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Monday Mailbag – What is Jeff Jackson’s biggest challenge?

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Photo credit:Tom Kostiuk
baggedmilk
6 months ago
Happy holiday Monday, Internet friends, and welcome to a fresh edition of the Mailbag to help get your week started and break down all things Edmonton Oilers. This week, we’re looking at Jeff Jackson’s biggest challenges, team toughness, the prospect pool, and much more. If you’ve got a question you’d like to ask, email it to me at baggedmilk@oilersnation.com or hit me up on Twitter at @jsbmbaggedmilk and I’ll get to you as soon as we can.
1) Alex asks – Jeff Jackson said in his introductory press conference that he’d like the Oilers to be best in class in areas such as scouting, analytics, and beyond. What do you see as his biggest challenge to tackle in year 1 of his tenure?
Jason Gregor:
To be best in class in all of them is most likely unrealistic, but I get why they have the goal to do it. I see the biggest challenge as constructing the plan that allows you to be the best. Which plan will automatically improve your scouting for instance? You can add more people to your analytics group, but more doesn’t guarantee success. It is about outlining the proper plan, and usually, you have to change and alter some things as you go, so for me, the biggest challenge will be setting up the strategy to ensure success. It will take time and there will be changes and tweaks to it as you go.
Robin Brownlee:
He said: “On the agent side of things, you do a lot of your own scouting of young kids. We used analytics, and I know the Oilers do. I’m going to look at all those things and try to best in class. It won’t happen overnight, but I’m going to dig in on all of the things that I know.” Year 1? Not sure. Jackson said he doesn’t feel the need to come in and re-invent the wheel. Early on, time might be best spent finding out who’s who and what’s what and then taking it from there. All that said, preparing to transition away from Holland being GM might be his single biggest task.
Tyler Yaremchuk:
The analytics department is always an easy answer. People have been on the organization for not having a big analytics department. I will simply say that Jackson should prioritize getting more quality hockey minds in the organization. Last year, Frank Seravalli reported that the Oilers had one of the smallest staffs in the league and that’s quite frankly unacceptable. There’s no salary cap for front office employees and the Oilers shouldn’t be afraid to spend.
Zach Laing:
His first step should be making hires to improve those areas. A stronger analytics department is needed to modernize the team, and a deeper, more robust scouting staff is, too. The fact the Oilers haven’t had an OHL scout in recent years is a perfect example of that.
Liam Horrobin:
I suppose the correct answer is analytics. Having a few more bodies on that side of things would be beneficial. However, I don’t expect the Oilers to live and die by analytics like some teams do.
Baggedmilk:
If Jeff Jackson can come in and fill some organizational holes — like, oh I don’t know, an Ontario scout for the biggest league in the country — then that would be a very strong start. There’s no cap on management and scouting staff, so the Oilers should have the best people they can in all of those spots. Work outward from there.
Dec 30, 2022; Seattle, Washington, USA; Edmonton Oilers forward Klim Kostin (21) punches Seattle Kraken forward Brandon Tanev (13) during the third period at Climate Pledge Arena. Mandatory Credit: Stephen Brashear-USA TODAY Sports
2) @oldoilersfan asks – I liked our team size last year, but losing players like Kostin as we have has me a little concerned again about getting pushed around. Thoughts?
Jason Gregor:
His tenacity will be missed, but I don’t see Edmonton suddenly getting pushed around. They were tied for 23rd in fights and 16th in hits. Their biggest intimidation factor is their power play. It will still be good, and if teams try to run the Oilers they likely will take a few penalties. Edmonton still has lots of team toughness for 2023 with Kane, Desharnais, Nurse, Kulak, Hyman and RNH who can fight if needed. They have enough physicality that I don’t see them getting pushed around.
Robin Brownlee:
Not concerned. Mattias Ekholm takes up some of the physical slack lost with Kostin and he plays a lot more so he has more chance to impact games. Desharnais and Nurse provide plenty of physical edge.
Tyler Yaremchuk:
They still have Vinny Desharnais, Darnell Nurse, and Mattias Ekholm on the backend. Even if they don’t fight a lot, those are guys who will stand up for their teammates. Losing Kostin sucks, but I’m not super worried about it from a fighting perspective.
Zach Laing:
I’m not overly concerned about it. Being tough on the ice is about a lot more than just having size.
Liam Horrobin:
I am not concerned about it. The Oilers still have Darnell Nurse, Evander Kane, and Vincent Descharnais to help fill that void. Additionally, the Oilers are a tall and strong team in general so I think they’ll be fine. With that said, I’ll miss Klim Shady too.
Baggedmilk:
I’m going to miss Kostin’s willingness to defend his teammates without even thinking about it. The Oilers have other players like that on the roster, but not at Klim’s spot in the depth chart. I’ll miss him. I do think they’ll be overall fine given the other guys they have.
3) @OilersPain asks – Who would you consider to be the Oilers best prospect at the moment? Who has the best shot at making the NHL jump sooner than later?
Jason Gregor:
Dylan Holloway. I know he played 51 games last season, but he didn’t play much and I see him as a young player still making his way. But if you are looking at players with no NHL experience, then I’ll go with Raphael Lavoie to be the first to make the jump, but I’m not sure how big of an impact he will make or how much opportunity he will get. I still view Xavier Bourgault as the one (with no NHL games) as having the most long-term potential.
