Mini Plot Hole

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It was set to activate on Tobi because Itachi didn't want Tobi to tell him everything that he told Sasuke about the Uchiha Clan and his brother Itachi...It was Itachi's attempt to kill Tobi to protect Sasuke. His plan failed though. Itachi could have beaten Sasuke but he wasn't trying to win, besides, Itachi was in a weakened state (coughing up blood and such...) Irrelevant though...Simply put, Amaterasu was set to activate on Tobi to kill him to hide the secrets from Sasuke. Sure enough, Sasuke was brain washed by Tobi...
 
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You are underestimating Itachi. Simply put, Itachi made what is known as a "Trigger Effect" so that right when Sasuke saw Tobi's Sharingan, left or right eye shouldn't matter, Sasukes Mangekyo would activate Amaterasu on Tobi. You are looking too into it. Itachi has no beef with Kakashi too (even though Obito and Kakashi share the same eyes) The Amaterasu was not meant for Kakashi...besides...the Amaterasu only activated when Sasuke saw Tobi's right eye
how is it stupid when now its obvious that they have the same sharingan
 
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