At first, Cas is sympathetic to Rowena.
He thinks WOW no wonder she's like THIS:
He actually seems to change his mind. He seems in near disbelief that Rowena doesn't love Crowley.
Cas has sympathy for Crowley's plight now:
Cas's brain begins to say: Maybe I had it backwards. Maybe Rowena is why HE is like THIS
In the script, Cas invokes the LOVE OF A CHILD. SPECIFICALLY.
He gives her a sympathetic smile, because in this moment, he feels wiser than she. He's BEEN the ambitious company man, the military-minded man, COMPLETELY sundered from his own emotions.
He sees her nihilism with a level of understanding that Rowena probably couldn't even comprehend.
He tries to tell AU Michael something similar in, funnily enough, an episode titled Nihilism:
In the next moment, Cas helps facilitate the sacrifice of "Rowena's child."
From Cas's POV, he's allowing the sacrifice of this man to prevent the losses of boys like the Styne kid, and to prevent Dean from murdering the world, and... it's a delicious bit of hypocrisy. This is Cas's old pattern of the greater good, the angelic soldier doing what he thinks is best in this moment. (Even if internally, like he told Sam, everything in him is screaming, "This is a mistake, Sam!")
And Rowena? Rowena wants her own freedom (from Sam's boot).
And Crowley? Crowley is enticed by revenge. As soon as Cas reveals that Rowena has to kill something she loves (and it's been shown by this point that Crowley already knows about Oskar), he says "I'm in."
And so. Crowley becomes his worst self again, killing innocents and going after Seth the way Lucifer went after humans:
Cas didn't know about "Seth," exactly... even if he knew of Oskar.
Crowley has been sitting on Oskar, waiting for just the right time to inflict on Rowena maximum pain and revenge. And he's so excited to watch her crumble.
He's a little bit like Lucifer at the end of season 13, so lacking in love that he delights in making people who love each other KILL each other.
Rejected by Rowena, Crowley goads her to kill the son she loves. Just like Lucifer, rejected by Jack, goads Jack to kill the father he loves:
Like Cas's war on Heaven/Raphael in season 6, and like Amara's destructive rampage against Chuck in season 11, most of Crowley's actions in season 10 have more to do with his family than Dean.
It's not as simple as, "I did it, all of it for you," or "all that I've done for you the past six months."
It digs even deeper. Cas becomes God-like to inflict punishment and a firm hand on Heaven, and Crowley becomes Luciferian to exact his revenge on Rowena.
Anyway, the point is! Cas starts to understand that maybe Crowley is what he is because of his tragic circumstances, and maybe he doesn't blame Crowley anymore.
You know, like how Rose was like SHE was because of her parental wound:
The thing is, that Rose and Crystal are like Dean and Crowley. Dean's unstable home life drove him to desperation, and Crowley led him straight to his own doom, straight to Cain.
And yeah, I've seen Dean compared to Rose before. But also... Crowley is also like Rose... and Crystal.
What Rowena did to Crowley led him into a workhouse. He died drunk in an alleyway, preyed upon by a demon.
And Sam feels like maybe he owes Dean, that it's his responsibility to help Dean because he benefited so much from Dean's sacrifices. Sam feels like he pushed Dean to the brink, just like this brother feels like he pushed his sister to the brink:
"So you didn't bother to tell the cops that, even when your sister turned up dead?"
"I was sort of the one who brought them out there in the first place."
There's so much complicated family stuff there!
(Not super coherent, but I had a lot of thoughts, okay?)
I think it definitely has implications for Chuck, too. This theme unites Crowley, Lucifer, and Chuck in a delicious, delicious way:
When Dean doesn't do what Chuck wants him to do, his manner of speaking mirrors how Crowley speaks to the rebellious Demon Dean, saying to Sam: invoking barbs like "crazy" and "stupid:"
While characters like Dean, Mary, and Cas occasionally go berserker and hurt the very things they were trying to protect, it is rarely out of spite.
Godstiel hurt Sam but started the season trying to protect Sam (rescuing him from the cage)!
Demon Dean turns on Sam, when Sam is the thing he's tried all his life to protect.
Mary didn't want to become the Natural Born Killer version herself, NBK!Mary... When she went to the Men of Letters, she wanted to put a stop to evil once and for all, protecting her children and giving them a free future.
Jack isn't like this either. When he learns he "isn't family," that he "isn't loved," he doesn't behave like Lucifer. He's more like Dean, throwing himself into the cause.
ANYWAY. I just think it's interesting.
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