lol Sasuke out classes Itachi in every category possible.
Tsukiyomi is the most powerful Genjutsu in Itachi's arsenal. Once ensnared, Itachi can torture the victim indiscriminately; for an amount of time determined by him.
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Tsukiyomi also possesses an incredibly small activation time.
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Defeating the jutsu requires not only superior Genjutsu aptitude to the user, but the Mangekyou Sharingan as well.
Itachi has multiple methods for deploying Genjutsu. Eye-contact can instantly place the target under Sharingan Genjutsu.
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Not only must you avoid Itachi's eyes, looking at his torso leaves you vulnerable to Utakata.
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Itachi can also discorporate his Karasu Bunshins, providing him with multiple allies; all capable of Sharingan Genjutsu.
His Genjutsu is almost impossible to defeat as well. Orochimaru was incapacitated by Magen: Kasegui.
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Kurenai - the strongest Genjutsu user in Konoha - had her Genjutsu casually reflected back on her.
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Itachi is also considered capable of controlling people from afar with Genjutsu.
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He is said to possess power over the Kyuubi, which the Databook states is the same ability used by Sasuke to control Manda.
The manipulations carried out through Genjutsu, have been incredibly wide-ranging. Deidara was tricked into almost committing suicide.
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Naruto was tortured psychologically, and he has proven himself adept at simulating entire battles.
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Itachi > Sasuke in Genjutsu
In a battle of minds, Itachi is unlikely to be outsmarted. With Sharingan insight and hailed as a prodigy that scored a 5 in intelligence, only someone with Shikamaru-level intellect should be able to outsmart him. Itachi should intellectually outperform or stalemate most others.
In his first showing, Itachi used multiple schemes to out-maneuver both Kakashi and Kurenai.
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When confronting Sasuke, he mixed Bunshin feints with their shuriken clash, leaving him thoroughly unprepared.
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In his latest showings, Itachi used basic Katons and kunai to maintain the initiative.
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Although not lacking in raw power, Itachi's skill allows him to use to use basic moves at even the highest level of combat.
Itachi > Sasuke in intelligence
Itachi's weapon skills are prodigious. Sasuke explicitly summoned shuriken in order to keep up during their clash.
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He also used basic kunai to blind the Rinnegan, from blind-spots no less.
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Itachi > Sasuke in Shuriken .