You've probably overpaid Nurse by around $700k and I'm willing to bet that based on his historical usage, Donato isn't much of an NHL center. Domingue seems pricey, but he might be a warranted upgrade over Starrett, who I desperately need to see bounce back after injury before I'm willing to consider him as an acceptable option for next year's backup position. Tippett really doesn't like using Russell on his off-side, and I'm curious as to why Bouchard can't crack this roster in its given state. If there's a season to move ol' Cowboy, it's this one.

A few things regarding Kassian though, and I'll try to break this down in a logic-oriented manner and keep my personal feelings about Kassian and the Oilers' brass out of it. Sorry for the long read lol

1. What about Zack Kassian is worth a $3M/3y extension?

His speed, physicality, and utility on the PK are all positives that any team would be willing to pay for. The glaring issue is his historical production: pro-rated to 82GP/season, over Kassian's 8-year career (excluding this season), he's averaged 24 points per season. It's a tad outdated, but as a quick resource, this (https://www.pensionplanpuppets.com/2011/9/27/2452941/common-misconceptions-how-much-should-that-forward-score) defines Kassian as a "good" third-line RW based on his historical production. Colin Wilson - as a slightly above-average third-line center (historically more valuable, higher historical production) - was projected to sign a three year deal at $2.52M per year via EvolveWild's 2019 projections. Kassian, his agent, and the fanbase are all out to lunch if they think he should make more than what Wilson was projected to make: they have similar utility, but Wilson produces more and plays a more valuable position.

The only way Kassian should be able to ask for that much money in a new deal is if he takes a one-year "prove it" deal. I agree that players should go out and be paid their worth, but this season's production anomaly does not reflect Kassian's historical value. Are we paying him for having one good season without accounting for the chance that it's a fluke? Are we paying him because he can put up 25+ points a year and might get suspended once or twice in the process? Are we paying a player with penalty kill utility $3M to spend over a minute per game in the penalty box, invalidating what he was paid to do? Are we going to commit term to a player who's playstyle is more likely to prevent him from playing all 246 games of his new deal? Should we ignore the inherent risk of signing a player reliant on his speed and physicality with a history of back and leg injuries?

I could be talked into $3M for a one-year deal (begrudgingly) or a two-year deal at under $2.5M. I balk at anything with three years of term or north of $2.5M with term. Keep in mind that Chiasson had a lesser production spike last year and we already regret his two-year deal.

2. Could Edmonton employ a more skilled winger in the #1RW slot? Alternatively, should they?

Edmonton's lack of a true, skilled top-line right wing is what keeps the Draisaitl-McDavid duo outside of "is this the top line in hockey" conversations. Compared to the world-ending Landeskog-MacKinnon-Rantanen or Marchand-Bergeron-Pastrnak trios, Edmonton does fall short in this category. I don't think the Oilers are suffering because of Kassian's inclusion on that top line, but if there's another level to be reached with our top line, it's unlikely that they'll get there with Kassian. Teams like the Leafs or Blackhawks - despite common criticisms - still perform well when rolling three skilled players on a line. If Draisaitl and McDavid are already projected to hit point totals unheard of since the turn of the millennium, what could happen if the Oilers found a third piece to produce alongside them? How much mroe dominant could that line be?

It's difficult to project because we haven't seen this line, this year specifically, perform in the playoffs. Goals typically are harder to come by beyond April, and while Kassian will for sure bring that much-needed physicality and forecheck while the top-line is deployed, I'm worried that the production won't be there. If Holland goes into the remainder of this season having not upgraded the middle-six scoring from where it is today, the burden of scoring in the playoffs will fall on the Draisaitl-McDavid-Kassian line. I do not believe that line to be as lethal as the aforementioned Avalanche or Bruin top lines, and would not expect them to be able to fully turn the tide in a game when the team truly depended on them.

The long-game is to assume one of Maksimov or Lavoie will develop into McDavid's long-term RW: the problem with a three-year Kassian deal is that neither Maksimov nor Lavoie are three years out from being able to assume that role. A short-term solution - even if they happen to be more expensive than Kassian at $3M - is going to be more desirable in order to get one of those skilled, physical prospects playing on the NHL roster full-time. This is where a two-year Kassian deal (as I suggested in my first point) starts to look better, as it rewards the player and suits the organizational plan moving forward.

3. If Kassian reverts back to a third-line forward, what happens to the rest of the team?

This is my biggest concern with extending Kassian. Assume for a minute that this year's projection truly is anomalous and that next season Kassian reverts to a 25+ point, third-line forward with PK utility and provides little-to-no substance upon being promoted back to the #1RW position. Kassian as a third-line winger on this team is a horrible outcome for this team.

Chiasson's bad deal last summer warrants he (at minimum) consumes a roster spot or costs $1M-ish against next year's cap upon being buried in the minors. If Chiasson is a roster player and is expected to produce in the neighbourhood of what a $2.1M forward should be producing, he'll be given third-line minutes. If Yamamoto is likely to break into the NHL next season, it's probably going to be as the #3RW. He'll need sheltered minutes for at least the first quarter of the season before progressing up the lineup, as his historical usage in the top-six has left fans (and I'm assuming management) wanting. Do we continue to employ an aging James Neal - who seemingly cannot score at evens this season - as a top-six option? Would Neal benefit from a slight reduction in icetime (read: #3RW minutes) with usage on the power play? If Chiasson is buried/traded, and Yamamoto is not an NHL-roster option by the onset of the 2020-21 season, and Kassian proves to be a good #3RW for the Oilers, the risk is keeping Neal in the top-six assuming his 5v5 game either returns or his PP production stays hot into next year, at which point it's likely that Edmonton is continuing to run sub-optimal lines and isn't really going to be considered a serious contender for a Stanley Cup next season.

