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Quite honestly, Itachi does not fit the definition of an anti-hero. First of all, an anti-hero is a protagonist who achieves goals and realizes ambitions that are the antithesis to that of a hero. Kishi establishes Itachi as an antagonist from the very start of the series, ergo he does not fit the bill of an anti-hero. He does, on the other hand, fit the bill for an anti-villain:
an antagonist who achieves goals and realizes ambitions that are the antithesis of a villain.
Really, all the discussion has been about is how much of a badass Itachi is, and essentially what his intentions are. This definition sufficiently establishes Itachi as an anti-villain. He is an antagonist, his goals are contrary to that of the two main antagonists of the series, which accounts for a portion of the anti-hero defintion. The outcome is not what he would have wished, that much is certain. But the implications of his chosen outcome was that he was never truly loyal to Akatsuki, or even the Uchiha clan, but rather he chose to remain loyal to Konoha; which is a direct contradiction to the where the loyalties of Madara, Orochimaru, and the rest of Akatsuki lie.
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