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Honestly, I think I'm just gonna go with Inconclusive due to my reasons, as well as Cisco's. I really think this could go either way depending on a shit ton of variables.
 
Would Nagato be willing to use his most powerful gravitational jutsus even though it would end up ruining his village, considering he is in-character?

If not, I vote for Jiraiya.
 
The way I see it, if it ends up in a situation where the Pains find Jiraiya and gang up on him in combat? Jiraiya get's eviscerated. If it's closer to Jiraiya avoiding that situation and focusing on stealth, taking out key targets? Jiraiya can use his Genjutsu to disorient certain pains, and manipulate the situation to where he takes down the Naraka Path, and stop's them from getting any revives. The Animal path is the next biggest target tbh, and Jiraiya can take that one out too, with Genjutsu. Slowly but surely, he starts to eliminate the various pains, with his Summons aiding him and him likely bringing copious amounts of equipment. Weather or not he ends up getting past The Deva Path after Nagato is forced to channel his Chakra into just the one body is hard to say, but I do think he at least beats most of the pains by sneak attacks, and can handle some of the other's afterwards. I'll say incon ig
 
I believe that Jiraiya will put up a much better fight compared to what happened in canon, but I don't think it will be enough for him to take the W.

Please correct me if I am wrong, but didn't Jiraiya fight the three weaker Pains, and get bodied by the stronger paths?

Pain even after fighting the entire village, and being fatigued after blowing up said village still ended up beating down Naruto with a better sage mode, full knowledge, and outside help, and the fight only continued after he got a rage amp with Kurama.

Unless Jiraiya can manage to hit all six paths with the frog song, I can't see him winning.

I vote Pain 6/10. Jiraiya puts up a better fight, but most likely still gets killed, or retreats.
 
I believe that Jiraiya will put up a much better fight compared to what happened in canon, but I don't think it will be enough for him to take the W.

Please correct me if I am wrong, but didn't Jiraiya fight the three weaker Pains, and get bodied by the stronger paths?
He didn't really get bodied by the stronger paths, and the three Pains he fought weren't really weaker per se. Sage Mode Jiraiya and the Pains are basically just relative.
Pain even after fighting the entire village, and being fatigued after blowing up said village still ended up beating down Naruto with a better sage mode, full knowledge, and outside help, and the fight only continued after he got a rage amp with Kurama.
Well, in his battle with Naruto, Pain also had prior knowledge of the frog genjutsu which allowed him to react accordingly. If he didn't have that knowledge, the remaining Pains would've been trapped and Naruto would've just destroyed them.
Unless Jiraiya can manage to hit all six paths with the frog song, I can't see him winning.
Well here, he has prior knowledge, so if he trapped the Naraka Path with the frog song, then the remaining Pains couldn't regenerate and Jiraiya could pick them off.
 
He didn't really get bodied by the stronger paths, and the three Pains he fought weren't really weaker per se. Sage Mode Jiraiya and the Pains are basically just relative.

Well, in his battle with Naruto, Pain also had prior knowledge of the frog genjutsu which allowed him to react accordingly. If he didn't have that knowledge, the remaining Pains would've been trapped and Naruto would've just destroyed them.

Well here, he has prior knowledge, so if he trapped the Naraka Path with the frog song, then the remaining Pains couldn't regenerate and Jiraiya could pick them off.
You raise good points. But I feel like it's still hard for me to call.

I'm changing my vote to Inconclusive. Whoever manages to get off their insta-kill moves first most likely wins.
 
Jiraiya would take this. Since he know about the secret of Rinnengan and its Abilities. Then he could just separate them from the start. Like He did before.. The Absorbing Jutsu have 6 second delay usage and Same as Shinra Tensei.. Nagato cant spam same abilities without a delay. When Jiraiya seperated those Six Path, they were useless, but this time since he know there 6 of em and some knowledge about Rinnengan.
 
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