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No, obito was never afraid of Itachi.
^^ This picture is a huge misconception....Obito attacked the leaf village when Itachi was a child right?
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This means that minato defeated obito when Itachi was 6. That was
7 years before the uchiha clan massacre took place (making Itachi 13). This is when itachi
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obito, & this is when they had that "deal". Obito was merely humoring Itachi for the plot's sake, obito could've attacked konoha in the 7 year time period before he even met up with Itachi, lol...
All in all, Itachi did nothing to stop obito's plans, he was simply a plot shield.