I hope everyone is feeling refreshed after the weekend because it’s time to get back to work with a brand new Mailbag! This week, we’re looking at the Duncan Keith trade, the Zach Hyman rumours, the Oilers’ Cup window, and more. If you’ve got got a question you’d like to ask, email it to me at [email protected] or hit me up on Twitter at @jsbmbaggedmilk and I’ll get to you as soon as we can.
Apr 15, 2021; Detroit, Michigan, USA; Chicago Blackhawks defenseman Duncan Keith (2) during the third period against the Detroit Red Wings at Little Caesars Arena. Mandatory Credit: Tim Fuller-USA TODAY Sports
1) Travis asks – The move has been beaten to death already but I’d like to know how everyone would rank the Duncan Keith trade on a score out of 1-10 and why?
Jason Gregor:
I’d say 6.9. (nice). He is better than the player they gave up. Taking the entire cap hit wasn’t ideal, but had Chicago retained 25%, if Keith plays poorly it won’t change much if he is a $5.5m cap hit or a $4.125m. It will end up not being a very good deal.
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Robin Brownlee:
Yes, it has. I’d say 7. I think Keith will be better suited to reduced minutes in a second pairing. He can still play. Brings experience and leadership. Knows what it takes to win. Price on the high end. We’ll see how much value is there in the next two seasons.
Cam Lewis:
2/10. Keith can probably be effective in a lesser role than he was playing on Chicago and I don’t doubt that he’ll bring intangible benefits to the group. That said, this was a massive market misread and being unable to get Chicago to retain the requisite cash in order for Keith to carry a cap hit around what he’ll be worth as a player at this stage is a huge loss.
I don’t understand what the rush was. This is the type of trade you make after you strike out on Alec Martinez and Jamie Oleksiak in free agency. Holland operated as though there was a bidding war on Keith, and that was most certainly very far from the case.
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Tyler Yaremchuk:
I rank it a 2 out of 10. They got a decent player and I do value what Keith brings to the table, but they grossly overpaid. It’s too much money for a 38-year-old defenseman and they have now locked the only second-round pick they have in the next two drafts so it can’t be used in another deal. It was not a good deal and Holland has no excuse for why he didn’t get a better deal.
Zach Laing:
I’d given it six Reid Wilkins’ out of 10. I’m really not a fan of the fact the Oilers had to eat the full salary even though I understand the acquisition cost could’ve been higher in that case. With that being said, my expectations are high for Keith. He needs to come in and play very, very good hockey for the Oilers based on the acquisition cost. Realistically, I’m not sure if that happens.
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Baggedmilk:
I’ll give it a 5/10. I totally understand why the organization would want a player like Keith around — the guy has won everything there is to win in hockey — but where points get knocked off is the cost of acquisition and not being able to have Chicago retain salary.
Mar 20, 2021; Tampa, Florida, USA; Chicago Blackhawks defenseman Duncan Keith (2) against the Tampa Bay Lightning during the first period at Amalie Arena. Mandatory Credit: Kim Klement-USA TODAY Sports
2) @RedFern7581 asks – With Keith on the roster, does Holland get any other vet defencemen or let the youth play?
Jason Gregor:
More youth won’t help. They need Larsson re-signed. IF they lose Kris Russell in expansion, I could see them signing another LD. I don’t see Lagesson as a great option as the third LD.
Robin Brownlee:
Not sure. Might depend on the status of Russell, who is available in the expansion draft.
Tyler Yaremchuk:
I would like to see both Adam Larsson and Slater Koekoek brought back. I think that would give them a good mix of veterans and young d-men. Kris Russel could be their seventh defenseman as well. It would be a pretty good blueline if they did that.
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Cam Lewis:
They badly need another right-handed veteran if Larsson walks. Even if he does stick around, they could use another. I wanted Oleksiak before the Keith trade and I still want him after the Keith trade.
Zach Laing:
I think he needs to add some more depth to the blueline. I’m very high on Mark Pysyk being one of them.
Baggedmilk:
I’m always of the mindset that all positions can be upgraded for the most part, but I don’t think that will happen. I think Larsson will get done and that’s what we’re rolling with.
Jan 11, 2020; Calgary, Alberta, CAN; Edmonton Oilers defenseman Oscar Klefbom (77) against the Calgary Flames during the second period at Scotiabank Saddledome. Mandatory Credit: Sergei Belski-USA TODAY Sports
3) @eakins_hair asks – With @Oscar Klefbom looking like he will not suit up at all for Edmonton this season and the Oilers needing another 1st pairing D-man, who do you think the Oilers could realistically obtain given they still have lots of players to sign and only so much cap space?
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Jason Gregor:
If they don’t get Larsson, they could take a big swing at Dougie Hamilton. If they lose Russell they will need another veteran. Slater Koekkoek is an option. I also like Jani Hakanpaa as an option if they lose Larsson. Their RD would be quite thin losing Larsson.
