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If they weren't allies, how could Obito just think about capturing both the
eight and nine-tails, and win a war in which he was challenging the 5 great
nations?

His only weapons were the clones of the white Zetsu, which, regardless of
their "copy ability", were such a big failure, and the Gedo statue, which was
his trump card. In that way, Obito would stand against an Allied Shinobi
Nation, who weren't weakened by the Edo Tensei reanimations, but obviously, he
wasn't expecting that Kabuto would search for him and offer a helping hand, so
I think that Obito was overestimated by Madara to think that he could manage a
plan with such a great magnitude.

And as second thought, what were his plans for resurrecting Madara? Losing
Nagato's 7th path, I'm curious how he would've managed this part of their
plan. It's kind of luck for both Obito and Madara, that the events turned out
as they are right now in the anime...


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naruto
What would've happened if Obito didn't accept Kabuto's help?


I think your hint goes in the right direction, Madara had counted on Nagato to
resurrect him, he didn't expect Nagato to betray their plan. And then Madara,
with Obito and Nagato's help, could have taken care of the five nations.

From wiki:

> Tobi was surprised by news of Nagato's death and, more so, his "betrayal",
> having wanted Nagato to save the Samsara of Heavenly Life Technique for him.


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I guess Obito will lose the war.

Obito seems to have underestimated the 5 nations. Maybe because he thought
that he can take advantage of their previous wars and conflicts and never
expected that the alliance will truly go in war as one allied shinobi rather
than fighting for their own nation.

As for plans on resurrecting Madara, I don't think he still plans to do so
since he said that he wants Nagato to use the 7th path on him and his current
actions shows that he wants to be the Juubi's jinchuriki himself and the one
to cast infinite tsukoyomi and I think he underestimated Madara on that one
too.


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With the rinnegan, he can defeat the five kage. Also he had gedo statue and 7
tailed beasts at his disposal. If you consider that kabuto never met him, then
there would be no itachi and no previous hokage and sasuke would have been on
his side. With an EMS sasuke, he can easily win the war. Even if sasuke never
joined the battle, he was able to take on kcm2 naruto, bee, kakashi and guy.
He would have found a way to retrieve some part of 8 tails and 9 tails chakra
either by using white zetsu or by his chakra absorption and gone for an
imperfect transformation again by making kakashi force him break the seal by a
chidori.


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