While some may say that Obito (pre-rinnegan) was not scared of Itachi, are we forgetting that he made a point of not going forward with his plan until Itach was dead? Are we ignoring Obito saying something along the lines of “if he (Itachi) knew everything about me, I’d (Obito) be dead.”??? (Now I will admit Rinnegan Obito/War Arc Obito could beat Itachi. I’m not debating all that tho, just pointing out things.)
Itachi was able to escape Kabuto’s control and even Kabuto was surprised by this. There was much more to this than Itachi escaping Kabuto’s control, like Itachi proving once again he is a very intelligent and strategic character. He anticipated that he would be reanimated and he pre-planned so that he could escape the control.
Now, the next things I’m about to say is very controversial but Sasuke was terrified of Itachi. While most of this fear came from the Tsukuyomi, Sasuke, in his prime, was afraid of Itachi, despite Itachi literally bleeding out right in front of him.
Another controversial thing is that Danzo was scared of Itachi. Now, this mostly comes from the fact that Itachi is a direct threat to Danzo, he could expose everything shady that Danzo was involved in and even threatened Danzo with it after the massacre to make sure Sasuke stayed safe. While I believe Danzo was afraid of Itachi, he also respected his abilities, he even tells Sasuke that his (Sasuke’s) Genjutsu is vastly inferior to Itachi’s.
