It's 2 years of Toews
Incorrect, the AGM was for 2022-23. It was a one-year rental of Toews.
a near point per game (60 pts in 70 gp in 19-20, didn't play last year), Selke calibre 1st line centre, at only 5.5mil, and you make (most) of the cap room by also giving up Kassian in that deal.
I bolded the part that concerns me the most. Toews was showing signs of a drop-off before going down for so long. I think a third line role, especially on like a shutdown line, would be the ideal role for someone of his skill and point in his career, but those kinds of pieces don't get the A-prospects in return. Perhaps a first and a third as we saw in the Foligno deal, but with how much of a cap hit Toews actually brings with him and that it's blatantly clear he'd only be the third-best pivot in Edmonton, why should he cost more than the aforementioned Kassian and a 2nd? Why must the Oilers keep doing the Blackhawks favours?
Kassian would cost more than a 2nd to dump imo.
I think this might be false during next summer. I think any team looking to keep itself close to the cap floor would take his remaining $5.8M across two years. Edmonton could even retain upwards of a million per season. I think the Coyotes solve this problem quite handily to be honest.
So you're giving up less than Holloway's value for 2 years of Toews 5.5. It's an absolute steal of a trade and to suggest otherwise is foolish. I like Holloway, but bringing in a capable 2-way leader like that with championship pedigree (who unlike Keith is actually still good) is worth far more than part of Holloway's value.
What kind of galaxy brain math is this? The Oilers are giving up - by definition - more than Holloway's value. Kassian and the 2nd are still assets with varying degrees of value and you're forgetting the part where Edmonton TRADES AWAY Holloway.
And how much of a leader can Toews (or Keith) be for that matter if both players were playing such roles in an environment that permitted the sexual assault of another player?
He immediately would give Edmonton the best top 9 in the league, allowing Drai+McD to play on the same line all the time while still icing a good 2nd line (Hyman-Toews-Yamamoto?) and then a good 3rd line (Foegele-Nuge-literally doesn't matter these 8 are already the best top 9).
Edmonton already has one of the best top-9 units in the league, adding Toews isn't going to do anything but enable Tippett to park his head further up his own ass by continuing to run Draisaitl with McDavid. Earlier you agree that he'd be a third-line shutdown center and now you're doubling back on that to finagle in some greater value than what the man can actually provide? Pick a lane and stick with it please.
Edmonton's problem of course remains terrible defense and streaky at best goaltending, but Toews would definitely improve their team defense.
He's a forward, and an old one at that. Toews will only do so much. If he's in a third line role at 5v5, then he's probably seeing no more than 12 minutes at even strength and maybe he gets the PK workload. Less than a third of the game. That's not going to be a substantial impact, especially for the cost paid to acquire him.
In the end it's a moot point because it's a horribly lopsided trade without the cap dump (Kassian) and the retention, and Chicago wouldn't entertain trading him anyway, but it instantly and significantly improves Edmonton's chances of winning the cup in the next 2 years while McDavid is at his most dominant with next to no downside. Plus you still have your 1sts, Bourgault, Lavoie, Broberg, etc. to go after immediate improvements on defense. Not that I think Edmonton is gonna do anything, because they've committed to their mediocre top 4 and are capped out but hey, dreaming is nice I suppose.
I think you touch on two key points here which ultimately defeat the idea of this trade:
1. The Blackhawks maintain a degree of sentiment to Toews and will enable him to retire as a Blackhawk.
2. The Oilers front office is life-threateningly allergic to math and other forms of sound, logical decision making and would never get out of their own ways to improve the team.
I really appreciate the gusto in which you approach the idea in general, but there needs to be some time to pause and consider the other side of the equation: Edmonton is in a disastrous cap situation next season and Holloway is going to provide supreme value in terms of his skill and his ELC. A nearly $6M third line center cannot be an option for the Oilers next season unless Keith retires, and in any case that money should be thrown at upgrading the blueline as much as possible: Smith's term and the organization's increasingly obvious projection of Skinner as next year's backup is going to leave even more question marks in net.