just jiraiya alone would eat up alot of itachis chakra. orochimaru uses ten thousand snakes and gaara turns the place around itachis feet to quicksand. end of fight
So basically you wanted to start a pointless flame war :l how bored can you get, we all know itachi gets raped. And there isn't any character who's healthy itachi, because he's never been healthy in his strongest according to manga facts