense.
On the "DFO Rundown," insider Jason Gregor boldly guaranteed that it's highly probable something transpires prior to the 2026 NHL trade deadline, and he'd be surprised if the two are still an item by then.
"I'll be surprised if after the trade deadline...the same two goalies are in Edmonton in Pickard and Skinner, I just think it's inevitable there's going to be a change there."

- Jason Gregor
It all hinges on how they perform this season. They were handed a second chance, and there's very little room for error.
General manager Stan Bowman remained faithful to his goalies a year ago by not pulling the trigger at last year's trade deadline. This year, patience won't be so lenient.
The Oilers have the talent to win it all, but without reliability in net, the narrative will be a broken record quickly. Edmonton needs to act now.
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Oilers Goalie Shakeup Coming? Jason Gregor Makes Bold Trade Deadline Guarantee

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