Itachi vs Jiraiya, who would win?

[AgentShayd]

I love Itachi and would want him to win. BUT it would be a very close match. It seems to me that some of you are counting Jiraiya out because obviously his character kinda got shifted out of the spotlight. He could have always out smarted Itachi in some way, or had something up his sleeve that Itachi would never see coming. The same can be said for Itachi. I will place my bet that this match just might be a draw...

[uchihamarina]

It would be a difficult fight for them both, but I think Itachi would win!

[PrinceofPeace]

Jiryria would easily get caught in genjutsu which Jiryria sucks at.
I do not see how Jiryria would get past Susanoo nor Amaterasu

WIthout Sm Jiryria is nothing

Itachi stomps

[MinatoXNaruto]

^^It's not SM Jiraiya?

Jiraiya gets stomped hard

[PrinceofPeace]

^ My point EXACTLY

[placeinthesun16]

itachi hands down third best uchiha after obito and madara

[NINE-TAILS-BIJU]

^no Itachi is #1 cause he's not scum like they are, but yeah Itachi would win this battle

[placeinthesun16]

best of the uchichas in comparison in power.

[Kananda]

Jiraiya is smart enough to avoid Itachi's genjutsu + Amaterasu and Itachi knows it. But I think Itachi would win just because he has the Sword and Mirror. If Jiraiya had intel on the 6 paths I think he could have won (with Tendo's powers dormant).

[scallanan]

Ok, to clear things up. Jiraiya and Itachi had the same moves as before and after the time skip. They just weren't shown for purposes that are quite obvious. Kishi needed to build up the level of attacks in Naruto.

So, to figure this out we need to go through each of their abilities.

Jiraiya = Yellow
Itachi = Black
Conclusion = Red

1. Strength
Well, first of all, how strong is Jiraiya? We know that he only got close to death twice in his life before his encounter with Pain. Once when Tsunade hit him, and the second time when Naruto's seal was weakened and Naruto went out of control. We know that he was feared everywhere, and thus we see him always gloating about himself. Konan was no match for Jiraiya, and Itachi and Kisame decided if it came down to it, that Jiraiya would be too hard an enemy to face, and that they'd only end up reaching a stale mate if both of them were to take him on. This is coming from Itachi himself. But that said, Itachi never underestimated his opponents, as seen many times. So those words probably don't sum up their powers correctly. Kisame also mentioned that Jiraiya was too strong for him, saying that he was "on a whole different level." Minato mentions that Jiraiya is the strongest ninja he's ever known at one stage too, and Pain mentions that he would not have beaten Jiraiya had he not known of Jiraiya's "secret." So in this sense, Jiraiya is to be utterly feared.
As for Itachi, we know that he was an incredibly quick learner, and from at an early age displayed superb talent. Tobi mentions that "Itachi never ceases to amaze [him]" and Kisame acknowledges Itachi as the stronger of the two. As mentioned above, Itachi never underestimates his opponents and always plans ahead. We know that he defeated Kakashi, Kurenai and Asuma easily without using much of his strength. Itachi graduated from the academy at age 7, mastered the sharingan at age 8, and became an ANBU captain at age 13. He also is one of the most skilled users in the Mangekyo Sharingan. We cannot go by Itachi's fight against Sasuke, so I think that's all we can gather of Itachi's strength.
I think strength-wise the two of them are totally feared throughout the ninja world. Each for different skills, but feared. Therefore, I think Itachi and Jiraiya are equal when it comes to people's experiences with them.

2. Taijutsu
Although Jiraiya doesn't use Taijutsu much, he is still very skilled in it. We see him stop one of pain's summonings (the splitting dog) with just taijutsu in his legs. Other than that, I don't think there are any other examples to be seen.
Itachi also isn't a specialized user in taijutsu although has shown much skill in it. He defeated some members of the konoha military police very easily with just taijutsu alone, he stopped sasuke's chidori in part 1 effortlessly despite all of sasuke's taijutsu training for the chunin exams. He can also use the body flicker technique adding to his evasion after a taijutsu move.
I think when it comes down to plain Taijutsu, Itachi has the upper hand. Jiraiya's physical strength may be a small bit better, but Itachi has more skill and technique. That said Jiraiya can use sage mode and when in this mode, has an overwhelming advantage over Itachi in the art of Taijutsu. But for plain Taijutsu alone, Itachi wins.

