Insider Expects Crucial Trade to Materialize for the Edmonton Oilers: ‘It’s Inevitable’

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Tom Banks
August 21, 2025  (8:16 PM)

The Edmonton Oilers.

Photo credit: Oil on Whyte

The Oilers need to make a big change, and according to Jason Gregor, it’s inevitable that they’ll trade either Stuart Skinner or Calvin Pickard this season.

The Edmonton Oilers have come so close over the past two seasons, falling to the Florida Panthers in the Stanley Cup Finals each time, and this summer, they’ve gone about shaking up their roster.

Stuart Skinner and Calvin Pickard Won’t Be the Oilers’ Tandem in the Playoffs, Per Jason Gregor

However, the changes may not be over, as Jason Gregor has addressed the team on the latest episode of the DFO Rundown, stating that when the trade deadline passes in 2026, the Oilers goaltending tandem will not be what it currently is.

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.

In his prediction, Gregor notes that either Calvin Pickard or Stuart Skinner will likely be on the way out, with many fans coming into this off-season expecting the move to happen before the 2025/26 campaign.

Ultimately though, it’s a move that needs to be made at some point, as the tandem have shown they’re not quite good enough to get the Oilers over the final hump, and with more goaltenders potentially becoming available ahead of the trade deadline, it’s a move that’s widely expected to happen.

Previously on HouseOfHockey

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