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It's already manga cannon Jiraya wins. Jiraya vs Pain
Taijutsu:
SM Jiraya has superior speed over any of the Paths. He was blitzing them left and right during that battle kicking them in the face before they could even react, sometime even despite Rinnegan shared vision(which was the only thing that was saving them from a taijutsu stomp). So in a 1vs1 taijutsu battle, SM Jiraya would always have the advantage, something stated by Jiraya later. However i'm perfectly aware of the Shared vision around 6bodies being a problem and would even be an advantage
However Jiraya already showed to be smart enough to prepare an interesting i must say, since he was able to block the Rinnengan share vision by using basic ninjutsus. Hiding a clone on the wall, he used a katon Dai Endan to cover Gakido's vision, while placing a already prepared yomi numa to stop human Path movements(who was already blind anyway because of Jiraya's kick) by forcing them to jump with a katon, and thus entering a 1vs1 situation that leads to his victory. So 1 point for Jiraya here
Ninjutsu:
Ninjutsu would be a problem though especially Animal Path and Deva Path from my point of view. He is perfectly able to handle Human Path and Narakara Path has nothing special than only reviving the other Paths though like he did in cannon even.
Summoning jutsu won't be a problem for Jiraya since it's already proven that he could smash them away with ease. Or simply destroy them with Pa and Ma combos like this one for example. Even the cameleon won't be a problem due to his detection barrier for him combined with Ma's all-living being tracking ability
Jiraya should kill Gakido very fast and with knowledge, it's what he will try first. After that, he can also use Senpou Goemon(something that was creating deformations on the environment including hard metalls in an instant without contact), which covers an insane range to put every Pain in difficulties. The Senpo Goemon is a particular dangerous move since because of the high temperature of the jutsu, it's even said to reduce everything to cinders in the databook
Genjutsu:
Pain has shown great vulnerability to Pa and Ma sound genjutsu. If he sets that up, it's a lost for Pain and with his superior taijutsu over the Paths, his variety of ninjutsu, or even kage Bunshin to make some Paths busy(Kage Bunshin able to use ninjutsus like Katon Dai endan themselves to keep some busy), i can see him able to pull it off, and in this case, the Paths are fighting all 6 with Jiraya having knowledge on it, so they are not escaping.
Taijutsu:
SM Jiraya has superior speed over any of the Paths. He was blitzing them left and right during that battle kicking them in the face before they could even react, sometime even despite Rinnegan shared vision(which was the only thing that was saving them from a taijutsu stomp). So in a 1vs1 taijutsu battle, SM Jiraya would always have the advantage, something stated by Jiraya later. However i'm perfectly aware of the Shared vision around 6bodies being a problem and would even be an advantage
However Jiraya already showed to be smart enough to prepare an interesting i must say, since he was able to block the Rinnengan share vision by using basic ninjutsus. Hiding a clone on the wall, he used a katon Dai Endan to cover Gakido's vision, while placing a already prepared yomi numa to stop human Path movements(who was already blind anyway because of Jiraya's kick) by forcing them to jump with a katon, and thus entering a 1vs1 situation that leads to his victory. So 1 point for Jiraya here
Ninjutsu:
Ninjutsu would be a problem though especially Animal Path and Deva Path from my point of view. He is perfectly able to handle Human Path and Narakara Path has nothing special than only reviving the other Paths though like he did in cannon even.
Summoning jutsu won't be a problem for Jiraya since it's already proven that he could smash them away with ease. Or simply destroy them with Pa and Ma combos like this one for example. Even the cameleon won't be a problem due to his detection barrier for him combined with Ma's all-living being tracking ability
Jiraya should kill Gakido very fast and with knowledge, it's what he will try first. After that, he can also use Senpou Goemon(something that was creating deformations on the environment including hard metalls in an instant without contact), which covers an insane range to put every Pain in difficulties. The Senpo Goemon is a particular dangerous move since because of the high temperature of the jutsu, it's even said to reduce everything to cinders in the databook
Genjutsu:
Pain has shown great vulnerability to Pa and Ma sound genjutsu. If he sets that up, it's a lost for Pain and with his superior taijutsu over the Paths, his variety of ninjutsu, or even kage Bunshin to make some Paths busy(Kage Bunshin able to use ninjutsus like Katon Dai endan themselves to keep some busy), i can see him able to pull it off, and in this case, the Paths are fighting all 6 with Jiraya having knowledge on it, so they are not escaping.