I mean he had his moments, but he still wasn't the same player. This year he regressed even more.
Correct. Father time remains undefeated after all. McDavid has started his slide and it will continue. He is still going to be in the Art Ross hunt for the next 3-5 years or so you would expect, as long as he maintains health, but his days of being 25% better than everybody else are very likely behind him. Forwards prime scoring years are generally a lot younger than most people realize, being in the 24-27 range for most players. The truly great players like McDavid tend to extend that range somewhat, as Kucherov, MacKinnon and even Drai this year, have shown.
His slight regression isn't the reason for my thoughts on the contract though, its purely based on math and a hard cap reality. You win the cup by having players on smoking good cap structure deals, because you win the cup with team depth, not by having the best 1 or 2 players. The NHL isn't the NBA, and the lack of an Oilers cup during the McDrai era should highlight this in technicolor for everybody.
Drai is already not on a team friendly contract starting this upcoming year. Bouchard won't be on a good cap deal starting this year. The only players we really have on good deals are Hyman, and you could make a case for Ekholm (if he recovers his health and play) and maybe Walman, and maybe Kulak. But that is it. We have a massive, massive overpayment to Nurse, a cap buyout penalty to Campbell to overcome and a Drai and Bouchard contract to overcome. Not because Drai/Bouch aren't worth it, but because they take up such a high percentage of our cap. I haven't even discussed the need to get out from the Kane, Arvidsson, and Henrique deals as well. We are in some serious cap trouble starting this year, and we need cap friendly contracts.
Now, why would McDavid be the person to focus on? From a team perspective, I don't think you do. You pay him what he wants because of who he is and that you can't replace him. From a team perspective, you try and fill out the roster with value contracts around him (so in other words you don't pay Frederic, a 3rd/4th line tweener $3.75 M for 8 years! lol). That is how I expect it will play out, and I suspect it will fail. The reason it will fail is because it is very difficult to find enough bottom-50% of the roster good deals to make a difference in the playoffs. Where you really need help is in your top end guys on good deals, like Florida has. Barkov makes $10, Turtle makes $9.5, Reinhart makes $8.6, Verhaeghe makes $7, Lundell makes $5, Jones makes $7 and Forsling makes $5.75. Every one of those players are top of the roster players on good to freaking AMAZING deals. Hyman is our only good player on such a deal, whereas Florida has SEVEN players on such deals. Pretty much their entire top-6 and 2/3rds of their top-3 D are on value contracts.
The only way the Oilers win a cup is if McDavid takes a massive, MASSIVE, team discount deal. Due to the fact that McDavid's market rate is around $16 M, he is the only chance the team has on making up the difference. McDavid could also easily afford to take an extremely team friendly deal for a short 2-3 year contract, and allow the team to build out around him with other players. He is going to finish with around $300-325 M CAD in career earnings, even if he played for free for the next 3 years, so money isn't exactly an issue for him. This is the only path forward for the team to win a cup, its the only way. Yes, we made it to the cup the last 2 years, but that was with Drai and Bouch on exceptionally friendly contracts of $8.5 and $3.9, and those days are done starting this year. McDavid was also still on a "decent" value contract at $12.5, but that is also over starting in 2026-27. The Drai and Bouch contracts might eventually turn into good contracts in the back half of those deals due to rising cap, but McDrai will be 35+ years old by then and the window will have closed. The only way for McDrai to win a cup in the next few years, is if McDavid takes a MASSIVE discount on his current contract. There could have been another way with the Drai contract coming in $2 M lower and Bouch coming in $1.5 M or so lower, but that ship has sailed. I don't blame Drai and Bouch for getting what they can, because they aren't McDavid, and don't make $5 M USD every year on endorsements alone. They don't already have $110 M USD in career salary earnings already, they needed to make their bank. But McDavid is different, and could very easily afford to play for free for 3 year if he wanted (although nobody is suggesting that obviously).
McDavid will not do this of course, but the Oilers (and his) fate will be sealed as soon as the contract is signed.