Wait....

[Namikun]

I just re-watched the Naruto vs Sasuke fight at the final valley and I thought by myself...did Itachi really want Sasuke to kill Naruto? He didn't know Sasuke wouldn't kill him, right ? That sick asswipe lol.

 

[Tobi98]

How the hell am I supposed to know?

 

[Hebi Sasuke]

Did Itachi knew Naruto was Sasuke's best friend? Think not.

 

[Its sasukebase]

i think he i did i dont kishi knew itachi wasn't evil himself at that point

 

[RedRobin]

Well Itachi killed all those people, Naruto would have been nothing . It would have put Obito's back for a while.

 

[Six Paths]

I don't know to tell the truth.

 

[Fuzzy Panda]

LOL at the time I think Itachi thought Sasuke had no friends. He probably meant kill your imaginary friend.

Silly Sasuke.

 

[SkyGodHorus]

Itachi was a wonderkind like Urahara. He knew pretty much everything. He may have been watching them for all we know and planned to hide Naruto from Akatsuki rather than taking him to them before Jiraiya showed up.

 

[BLAZE]

Itachi wanted to save sasuke by any means possible then what's the problem with that
he did kill his own clan including maybe children wasn't that sick

 

[Young Vongola]

He said Sasuke's best friend. It didnt matter who it was lol

 

[The7thHokage]

Itachi didnt know who Naruto was, and he didnt know he was Sasuke's best friend lol.

If he had known it was Naruto things would have been way different.

 

[ANiMUS]

TBH, I wonder how Itachi was expecting Sasuke to be able to go back to the village as a hero if his plan involved Sasuke killing a fellow Konoha shinobi......................................It seems rather stupid, maybe he didn't think Sasuke would be able to pull it off and instead wanted Sasuke to seek him out when his friend died in battle or something.

 

[ShiroT]

he told him to kill his best friend but he didnt mean naruto at the time since sasuke didnt really have any friends