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Originally Posted by itachi-san314
^back when itachi told sasuke he had to kill his closest friend, sasuke and naruto were not friends. sasuke probably didn't even even know naruto existed. there's no way itachi could have seen that coming. he probably assumed it would be an akamichi or an aburame or someone who could have easily been swept under the carpet and not given sasuke away as a murderer
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More likely it was Itachi's back-handed/reverse psychological way of telling Sasuke to get a friend. Or, it was his way of making sure Sasuke (who was always deemed to be very emotional) didn't have the guts to kill his friend. As Hunter said, the whole 'kill your best friend' thing is somewhat fake. It can work that way, but it can also work in quite a variety of other ways. Consequently, we have to look at what Itachi hoped to accomplish by telling Sasuke to kill his friend, rather than treating the information as a true maxim for attaining the MS.