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Monday Mailbag: What are the Oilers’ biggest needs to remain a Stanley Cup contender?

Photo credit: Perry Nelson-Imagn Images
By baggedmilk
Jun 1, 2026, 09:00 EDTUpdated: Jun 1, 2026, 00:17 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’ needs to get back on track, re-signing Jason Dickinson, Darnell Nurse, 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 ImagesMay 26, 2026; Las Vegas, Nevada, USA; Vegas Golden Knights and primary owner of the Vegas Golden Knights Bill Foley are presented with the Clarence S. Campbell Bowl by Deputy commissioner of the NHL Bill Daly after winning against the Colorado Avalanchein game four of the Western Conference Final of the 2026 Stanley Cup Playoffs at T-Mobile Arena. Mandatory Credit: Stephen R. Sylvanie-Imagn Images
1) Tashmid asks – What changes do you think the Oilers need to make to realistically get onto the same level as Vegas? The Marner signing really elevated them, whereas Edmonton still feels uncertain, both coaching-wise and contract-wise, despite having elite talent.
Jason Gregor:
They beat Vegas last year, and this year they were hurt. I don’t think Vegas is significantly better than Edmonton. Oilers don’t have a head coach at the moment, but once thatis resolved, I suspect the uncertainty about coaching will shrink. Vegas has more money allocated towards the cap next season than the Oilers currently do. Edmonton needs to ensure they re-sign Connor Murphy. There are no RDs better on the market. Start there. Biggest area Edmonton has to improve is their commitment to playing sound defensively. Do that, and they will be close to Vegas.
Tyler Yaremchuk:
I’ve said for a while now that they need to stop dealing with the mushy middle when it comes to offseason adds. You can find $3-4m wingers at the deadline for cheap if you need scoring depth. In the summer, they need to go for the big dogs. Go big game hunting and add legit, impact pieces. That’s why this summer I want to see a trade for someone like a Jordan Kyrou versus signing someone like Boone Jenner.
Liam Horrobin:
There isn’t much difference between Vegas and Edmonton. Vegas got hot at the right time and had players return from injury, rather than getting injured. Obviously, Carter Hart has played great too. If Edmonton can add a top-six winger and a goaltender, then they’re right there, too. Easier said than done, of course, but that’s my wish list. The players I’d acquire are Jake DeBrusk and Sebastian Cossa.
Baggedmilk:
I think they’re closer to Vegas than we’re maybe giving them credit for. That’s not to say that there aren’t still upgrades to find, but I don’t think the Oilers are so far out that the task is impossible either. The high end talent is here. Now we (still) need the right supporting cast.
© Jerome Miron-Imagn ImagesMar 12, 2026; Dallas, Texas, USA; Edmonton Oilers center Jack Roslovic (28) and center Jason Dickinson (16) skate off the ice after Dickinson scores a goal against the Dallas Stars during the second period at the American Airlines Center. Mandatory Credit: Jerome Miron-Imagn Images
2) Oilers fan in Van asks – There were reports on social media that the price for Jason Dickson could go as high as $5 million in free agency. I enjoyed what he brought to the Oilers, but would a price tag like that not make him too rich for Edmonton to pursue? Would he be worth it at that number with limited offensive upside?
Jason Gregor:
He has scored more than nine goals once in his career. I like him. I like his approach to being good defensively, but aside from one 22-goal season, he has yet to contribute much offence. Hard to pay a third-line C $5.5m when he doesn’t produce much offence. At that price I’d let him walk. I’d look at Michael McCarron, big, right-shot C who is physical, can win draws and kill penalties. He won’t cost close to that much.
Tyler Yaremchuk:
Not a chance. A good organization finds a cheaper player to fill that spot. Spending $5.5m on a third line centre is not a luxury that the Oilers are in a position to afford.
Liam Horrobin:
I wouldn’t touch Dickinson at $5.5 M. I’d honestly worry about signing him for anything more than $4 M. While I live his defensive style, he doesn’t provide much offence. Yes, he had a good four games in the playoffs, but that doesn’t warrant that high of a contract. I’d opt to trust and develop Josh Samanski and acquire someone at the deadline, or I’d find a cheaper option via trade.
Baggedmilk:
I think that’s a little rich for me. I thought he would actually have to take a discount based on the lack of goal production since he signed that last contract, but I guess he’s aiming to cash in on a thin free agent class. That one would make me nervous.
