Obito was Frightened of Itachi (Kishimoto's words)

Itachi Uchiha Solo King

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Itachi was the only thing keeping Obito in line for part one & two.
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Obito was the one to flee from Itachi.

The only movie written by Kishimoto pretty much shows this:

Itachi shows up to rescue Sakura and immediately realizes that physical attacks won't work:
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[/SPOILER]

Itachi says he knows a way to hurt Obito in spite of Kamui:
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FYI, constantly keeping his distance is how Obito kept even Kamui a secret from Itachi.
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He kept it a secret from no other ninja...
Obito thought Itachi was THE SHIT, bra.

Obito was constantly amazed by Itachi...
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Conclusion:

Obito was incredibly, incredibly cautious of Itachi & kept his distance

He was too frightened to send Pain to destroy the leaf while itachi was a live so knowing that kakuzu and hidan wouldnt be able to harm the leaf he sent them to die

He even stayed out of Akatsuki when Itachi was roaming.

(So Madara Orochimaru and Obito have that in common.)

 
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Jasey

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Infinite detention... You are very brave my friend lol
 

Angelic.

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fail. obito isnt afraid of him, only his aids
 

RasenUchihaChaos

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He was wary of itachi Tough people don't like to admit e manga states that they say obiot could beat itachi no diff yet if that's e case why itachi never warp way around itachi cuz he knew itachi figure it out just like konan did and kill him
 

Sasori

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Images are just done wrong.

Ot: He was just waiting till Itachi died since he knew he was a spy.
 

Koro

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This is the worst BBCode formatting I've seen in my life.

OT:
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Sirius Black

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If you are an Itachi Fan (Fapboy). Than don't make threads where people start bashing him.
 

Drackos

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I'm sure he was just wary of him. Not absolutely frightened by him. None of the Akatsuki are fodders. He probably saw him as more of a nuisance to take head on and probably just wanted to wait him out.
 

Jasey

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Shut the hell up!!! Women are not allowed to talk unless they get permission. Go back to the Kitchen Konan!!!

Hey, Villain,
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Chie

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Obito was cautious of him shown by his words in the canon manga and the way that Kishimoto portrayed him in the RTN movie that he devised the script for...he ran away from Itachi. ._.
 

RasenUchihaChaos

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Funny thing is even Nagato could have beat ms obiot since konan knew about kamui and its limit pretty sure she told Nagato
 
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