Sam & Crowley; Jack & Oskar
I can't decide if Jack would commiserate and win Fergus/Crowley over or not. Because it's about the order of operations.
Jack had a "shitty" father, just as Fergus did, but Jack won Rowena over with just a few damn words:
Rowena fell head-over-heels for Jack, and she behaved with him (saving him when he was sick) in a way not unlike OSKAR.
Jack is the foster "son" with a "new, younger man" (Sam).
Crowley might hate him on Rowena-grounds alone.
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And all OSKAR says is: I hope I haven't hurt you (by letting myself get caught and brought here like this).
ANYWAY
What Crowley's doing here...?
This isn't unlike how Crowley behaved with Sam in the previous season, making him (and Dean) "UNDO" the people they saved:
Aside//
As much as he hates Crowley, Sam is in season 10 becoming more like him (and also like the dark scientist-type: MoL Cuthbert). While Sam is critically different in that he's not doing this for the sake of cruelty itself, it's still some heavy collateral damage he's engineering in order to save his family.
But whereas Dean is reeling from a newfound empathy and humanity for the absolute horror show-reality of being a demon in Hell (Dean and Claire Novak are absolutely mired in forgiveness in s10), Sam is still bent on revenge...
...and for his part, Crowley himself is a lot like Sam, too.
Crowley keeps lying to others and himself, sidestepping his part in dangling Dean to Cain (he never EVER apologizes, only pragmatically tries to "help" ...but mostly uses it as an opportunity to hurt his mother).
It's sooooo crunchy how Crowley SAYS he's doing Hell favors in a season where what we actually SEE onscreen is him continuing to abuse his underlings and struggle under the weight of a continued LACK OF RESPECT.
(Which is... also beautifully illustrated through Demon Dean-humanity, who IMMEDIATELY and INSTANTLY chafes against how Crowley rules and... even dare I say gains more respect as a leader than Crowley for the actual two seconds he's around?)
ANYWAY
Maybe deep down, both Crowley and Sam WANT to be leaders... and can't understand why they struggle so much with it. (Compare this with Dean and Cas who are assumed de facto leaders often, but theyFEAR becoming cruel/authoritarian rather than starting there.)
i.e. Crowley never apologizes for his manipulation or for the MoC. We see him sidestep the opportunity to do so in Inside Man with "So she's a liar," and "Must run in the family." Then Dean sadly pivots, because he realizes he's not going to get that kind of care, not even as a friend, while Crowley meanwhile sucks up the Dr. Phil opportunity to talk about his own problems with his mom.
And Sam to my knowledge... never apologizes for Oskar. At least not onscreen. I think it's possible with how close Rowena and Sam become that it came up at some point in their relationship.
OR as I've said before, weirdly, their cut-throat desire to sacrifice others for love is something they LIKE about each other (SEE: Funeralia for example.) In Rowena's world, motive counts. (x, x, x)
Because Sam's (and Cas's) motive in killing Oskar was protecting family, she could respect that. And so, she brought the weight of her revenge on Crowley, whose motive was really mostly personal, just absolute cruelty.
Once Rowena helped send Gavin back to his timeline and hurt Crowley in the same way she was hurt, she likely considered the issue a closed circle. (And again, in that moment, Crowley turns his ire on HER, not Sam and Dean for their impersonal part in Gavin. Because they're not family to him in the same way Rowena is.)
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ANYWAY
Sam Crowley parallels drive me insane. Oskar Jack parallels drive me insane, too.
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EDIT: This scene with Crowley above circles all the way back again in 13x23 with the Lucifer-Sam-Jack confrontation. It just NNNNNNGH
The Lucifer-Crowley parallels will drive you insane too, with crucial aspects of their personalities aligning at numerous crossroads. Here, Crowley makes Rowena kill the family she loves (Oskar) & in 13x23 Lucifer wants Jack to kill the family he loves (Sam).
ANYHOO There's a 50/50 chance that Crowley would DESPISE Jack, at least at first, but because of ROWENA













