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#with his fancy wine and clothes and relationship with both koyou and his mackerel
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hot take (? maybe? i don't fully know what the general stance is on this) but i don't think chuuya would've left the mafia with dazai
not because their bond is shallow (sike, fyodor) but because i think chuuya found his grip in the mafia by the time the dark era rolls around. he entered the mafia because of dazai yeah but they both have lives outside of each other still. after everything that happens in fifteen, koyou being in the mafia, and also just chuuya's unwavering loyalty - which he swore to mori, however unfortunately but it's still the truth - i think he would've let dazai go alone.
but there's that other thing though; his bond with dazai. his very significant bond with dazai. that's why i think he would've let dazai go; as long as dazai isn't leaving because of something he did, or plotting to like, burn the mafia down, i don't think he would've been particularly bothered beyond the 'dealing with traitors' business but honestly lets be real if you're important enough in the mafia, being a traitor or threat or enemy means jackshit (tachihara, verlaine, chuuya, even dazai is literally invited back by mori lmao).
i can see chuuya just tsk-ing and waving him off like "you probably have an escape route planned so i'm not even gonna bother pursuing you, won't give you the satisfaction of dying quickly either, you do you bastard, imma go celebrate with wine now, don't die i'm still gonna kill you someday, see ya." or like. you know. some rough approximation of that.
i think if dazai actually told him, considering what i know of his character thus far, chuuya would've helped him leave or, at least, rolled his eyes and looked the other way and do essentially a scripted song and dance of hunting him down with everyone, including mori, knowing full well that a) dazai won't be found unless he doesn't want to be, and b) the only person remotely capable of finding him would just punch him in the face then let him go again
skk would probably just keep up their usual bickering nonsense via randomly breaking into each others places (i.e. dazai because he's now broke and chuuya exclusively breathes designer air) and even if they don't interact for long periods, they would easily slide back into their dynamics whenever they do, as it is in canon except they'd likely manage to be even more in-tune and annoying with each other.
(also the ADA would know about the mysterious rich redhead whose number is listed as "dazai's dog" to call up when dazai is up to his shenanigans so he can come over and kick discipline into him. guessing who the hell he is another one of their mysteries and they know it ties in with dazai's old job, just not how. ranpo cackles everytime he shows up. he and kunikida meet up for lunch to bitch about dazai.)
tl;dr, imo skk could've been skk for the missing four years with chuuya still being an executive and dazai stiill being a detective if only mister cyclops there chose communication over blowing a car up, because i do believe chuuya would've let everything play out the same as in canon except he and dazai wouldn't be cut off the whole time
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