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Well an fight between Sasuke and Itach would be interesting.
Just think of the fact that they predict eachothers movments, what a strange fight that would be
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I doubt Sasuke would gain that much experience in just 3 years, compared to Itachi. So Itachi will still have the upper hand on that fight.
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I think the theory on Itachi killing every1 was to keep the power away from the hands of the Akatsuki and is now undercover.
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Itachi probably knew what Oro was gonna do or something. Or Oro tried what he did with Sasuke to Itachi...