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how much do you think chuck was actually affecting the movement of the plot throughout the series?

personally, i think he was just observing them from season 6 to season 10, but then he actually had to get involved upon amara’s return. and i do like the theory that he was responsible for the “vision” that cas thought he saw from jack, and that he kinda let mary get killed after cas’s prayer in 14x17, before again becoming fully involved throughout season 15. but for the other seasons 1-5, most of 12-14, and really for the overall universe, idk how much can, or should, be ascribed to chuck’s machinations. like i can never decide which route would be most satisfying for me as a viewer, and so i’m just curious as to what your opinion might be :)

Jack visions theory

Probably helps just to say starting off for anyone who might be coming from a different perspective, that my own understanding of Chuck's machinations in Supernatural (at least when it comes to Sam, Dean, and Cas) do not involve directly violating their free will. Chuck's machinations involve shaping the experiences around our characters to convince them to make the choices Chuck wants them to make. For example, when Dean tosses the gun aside in 14.20 and refuses to kill Jack, Chuck shouts "Do it!" instead of putting some kind of mind whammy on Dean that makes him kill Jack because Chuck either can't do that or won't do it because it wouldn't get him off. Chuck needs Dean to do what Chuck wants him to do (kill Jack) because Dean was brought to a point psychologically where he chose it. The same thing is true of Sam in season 4. The demons or the angels or Chuck don't operate Sam like a robot—they slowly convince him to take one turn after another based on the psychological state he's in, the things happening around him, and the things being whispered in his ears until he's killing Lilith and Lucifer's cage is opening, and Ruby says,

No. It wasn't the blood. It was you... and your choices. I just gave you the options, and you chose the right path every time. You didn't need the feather to fly, you had it in you the whole time, Dumbo! I know it's hard to see it now... but this is a miracle. So long coming. Everything Azazel did, and Lilith did. Just to get you here. And you were the only one who could do it.

I refer to Chuck's influence on the narrative as causality rather than fate. I have a tag for this called #spn and causality. 4.18 goes to great lengths to show how difficult it can be to subvert causality. For example, Dean tries to defy the writing by moving himself and Sam to a different hotel than Chuck wrote them to be in, but the motel's neon sign goes out, causing the name of their motel to "change" to "The Red Motel"—the motel Chuck wrote. ("No matter what details you alter, we will always end up here" etc etc). However, this episode goes on to show that it is possible to leap out of causality's flow. Chuck's control of the narrative ultimately works via anticipation. If he can anticipate his creations choices, his writing realigns everything with the narrative. If they do something he is unable to anticipate? They can leap out of his narrative just long enough to make a difference.

How do they leap out of causality's flow? Two things together: Dean and Cas. Quoting myself here in this post:

Leaping out of causality is something Dean and Cas do together in 4.18, 4.22, and 5.22. In 4.18, Dean pleads with Cas to help him save Sam, even though Cas thinks what’s going to happen is fate and can’t be subverted. Cas doesn’t personally act, but he gives Dean the idea that Dean then executes, leading Chuck to say “What are you doing here? I didn’t write this.” In 4.22, Dean pleads with Cas again. They again fight about the inescapability of destiny. This time, it’s Dean’s pleading but Cas’s actions—flying Dean out of the green room (somewhere Dean is incapable of escaping from on his own). Chuck says when they pop into his house, “Wait. T-t-this isn’t supposed to happen” and then “Yeah, but you guys aren’t supposed to be there. You’re not in this story”. In 5.22, after Lucifer takes Sam over (something that was foretold to happen in Detroit), Cas and Bobby despair, but Dean refuses to give up and calls Chuck, who says, “Oh, uh, Dean. Uh, wow. I, uh, I didn’t know that you’d call.” Then Dean goes to Stull Cemetery alone. However, the moment that Michael begins to walk up on Dean and says, “You little maggot. You are no longer a part of this story!” Guess who suddenly appears with a holy oil Molotov cocktail?

Dean and Cas are something Chuck seems to have a lot of trouble anticipating. I think this is true both individually and as a unit. Individually, Dean is the narrative heart, to an extent that his capacity for love is always exceeding the bounds that Chuck anticipates, leading to confounding leaps like showing up at Stull in "Swan Song" and dropping the gun in "Moriah" and saving the world with the power of love in 11.23. Dean in turn pleads with Cas with that heart, and Cas is angel with a crack in his chassis straight of the line. Naomi/Chuck cannot get Cas to do what he's "supposed" to do no matter how many times he's reprogrammed. He has Loving Dean Winchester/Humanity (same thing) Disease and it's incurable no matter how many lobotomies are attempted.

