Naruto and Jiraiya probably have a great Chemistry going since they have both trained a decent amount together. Sasuke and Itachi have not although Sasuke seemed to be reading Itachi well when he fought him. Unless its Tsukiyomi, Genjutsu wouldn't really be helpful since there are multiple people and it takes about a split second to force chakra into your partner. Sasuke's Tsukiyomi Sucks. Itachi's is REALLY OP but he needs to look into the user's eyes.
Naruto vs Sasuke:
If we leave Kyuubi Mode and EMS mode out (we should since we don't know their power really), Sage mode surpasses MS
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before the Susano was complete but with Susano complete they might be similar in strength. Sage mode makes Naruto better at Taijutsu (frog fu). Sharingan predicts trajectory but forg fu doesn't have to make contact to have impact. Expanding throwing Rasen Shuriken (i'd like to believe) is better than Raikage's punch (which broke susano) so it might be able to Break the Susano. Susano's weapon so far has seemed really lame since its got no sealing thing like Itachi's. Sasuke's Amaterasu control wouldn't protect him against a Rasen Shuriken since he won't make any contact with Naruto although it would become bigger and meaner because blaze style would feed on the wind. Also a susano can't really 'dodge' the Rasen Shuriken if Pain couldn't. Naruto is decently quick so he might be able to dodge the Amaterasu since sasuke can't sustain it for long (
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). Naruto's skill with Kage Bunshin is unparalleled and In sage mode even each one of his Taju Kage bunshins can have a chou rasengan (as seen against kyuubi). Sasuke would be screwed. In sasuke's defense, I think his summon (the hawk) could be a pretty troublesome thing for Naruto. The only way I see Naruto getting to the Hawk was the Clone throwing him around (which he has been doing since Gaara arc in Naruto). Frogs suck against flying summons (as seen in the pain arc) but Gamabunta can do a Water style jutsu and Naruto has wind which in Sync with water will destroy sasuke's fire jutsu since wind's weakness to fire will be nulled. Although harem no jutsu won't work on Sasuke since he is gay (he doesn't do it with Sakura or Karin or Ino), Konoha's secret hidden Taijutsu Sennin Goroshi is bound to **** him up pretty bad (as happened to Gaara).
-Naruto Wins
Jiraiya vs Itachi:
Its already been mentioned how Itachi said that Itachi+Kisame could only hold Jiraiya in a stalemate so i am thinking Itachi can't be that much stronger than Jiraiya individually.
Jiraiya's biggest disadvantage would be his speed. Itachi has got do be much faster. Speed can cost him not being able to dodge Amaterasu and that would probably be the end. (That being said, i don't remember ever seeing Itachi 'dodge' anything) So its all a question of whether the Amaterasu hits. Susano isn't going to do shit because (a) Totsuka sword moves pretty slow. Sasuke didn't dodge it because he couldn't move since he was exhaused. I did say jiraiya was slow but he can't possibly not dodge that or he wouldn't be a sannin. It would be interesting to know if Chou Odama Rasengan can break the susano. If it can't, all Jiraiya has to do is outlast the susano. Eventually it will take a toll on Itachi's eyes and then it will be too easy to beat him. So i think all the Totsuka advantage is pretty lame. Totsuka only hit Orochimaru and thats because he was a GIANT 8 HEADED SERPANT. Jiraiya has Earth and Fire Techniques. Doton: Doryu Hiki or Earth wall has always been shown to pop up REALLY quick. It might be his only defense against an amaterasu. Jiraiya should use summoning technique twice and let both summons buy time for him while he goes Senni Mode. As far as Tsukiyomi is concerned, not looking is not that much of a disadvantage since He can use the Barrier technique so as to feel Itachi's every movement and so he would know what itachi was upto. If he was in Senni Mode (I think he should be only because we are comparing all these characters in their prime so far) then he would have no trouble with genjutsu and old lady frog shima would beat the shit out of Itachi (like she did to the Chameleon). I think MS aside, Jiraiya would beat Itachi all to easily because he would have earth and fire types from himself, water from shima and toad oil to enhance fire. A rather crude way to not get hit by the amaterasu would be to cast a ninjutsu towards it. We saw sasuke dodge it when his goukakyuu was still going. As far as Jiraiya vs Itachi is concerned it really seems to come down to how much time Jiraiya lasts. If itachi is unable to strike him with the Amaterasu, its game over (To know why, check out Itachi's stamina in the 3rd databook released...2.5 compared to 5 for jiraiya).