Stephen R. Sylvanie-Imagn ImagesMar 8, 2026; Las Vegas, Nevada, USA; Edmonton Oilers defenseman Darnell Nurse (25) warms up before a game against the Vegas Golden Knights at T-Mobile Arena. Mandatory Credit: Stephen R. Sylvanie-Imagn Images
3) Terry asks – With all the talk about trading Darnell Nurse this summer. Would a new, demanding coach like Cassidy or Laviolette be able to get the nurse to limit giveaways and mistakes through proper structure and accountability?
Jason Gregor:
To me, it is about his decision-making. A coach can only help out so much, as it comes down to the player making the split-second decision. Those two could help, but it is more about who is running the defensemen. Any player is tradeable, and if the return doesn’t make Edmonton worse, I can see trading him, but giving him away to free up cap space would be a bad decision. It has to be a hockey trade that the team feels makes the team, at least equal.
Tyler Yaremchuk:
No, I don’t think so. We’ve seen Nurse struggle with plenty of different coaches, it’s not like the issues in his game just started popping up once Knoblauch took over. He’s certainly capable of having a better year than he did but he also isn’t so bad that he’s unplayable. The contract just sucks.
Liam Horrobin:
I don’t think the previous coaches let Nurse just get away with giveaways, so I’ll say no. The problem with Nurse isn’t necessarily his on-ice play, but that he’ll never play up to his $9.25 million contract.
Baggedmilk:
I doubt any of Darnell Nurse’s coaches have let him make mistakes without talking to him about it. Like Liam said, he makes more money than anyone is happy with, and the expectation is that he plays up to his pay grade. Not gonna happen, but I too would have sprinted to the fax machine to sign that contract.

Apr 7, 2026; Salt Lake City, Utah, USA; Edmonton Oilers defenseman Evan Bouchard (2) prepares to shoot against the Utah Mammoth during the second period at Delta Center. Mandatory Credit: Rob Gray-Imagn Images
4) Clay asks – Given that Evan Bouchard took a high hit and was injured at the World Championships, do you see any scenario where a Cup-contending hopeful like the Oilers would not allow their players to attend?
Jason Gregor:
Doubt it. It is rare to see a player injured by a headshot at the World Championships.
Tyler Yaremchuk:
No. I think they could suggest that certain players don’t go but for someone like Bouchard, who wants to be on future Olympic and World Cup teams, I think the team has to respect that this is important to him.
Liam Horrobin:
No, that should never happen. Representing your country is an incredible honour, and it would be selfish for teams to prevent players from doing that. Additionally, Evan Bouchard wants to play for Canada at the Olympics and World Cup, so he needs to showcase himself while wearing a red Maple Leaf. Opportunities like this shouldn’t be limited.
Baggedmilk:
I doubt it. I think if their NHL team is out of the playoffs and they want to represent their country, it’s pretty tough to tell a guy that’s not an option.
Ron Chenoy-Imagn ImagesMar 10, 2026; Denver, Colorado, USA; Edmonton Oilers center Jason Dickinson (16) defends on Colorado Avalanche center Nazem Kadri (91) in the second period at Ball Arena. Mandatory Credit: Ron Chenoy-Imagn Images
5) Ed M. asks – The Avs have had another disappointing playoff run. They were the biggest buyers (and now the biggest losers) of the trade deadline madness, giving up two 1sts and a 2nd. Since the 22 Stanley Cup, the Avs have had 4 disappointing playoff runs, have about $5M in cap space, and their next 1st-round pick is in 29. If the Oil were in this spot, is there any way the coach and GM could survive?
Jason Gregor:
Blaming the coach is too easy. Avs are a good team, but Vegas played better for four games. It happens. But to answer your question, in Edmonton, the coach and GM would pay the price, as under Daryl Katz, the organization has shown a willingness to fire the coach (especially) and the GM, even when they have success.
Tyler Yaremchuk:
The good news is they got a piece like Kadri who is under contract and can help them next season. They are in a bit of a tough spot. I’m not sure if this summer is the one where they’ll make sweeping changes but if next year doesn’t go well, they could have to start asking some tough questions about a core that’s only been past the second round twice in the last decade.
Liam Horrobin:
Once you win the Stanley Cup, you have a longer leash. So yes, if that situation were in Edmonton, they’d still be in their positions. At the end of the day, Bednar led Colorado to a Stanley Cup, and McFarland does everything in his power to give them an opportunity to do it again year after year. The grass isn’t always greener on the other side.
Baggedmilk:
I think Bednar will get more leash because the Avalanche have already won under his watch. Different situation here in Edmonton, but if that happened here, I wouldn’t be surprised to see a housecleaning up top.
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