SM Jiraiya vs Third Raikage

Lariatoo

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Location: Forest of Death
Distance: 30 meters
Intel: None
Restrictions: None

Conditions: Jiraiya starts in Sage Mode with Ma and Pa on his shoulders

Who wins?

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Gold Lightning

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Jiraya wins med diff. With sage sensing and perception, he should be more than capable of reacting to Raikage, just like Naruto did. Jiraya will probably attack with hair senbon and rasengan from close and realise they are ineffective. From then on Shadow clones will be able to cause confusion and allow Jiraya to buy time.

Once toad genjutsu is prepped and cast, Raikage cant evade it. After being subdued by the genjutsu, a toad gourd can be used to seal the raikage inside and then thrown into the stomach acid.
 
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Beans2

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No intel? Raikage is a simple enough fighter anyway so that's a heavy advantage for Jiraiya. Anyway, Jiraiya wins with frog song genjutsu. First he will use Yomi Numa to turn the ground below him into a swamp. Then Shima will summon two boss toads to distract the Raikage, and Jiraiya can leave a shadow clone with them to also buy them time. Then the real Jiraiya will summon one of his barrier toads ( ), which he will crawl inside, then the toad will hide in the swamp. Ma and Pa can safely prepare their genjutsu inside the toad, with Raikage having no idea where they are in the massive swamp. Then when the genjutsu is ready, Jiraiya will summon a big toad below him to push away the mud like it pushed away sand ( )-( ), and it will push Jiraiya above the swamp. Once Raikage hears the genjutsu, he will become paralyzed and his raiton shroud will be deactivated. After that all it takes is another Yomi Numa, and Raikage will sink into the swamp and drown.
 

Lariatoo

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Jiraya wins med diff. With sage sensing and perception, he should be more than capable of reacting to Raikage, just like Naruto did. Jiraya will probably attack with hair senbon and rasengan from close and realise they are ineffective. From then on Shadow clones will be able to cause confusion and allow Jiraya to buy time.

Once toad genjutsu is prepped and cast, Raikage cant evade it. After being subdued by the genjutsu, a toad gourd can be used to seal the raikage inside and then thrown into the stomach acid.

No intel? Raikage is a simple enough fighter anyway so that's a heavy advantage for Jiraiya. Anyway, Jiraiya wins with frog song genjutsu. First he will use Yomi Numa to turn the ground below him into a swamp. Then Shima will summon two boss toads to distract the Raikage, and Jiraiya can leave a shadow clone with them to also buy them time. Then the real Jiraiya will summon one of his barrier toads ( ), which he will crawl inside, then the toad will hide in the swamp. Ma and Pa can safely prepare their genjutsu inside the toad, with Raikage having no idea where they are in the massive swamp. Then when the genjutsu is ready, Jiraiya will summon a big toad below him to push away the mud like it pushed away sand ( )-( ), and it will push Jiraiya above the swamp. Once Raikage hears the genjutsu, he will become paralyzed and his raiton shroud will be deactivated. After that all it takes is another Yomi Numa, and Raikage will sink into the swamp and drown.

And with Full intel?
 

super yang

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jiraiya changes dimensions, gets into sage mode & wins.

frog song + enchanted swords
or frog call stun + sage enhanced lion mane rips his throat out of his mouth
or clone feint -> toad shadow possession -> make raikage stab himself
or drown & boil him alive in Goemon(or acid lake) after frog lobotomy(shimas tongue thru his eye->brain)
.........
 
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