Board Thread:Versus Debates/@comment-38812954-20191010013440/@comment-43403813-20191011130121

I'd say Itachi is superior to Madara in terms of his usage of genjutsu, but Madara wouldn't be that far behind him. He's used genjutsu on plenty of occasions, such as against a fodder ninja about to axe him when he was fighting the Alliance, or when he used it on Ay whilst fighting the 5 Kage.

Madara would be able to break out of it after a couple seconds without too much trouble. It's just Itachi's choice whether he would want to expend so much chakra on a technique that might not even faze Madara. And even if Itachi chooses to, I am 95% sure that any physical torture used against Madara would not have as great of an effect as it did against kakashi.