3. Ninjutsu
Jiraiya specializes in Ninjutsu, and has a wide variety off techniques, both offensive and defensive. Jiraiya's most well-known move was the rasengan of course, and Jiraiya showed skill in expanding his rasengan to large sizes. Jiraiya could grow and sharpen his hair for both offense and defense, and was able to use two chakra natures - earth and fire. Jiraiya was said to be able to perfect every move, even simple moves that Genins learn, such as the "Transparency Jutsu" which he used frequently to spy on women. Jiraiya is also adept at using barrier ninjutsu, seen when he used "Barrier: Canopy Method Formation" against Pain to detect his chameleon summon, and "Barrier: Toad Gourd Prison" to trap people in the belly of a toad. Jiraiya was called the "Toad Sage" and had many toad summonings including Gamabunta. Jiraiya could use "Ninja art: Toad mouth trap" as seen against kisame and itachi, and could spit oil from his mouth. He also could use "Toad Subjugation Shadow Manipulation Jutsu" which allowed him to manipulate people by becoming their shadow, or hide in any other shadow. He could also hide inside small toads to get away.
Itachi didn't specialize in Ninjutsu but as an Uchiha was again highly skilled at it. Of the ninjutsu he did posess, they were all of a very high level, and had great power and destruction. Itachi could do a lot with his clones. His "crow clone jutsu" allowed him to create crow clones without the use of handseals. He could also create explosive clones or change his shuriken into crows. Itachi as an Uchiha, had an affinity for fire, and could create monstrous fireballs

Spoiler:

that were enough to bother Samehada in his fight against naruto and killer bee. Itachi could also use water style, and was able to perform jutsus such as "Water Style: Water Fang Bullet" and "Water Style: Water Dragon Jutsu."

Between the two, I think Jiraiya's Ninjutsu is way too much for even a skilled Itachi. His perfection in his jutsu and his variety of jutsu makes him unpredictable and extremely powerful.

4. Other techniques
Jiraiya, like Naruto, can use sage mode. The only problem is that he cannot enter it by himself, nor can he use shadow clones to build it up for him, so he counters this problem by summoning toads to defend for him. Fukasaku and Shima have to attach to Jiraiya's shoulders in order for him to enter this mode. In sage mode, Jiraiya has a great enhancement in his senses and abilities. His physical power goes through the roof, as does his jutsu and speed. He relies on Fukasaku and Shima to perform genjutsu if necessary. He can use "Sage Art: Bath of Boiling Oil" when in this mode as well, one of his most powerful ninjutsu techniques that use Fire, Oil and Wind. Another problem with Sage mode is that it runs out after 5min or if he uses too many strong moves, giving Itachi the upper hand as his strongest techniques can only last for that length of time. A second transformation into sage mode would most likely not occur as Itachi would know what to target the second time round.
Itachi had extreme talent in handling his weapons as seen numerous times in the series. His shuriken jutsu is one example (the one he was teaching sasuke as a child). Sasuke mentions at one point that Itachi is so skilled at using weapons that he would even beat his father (this was when Itachi was still young). Itachi's main weapon would be his sharingan. As mentioned before, Itachi showed more promise than any other Uchiha with his sharingan. He, along with Shisui, were considered to have the best set of eyes. Itachi's normal sharingan was even tough to fight against. Kakashi mentioned that Itachi was the true successor of the sharingan once. He could merely point at someone to put them under genjutsu, and

Spoiler:

could manipulate people from a long distance, according to Ao. Itachi could also use the two forbidden techniques, Izanagi and Izanami. With them, he could easily escape death, or trap his opponent in an infinite loop.

Itachi's Mangekyo sharingan was even more powerful, which he awakened the day Shisui died. Itachi's three strongest jutsu came from this eye. Tsukuyomi could trap an opponent for days in the most horrible and realistic genjutsu, which is enough to shatter anyone's will. We saw this used against kakashi and sasuke. Amaterasu was a black flame in which Itachi could control with ease. Even when trying not to hit sasuke, he managed to get sasuke engulfed in it. His most powerful jutsu, Susano'o had the Totsuka blade and the Yata Mirror. This allowed him to deflect all attacks and seal his opponent forever by touching them with the Totsuka blade. Itachi had such mastery over his sharingan that he could keep it turned on for long periods of time. The drain from his chakra supplies were very minimal and even with his low levels of chakra, he could use very powerful moves many times.
Itachi in my opinion beats Jiraiya in "other techniques." He specialized and had complete mastery over the sharingan, an already highly powerful dojutsu, something that is so hard to dodge (amaterasu, tsukuyomi, genjutsu, susano'o), so hard to break through (susano'o defense, or use amaterasu around him as a shield) so hard to fight against (like guy said, the only way to counter is to predict movement by looking at their feet/hips; and the sharingan can predict and see through almost any movement) and even if you can get through all that, Itachi can use

Spoiler:

Izanami/Izanagi as a means of escape for certain victory.

