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Monday Mailbag: Did the Oilers give Calvin Pickard a raw deal?

By baggedmilk
Feb 16, 2026, 09:00 ESTUpdated: Feb 16, 2026, 00:10 EST
Good morning, everyone, and a happy Monday to you all. As per tradition, I’ve got a brand new mailbag set to go after taking your questions and sending them to the crew for their takes. This week, we’re discussing the Oilers’ coaching noise, Paul Coffey’s return, Leon Draisaitl’s comments on the team, and more. If you’ve got a question you’d like to ask, email it to me at baggedmilk@oilersnation.com or on Twitter at @jsbmbaggedmilk, and I’ll get to you as soon as I can.

Dec 29, 2025; Winnipeg, Manitoba, CAN; Edmonton Oilers goaltender Calvin Pickard (30) and Edmonton Oilers goaltender Connor Ingram (39) celebrate their victory over the Winnipeg Jets at Canada Life Centre. Mandatory Credit: James Carey Lauder-Imagn Images
1) Garrett asks – Calvin Pickard’s agent seemed to imply that he got the raw end of the deal when compared to Tristan Jarry and Connor Ingram. Do you think Pickard should have been given more of a chance to prove himself against the other two?
Jason Gregor:
His main point was that Pickard has a stronger playoff track record. When Skinner was traded, Jarry started three of the first four games and got injured in his third start. Pickard came in and then started the next game. Then Ingram started the next three, then they rotated, Pickard, Ingram, for the next six before Ingram started the seventh game. Then Jarry returned, and Pickard didn’t play again. They knew what they had in Pickard and opted to go with the other two. We will see how it plays out down the stretch, but I’m not sure that Pickard getting one start when Ingram started three in a row would have changed much.
Tyler Yaremchuk:
No. He was statistically one of the worst goalies in the NHL for the first two months of the season. If anything, he’s lucky he got the leash he did.
Woz:
It’s tough to say. He was splitting the workload specifically with Skinner before he got traded. His numbers haven’t reflected well when given the opportunity. I think the Oilers wanted a change of scenery in net, and, unsurprisingly, Pickard’s agent went on the defensive for his client.
Baggedmilk:
Numbers don’t lie, and pro sports are cold. I love Calvin Pickard for what he did in the playoffs, but if the backup spot is between him or Ingram, the numbers tilt one way over the other. Agents gonna agent, man.

Feb 13, 2026; Milan, Italy; Connor McDavid of Canada in action with Michael Fora of Switzerland in men’s ice hockey group A play during the Milano Cortina 2026 Olympic Winter Games at Milano Santagiulia Ice Hockey Arena. Mandatory Credit: Geoff Burke-Imagn Images
2) Kevin asks – When are we going to see Connor McDavid hitting like a truck in an Oiler jersey?
Jason Gregor:
You have. People just forget. He’s had some big hits in the NHL, and I expect he will again.
Tyler Yaremchuk:
We see him find this level every playoffs. Maybe it doesn’t quite come through with big hits, but he cranks up the intensity every spring in an Oilers jersey, and I don’t like pretending that he doesn’t.
Woz:
McDavid loves to bring the physicality when the games matter more. We’ve seen him drop guys on the ground during the playoffs. I remember his first playoff game in 2017, and he laid a Sharks player out flat on the ice in his first few shifts.
Baggedmilk:
We’ve seen Connor truck some people in the playoffs when the games matter most. He elevates for those games, and that’s what’s happening in the Olympics.