Robin Brownlee:
Why not Bear in that pairing with Nurse? Money might be better spent up front or in goal.
Cam Lewis:
I would like to see Nurse and Bear, Oleksiak and Larsson, Keith and Bouchard.
Tyler Yaremchuk:
Duncan Keith is pretty clearly their Klefbom replacement. If they bring back Larsson, I think that’s it for additions on the blueline. They’ll focus their attention on improving the forward group, as they should.
Zach Laing:
I don’t think they need another top pairing defenceman. I think Ethan Bear will take a big step forward in his game this year on the top pair alongside Darnell Nurse.
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Baggedmilk:
The gamble has to be that Ethan Bear can get back to playing well with Darnell Nurse, right?? Has to be. I doubt they bring in another veteran d-man.
Apr 18, 2021; Vancouver, British Columbia, CAN; Toronto Maple Leafs forward Zach Hyman (11) skates against the Vancouver Canucks at Rogers Arena. Canucks won 3- 2 in Overtime. Mandatory Credit: Bob Frid-USA TODAY Sports
4) Geoff asks – It’s been reported that the Oilers are among the frontrunners for @Zach Hyman but this seems to me like an opportunity to overpay for a player with a career-high of only 41 points. What is the max dollar and term that you would be comfortable paying Hyman if you were in Ken Holland’s shoes?
Jason Gregor:
My max is $5m on a four-year deal, which won’t get it done. I might be enticed to go five years, but that is the longest. Term kills you in free agency. There are many LW available. No need to overpay on term or money.
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Robin Brownlee:
Wouldn’t be enough to get him. 5x$5.5M
Cam Lewis:
This is a risky contract. Hyman has done well with the Leafs but pretty much exclusively as a linemate of Auston Matthews and Mitch Marner. I think he would be a great fit for Connor McDavid given he crashes the net and forechecks well, but you can’t fork over too much cash for complimentary players. Hyman also plays a very crash-and-bang style and has been injured in the past. There’s a good chance his game won’t age well.
Tyler Yaremchuk:
The max I would personally go is $5.5 million per year on a five-year contract. I believe that is an overpay, but I understand that to get a good UFA forward, you often need to overpay. I would not go any higher than that but my current fear is that Holland will feel pressured to give him more term than that to get the deal done. Term is often what kills teams in free agency.
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Zach Laing:
Five years and $5-million is about as far as I’d be comfortable going. Hyman is a good player but the Oilers have been in this situation before and been burnt (i.e. Milan Lucic). As I wrote about Friday, I think Gabriel Landeskog is a safer option in a similar price range.
Baggedmilk:
$5.25×4 would be my max but I know that won’t get the job done. The guy has a career-high of 21 goals and 41 points so I don’t really understand the hype. If you’re going to overpay on an UFA winger, make it Gabriel Landeskog.
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Apr 19, 2018; Columbus, OH, USA; A view of official game pucks with the Stanley Cup logo prior to the Washington Capitals against the Columbus Blue Jackets in game four of the first round of the 2018 Stanley Cup Playoffs at Nationwide Arena. Mandatory Credit: Aaron Doster-USA TODAY Sports
5) @TheMadHatter asks – I hear the buzzwords like “win-now mode” or “Cup window” get thrown around, but realistically, is Edmonton really in a position to be in a Cup window after two dismal playoff exits? They may be in win-now mode but is it really a playoff round? playoff run? Or a cup run?
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Jason Gregor:
I don’t like Cup window as that can extend to 10 years. Win now for me equates to winning at least one round in three of the next four years. You never know when an upset can happen, just ask the 2019 Lightning. But Edmonton needs to win a round and then anything can happen like Montreal this year.
Robin Brownlee:
Win-now doesn’t mean a Cup next season. It means progressing into legit contention by getting into the playoffs and getting more rounds in year after year. There is a window and it’s the next 4-5 years with McDavid and Draisaitl in their prime years.
Cam Lewis:
I mean, you have the last two Hart Trophy winners on your team and they aren’t getting any younger. If the goal isn’t to win right now, I’m not sure what you’re doing.
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Tyler Yaremchuk:
They absolutely are. They have a lot of the key pieces needed to win a Stanley Cup already (Draisaitl, McDavid, and Nurse). The hard part is done for Holland and the Oilers, they just need to surround those guys with some decent support. That’s why we should be talking about them being in their “Cup Window.”
Zach Laing:
The Oilers are in a win-now mode. They have to be given the fact the years are dwindling on Connor McDavid and Leon Draisaitl’s extension. It’s time for the Oilers to go all-in.
Baggedmilk:
At this point, I don’t really care what terminology people use as long as the Oilers can get into the playoffs and make some noise beyond a stuttering wimper.

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