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Translations: Gintama 515 (2)
Jiraiya is an underestimated weapon. His best sellers might win a lot of people's heart and will offer us a worldwide support and which is better than being supported when you want to dominate the world ?
Minato and Naruto one for biju bomb the other to teleport the bijuu bomb to set example for those who don't think am serious
But since where going with five then
Shikamaru or Shikaku : for tactical purposes
Madara : Strongest punk right there
Obito : Assassination purposes
Hashirama : One of the strongest punks there
Itachi : For manipulation purposes
Anyone who omitted Shikamaru there, should read the Ravages of times or Romance of the Three Kingdoms to understand the importance of advisors
all the uchiha dudes:
hashirama or naruto