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Trans!Zenkichi angst time!
(tw: transphobia, deadnaming, various forms of harassment and assault)
Now let's face it, the guy has had it rough from day 1. Nobody wanted anything to do with him when he came out, his own family included. Aoi and her own family are what helped him keep going, even providing the means to get top surgery which was one of the happiest days of his life. He was treated decently enough at first when he started his job (after having Akane via a donor)... That is until his full information was leaked out somehow.
He wasn't able to legally change his name yet so his deadname was still in his files. He suspects a petty co-worker but the damage was done anyways as it gets followed by deadnaming, bullying, and full on harassment. To them, he has no voice at all and he can't do anything about it... And he started to believe them. Especially after Aoi's passing. It all got worse for him: Insults, slurs, sexism, even unwanted attention.
When the PTs found out and accepted him, his surprise was evident but then happy for the first time in a while. His recovery begins a bit. His interrogation however nearly undid it all as the beatings escalated along with getting threats should he refuse to fess up. I'm pretty sure we all know the types of threats and comments he had gotten before Sae intervened. Didn't stop him from being anxious and even scared out of his mind regardless of the outcome. Before he could even wonder whether they were serious or not, they grab him and he full blown starts to panic. They don't go far though as Sae shows up before anything else could happen. They deny any attempt at wrongdoing but she wasn't convinced at all. He ended up more traumatized and he still feels banged up from the whole thing. Learning that Akane has a Jail now was basically the straw that broke the camel's back. It doesn't stop him from wanting to step in to help though, even if it kills him.
Fast forward to his awakening and next to getting top surgery and having Akane with Aoi, it was the happiest moment of his life. He didn't even know what to expect but gaining Valjean, a distinctively male Persona on top of it, and then his Thief outfit gave him such an overwhelming feeling of euphoria. He felt liberated and free now, more comfortable in his own skin.
Look, all I'm saying is: Trans!Zenkichi HC is gives me strong feelings here and he would have undoubtedly went through more hell and trauma before then feeling strong gender euphoria after awakening. That and giving his co-workers the middle finger at some point too.