Mei Terumi
Old Hiruzen
Gengetsu Hozuki
Tsunade Senju
3T Itachi
Hebi Sasuke
3T Kakashi
Kakuzu
Sasori
Deidara
Kills: Mei, Gengetsu, Sasori, Itachi, Kakuzu
With:
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Gengetsu has no counter Itachi has no counter. Kakuzu has no counter. Mei can use a big ass Suiton but if it comes to whose shooting their move longer (because Mei can shoot a Suiton for a long amount of time), Jman still trumps her in chakra and will keep spitting fire while Bunta spits the oil. She gets roasted alive. Sasori can defend with Iron Sand but high heat demagnetizes his sand and it will dissolve and he'll be roasted as well.
Kills: Kakashi, Hebi Sasuke
With: Various jutsu. Their main area is CQC but its also the worst against Jiraiya. If they get close they are crushed and impaled to death with Needle Jizo/Wild Lions Mane and nothing they will do will free them. Its as hard as steel and easily crushed Animal Paths boss summon. Sasuke can survive with Oral Rebirth but hes done for if he uses that due to chakra drain. Manda is slightly superior to Gamabunta but they can out number him because Gamabunta can summon Gamashiro or Gamaken to aid him.
Kills: Hiruzen
With: Outlasting him.
Loses: Deidara, Tsunade.
Because: C4, Tsunade can tank anything he dishes out and outlast him.
Kills: Mei, Gengetsu, Sasori, Itachi, Kakuzu
With:
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Gengetsu has no counter Itachi has no counter. Kakuzu has no counter. Mei can use a big ass Suiton but if it comes to whose shooting their move longer (because Mei can shoot a Suiton for a long amount of time), Jman still trumps her in chakra and will keep spitting fire while Bunta spits the oil. She gets roasted alive. Sasori can defend with Iron Sand but high heat demagnetizes his sand and it will dissolve and he'll be roasted as well.
Kills: Kakashi, Hebi Sasuke
With: Various jutsu. Their main area is CQC but its also the worst against Jiraiya. If they get close they are crushed and impaled to death with Needle Jizo/Wild Lions Mane and nothing they will do will free them. Its as hard as steel and easily crushed Animal Paths boss summon. Sasuke can survive with Oral Rebirth but hes done for if he uses that due to chakra drain. Manda is slightly superior to Gamabunta but they can out number him because Gamabunta can summon Gamashiro or Gamaken to aid him.
Kills: Hiruzen
With: Outlasting him.
Loses: Deidara, Tsunade.
Because: C4, Tsunade can tank anything he dishes out and outlast him.
jiraiya is underrated in my opinion here's why:
has access to 4 elements- fire release, wind release, earth release, water release plus ying and yang release
has imperfect sage mode- access to sage art techniques, imperfect sage mode can tank anyone below kage level and and he can take on kage level shinobi with this alone
powerful ninjutsu- powerful fire release jutsus, barrier techniques, rasengan variants, sage art jutsus, frog kata, hair jutsus, toad jutsus
can summon toads e.g gamabunta- he can tank anyone below kage level and take on kage level shinobi with this alone
cooperation ninjutsu- he can use powerful cooperation ninjutsu techniques with toads e.g toad oil flame bullet, wind release water gun, high level sound base genjutsu with fukasaku and shima, sage art goemon etc.
nagato even admitted that jiraiya would defeat him if he knew about the secret of his 6 paths technique

So whats your point in listing the skills of Jiraiya when they are all countered by the likes of 3 tomoe Itachi,Kakashi or hebi Sasuke? Not to mention some of them ain't even base Jiraiyas skills.
All three of Itachi,Kakashi and Sasuke can force the toads to pact with them via sharingan genjutsu, forcing Jiraiya to dispel his summonings. Plus Kakashi can get rid of them with his raiden if its needed.explain to me how 3 tomoe itachi, kakashi or hebi sasuke can counter jiraiya's techniques. jiraiyas barrier canopy method will limit their close combat/taijutsu. i don't see how 3 tomoe kakashi can take on jiraiya's summonings e.g gamabunta, gamaken etc. kakashi has all 5 elements so he can cancel out some of jiraiya's techniques but he will lose on chakra and stamina. yes itachi can cancel out jiraiya's fire release techniques with water release but can 3 tomoe itachi take on jiraiya and the toads? itachi's elements are - fire release, wind release and water release. jiraiya's are fire, wind, water and earth. itachi is an extremely intelligent shinobi and is a master of genjutsu but i see jiraiya defeating him
1) because of his jutsu diversity 2) because of the overall power of his jutsu's. don't get me wrong, i think MS itachi can beat jiraiya but not 3 tomoe itachi. hebi sasuke might have a chance because he can summon snakes e.g aoda to counter jiraiya's toad summonings but apart from that i don't see what else he can do, his raiton will cause jiraiya trouble but i see jiraiya ultimately winnning.
Mei Terumi- Jiraiya can win
Old Hiruzen - Jiraiya wins
Gengetsu Hozuki- Jiraiya wins if he manages to destroy the clam before the mizukage shoots a bullet through his skull
Tsunade Senju- Jiraiya wins
3T Itachi- Jiraiya wins
Hebi Sasuke- Jiraiya wins mid diff
3T Kakashi- Jiraiya wins low diff
Kakuzu- Jiraiya wins mid diff
Sasori- Jiraiya obliterates him
Deidara- Jiraiya wins this mid/high diff
All three of Itachi,Kakashi and Sasuke can force the toads to pact with them via sharingan genjutsu, forcing Jiraiya to dispel his summonings. Plus Kakashi can get rid of them with his raiden if its needed.
How the barrier helps Jiraiya in taijutsu? He needs to hold his hands in clap to maintain this jutsu so his taijutsu would be limited.
Kakashi can hide underground from Jiraiyas expanded techniques, Sasuke can avoid them through flying up.
Plus in close combat Jiraiya must keep his eyes away from the sight of his opponent's sharingans so he has to rely on his barrier but that also makes him vulnerable as i explained above.
Moreso, I don't recall Jiraiya using wind element, could you refresh my memory with a scan?
All they have to do is to get close to Jiraiya and then they have this match in their bags.
1) You are not enlightened upon Kakashi's genjutsu feats, its clear.1) kakashi won't be able to put gamabunta in a genjutsu. so jiraiya beats kakashi
2) jiraiya doesn't need to clap his hands to maintain the barrier, he clapped his hands because he was summoning shima and fukaksaku. so kakashi, itachi and sasuke will be limited in taijutsu vs jiraiya
3) jiraiya can look at 3 tomoe sharingan in the eyes it's only itachi's mangekyo sharingan where he can't look at him directly in the eye.
4) rasengan is a wind element jusu
5) you're right, itachi and sasuke can put the toads in a genjutsu, so yeah i agree with you that sasuke and itachi can defeat jiraiya if they can put the toads in a genjutsu
jiraiya beats kakashi but loses to sasuke and itachi if they can put the toads in a genjutsu
Rasengan in itself just a superfast chakra flow without any elemental enhancement.nah im serious,Can't tell if you're trolling or serious bro. SM restricted. Bolded ones stick out a lot
c4 won't do anything to jiraiya if gamikichi, fukasaku or shima can reverse summon him. he defeats tsunade, his coorporation ninjutsus and barrier canopy method formation will be tough for tsunade to handle
nah im serious,
as for the bolded ones, you had Hebi Sasuke, and 3T Kakashi, well the former gets defeated without too much diff whilst the latter gets nearly stomped,