Robin Brownlee:
I think Dylan Holloway has a chance to be a factor this season after getting into 51 games last season.
Tyler Yaremchuk:
Does Raphael Lavoie count? If he does, then he’s probably my answer. Dylan Holloway is right there too. If they become impactful NHLers next season, then the Oilers could have one of the deepest forward groups in the NHL.
Zach Laing:
Our prospect writer Bruce Curlock is in the midst of writing up his top 20 Oilers prospects. I, however, am not sure if there’s one prospect above the rest. Edmonton has a number of good prospects, so you could make the argument for any of Beau Akey, Phil Kemp, Xavier Bourgault, or Raphael Lavoie being the top prospect for a variety of reasons.
Liam Horrobin:
Dylan Holloway is the Oilers best prospect and it’s not particularly close. One day, I think Matvey Petrov can take that step to being the #1 but he’ll need time in Bakersfield first.
Bagged milk:
Holloway or Lavoie have the chance to make the biggest impact this year unless you still consider Philip Broberg to be a prospect.
Jun 26, 2023; Nashville, Tennessee, USA; San Jose Sharks defenseman Erik Karlsson talks with members of the media after the 2023 NHL Awards at Bridgestone Arena.
4) Ed M. asks – The Karlsson trade has come down. It was reported by Friedman that the Sharks were asking last season for multiple 1st rounders for Karlsson. They settled for a 1st and a bunch of veterans with bad contracts. They also had to toss in a 3rd and don’t get much cap relief this year and only some next year. Are you surprised by the poor return the Sharks received? Was Grier overvaluing Karlsson last season?
Jason Gregor:
What you want and what you receive are two different things and this proved it. Grier opted to take less of a package in exchange for retaining less salary. Ultimately he didn’t get very much. He is hoping he will be able to move Hoffman for a pick at the deadline and the same with Rutta and Granlund, but likely at next year’s deadline when they are in the final year of their deal. I felt San Jose did the worst of the three teams and I wonder if Grier’s inexperience was a factor. I don’t know what direction the Sharks are going. They don’t seem to be fully committed to a rebuild and that will only extend their pain.
Robin Brownlee:
Not surprised. The market changes and when a player wants to move along — he wants to play for a contender — the team trading him doesn’t hold all the cards. Bit of an eye-opener for rookie GM Mike Grier here.
Tyler Yaremchuk:
I’m just surprised they didn’t bite the bullet and retain more money to maximize the return. If they would have just kept 50% of Karlsson’s deal, they very well may have gotten multiple first-round picks. Instead, they settled for a poor return to save money. Not a great way to do things in my opinion.
Zach Laing:
I’m not surprised at all at the underwhelming trade. The Sharks clearly valued the ability to have cap space over the next number of years, rather than being able to acquire the best assets possible in a deal. In my eyes, that’s a massive mistake. San Jose actually added $2.25-million to their books through this deal. It really makes no sense whatsoever.
Liam Horrobin:
Grier overvalued Karlsson but it was the right thing to do. You’ve got to see if somebody bites on it. The return in the end was underwhelming thought which suggests the offers weren’t good from other teams either. I think when we hear rumours like that in the future we should take them with a grain of salt. Rarely in the NHL will we see crazy deals with multiple first round picks and prospects.
Baggedmilk:
That contract was a monster and moving it was always going to be difficult, especially if the Sharks weren’t willing to retain half. They weren’t willing to do that and the return reflected that.
5) David O. asks – Why don’t the Elks and the Oilers have a better partnership? It seems like they are just two distant roommates inhabiting the same city but there’s very little cross-promotion of any sort. Obviously, the Elks would be the big beneficiaries but building a better sports culture and a culture of attendance to sporting events feels like it would also be good for the Oilers.
Jason Gregor:
In what sense? They have never had massive cross-promotion in the social media era. I do wonder if part of that is due to both being bad for the majority of it. How much do the Blue Jays and Maple Leafs cross promote for instance? I’d be curious about how you think they could be better partners. We all know the Oilers are the big dog in town, and if they tweeted a few times about the Elks it would help, but what would help more is if the Elks finally won a home game.
Robin Brownlee:
A culture of attendance? People don’t go to Elks games because they stink. With 22 straight losses at home, they’re historically bad. There’s nothing for the Oilers to cross-promote and the seasons don’t overlap much. Even at the best of times, the CFL is a big step down from the NHL in terms of widespread fan interest and this is far from the best of times.
Tyler Yaremchuk:
It would be a good move by the Oilers and it would only create a stronger sports atmosphere in the city. I don’t see a downside to it and I don’t know why they don’t work together more. It probably has something to do with money.
Zach Laing:
If there’s one thing we know about professional sports organizations in Edmonton, it’s that they love to make things hard on themselves. *shrug*
Liam Horrobin:
I am not sure but you are correct. The Elks need to do many things differently but getting the Oilers in the picture would be much better for them. Evander Kane did go out earlier in the season but we haven’t seen anything else since. However, even without the Oilers in the picture, the Elks can do better at promoting their games and making it a better event. The Edmonton Riverhawks are a perfect example of what a team can achieve in this city even if they aren’t called the Edmonton Oilers.
Baggedmilk:
Like in the Carnival of Champions days! I think it would be nice to see some cross promotion but it seems like neither side really cares so the only ones talking about it will be us.

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