All things considered, the Oilers' brass has to be damn sure that Kassian can maintain top-line production over the next two seasons or he shouldn't be resigned. Neal is going to need to find less time on the roster as he ages and if Yamamoto ever decides to live up to his potential, his launch pad is likely in the spot Kassian would otherwise occupy. Nobody in their right mind should be willing to justify Kassian as a fourth-line forward making more than he does today, so I refuse to consider that an option.

TLDR; Kassian at $3M/3y is a bad bet and an even more horrible contract given his comparables, Edmonton's deployment, and the organizational plan.

I don't want to lose Kassian for nothing but when I made the Part 3 of this it became apparent that you're right that Kassian starts to be more of a blockage then anything. Lavoie should be ready by 2021-2022 I think. I'm not a fan of Yamamoto and don't think he's capable of improving that top line. I think he can play in it, I just don't think they get substantially better. Ideally Kassian would be on a two year deal for under 3 mill, and we can move chiasson and Kassian slides onto the third. I would welcome a Gauthier and pick for JP swap as I feel Gauthier would improve that line as well as creates competition with Lavoie. I like Kassian for the grit he brings to the Oilers but my personal opinion is he's a bottom 6 forward, albeit a good one and holds the top line back to a degree. The biggest problem is who replaces him now and down the road. If JP had developed better I'd be looking at him. Maybe Lavoie, but like you said that's the long game. I think both Yamamoto should be traded as should JP. Kassian resigned on a two year deal even if we have to pay him 3 and force him farther down the lineup. @ConnorsCousin replaced Donato with Staal and that may serve us better for now. If you look at part 3 I have Donato replacing Neal but that's a big risk that he'll improve significantly. Thoughts on who the Oilers should pursue for a top 6 forward? Rangers fans want to much for Kreider and I feel he could get 6 mill plus this summer. Zucker I doubt waives to come here. Toffoli strikes me as a rental and not necessarilly a good one. Maybe the Oilers can get AA? Also as far as Domingue, I don't know who they'll take but needed a backup and figured 1.5 is good for a backup. Donato, Idk about him as a centre although it says he plays any position, hoping the third line is a safe place for him with more responsibility. I had cap space that's why i kept Russell, I think Bouchard could, but I haven't gotten to see him really since I don't watch the Condors games so wasn't sure how his development has come along.

I'd start looking at Kassian as our own in-house rental than we're losing him for nothing. You know you can't really afford him if you keep him, but his skillset is only going to aid you in the playoffs. You're trading having him long-term for a possibly deep run at a cup this summer.

I've damn-near beaten my own head in trying to figure out which wingers to pursue by this TDL and into next season. There aren't a ton of options.

Kreider would be an okay rental, but if he signs for anything bigger than the Nyquist deal he's a detrimental piece in 3 years. Names like Craig Smith and Vlad Namestnikov are okay options, but they're kind of like the bottom-of-the-barrel options in my opinion. I don't have personal issues with Athanasiou but I've eaten a ton of criticism in AGMs that I've acquired him in due to how inept he can be defensively and that he's never really produced well beyond his one 30-goal season. Minnesota seems incredibly hesitant to trade Fiala, and any of Tampa's expendable forwards won't be made available until the summer. I'd personally stay away from Toffoli due to his footspeed, inconsistency, and what's bound to be an absurd ask from the Kings. Hall's too expensive to pursue now or in the offseason. Zucker's NTC - as it was recently explained to me - is due to his family being unable to leave the states without some big legal process. It's easier for him to stay in America, and I don't fault him for that.

Every now and then I allow myself to think that Columbus could part with Bjorkstrand, but I haven't actually delved into what it would cost. If they're looking to start building again, picks this year is definitely their price. I like Donato as an upgrade to the #3LW position, and if he can be had for next year's 3rd Round Pick, I'd jump on it. Staal I feel would still be kinda pricey and that you'd have to chose between him and a #2LW in order to make a trade work. Kinda why I like Bjugstad as a #3C; he's never goign to be cheaper than he is today and he has a track record of being much better than what we've seen in Florida. But if the price was right, and as weird as it would be, I could live with Staal as the third-line center for the next two seasons.

I'm still on board for Gautheir and a pick for Puljujarvi, but I'm starting to see that more as a draft-day move than a today move. Carolina could probably be talked into moving their second round pick if it's high enough, and I think Holland is banking on either that or the NYR 3rd Round Pick being a really high third rounder. Gauthier's size and speed could make him a good substitute for Kassian in that #1RW role until one of Maksimov or Lavoie usurp him for it.

I don't think Ken will make a move with Nuge out as he wants to see who's going to step up, the problem with that is that we could lose some crucial games here. As far as Kassian goes, you realize if we let him walk this summer the moment the Oilers start losing the first thing people will say we need is a physical winger to play with McDavid and not more depth like we know they will need. I think Bjorkstrand would cost to much since I can't see them going for JP or Yamamoto.

I'd like Bjugstad provided their was retention on that, I think i saw an AGM team that had him for a pretty reasonable price. I think if Wild did sell Fiala it would have to wait a couple months as he's producing again. Thoughts on Galchenuk in free agency? Think he skated with McDavid at biosteel or something a couple years ago, wasn't coached by Tippett before but he might not fit Tippets style.

Also is it just me, or do the Oilers seem to ALWAYS get caught puck watching when they get scored on. I swear it feels like every time they leave somebody wide open because everyone and i mean everyone is watching the puck, including the top guys.