Itachi and Madara meeting each other

[Bad Touch Yakushi]

Madara didnt turn into a bitter old man. He manipulated everything, including Obito. With Obito, he set the terms and gave Nagato his Rinnegan to resurrect him. He's the only villain or as I call him "Anti-hero" who achieved his goal before Black Zetsu betrayed him.

Itachi on the other hand, obeyed Danzo and the elders. He just bent over and obeyed them like a good girl. He sacrificed everything for a village oppressed, dehumanized, discriminated against his own family. And that is why he's a traitor and Sasuke being forced to accept Konoha's corrupt ideas just for him is an insult.

Plan or not he still left the village disgraced and vengeful. He then stewed by himself on this plan until old age, i'd call that bitter. He's still cooler for it but it's an important part of the character that he spent decades wronged.

 

[Frois]

Itachi would die from aids before he could touch Madara.

He only has HIV, and that's from having **** with foddera