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Monday Mailbag: Why can’t the Oilers hold a lead?
Edmonton Oilers vs Dallas Stars
Photo credit: Jerome Miron-Imagn Images
baggedmilk
Nov 10, 2025, 08:00 ESTUpdated: Nov 10, 2025, 10:54 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 why the Oilers keep fumbling leads, buying in vs. systems, the PK’s slide, 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.
Detroit Red Wings
Oct 19, 2025; Detroit, Michigan, USA; Detroit Red Wings center Emmitt Finnie (58) celebrates with left wing Lucas Raymond (23) and center Dylan Larkin (71) after scoring a goal against the Edmonton Oilers during the second period at Little Caesars Arena. Mandatory Credit: Rick Osentoski-Imagn Images
1) Lyle asks – Are the Oilers struggling at 5v5 because of systems, or is this just a group that hasn’t fully bought in yet?
Jason Gregor:
I can’t believe their system says don’t get traffic in front and take the puck to the net. But the coach could make players more accountable and say it is now a requirement to go to the net more. So I’d say it is a combination of the players and coaches needed to do more to generate more offense.
Baggedmilk:
They’re playing country club hockey right now, and I can’t imagine the coaching staff is suggesting staying on the perimeter and looking for the perfect pass instead of making a play toward the net. Either way, the players look like they don’t care. That’s a massive problem.
Edmonton Oilers vs Dallas Stars
Nov 4, 2025; Dallas, Texas, USA; Dallas Stars center Wyatt Johnston (53) and right wing Mikko Rantanen (96) celebrates a goal scored by Rantanen against Edmonton Oilers goaltender Stuart Skinner (74) during the second period at the American Airlines Center. Rantanen scores his 300th career NHL goal. Mandatory Credit: Jerome Miron-Imagn Images
2) Oilers fan in Van asks – What are you seeing when you watch this team cough up leads repeatedly?
Jason Gregor:
They’ve made some egregious errors to give away leads. Lack of focus has been a theme.
Baggedmilk:
They’re playing not to lose instead of playing to win. They look scared, timid, and that lack of assertiveness is blowing up in everyone’s faces.
Edmonton Oilers Connor McDavid Zach Hyman
May 25, 2025; Edmonton, Alberta, CAN; Edmonton Oilers left wing Zach Hyman (18) and center Connor McDavid (97) celebrates a goal scored by McDavid against the Dallas Stars during the first period in game three of the Western Conference Final of the 2025 Stanley Cup Playoffs at Rogers Place. Mandatory Credit: Perry Nelson-Imagn Images
3) Ed M. asks – The Oil are on the verge of getting some guys back off the IR. Regula is back, Hyman and Janmark are close. Kapanen unsure. There is little doubt that Hyman will help. But what about the others? Will they help? Or will they be put on waivers/traded?
Jason Gregor:
I think Regula can help, but, like Janmark they are depth guys. They will help in small doses, but they aren’t difference makers.
Baggedmilk:
Right now, there are a bunch of players who aren’t helping at all. Hyman will help, and Janmark will bring some speed to the bottom six, but I honestly don’t know who is most deserving of staying or going right now.
Edmonton Oilers Stan Bowman Kris Knoblauch
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
4) Pat asks – When polls are taken ranking front office operations around the league (the Athletic), the Oilers never make the top 10 (maybe not even the top 20). Why does the Oilers front office rank so poorly? What are they not doing well?
Jason Gregor:
Any poll that is anonymous I don’t put much stock in. EDM has been to two Cup Finals and a Conference Final in the past four seasons. Suggesting their front office has done nothing that would rank them top 10 at least once seems rather idiotic to me.
Baggedmilk:
I mean, that’s tough when the Oilers were the second best team in each of the last two seasons, but it’s probably because some of the same issues we’ve had in those two losses are still plaguing them right now.
Detroit Red Wings celebrate goal
Oct 19, 2025; Detroit, Michigan, USA; Detroit Red Wings center Dylan Larkin (71) celebrates with defenseman Axel Sandin-Pellikka (44) after scoring a goal against the Edmonton Oilers during the second period at Little Caesars Arena. Mandatory Credit: Rick Osentoski-Imagn Images
5) Brian asks – The Oilers’ power play is still lethal, but their PK is starting to slip again. What’s missing?
Jason Gregor:
The penalty kill is 81.8%, which is tied for 12th. It is 81.5% in their last 10 games and 81.3% in their last five. It is 84.6% in their last three games. Brian it hasn’t slipped at all. It is been fairly consistent. There are many issues on the team, but PK, isn’t a main one right now.
Baggedmilk:
5v5 is the biggest issue for me, and it’s not close. Special teams are fine imo.

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