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Monday Mailbag: How long do the Oilers wait to hire their new head coach?

By baggedmilk
May 25, 2026, 09:00 EDTUpdated: May 24, 2026, 22:48 EDT
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 timelines, pressure on the management, Cup or bust, 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.
Stephen R. Sylvanie-Imagn ImagesNov 10, 2025; Las Vegas, Nevada, USA; Vegas Golden Knights head coach Bruce Cassidy takes questions during a presser after the Florida Panthers defeated the Golden Knights 3-2 at T-Mobile Arena. Mandatory Credit: Stephen R. Sylvanie-Imagn Images
1) Alex asks – How long should the Oilers be willing to wait for Bruce Cassidy before moving on to a Plan B?
Jason Gregor:
No rush. Wait until Vegas is out. You don’t need a head coach right away. If they believe Cassidy is the guy, then wait, if not do an extensive search and interview other coaches.
Tyler Yaremchuk:
This is an interesting question for a few reasons. Bruce Cassidy is clearly the best candidate out there and other than Peter Laviolette, I’m not sure if there is another great option out there. So if I’m the Oilers, I would be talking to Laviolette and keeping a close tab on his situation and if he starts interviewing in other spots, I would jump and make sure I get him. If Laviolette isn’t close on another job, then I would wait as long as possible for Cassidy.
Zach Laing:
I question whether the Golden Knights will even grant the Oilers permission to speak with him, let alone before their season is over. While the team received permission to speak with Craig Berube, we haven’t heard anything about a formal conversation in the last week. The team needs to broaden this search, and getting in touch with Peter Laviolette is a great place to start.
Michael Menzies:
They have to be willing to wait a while – at least until Vegas is eliminated, which is looking like more of a mid-June thing than an immediate one. The issue is…do they know what Plan B is? I’m not sure they do yet. The first full week of a coaching search hasn’t quite been the interview-laden period one usually hears about.
Baggedmilk:
I think they need to get their coach in place before the NHL Draft, because you’d want them around for the trade and selection talk that happens over the weekend. Same goes for free agency.
Kiyoshi Mio-Imagn ImagesApr 24, 2026; Anaheim, California, USA; Edmonton Oilers center Connor McDavid (97) heads to a penalty box during the third period against the Anaheim Ducks in game three of the first round of the 2026 Stanley Cup Playoffs at Honda Center. Mandatory Credit: Kiyoshi Mio-Imagn Images
2) Cliff asks – Is there another organization in the NHL with more pressure to get things right than the Edmonton Oilers? How can they avoid making panic moves just because the team is on a McDavid countdown clock?
Jason Gregor:
The Dallas Stars are in a similar boat. In the last seven years, they’ve been to the Cup Final and three Conference Finals. I see them in a similar boat, but I’d argue this summer is bigger for them as they have to make a decision on Jason Robertson. Do they pay him or trade him? But the Oilers SHOULD NOT make panic moves. I argued the Jarry trade was a panic move. Be creative, be aggressive, but don’t panic.
Tyler Yaremchuk:
No. Connor McDavid is the best player in the world and if this season goes poorly for the Oilers, then they could very well lose him. No other team has that kind of ‘win now’ pressure.
Zach Laing:
No, the pressure is massive in Edmonton. They could avoid any more panic moves by replacing Stan Bowman.
Michael Menzies:
Probably not. If McDavid is the game’s best player and the best one without a Cup, then it’s the Oilers with the most pressure. The thing is, the Oilers have felt this pressure for a decade and therefore have already made panic moves. There’s no guarantee either way. The surest way to avoid a panic move is to have a very quiet summer…is that good? Maybe it is. Either way, Bowman needs a steady hand threading this needle.
Baggedmilk:
No, and I really don’t think it’s close. And they’ve done it to themselves. Smartest people in the room, always have been.
Baggedmilk/OilersnationStan Bowman Edmonton Oilers GM free agency live blog
3) James in Peterborough asks – With the relatively weak Free Agent class this year, looking internally might prove the most prudent. How many players within the organization could reasonably be on the club’s NHL roster in the fall and stick?
Jason Gregor:
Isaac Howard is the main one I see. Josh Samanski should be a regular as well. Quinn Hutson will push for a spot, but I don’t see room for him and Howard in the top nine. Alec Regula, after finally getting to play some games, will push for a roster spot in camp.
Tyler Yaremchuk:
I think both Josh Samanski and Ike Howard are close to locks. The Oilers will likely need them to be key players next season. Outside of that, I think Quinn Hutson should be able to make a push, and I’m curious what Owen Michaels can do, but my expectations for him are low. Connor Ungar would be the one wildcard between the pipes.
Zach Laing:
Isaac Howard is front and centre in those talks. If the Oilers get an entry-level contract done with Maxim Berezkin, he’ll be a top candidate too. Quinn Hutson and Roby Jarvëntie will likely see NHL games next season.
Michael Menzies:
I think the two with the best shot are Isaac Howard and Maxim Berezkin (if he indeed signs). Then, Quinn Hutson and Alec Regula. That’s based on where they finished their seasons and assumes Josh Samanski is entrenched as an Oiler.
Baggedmilk:
Imma say Isaac Howard, Josh Samanski, and Quinn Hutson will spend the bulk of the full-time or call-up time on the NHL roster next year.

