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#<- said as a fellow gemini (also derogatory)
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When discussing or analyzing Dazai, one thing I hope you will keep in mind when reading anything I write about him is that from my perspective, he is always, always both.
What do I mean by this? Well, I find there tends to be a general split among people who hold the opinion that "he's a manipulator and will always be manipulative" and "he's doing his best to be good and helpful and live up to Oda's last wishes for him", of which, neither is completely right - because he is both. But even among the people who hold to this dual-nature interpretation, I find that his individual actions and motivations still tend to be thought of in a dichotomous manner - is it manipulative, or genuine?
Again, I think it's always both.
Dazai has a very pragmatic view on a lot of things - he is always looking for the usefulness of things and people so that the situation turns out in his favour. He's incredibly adept at this, and his prediction and placement and careful reveals are all manipulation tactics to get his allies and enemies doing exactly what he needs them to. I don't think anyone can contest this since we see it over and over in the series.
But that's not all there is to it. He's not solely manipulative and he does, to some extent, sympathize with others - I think there are several instances of this in the series, but I want to stress that this has been apparent since Chapter 1!
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For context, Dazai is recalling what Atsushi said to him a few minutes earlier, but it's very interesting that it should be this specific part of the conversation. He could've flashed back to the part where Atsushi said he had nowhere to go; no money, no food - he is about to trick him into joining, after all, and this is the key piece he uses to basically force Atsushi into the Agency. But instead it's Atsushi's self-deprecation that catches his attention, and it really does, because even during the conversation, he turns to look at him after he says this with an odd expression.
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You could say that this makes Atsushi easier to manipulate, if that's your angle, but that can't be solely it, because in the later conversation with Hirotsu, we know Dazai was planning to bring Atsushi into the Agency and set him up as one half of the new Double Black the moment he met him. The panel shown there is the riverbank, set much earlier in the day than this scene. He was already planning to pair him with Akutagawa since he figured out he was the tiger, so what's with this reaction?
Well. Sometimes the simplest explanation is the best.
He manipulated Atsushi into joining with the intention of utilizing him in his future plans. He also helped him and gave him a place to belong, and importantly, he likes this kid! It's both.
I think much of it might be that his brain just kinda works way too fast - he's such a natural at crafting these elaborate plots and seeing how things connect and gathering useful people like resources that it's practically automatic - though this is not a great means when you're trying to be a kinder person. There's an omake, I believe, that has him saying "I like using my head for justice", i.e. using these underhanded means to act for the better. Not great, but those are the kind of gifts he has. He's way more suited to exploitation, but is choosing to use these tactics to save people now, which is quite reminiscent of what he tells Kyouka. Kyouka's talents lie in killing people - when what you're good at isn't who you want to be, what do you do? Well, I expect you use what you have, even if it's not ideal.
Now, about the current situation with Sigma - I think he definitely likes him, and is intrigued by him and his situation. We did get a little thought bubble where the guy amusedly compares him to Atsushi, and you can't tell me he doesn't care about Atsushi (listen to the onsen drama cd, or read 55 Minutes if you somehow don't believe me). But also, it's undeniable that Sigma is in a very vulnerable position of being homeless and having had no one be genuinely kind to him before. His trust is very easy to earn, and with the latest chapter, Dazai has now saved his life multiple times. There is, as always, a practical purpose he needs him for. And I have to be somewhat amused because Dazai is quite literally telling Sigma everything he ever wanted and needed to hear. It's a brilliant means of quickly endearing himself to Sigma - but I don't think that's all it is.
Look. The most honest moments we get in this series from Dazai are, interestingly for an expert manipulator, when people are at their most vulnerable. In spite of every pointlessly cruel act he inflicted on Akutagawa, his first meeting with him was open and transparent; much like the orphanage director, it seems he thought this treatment would make him strong and adaptable (he's wrong but that's not the point of this). He cuts Kyouka off in irritation and says "don't give me that" when she implies that she would fail the entrance exam. He tells Atsushi it's normal to cry after losing a father figure and to feel however you feel, even if that person caused you nothing but incredible pain and cannot be forgiven. He refuses to entertain Sigma's assumptions that Dazai sees himself as a superior being to him.
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Selective honesty can also be utilized to great effect; Mori does this, and undoubtedly it serves this purpose for Dazai too. But I want to stress that I do sincerely believe this is all still honesty from him. Manipulation, or genuine?
Both. It's both.
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