My consensus: Itachi and Jiraiya both have different fighting styles. Jiraiya is close to mid range combat, with the use of summonings and high level ninjutsu. He has quite a good defense, and can even get out of normal genjutsu. If he can manage to get into sage mode, his speed would be on par with Itachi's and his strength even better. Itachi on the other hand can fight in any range distance. He has both the ultimate defense and the ultimate attack, and even if he doesn't use them, he is very fast and intelligent, and can plan ahead shockingly far. His genjutsu is to absolute perfection and even if his opponent can manage to bypass all of this, he has the

Spoiler:

use of izanagi and izanami to save him and ensure victory.

The combination of being able to predict and counter fast movement, along with the fact that Jiraiya can't look into his eyes, makes him already virtually impossible to face (and this is only with a normal sharingan). In my opinion, no matter how much I love Jiraiya, and no matter how strong Jiraiya is, he just isn't the right opponent for Itachi. Only few enemies can even get close to beating Itachi, and Jiraiya isn't one of them. As we know kakashi is extremely strong, yet facing itachi proved way too much for him. Sasuke was on the verge of death against an Itachi who's body was failing him, and his intentions were never even to kill Sasuke (and they say you can only beat a sharingan user with a sharingan and sasuke couldn't do it with itachi not even trying).

Spoiler:

His speed was so great that he could keep up with Naruto and Killer bee in their tailed beast forms.

Winner is definitely Itachi. The only hope Jiraiya would have is trapping him in genjutsu, or fighting outdoors and summoning gamabunta.

[placeinthesun16]

i just gotta say that jeriaja never stood a chance against pain since he was able to take on 6-9 tail fox on battle. if nagato/pain wasnt weaken because of him using the statue he would of being undefeatable even to naruto. this is base on the fight when nagato was reincarnated where he was kicking killer bee,naruto and itachis ass. at the same time.

jeriaja was defeated by the 4 tails. quite easy and nearly kill. while orochimaru was able to take it head on.

but itachi would win thought he can use susano and had 2 legendary weapons.agaisnt jeriaja.

[Jose]

Itachi isnt the type to go MS right away like Sasuke so Jirayia will most likely be.in control through out the whole match until Itachi uses Susanoo then he gets sealed.

[konoha chimp]

As much as I love Jiraiya I have to give this want to Itachi
To put it simple: Itachi plays against Jiraiyas' strengths and however, both characters in my opinion or two of the best out of the whole Manga/Anime

[SmellyDump]

Itachi with all his overpowered secret techniques and such and if Itachi were about to die to Jiraiya I'm pretty sure that Itachi could pull something off like Izanagi and then kill Jiraiya easily.

[Hyugga101]

Tie, Itachi has:Amertrasu,Tsukuyomi
Jiraiya has:Sage mode,Rasengan

[EnigmaNinja]

itachi said himself, if they were to fight one another they would both die. Although their is a better chance that just one of them would die, itachi makes it seem very close but overall ill go with jiraiya. He is a beast in sage mode much more experienced than naruto.

[scallanan]

Originally Posted by EnigmaNinja

itachi said himself, if they were to fight one another they would both die. Although their is a better chance that just one of them would die, itachi makes it seem very close but overall ill go with jiraiya. He is a beast in sage mode much more experienced than naruto.

Itachi never underestimated an opponent. Therefore his words about fighting vs jiraiya are swayed. Also, naruto mastered sage mode. Jiraiya didn't. Naruto has surpassed his master

[DrKage]

If both gets their full compliment of abilities, Jiraya. Sage mode with Ma and Pops on his shoulders, Itachi can't stop it. Ma and Pop could snap him out of genjutsu, he'd probably be fast enough to avoid anything Susanoo could throw at him (and please, Danzo was an old half cripple, while a strong ninja, probably not nearly as speedy as a sage mode Jiraya) and while he couldn't put out Amaterasu, he could seal it away. Also, while Itachi (with Kisame) had no hesitation fighting against Guy and Kakashi plus whoever else Konoha had present atthe time, he definitely backed off when Jiraya came around.

[Kakashi2806]

Very close, almost tie, but Itachi wins in the end.

[MinaKushi]

I think itachi will win because he has the susano'o and amaterasu, it'd be a close fight though