In the season 1-5 setting, Chuck is actually fairly hands off despite all of this being his prophecy foretold. He told the archangels that everything would end with Sam and Dean as the vessels for Lucifer and Michael (5.08) and Lucifer passed these stories on to his princes, and the angels and demons brought that prophecy to fruition—including with deliberate meddling in the Winchester/Campbell bloodline (5.13, 5.14). Heaven and hell act as Chuck's hands and feet, carrying out his plan out of desire and (in some cases) religious fanaticism. Because Chuck's so painstakingly worked on this narrative and everything is set up in advance, he can just watch it play out. When he interferes directly, it's actually to give Team Free Will a better shot at subverting him. Chuck only directly interferes in

4.22/5.01 to transport Sam and Dean to the plane, un-demon blood Sam, and resurrect Cas

5.22 to resurrect Cas again

All that said, I think season 1-5 is the original Chuck canon, which is subverted by Team Free Will working together, and most specifically, by Dean and Cas interfering in ways Chuck did not anticipate. And Chuck was fine with this. His narration at the end of "Swan Song" reveals that he's pleased, even if the story turned in a direction he didn't anticipate (maybe the Michael and Lucifer story started to bore him—they bore me, and him wanting Sam and Dean to mirror them so rigidly was rather uninspired).

I get the sense that Cas is probably a good litmus test for whether Chuck's entertained or not by the story subverting his expectations, because Cas is not "supposed" to be a part of the original story, but Chuck keeps bringing him back anyway. And yet, somewhere down the road, Cas falls wildly out of favor with Chuck, and Chuck is hurling rage at him for never doing as told—the very thing he seemed to like about Cas at first.

Maybe I'll see things that will make me change my mind as I work through seasons 7-10, but so far, I agree with you that season 6-10 seems to be a mostly "hands off" period, with Chuck only arguably interfering once, to bring Cas back a third time in season 7, depending on how seriously/literally you take Daphne's recollection of events in 7.17:

EMMANUEL/CASTIEL A few months ago, she was hiking by the river, and I wandered into her path, drenched and confused, and... unclothed. I had no memory. She said... God wanted her to find me.

It's not necessarily clear exactly where Chuck loses interest (or if for example, Cas might fall out of favor with Chuck before Sam and Dean do). Chuck shows up in season 10's "Fan Fiction" to see a play of his work, so he was clearly feeling fond enough to celebrate his handiwork in an very non-prestigious but intimate setting. But when Chuck shows up in season 11's "Don't Call Me Shurley", he talks to Metatron about traveling (to his other universes, perhaps?). Chuck's writing his memoir, and Metatron claims it's full of self-doubt and nebbishness. Chuck's apathy jumps out to Metraton quick too. Metatron criticizes Chuck for writing only two paragraphs on the archangels in his memoir, lending to the notion that Chuck had come to a point where they bored him. Metraton tries to remind him that Lucifer was his favorite because he rebelled, but Chuck then denies that Lucifer was ever even his favorite! He doesn't like this rebellion thing so much anymore... which might also tip his hand as far as how he's beginning to feel about Team Free Will. I think it's likely that Amara is the catalyst for his change of heart, but I'll have to wait until I circle back to season 11 to have a fully formed conclusion on this.

Then we get seasons 12-15 where—at least arguably—Chuck begins planting the seeds for a new final ending, trying to force Dean into the role of Michael—the son so loyal to him that he killed his own brother. The problem is that Dean's never really been like Michael, and that's the whole reason season 5 never worked. It's also the reason "Moriah" doesn't work. Lilith claims in season 15 that Chuck has a creepy obsession with Dean—Dean specifically. Dean whose loyal love fills Lucifer with such seething jealousy in "Swan Song" that he loses control of Sam's body just as Dean's pleading brings Sam's consciousness to the surface to fight. That same loving heart thaws Amara toward Chuck in 11.23, and I think Chuck... decides that he does not like this. It is something beyond his capacity to express or to anticipate and write around. It is transformative, causality-defying love, that ruined his original ending (and he's BORED and TIRED). And has given Cas Winchester Derangement Syndrome so he can't be controlled. He decides that he hates Dean Winchester's heart, and he tries to obliterate it out of existence and force Dean into the Michael role once and for all.

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#11.23