Why did Itachi use Tsukuyomi on Kakashi?

SQY

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Because he was an Akatsuki Member. And he is not on Konoha's side. He simply trusted the Village, he really cares for his Brother. The people of the village do not matter to him.
 
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The people of the village do not matter to him.
Okay, so that's why he killed his entire family (with the exception of Sasuke and Obito) for the sake of the Leaf, and because he was ordered to. That must also be why he programmed Shisui's eye to make Sasuke "protect the leaf", and even if that failed, it was still his original intention.
 

Itachi Rane

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either kishi wanted us to believe he was evil or maybe itachi wanted to show kakashi his powers so that kakashi knows the extent of itachi's genjutsu abilities and thus trains to be prepared enough in case they meet again....
 

Wanheda

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The answer is above but because since Kisame is an Akatsuki member so itachi had to make a scene for it to look he doesn't care about the people of Konoha but he actually trying to help and he cares for his brother Sasuke.
 

Stark

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He wanted to see if Kakashi was powerful enough to protect/train Sasuke, so he wanted to see how strong he was in all aspects of combat including Genjutsu.
 
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