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What do you mean "beaten sasuke a lot of times"? He isn't one of the "bosses" like Kabuto or Orochimaru, he's just a forest fight that I know of... and If I'm getting it, how would Itachi fit into it after you have beaten Orochimaru? They are not comrades or partners and really have nothing in common after Orochimaru defected from Akatsuki...
i think hes just asking for itachi to be added like another mini-boss.
Maybe we can drop Orochimaru to 14,you have to beat him to go to lvl 15.Then beat Itachi at 15 to go to the next rank.I think that's what they ment.