4) Ed M. asks – Given that “Cup or bust” seems to be the expectation by many. Although Katz’s expectations are the only ones that count. Do you think Stan Bowman and/or Jeff Jackson will be fired if there is no cup in 2027? If not, what team performance will be required of SB and or JJ to keep their jobs?
Jason Gregor:
Too hard of a what-if. If the only way to retain them is a Cup Final, then they could make desperation moves, and that won’t help. I’d say the team needs a strong regular season, and if they win two rounds, then they’d have a strong case to stay. Doesn’t mean they will, but they need a good summer that includes no glaring overpayments and a creative trade to bolster the roster. Otherwise, I could see them on a short leash.
Tyler Yaremchuk:
Yes. They have to be gone if a Stanley Cup isn’t won in 2027. That’s how high the stakes are. This upcoming season either ends with a Stanley Cup banner or it goes down as a failure.
Zach Laing:
Stan Bowman got his bullet in firing Kris Knoblauch, so nobody’s seat is hotter in Edmonton than his. Jeff Jackson should be right out the door at the same time whenever that happens.
Michael Menzies:
I don’t think it’s a guarantee they’re fired. To me, it matters when and how they lose. Do Bowman’s additions this off-season, or seasons past, benefit the team? Or do glaring issues like Tristan Jarry help sink them? That’ll be the key. If they go to the third round and further, they’re probably both safe.
Baggedmilk:
They’ll get sent out as a 2-for-1 if these next two years go sideways, I can guarantee that.

5) Alex asks – We’ve officially hit patio season, and I want to know what is the ideal patio drink and appetizer that you’d order on a hot summer day in Edmonton?
Jason Gregor:
If it is just one or two, then I 20 oz pint of your favourite beer. The best appetizer for the patio is nachos.
Tyler Yaremchuk:
Ice cold lager (or a hazy IPA if we’re going the craft route) and something light when the sun is out. The cold beer is what’s really important here.
Zach Laing:
Now we’re getting to the important questions. It’s mathematically impossible to have a bad time on a patio when you have a Corona with a lime and some nachos.
Michael Menzies:
Either a cold beer like a Canadian or Budweiser, or if I’m craving something lighter, a Vodka-7. If it’s hot and daytime, I’m probably not eating outside on a patio, to be honest. The sunshine and heat equal a beverage to me. If it’s later and cooler, twist my arm for Bruschetta.
Baggedmilk:
Oh, great question. Couple of different ways we can go here.
1) A nice cold beer and wings are always elite. Either a pint or one of those team towers with the ice cylinder down the middle.
2) Margaritas and nachos. It’s a fiesta!
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