Kakuzu, with average difficulty.
You guys take it too easy. First of all, the most important fact you seem to forgett: Jiraiya needs about five to ten minutes of preparation in order to enter Sennin Modo. Pain was only sending animals after him back then. But if Kakuzu gets serious (which means that apart from him and his Jiongu strings four flying creatures capable of using elemental attacks on a very high level are after him) Jiraiya won't have time to prepare.
Even if he would manage to enter Sennin Modo, however, it doesn't mean certain victory. Ma's & Pa's Genjutsu would be Kakuzu's certain defeat, yes, but like Jiraiya's Sennin Modo itself it needs some time to be prepared, time they don't have during this fight. Jiraiya may be able to take out several masks with Rasengan or Senjutsu techniques, but the same goes for Kakuzu's beasts. The difference is that Kakuzu's beasts can fly, which means that they're harder to hit. Their attacks also cover larger areas than any of Jiraiya's known Jutsu, except for Doton: Yomi no Numa. His huge toads aren't that much of a problem here, since techniques like Katon: Zukkoku (at worst combined with Fuuton: Atsugai) could get rid of them.
Last but not least, even if Jiraiya could defeat Kakuzu's beasts without being killed, I don't see how he intends to hurt Kakuzu himself. Doton: Domu, his hardened body technique, is one hell of a Jutsu and obviously underestimated by some of you. It makes his body (according to Kishi's latest databook) as hard as a diamond and is activated in an instant. The only way to pierce that technique is using Raiton (like Kakashi did) - an element Jiraiya can't use - therefore it makes Kakuzu nearly untouchable against him. Admittedly it needs to be mentioned that Kakuzu's speed decreases pretty bad while he's using Domu, due to the increased weight of his body. Yes, that's also written in the latest databook.
Some of the circumstances I described only count if the battle takes place in a wide, large area, like the desert where Kakashi, Shikamaru & co were fighting Hidan & Kakuzu.
You guys take it too easy. First of all, the most important fact you seem to forgett: Jiraiya needs about five to ten minutes of preparation in order to enter Sennin Modo. Pain was only sending animals after him back then. But if Kakuzu gets serious (which means that apart from him and his Jiongu strings four flying creatures capable of using elemental attacks on a very high level are after him) Jiraiya won't have time to prepare.
Even if he would manage to enter Sennin Modo, however, it doesn't mean certain victory. Ma's & Pa's Genjutsu would be Kakuzu's certain defeat, yes, but like Jiraiya's Sennin Modo itself it needs some time to be prepared, time they don't have during this fight. Jiraiya may be able to take out several masks with Rasengan or Senjutsu techniques, but the same goes for Kakuzu's beasts. The difference is that Kakuzu's beasts can fly, which means that they're harder to hit. Their attacks also cover larger areas than any of Jiraiya's known Jutsu, except for Doton: Yomi no Numa. His huge toads aren't that much of a problem here, since techniques like Katon: Zukkoku (at worst combined with Fuuton: Atsugai) could get rid of them.
Last but not least, even if Jiraiya could defeat Kakuzu's beasts without being killed, I don't see how he intends to hurt Kakuzu himself. Doton: Domu, his hardened body technique, is one hell of a Jutsu and obviously underestimated by some of you. It makes his body (according to Kishi's latest databook) as hard as a diamond and is activated in an instant. The only way to pierce that technique is using Raiton (like Kakashi did) - an element Jiraiya can't use - therefore it makes Kakuzu nearly untouchable against him. Admittedly it needs to be mentioned that Kakuzu's speed decreases pretty bad while he's using Domu, due to the increased weight of his body. Yes, that's also written in the latest databook.
Some of the circumstances I described only count if the battle takes place in a wide, large area, like the desert where Kakashi, Shikamaru & co were fighting Hidan & Kakuzu.
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