Originally Posted by Wolverine
On a random thought... why didn't Itachi ever use Izanami on Obito? It is suppsoed to be the strongest Genjutsu...
Koto is the strongest genjutsu not Izanami.
Itachi had a plan and that plan involved having his eyes taken by Sasuke. Losing one eye would have fucked up that plan.
Also, Izanami requires that you engage your opponent in combat UNTIL Izanami is ready and trying that on someone who he thought was Madara, who could warp away at any given time, would be a futile. Tobi could just warp away and Itachi left standing there with one eyr.