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 It's a tad outdated, but as a quick resource, this (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.