Tobi ( MS ) VS Jiraiya , Orochimaru and tsunade

niceday

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Tobi will use his phasing ability and they wont be able to touch him. tobi will then use his space–time ninjutsu on them and send them to another dimension.
 

salamander uchiha

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Orochimaru told suigestu that he was interested in his war, backing off from interfering.
Jiraiya lost to Jiraiya and Tsunade called him an invincible immortal.

Tobious got this one. He’ll put Orochimaru in a powerful ocular genjutsu (since both Itachi and Sasuke whooped his ass with one).
He’ll impale Jiraiya with six path black weapons just like how Pain killed him with 4 of them. Lastly Tsunade will be warped into kamui for later purposes. Probably dress her in a Rin outfit.
@bold: damn bro thinking like a true good boy.

OT: what Rikudou Tobi said.
 

HowDidIGetPrem

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I would say Tobi wins, but Tsunade is a very real threat for him. The moment that she understands releasing chakra when she THINKS she'll make contact with him is only a waste is also the moment she stops releasing any of her chakra for attacks. I understand that Tobi's chakra constraints may as well be nonexistent, but they're still there. The guy simply isn't outlasting them unless he can find the opportunity to do major harm to Jiraiya and Tsunade multiple times as a method for them to dispense their chakra through healing. Pretty unlikely given how well Kakashi and Gai did against him.

Opposed to Tobi's useless state, the Sannin still can either bait Tobi or have hax ready for him if he doesn't take the bait.

1.Frog Song has two vulnerable & visibly plotting toads just begging for Tobi to attack them. They either snare him if he doesn't take the bait or becomes predictably tangible when taking the bait. Keep in mind that Tobi wouldn't know they're casting a genjutsu unless the dumb frogs actually say it in front of him.

2. It may be possible for Tsunade to give everyone her slugs and have the slugs reverse summon others/herself into Kamui if anyone is caught(this one's a bit of a stretch). Hell, it may be possible for Jiraiya & Orochimaru to share little frogs and snakes between each other and achieve the same thing. This would either discourage Obito from absorbing anyone if he catches on, or allow two characters to attack from the inside & escape Kamui if he foolishly sucks anyone up. Jiraiya can may be able to sense that Obito is gone & thus uses s/t jutsu to devise this counter & Orochimaru may have the analytical ability to reason this out as well.

If 1 nor 2 puts him down, he still isn't outlasting him.
 
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Scryed

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No. He survived Konami jutsu with a genjutsu, which he can only use once.
I think he's referring to the genjutsu used after Izanagi when he said, "once this genjutsu ends, so will your life" although it's unclear whether she died because of the genjutsu or because of the rod he impaled her with.

Ot: Obito wins after controlling Orochimaru like he did with the perfect Jinchuuriki to have him fight Jaraiya while he deals with Tsunade first.
 

Uverdore9

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Now that I think of it the Sannin wins. Frog Song and Frog Call can oneshot and Kusanagi blade slices through Obito's neck when the 5 minute time limit is over.
 
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