Jun 3, 2025; Edmonton, Alberta, CAN; Edmonton Oilers general manager Stan Bowman along with Oilers head coach Kris Knoblauch are seen during media day in advance of the 2025 Stanley Cup Final at Rogers Place. Mandatory Credit: Walter Tychnowicz-Imagn Images
3) Macyn asks – Are you expecting the Oilers to try and make a splash at the trade deadline or would you predict a year of nibbling around the edges?
Jason Gregor:
I think they need to make a key upgrade, either for a top-six LW or a second-pair RD, but the latter would require moving out a significant salary on the blue line, I think.
Tyler Yaremchuk:
I think it will be more nibbling. I think a good third-line centre, a solid depth winger and a bit of added depth on the blueline is way more likely than a true impact top-six forward. A player like Boone Jenner would be interesting and would be a guy who could move around the lineup, though.
Woz:
If they can move some money out and create flexibility with their cap situation, they will attempt to make a splash, I believe. Who the player will be is hard to say right now, but many signs point to a bottom-six player who can make an impact.
Baggedmilk:
I remember when the Ekholm trade happened, the Oilers had next to no cap space, and none of us saw that one coming. So, my approach to the deadline these days has been to wait and see. I always hope for big swings, but I never really expect them to happen.

Apr 21, 2025; Los Angeles, California, USA; LA Kings center Phillip Danault (24) and left wing Kevin Fiala (22) enter the ice during game one of the first round of the 2025 Stanley Cup Playoffs against the Edmonton Oilers at Crypto.com Arena. Mandatory Credit: Kirby Lee-Imagn Images
4) Ryan asks – Kevin Fiala had a major injury in Friday’s game between Canada and Switzerland, which is the exact kind of injury NHL teams probably use as an excuse not to go. Do you think having a player lose the rest of their season like that should be a factor in deciding whether or not NHL athletes participate in future games?
Jason Gregor:
Fiala could have been injured in the NHL just like Brayden Point, Anthony Cirelli, Seth Jones, Jonas Brodin and Simon Edvindsson were leading up to the tournament, not to mention Brad Marchand is banged up and so are others. It 100% should not be a factor. Injuries can occur at any time and players know it. They will all gladly take the small chance of an injury in the Olympics instead of not participating.
Tyler Yaremchuk:
No. Injuries happen and if you were to ask every player there, they would all say that the risk of injury is worth it for the chance to compete for their countries. Sucks for Fiala and Kings fans, but it’s not a reason to stop going to the Olympics.
Woz:
The players know the risks, and the only downside to the Olympics is the timing of the event. If this was in the summer or early fall, I don’t think it would be much of a conversation, but the players want to play on this stage as much as they want to play in the Stanley Cup Finals.
Baggedmilk:
It would be the owners who wouldn’t want their guys to go over and get injured. That really sucked for Fiala because it was such a freak accident, but you’d have a hard time preventing these guys from representing their countries. They know hockey isn’t tummy tickles.

Feb 13, 2026; Milan, Italy; Connor McDavid of Canada celebrates with teammates after scoring their first goal against Switzerland in men’s ice hockey group A play during the Milano Cortina 2026 Olympic Winter Games at Milano Santagiulia Ice Hockey Arena. Mandatory Credit: Geoff Burke-Imagn Images
5) Glenn asks – We’re a week into the Olympics now, and it’s remarkable how many unique sports are played as part of the games. Are there any sports, athletes, or performances that have particularly caught your attention so far?
Jason Gregor:
Kingbury is amazing. The Skeleton is wild to watch. Downhill skiers are absolutely fearless. The ski and snowboard cross is on the edge of falling at every turn, it seems. And moguls at that speed, and then you mix in aerials with it. Wild stuff. And short track speed skating is amazing theatre. I respect and enjoy watching any event, to be honest. I love it.
Tyler Yaremchuk:
I love all the snowboarding and skiing races. The events where they combine speed with pulling off these elaborate tricks. It’s crazy. I’m also a die-hard curling fan, so I’ve been glued to that. Watching all the casuals freak out over the Marc Kennedy situation has been both frustrating and hilarious. Real curling fans know that this is a non-story.
Woz:
No sport in particular, I’ve been locked into hockey. Shoutout to Damian Clara for his performance for Italy against Sweden.
Baggedmilk:
All of them. Cross-country skiing, moguls, speed skating, skeleton, snowboard half-pipe/big air, ski jumping… they’re all nuts and awesome to watch. I love the Olympics.
PRESENTED BY DAILY FACEOFF’S OLYMPIC COVERAGE
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Breaking News
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