OilersNation has no direct affiliation to the Edmonton Oilers, Oilers Entertainment Group, NHL, or NHLPA
Monday Mailbag: How should the Oilers approach shallow free agency pool?
Edmonton Oilers Stan Bowman Jeff Jackson
baggedmilk
May 18, 2026, 09:00 EDTUpdated: May 18, 2026, 11:02 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 needs, Vegas dragging their feet with Bruce Cassidy, free agency, 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.
Edmonton Oilers Kris Knoblauch
Apr 7, 2026; Salt Lake City, Utah, USA; Edmonton Oilers head coach Kris Knoblauch watches play against the Utah Mammoth during the first period at Delta Center. Mandatory Credit: Rob Gray-Imagn Images
1) Yves asks – Assuming a new coach isn’t hired by the time this is posted, what type of coach do you think best suits this Oilers group? Do they need a more militant style coach after the softer touch of Kris Knoblauch? Do they need a defensive specialist based on their goals-against struggles from last season?
Tyler Yaremchuk:
They need a coach with a bit more of a fiery personality. The Oilers sleepwalked their way through the regular season and I really think that if they had a coach who was a little harder on them and maybe held them a little more accountable at times, they would have found their game for longer stretches than they did. I think a defensive specialist is fine, but I also don’t think Knoblauch was a bad defensive coach. I just think they need a new voice.
Mike Menzies:
Usually, a coaching successor completes the yin-yang cycle. With that in mind, a demanding coach who will hold everyone accountable equally is what they’ll look for. Or as Bowman called it, “compliance.” Carrot, stick. Carrot, stick. So on, so forth.
Zach Laing:
They’re looking for a coach along the lines of a Bruce Cassidy, a Peter Laviolette, or a Craig Berube. Three names we’ve heard firmly, or loosly linked so far. The first two are the best options and No. 3 is about as far from the guy they should hire, but all three are known for not being docile, that’s for sure.
Baggedmilk:
I think they need someone with a little fire behind them. I want to see someone who can teach well, but isn’t afraid to blow his stack when things go sideways. I want to see a coach who defends his team and players instead of taking everything so calmly.
Bruce CassidyMatt Krohn-USA TODAY Sports
Mar 30, 2024; Saint Paul, Minnesota, USA; Vegas Golden Knights head coach Bruce Cassidy looks on during the second period against the Minnesota Wild at Xcel Energy Center. Mandatory Credit: Matt Krohn-USA TODAY Sports
2) James asks – Even though it’s annoying that Vegas is stalling on Bruce Cassidy speaking to other teams, do you not respect their willingness to make unpopular decisions in the name of gamesmanship with a division rival?
Tyler Yaremchuk:
No. It creates unnecessary noise. Just like John Tortorella not doing media after they won their series in Anaheim. There really isn’t actually a competitive benefit to it. Bruce Cassidy is eventually going to get permission to interview in other spots, and eventually, Torts will have to speak to the media. It’s just attention seeking in my eyes.
Mike Menzies:
I would only hope the Edmonton Oilers would do the same thing to the Vegas Golden Knights if the roles were reversed.
Zach Laing:
What’s the gamesmanship here, though, besides making themselves look back? Nobody is looking at this and saying, “ah, those Golden Knights sure showed the Oilers this time!”
Baggedmilk:
If it didn’t annoy me so much because the Oilers got caught in the crossfire, I would absolutely respect it. Vegas very much has this Darth Vader vibe, and they really do not care what anyone else thinks about their decisions.
Edmonton Oilers Connor McDavidKiyoshi Mio-Imagn Images
Apr 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
3) Tristan asks – Connor McDavid’s two-year extension kicks in on July 1st, but don’t the Oilers really only have one year to impress him enough for another one? They wouldn’t just let him walk to free agency, would they?
Tyler Yaremchuk:
I would. You’re never going to get market value for Connor McDavid and while I understand the logic of ‘you need to get something for him’ I also put a lot of value on trying to win a Stanley Cup with him in that second year and having that convince him to stay. If he asks out, then it’s a different story, but I would prefer to take another run with him even if it means potentially letting him walk for nothing.
Mike Menzies:
Provided arrows are up, and the team is where it needs to be, it’ll be both seasons. If screw-ups continue, then it’s one ugly off-season of conversation. I don’t see the scenario in which the Oilers trade McDavid unless he requests it. They can’t win a McDavid trade anyway, the teams he’d waive to would have to have that cap space, never mind the Oilers are pulling the chute on their own season by dealing McD. I expect it’ll be both seasons, with the first informing how the second year goes.
Zach Laing:
Next question.
Baggedmilk:
Stop. I refuse. We’re not doing this already.
Stan Bowman Edmonton Oilers GM free agency live blogBaggedmilk/Oilersnation
4) Oilers fan in Van asks – The 2026 free agency crop isn’t exactly a deep group this summer. Do you think that benefits the Oilers because of their swings and misses over the last couple of years, or do you think this will force overpayments on lesser players?
Tyler Yaremchuk:
It’s a horrendously weak class, which means there will be some real sticker shock when it comes to some of the contracts handed out. Where this hurts the Oilers is that it could drive up the price for guys like Dickinson, Murphy and Kapanen. As much as those guys might want to come back, some team might be willing to grossly overpay them due to the lack of other quality options.
Mike Menzies:
Unfortunately, their big swings and misses are in the exact tier of players available in FA this year. Charlie Coyle got 6×6 the other day. Funny money again on Canada Day? I could see it. I’d be more concerned about their own pending FAs and trades at the moment.
Zach Laing:
The Oilers would be wise to wait out the free agent market this year. Not only for the reason of their last two July 1’s, but because this class is brutal.
Baggedmilk:
I think it’s bad news because with fewer guys available, the cost for all of them will go up. Supply and demand. That’s scary for a team that hasn’t exactly hit home runs in free agency over the last couple of years.
Edmonton Oilers Darnell NurseKiyoshi Mio-Imagn Images
Apr 24, 2026; Anaheim, California, USA; Edmonton Oilers defenseman Darnell Nurse (25) shoots the puck ahead of Anaheim Ducks center Mason McTavish (23) during the first period of game three of the first round of the 2026 Stanley Cup Playoffs at Honda Center. Mandatory Credit: Kiyoshi Mio-Imagn Images
5) Paul asks – Do you think it’s realistic that a larger contract or a core piece gets moved out this off-season? If so, who is your bet?
Tyler Yaremchuk:
I don’t think it’s possible. Hyman and Nugent-Hopkins are still providing really good value considering they make under $6m per season. Bouchard and Draisaitl aren’t going anywhere. That’s kind of the core. I don’t think they’ll trade a Matt Savoie either. They don’t have a lot on the roster that they could or should move this summer outside of the obvious cap dumps.
Mike Menzies:
It’s certainly more realistic that the team returns as it’s built now, because any other move is complicated. If Nurse says no, then it’s no. But if the organization is in the ruthless business, which they appear to be right now, then they could make it hard on their assistant captain wearing a defenceman, who might boost in value a bit playing at the Worlds. Whether the core is still as good as it was in 2024 and 2025, and whether it can win a Stanley Cup in 2027 or 2028, is a fair debate. Just because they got there before, does that mean it will happen again? At least for 2027, the only piece at play is Nurse.
Zach Laing:
Two names could fit the bill: Darnell Nurse and Tristan Jarry. But both come with bloated contracts, and breaking even in either potential trade is unlikely.
Baggedmilk:
Unless Darnell Nurse waives his NMC, then no.

PRESENTED BY STAKE