Rowena & Crowley back the wrong horse, over and over and over...
Everyone remembers Rowena's tragic clinging to Lucifer in season 11, and how it ended up for her. Upon learning she's the only one that can put him back in the cage, Lucifer pragmatically snaps her neck--a form of cold, indifferent insurance:
Ah, the tragedy of Rowena's desire to have security. Rowena wanted to be loved and protected by Fergus's father. She wanted to be appreciated and protected by Lucifer.
Crowley remarks that she's always looking for the biggest, baddest beast in the room to hide behind.
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In 11x23 Alpha and Omega, we see Rowena cozying up to her newest target, Chuck:
ROWENA: [Crowley mocks her as she speaks] Charles, I'll put the kettle on. My mom always said, there's nothing a nice wee cup of tea can't fix.
...
CROWLEY: It's what she does. Find someone with power...cozies up...digs the claws in. [As he’s talking, Crowley walks over to a cabinet, opens a door and takes out a bottle of Craig]
CHUCK: Hmm. Yeah, well, I'm not helping anyone right now, obviously. She's been...nice.
CROWLEY: For now.
Funny sidenote: As Rowena moves in on Chuck, getting sweet on him, she starts calling him "Charles," a little nugget for how she'll later call Sam "Samuel," and Cas, "Hello, Castiel."
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Ahem. Anyway. The thing is, that yes, Rowena totally does this. We can't really blame her when we look at the tragic happenstances of her life. During the course of the series, we see her make numerous moves to gain favor will powerful beings:
SEASON 10
We see her volleying to make Crowley sit upon a stronger, more secure throne.
SEASON 11
We see her cozying up to Lucifer and getting killed for her trouble.
Next, we see her coming back from the dead to move in on Amara.
She's kind of playing both sides, but she gets sweet on Amara here: "Oh, I can be useful...And even if it is born out of my own self-interest, I-- I care about you. I'm someone you can talk with. Confide in. Have you... have you ever had that? Oh, you don't have to be (alone), darlin'!"
Then, as I mentioned above, she cozies up to Chuck, and Crowley snarls many a nasty word about her.
SEASON 12
We find Rowena trying to date rich men and lying about her background, painting herself as a posh, well-to-do ballerina.
In an abrupt about-face to insulting Cas (she called him a fish in season 10), we see that Rowena has flipped on her appraisal of him.
Now, Castiel is super hot. He's "the handsome, strong angel," an ideal partner/protector. So, she hits on him. A lot.
Despite her memory of "Cas's face" as Lucifer snapped her neck, her dogged attraction to Cas blooms sometime in season 12.
Perhaps, it's when she and Cas and Fergus are hunting Lucifer together.
(In the same time frame, Crowley is also hanging off Cas's arm, keeping him company, trying to be oddly "cutesy," singing in the car, etc. It's...hilarious. You get the mental picture of them both trying their hardest to get his attention.)
SEASON 13
Season 13 brings us her library tryst with Gabriel.
She says she's motivated by trying to heal his wounded virility/grace/pride, but it's at least partially about his status as an archangel.
And of course, there's security in Sam(uel), but it's all twisted up with him being her executioner, not just her protector.
But in being her "destiny," he also functions as her security. It's very complex. (And kinda sexy.)
SEASON 14
Rowena will hit on Cas as later as season 14's Ouroboros, saying his full name in a similar coo to how she says, "Charles and Samuel." -> "Hello, Castiel."
Castiel, for his part, tends to be a little flustered by her, straightening up and saying, "Hello," back.
SEASON 15
Finally, in season 15, somewhat hilariously, Rowena moves in on Arthur Ketch.
But it's a little different this time, reflecting a more confident, in-control, and emotionally integrated Rowena.
She seems to be genuinely interested in him for his wry, science-loving personality. They banter.
She and Ketch mutually harass Dean for details about the other, like schoolyard crushes.
They had a battle connection in the past, have fought together and helped one another re: resurrection spells, but it is only now that they’re healthy and healed that they can actually see each other.
Rowena throws Dean a breathless, thankful look when he saves Ketch (for her).
She’s reformed, Ketch is reformed. It’s heartbreaking just how excited she is about him. He instills a her hope in her, for the future. (But he won’t sell out his friends. He dies. She won’t let the world die, so she dies, too.)
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But Crowley does the same friggin' thing, doesn't he? He is so her child, a tragic mini-Rowena, despite his efforts to look like a big, bad Hell-king. 💔
SEASON 5
When we meet him, we see him backing the Winchesters re:the Colt.
In his early appearance, he does this because he thinks Lucifer is going to wipe out demon-kind.
That gamble goes okay for Crowley, mostly.
SEASON 6
Sometime in this timeframe, he is given the role of Hell-king as a consolation prize, by Ramiel, prince of Hell, who honestly doesn't give a fuck.
In season 6, Crowley backs Castiel. Cas's got magnetism and sex appeal.
As the original "angel's angel" in Heaven, he's a strong frontrunner in Heaven's Civil War simply by popularity alone. So, Cas is the horse Crowley decides to bet on.
Then, Cas turns out to be duplicitous, cunning, and too devoted to his human family to be controlled. He’s way more than Crowley can handle.
There are glimmers of this power imbalance, when Cas on occasion has had enough of Crowley's innuendo-laden threats, like when Cas snaps and crushes him into a wall, for example. But on the whole, Crowley ignores this. It's his tragic hubris.
Eventually, Cas overwhelms him and seizes power, and the whole thing turns out to be a frightening blow to his position.
