Pickard’s agent reveals why the goalie chose loyalty and opportunity with the Edmonton Oilers, even amidst a crowded crease and waiver uncertainty.
The goaltending situation in Edmonton is somewhat messy. Starting the 2025-26 season with Stuart Skinner and Calvin Pickard as the 1A and 1B options, Skinner is now in Pittsburgh, and Pickard recently hit and cleared waivers. The Oilers are now trying to close the season out strong with Tristan Jarry and Connor Ingram.
All of this has left Pickard in an awkward spot, but according to Pickard's agent, Ritch Winter, even with options, leaving Edmonton wasn't an option his client considered.
Speaking candidly about the situation that saw Pickard become a third-string goalie, then go on waivers just ahead of the 2026 Winter Olympic break, Winter explained that despite the uncertainty surrounding the Oilers’ crease — and competition from Tristan Jarry and Connor Ingram — Pickard never seriously pushed for a fresh start.
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“There’s so many factors that go into winning,” Winter said, pointing to Pickard’s playoff résumé and the respect he’s earned inside Edmonton’s locker room. He believes Pickard was and is solid, but that his off-ice presence is just as important as the numbers he's putting up.
Winter highlighted Pickard’s 9-2 playoff record over the past two seasons and noted how quickly teammates rallied behind him when he cleared waivers. Leon Draisaitl took to social media within seconds, calling Pickard “maybe the best teammate we’ve ever had.”
Pickard knows that this group of Oilers is special. And, even if he's on the outside looking in, he's not completely out of the mix. With a chance to earn back his spot and with so much already committed to this group, he didn't want to leave his friends.
Winter said he and Pickard discussed the options available: a trade, a possible contract termination, staying in Edmonton as a third-string option and not playing, or a move to the AHL. When weighing his future, Pickard evaluated both opportunity and environment. Winter admitted they briefly explored alternatives but ultimately concluded there wasn’t “enough differentiation” between Edmonton’s three goaltenders to justify starting over elsewhere.
In other words, while they hold nothing against either netminder, Pickard and Winter don't believe that either Jarry or Ingram has necessarily cemented themselves in the role of starter and backup. Both have played well at times, but both have also struggled. So too, there are times that the Oilers don't play well in front of either one, something they've been known to do in front of Pickard. Winter suggested it shouldn't be that way, but it often is.
And, even if it turns out to be that both keep those spots, where else would Pickard go that was better than where he is?
Calvin Pickard had no desire to leave the Oilers. Photo by:
© Walter Tychnowicz Imagn Images“It’s not easy,” Winter said of finding a better situation around the league. He argued that 24 teams are out of the mix right away because they aren't really contenders. Others have salary cap issues they have to address.
Instead, Pickard chose familiarity, relationships, and a culture he believes in. Winter stressed that some players might be shaken by waiver uncertainty — but not Pickard.
“It might break another guy. It just motivates him.”
With the playoffs approaching and Edmonton still sorting out its goaltending picture, Winter made one thing clear: he expects Pickard to be right in the middle of it.
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