In what situation would they have met?Like, did he make them not meet each other so that it wouldn't be weird? I think Madara would win but seeing him defeat Itachi would be kinda sad, if Madara doens't win then that's weird too.
You gotta take into account their missions as edo.
I'm pretty sure Nagato and Itachi's job was to literally cause mayhem on non combative. So they would be away from the fight.
Madara was used against the army and to capture Naruto.
When Itachi broke free, running to fight another immortal person would have been retarded, even if he could totska blade him. Because he isn't the only threat.
Kabuto had some scary mother-fuckers running around and not everyone has fuinjutsu or even capable of defeating them.
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