So, Crowley goes running to the brother Raphael, which is another bad gamble. Castiel straight-up kills him, and Crowley is forced to flee and go into hiding.
SEASON 7-8
In seasons 7-8, Crowley vies for control of the prophet Kevin, torturing and killing those around him.
He makes sure to kill Meg, who is in his mind a Lucifer loyalist (she's actually a Castiel loyalist at this point, but the Lucifer label sticks).
SEASON 9
In season 9, Crowley manipulates a series of events to allow him to dangle Dean to Cain in a bid to transform Dean and destroy Abbadon, the newest threat to his position.
(Crowley won't suggest taking the mark on his own; he won't risk his own neck.) Afterwards, he scoops “demon” roofied Dean up, like spoils of war, a dark parallel to the pimp-demon in Girls, Girls, Girls (and Randy).
SEASON 10
In season 10, this bites him in the ass, too.
Demon Dean proves too much to handle, a liability on the job, as he refuses to perform the cold, capitalistic mercenary duties of Hell.
"The little prat’s bad for business. He’s uncontrollable. Must be the Mark."
In a scene similar to Cas crunching Crowley into a wall, Dean too throws Crowley down. Demon Dean will not be cowed by Crowley, and he will not be a sidekick, little bitch, or Queen to be "controlled."
So, Crowley goes running to the brother, Sam. He “sells him out" to Sam.
And then Crowley goes running to revive Castiel again, to deal Dean. Dean is now a problem (the problem-that-solved-his-original-Abbadon-problem).
And around and around Crowley goes.
Despite everything, Crowley softens to Dean. Crowley's a little bit human now, and it shows. As he softens, his mother appears, making things much more complicated.
SEASON 11
Crowley tries to muster up the glory of his former evil self--he kills a bunch of poly/queer swingers for no real reason.
Then, Crowley sees a new opportunity to sway a powerful being, and we get Crowley unsuccessfully trying to mold Amara as his newest weapon of mass destruction.
Like with Demon Dean, he strikes fast to scoop her up when she's “vulnerable” and "new,” to get her under his sphere of influence.
Then, it goes badly, as this always does for Crowley. Amara breaks “Uncle Crowley's”arm and runs away.
In this season, Crowley goes to bat for Cas again, trying to detach him from Lucifer and screeching angrily at Cas as Lucifer beats Crowley up.
In fact, in that brief moment before Crowley even goes to bat, he's actually smiling at Dean and Cas as they reunite, as Dean says, “Cas, we don't have a whole lot of time, okay?"
Crowley is a softie. Cas is his kinda-friend, and Crowley wants Dean to be happy. Crowley's changed.
At the end of the season, we briefly see Crowley complaining about Rowena cozying up to Chuck, while he moves to cozy up to Billie. (Really, Crowley? Stop doing the thing that gets you burned, man.)
SEASON 12
Enter season 12, and Crowley works with his mom again. He and Rowena form an uneasy alliance, and both begin to see family in a slightly new light.
They trust each other a little more, and they hurt each other to try and solve their mutual pain re: Oskar and Gavin.
Hilariously, they both start seeing Castiel in a fresh light this season. It's like, in watching his devotion and chivalry to his family, and as their understanding of family shifts, they've mutually decided that he's dependable and thus desireable. (The "blue-collar, family-oriented soldier.")
So yeah, season 12 finds Crowley cozying up to Castiel again in order to lock away Lucfier--with Crowley being overly friendly and flirty and sing-songy to the point that Cas just might bash his own head in.
(In this same timeframe, Rowena warms to Cas, so you have this implication that they're both hanging off his arms adoringly, and he is tired as fuck of dealing with them. I'm sure Cas's tendency to get a little flustered and sweet with Rowena is something that would drive Crowley insane on multiple levels.)
Crowley even risks his life for Cas against Vince!Lucifer. (He wants Cas to be his friend so badly in this era, oof.)
Then, he saves Cas against Ramiel, thanks in large part to his bond with Dean, and Dean thanks him for it.
Crowley, like Rowena, will take any form love. Any friendship. Any comradery. Even scraps. They've got the same neurosis.
Anyway, in season 12 we also have the team-up of the century, where Crowley works with Rowena to send Lucifer back to the cage. Victory!
And Crowley has another fatal misstep. His last one ever, perhaps. He thinks, yet again, that he can outsmart another overpowered beast in order to buy his own security.
And so, he locks Lucifer in Nick's body, Ma'lak box-like, and tries to out-bark and out-dominate him.
Horribly, Lucifer doesn't even appear that threatened or upset. Even when he's being humiliated, the demons under Crowley flock to Lucifer. (It's not fair!)
Lucifer seems quietly amused, like he's waiting for his moment to strike, just as Cas behaved in season 6, quietly tolerating Crowley's goading because he was not actually threatened by him.
(Crowley is no Azazel or Dagon or Ramiel or even Asmodeus.)
And it's fatal. It goes badly. Crowley's gleeful crowing of brains-versus-brawn blows up in his face.
He escapes by the skin of his teeth, and goes running, tail tucked, to tell the Winchesters what he's wrought.
Sam and Dean are horrified, realizing that Jack, Kelly, and Cas are in danger, and so they speed towards them in hopes of warning them in time.
Crowley seems a little hysterical and fatalistic, deciding to back the Winchesters one last time, because, "life is meaningless," and "what's the point of it all."
Crowley lost everything for a job he hated, so he commits suicide, because he's tired and worn down.
He has become like Raphael, "we just want it to be over."
Crowley falls to nihilism.
And Rowena despairs. 💔💔💔
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