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Originally Posted by knubbe
Those "fancy eye tricks" pretty much mean automatic win for Itachi if you look him in the eye at all. If you're forced to not look at his eye and focus on his feet as Gai suggests you're at a disadvantage then too. The only person who could pull that off effectively is probably Gai himself and we know too little about either Itachi or Gai to predict how that fight would go.
Anyways my vote goes to Sakura since she obviously owns Naruto for free, and Naruto in his prime is in theory uber strong and Sakura > Naruto.
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We've seen him do it on Kakashi, and on Sasuke, neither of them are even contenders for being the strongest ninja. We do know that it is Genjutsu, but we don't know if it is counterable. We do know that the only two people we've seen him do it on didn't know a way to counter it. I doubt Itachi invented the technique himself, so some of the more experienced Ninja, like Jiriaya, probably know about it, and maybe a way to get around or counter it.
The fact is that everything about the all powerfulness of this guy is just assumed off of the outcome of two fights. One against a strong, but not anywhere near strongest, ninja, and one against a crap little guy like Sasuke