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What would they say to each other if they met.
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It would be a very quotable conversation.
Madara would just smile as they talk about peace, how their ideals are conflicted, and argue about who's right.
Itachi: Forcing people in an eternal genjutsu way not the right way. On top of that, you manipulated everyone for your own personal gain.
Madara: I did everything, so people can live in peace. I did not attend for the possibility of everyone turning into Zetsu and Kaguya's resurrection. What have you done? Oh, that's right. You manipulated your brother and obeyed the elders of the village like a good dog.
Itachi: I sacrificed my happiness and my family for the sake of the village and the safety of my brother.
Madara: The same village that discriminated, oppressed, and treated our clan like dogs since Tobirama's reign. You turned your brother against the village and forced him to live with the pain for sake of the villages' corrupt ideas. You have no right to judge.
Itachi: I did what I had to.
Madara: (Chuckles) You did what they wanted like a good girl!
Their conversation would be something like that.
Itachi would slap Madara's ass and hold it in his palm for 2 seconds, whilst smiling with a sinister grin.
Madara would step on that traitor like a bug with his Perfect Susanoo before that happens.
:kk:
Sorry, but Foddera stands no chance against the god of memes.
They're complete opposites when it comes to complying with the Leaf.
In that way Itachi was cuckolded by Konoha whilst Madara chose to become a bitter old man sucking Hashi DNA til he went senile. Not sure who got off better.