okay first and foremost, this doesn’t 100% line up, but it also makes too much sense for it not to at least be a theory...
also shoutout @voguecas for actually giving me the motivation to finish this mess (they make very good edits check them out or perish
)
also shoutout @voguecas for actually giving me the motivation to finish this mess (they make very good edits check them out or perish

let’s start with exhibit a: cas seems to know how to leave purgatory.
when dean asks how they leave at the end of 7x22, cas says “we’re much more likely to be ripped to shreds”. imo, that implies that he knows they could & it’s just unlikely that they will.
when dean asks how they leave at the end of 7x22, cas says “we’re much more likely to be ripped to shreds”. imo, that implies that he knows they could & it’s just unlikely that they will.
cas worked for heaven for 1000s of years and chuck/god sealed purgatory up himself, so it’s not hard to imagine that he heard about how god made a human portal for purgatory.
it’s also telling that cas knew where they were as soon as he and dean arrived in purgatory.
he just seems very informed about where they were immediately when he and from the start.
he just seems very informed about where they were immediately when he and from the start.
exhibit b: benny tells dean about the portal
the first question we have to ask is: how would benny know about the portal? it doesn’t make sense that he, or any other monster, would know how to leave purgatory, especially since they’re meant to be trapped there.
the first question we have to ask is: how would benny know about the portal? it doesn’t make sense that he, or any other monster, would know how to leave purgatory, especially since they’re meant to be trapped there.
obviously, it could just be that the portal is a purgatory legend or something like that, and because dean is the first human to be there this is the first opportunity to test it, but the next part can rebut that...
exhibit c: how benny talks about the portal
when benny tells dean about the portal, he says “at least that’s the rumour”, which implies that someone told him about it (although admittedly this could also be evidence for the legend theory).
when benny tells dean about the portal, he says “at least that’s the rumour”, which implies that someone told him about it (although admittedly this could also be evidence for the legend theory).
what makes me think it was cas, is that benny prefaces his last statement with “god has made it so”. even though cas has left his role in heaven at this point, this still sounds like something he would say (pls see the second image for an example of cas saying something similar)
exhibit d: cas is a soldier
if we accept that cas does know how to leave, then we have to explain why he didn’t help dean find the portal faster. we all know that cas left dean to protect him, but it seems out of character for him to let dean stay there for so long if he does +
if we accept that cas does know how to leave, then we have to explain why he didn’t help dean find the portal faster. we all know that cas left dean to protect him, but it seems out of character for him to let dean stay there for so long if he does +
know an escape.
my theory is that, because he’s keeping the leviathans away from dean, he doesn’t want to risk getting anywhere near him, and that way he can’t tell dean how to leave directly.
my theory is that, because he’s keeping the leviathans away from dean, he doesn’t want to risk getting anywhere near him, and that way he can’t tell dean how to leave directly.
if this is the case, being an ex-soldier of heaven, cas is a strategist in protecting humans and so it would make sense for him to find another way let dean know, like perhaps spreading a “rumour” about an escape from purgatory.
(there is more support for this in the next part)
(there is more support for this in the next part)
exhibit e: benny is a good vampire
so now we have to ask, if cas were to spread this rumour, or send some to find dean directly, why would he choose benny?
benny happens to be a vampire with more humanity than most, in that he doesn’t feed on humans, as we find out in 8x05
so now we have to ask, if cas were to spread this rumour, or send some to find dean directly, why would he choose benny?
benny happens to be a vampire with more humanity than most, in that he doesn’t feed on humans, as we find out in 8x05
again cas is a strategist. obviously, although benny doesn’t feed in purgatory, cas would still want to make sure the person he sent to dean wouldn’t harm him.
so let’s say cas comes up with the deal benny makes with dean and suggests it to benny, and then leads him to dean (note that benny reaches dean just as he’s in trouble
), he also knows that dean sticks to his word when he makes a deal, so he’d want to make sure that +

the monster wouldn’t harm anyone topside once dean got him there. if cas needs a monster to help dean escape purgatory, benny would be his best bet.
exhibit f: benny is against finding cas
when benny proposes the deal to dean, he initially doesn’t want to find cas. what is the reason for benny to not want cas to come with? dean is his only way out, so it’s in his best interest to appease him.
(see images for evidence)
when benny proposes the deal to dean, he initially doesn’t want to find cas. what is the reason for benny to not want cas to come with? dean is his only way out, so it’s in his best interest to appease him.
(see images for evidence)
it’s not hard to imagine that cas would tell benny to discourage dean from finding him. cas knows that dean trying to find him would not only be put dean at more risk, but would also a threat to cas’ plan to stay in purgatory and “do penance”.
finally exhibit g: the tension between cas and benny
when deancas reunite, dean introduces benny to cas. there’s something about the way benny looks away before he greets cas, and especially the way cas doesn’t even really acknowledge him, that feels off +
when deancas reunite, dean introduces benny to cas. there’s something about the way benny looks away before he greets cas, and especially the way cas doesn’t even really acknowledge him, that feels off +
like they’re trying to hide that they know each other.
if dean finds out benny knew where cas was or that he was discouraging him to find cas even though he knew he was okay, his with him deal would be off, & benny would be stuck in purgatory.
if dean finds out benny knew where cas was or that he was discouraging him to find cas even though he knew he was okay, his with him deal would be off, & benny would be stuck in purgatory.
again, it’s in his best interest to keep quiet.
however, this does bring up the question, why did benny ask cas why he left dean when they were finally reunited.
arguably, this seems to go against this entire theory, but there are some possible explanations that could fit.
however, this does bring up the question, why did benny ask cas why he left dean when they were finally reunited.
arguably, this seems to go against this entire theory, but there are some possible explanations that could fit.
explanation 1: after seeing dean pray to cas every night, despite not getting any response, benny gets mad at cas for leaving such a loyal friend/a person benny has grown to respect.
explanation 2: benny thought it would help their cover to ask that.
explanation 2: benny thought it would help their cover to ask that.
tl;dr: cas knows how to leave purgatory, but doesn’t want to put dean at risk of the leviathans by telling him directly, so he makes a deal with benny to help dean out, and then when they are all reunited, keeping the secret from dean causes a lot of tension +
especially if we consider that benny knows cas’ real intentions.
obviously there are some things that don’t quite add up about this headcanon here and there, but it’s interesting, and not too out of character imo.
thanks for reading! have a good day
obviously there are some things that don’t quite add up about this headcanon here and there, but it’s interesting, and not too out of character imo.
thanks for reading! have a good day


the amount of typos in this thread pls look away it’s 4am here
