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’ off-season needs, Edmonton’s Cup window, a long summer for the boys, 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.

Have yet to win, so hard to really compare the two, also McDavid isn’t at the end of his career. Edmonton has two more years, at least of McDavid. I know many have said he will leave if they don’t win, but they said that in the final few years of his last deal. I think the Oilers have some key players who are young in Bouchard, Podkolzin, Savoie and maybe Howard, depending how he develops. Yes, some other guys are older like Ekholm, RNH and Hyman, but 97 and 29 are still in their prime.

Yes. I think we are. If things go well next season, then it certainly would buy the Oilers another year to prove to Connor McDavid that they can continue to be a consistent contender. But if next season goes poorly? We could be heading towards some dark times.

Come to think of it, maybe we are. While Connor McDavid’s two-year extension kicks in, it is, in a sense, a one-year deal, as next summer the Oilers will be back to square one, figuring out their superstars’ future.

It’s hard to know. The Last Dance in 1998 with the Chicago Bulls had a much more definite tone because Michael Jordan was 35 at the time and had already retired once. The reported rifts with ownership were well-known. It may be the Last Dance for the core as currently structured with the ages of Hyman and Nugent-Hopkins. So we don’t know, but it’s as close as it’s ever been.

I refuse to put this kind of energy into the Universe. How dare you? No. I say no.

Ensuring the team plays solid defensively and manages the puck in the offensive and neutral zones.

Figuring out the goaltending is a very obvious one, but they need to find a way to build a more complete forward group that can win games in different ways. That probably starts with adding one more high-end piece to the top-six and continues with finding depth players who can succeed in the roles that the Oilers need. Jason Dickinson did exactly that. Josh Samanski did that. They need more players like them.

Well, he needs another top-six/nine winger, potentially another defenceman, and to fix the goaltending issue. If that sounds familiar, it’s because it’s literally the same things that have been needing fixing for uh… years now. Goaltending is priority No. 1, though.

The gap between his philosophy and methodology and those of the coach. They appear disjointed. They are not working as one.

Stop spending money on a couple of middle-six UFA forwards and shoot the moon on a first liner that has a track record for scoring. Do it. Goalie too… again. Maybe a coach.

Sure it will help them, both mentally and physically, and it should re-energize them after losing in the first round.

I think it could. I also think a really disappointing early exit could light a bit of a fire in this group. Take a summer off, go five months without playing a meaningful hockey game and come back next fall ready to dominate the NHL, not just sleepwalk through the regular season.

Absolutely. The players themselves have said it, and even if they found a way through Anaheim in Round 1, how deep could this team really have gone with the injuries? Getting bounced in the first round, given they weren’t going to be able to contend with the injuries, is a best-case scenario.

Of course, it can be beneficial. What concerned me, anyway, wasn’t that they lost. It’s how they lost.

I guess. It will definitely be good for their bodies, but probably not for their spirits. Father Time is undefeated.

Yes, without a doubt. If the Oilers have a healthy McDavid, Draisaitl, Dickinson and Henrique, or three of those four, I think their odds of winning the series improve significantly. The Oilers have a good team, but they need to respect the regular season and show they are committed to playing sound, smart hockey right away. They can’t feel their way into another season.

It’s going to be a challenge. They’ll need to make their dollars and assets stretch pretty far but Stan Bowman is paid pretty well… it’s not unfair to ask him to make some sharp moves that push this team back to being a true Stanley Cup contender. There might also have to be some tough decisions made along the way and with time running out when it comes to Connor McDavid’s extension… he better be right.

The Oilers will be in win-now mode for as long as McDavid and Draisaitl are in town.

The idea is that this season was an outlier and that the Oilers are much closer to the SCF teams than this year’s team. Only time will tell if that’s true, but I’d lean to the former. However, they’ve rarely been an elite regular-season team in the McDrai era. Bowman said that he doesn’t expect a “dramatically” different roster. I think that’s probably realistic. Whether that’s right or wrong? I’m not certain.

Spend every draft pick and future for the rest of time if it means actually winning with the two best players on earth in Edmonton.

Depends who you talk to in regards to overreaction. If you want to find overreaction it is out there. But each team is different. The Avs won, and winning in 2022 gives fans and critics something to fall back on, however, Carolina has never one and I don’t hear much about their window closing or players wanting out. Each case is different. The Oilers have high internal standards, as they should, and if the public pressure is high, that is to be expected. But it isn’t realistic to think each team will be viewed in a similar vein. No other team has Connor McDavid and Leon Draisaitl, and while it is a blessing for Oilers fans, it also brings higher expectations.

I think that’s because you aren’t an Avs fan. Yes, we hear more about it from the national media in Canada because we are a hockey crazed country and there are only seven Canadian teams for the Sportsnets and TSNs to cover but make no mistake, there are Avalanche fans out there who are livid with how things have gone the last few years. Also, winning a Stanley Cup does soothe some of the pain.

The difference is that the Avs won the Cup.

If the Oilers had won the Cup in 2024, there wouldn’t be so much fervour. But they didn’t. I agree that perhaps we have taken winning playoff series for granted over the past years. For example, the Oilers have won seven rounds to the Lightning’s zero since 2023. The Lightning have pressure now after losing four straight series, but they can still be reassured that they climbed the mountain twice. Winning cures all. There’s noise because Connor McDavid is about to turn 30 and hasn’t won a Cup. If McDavid leaves without a Cup, that will hang over the franchise and, by consequence, the fans forever. In every hockey conversation you have with non-Oilers fans, it will be used against you. I don’t blame anyone for being anxious.

The Avs won. The Oilers haven’t.