Jiraiya vs Orochimaru

the snake has better usage of tactics, but pervy sage is stronger and has better back up summons.

I think Jiraiya punishes both Kakuzu and Orochimaru.

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill. 

Jiraiya stomps them.

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

" @iLLituracy said:

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

With Orochimare willing to kill and not effin around? No. Orochimaru can win without Kakuzu. "

jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl.

" @Cosmic_Falcon said:

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

Oro's kuzanagi sword can grown to a very long length in the fight against 4 tailed Naruto. He can cut through Jiraiya. He's most likely on par with Jiraiya in the speed department when he's a sage. He also has crazy regenerative ablities, is virtually immortal, and alot of powerful techniques. Jiraiya has Ma and Pa for genjutsu but Oro can strike them before that happens.  Basically,  Strength: Jiraiya obviously Durability: Orochimaru for obvious reasons. Speed: Tie Techniques: Both have different kinds of jutsus but I'd probably go with Jiraiya for tax consuming jutsus but can spam it while Oro has the special unique ones that can enable him the victory.  We have already seen that manda > Gamabunta. Oro has better summons outside of Ma and Pa which owns all snakes, Oro has the Kuzanagi sword, has jutsu's that involve moving in the ground without digging, can regurgitate himself, 8 headed Yamato snake, and reanimation. "

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

" @Susanoo said:

" @iLLituracy said:

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

With Orochimare willing to kill and not effin around? No. Orochimaru can win without Kakuzu. "

When does Orochimaru mess around other than his fight against Team 7 during the Chunin Exams. As far as I can tell he's very much tried in all of his fights and based on his showings against Sarutobi, where he almost lost his life AND had the help of the first two Hokage [who Jiraiya is stronger than, especially since Sarutobi was too old to keep up].  Orochimaru WAS the strongest of the three of them once upon a time, but Jiraiya is stronger based on showings. "

" @Susanoo said:

" @Cosmic_Falcon said:

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

Oro's kuzanagi sword can grown to a very long length in the fight against 4 tailed Naruto. He can cut through Jiraiya. He's most likely on par with Jiraiya in the speed department when he's a sage. He also has crazy regenerative ablities, is virtually immortal, and alot of powerful techniques. Jiraiya has Ma and Pa for genjutsu but Oro can strike them before that happens.  Basically,  Strength: Jiraiya obviously Durability: Orochimaru for obvious reasons. Speed: Tie Techniques: Both have different kinds of jutsus but I'd probably go with Jiraiya for tax consuming jutsus but can spam it while Oro has the special unique ones that can enable him the victory.  We have already seen that manda > Gamabunta. Oro has better summons outside of Ma and Pa which owns all snakes, Oro has the Kuzanagi sword, has jutsu's that involve moving in the ground without digging, can regurgitate himself, 8 headed Yamato snake, and reanimation. "

But in sage mode, Jiraiya is far stronger in speed and strength.  
 
He also has better summons IMO. 
 
@Ego said: 

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

 This is not true at all. Jiraiya didn't know who pain was, anything about his technique or what would happen. Naruto would NOT have beaten them if Jiraiya did not fight him first and pass on all the intel about the bodies. It was that battle that let Pa Toad tell Naruto about each and every single enemy.   Pain also commented that the fight could have been a lot different if Jiraiya knew about his abilities.    "

" @iLLituracy said:

" @Susanoo said:

" @iLLituracy said:

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

With Orochimare willing to kill and not effin around? No. Orochimaru can win without Kakuzu. "

When does Orochimaru mess around other than his fight against Team 7 during the Chunin Exams. As far as I can tell he's very much tried in all of his fights and based on his showings against Sarutobi, where he almost lost his life AND had the help of the first two Hokage [who Jiraiya is stronger than, especially since Sarutobi was too old to keep up].  Orochimaru WAS the strongest of the three of them once upon a time, but Jiraiya is stronger based on showings. "

Fights in part 1 aren't exactly that special compared to part 2. 3rd Hokage even said Orochimaru was the most powerful of the 3 sannins and that he surpassed himself as well. Orochimaru was very confident in the sannin fight against both Tsunade and Jiraya despite being handicapped. Jiraiya is stronger, but Oro is more versatile and is virtually immortal. He'll kill Jiraiya before Jiraiya kills him. If he can at all. "

" @SlimJ87D: Jiraiya is stronger than Orochimaru but not faster. They are most likely on par with each other. Orochimaru was fast enough to keep up with 4 tailed Naruto. Sage Jiraiya's speed from what I've seen, is as fast as Orochimaru. Orochimaru has better summons minus those uber frogs, more versatile techniques, vast healing and regenerative capabilities, and is virutally immortal in the ninja world. "

" @SlimJ87D said:

" @Susanoo said:

" @Cosmic_Falcon said:

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

Oro's kuzanagi sword can grown to a very long length in the fight against 4 tailed Naruto. He can cut through Jiraiya. He's most likely on par with Jiraiya in the speed department when he's a sage. He also has crazy regenerative ablities, is virtually immortal, and alot of powerful techniques. Jiraiya has Ma and Pa for genjutsu but Oro can strike them before that happens.  Basically,  Strength: Jiraiya obviously Durability: Orochimaru for obvious reasons. Speed: Tie Techniques: Both have different kinds of jutsus but I'd probably go with Jiraiya for tax consuming jutsus but can spam it while Oro has the special unique ones that can enable him the victory.  We have already seen that manda > Gamabunta. Oro has better summons outside of Ma and Pa which owns all snakes, Oro has the Kuzanagi sword, has jutsu's that involve moving in the ground without digging, can regurgitate himself, 8 headed Yamato snake, and reanimation. "

But in sage mode, Jiraiya is far stronger in speed and strength.  
 
He also has better summons IMO. 
 

@Ego

 said: 

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

 This is not true at all. Jiraiya didn't know who pain was, anything about his technique or what would happen. Naruto would NOT have beaten them if Jiraiya did not fight him first and pass on all the intel about the bodies. It was that battle that let Pa Toad tell Naruto about each and every single enemy.   Pain also commented that the fight could have been a lot different if Jiraiya knew about his abilities.    "

no jiraya was winning but they keep comming back to life. and he was eye balling the girl and lost distraction and started to run off. "

the only thing that made orochi "more powerful than the 2 other sanjins" was becuase of his immortality jutsu and his preptime genius.

" @Susanoo said:

" @iLLituracy said:

" @Susanoo said:

" @iLLituracy said:

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

With Orochimare willing to kill and not effin around? No. Orochimaru can win without Kakuzu. "

When does Orochimaru mess around other than his fight against Team 7 during the Chunin Exams. As far as I can tell he's very much tried in all of his fights and based on his showings against Sarutobi, where he almost lost his life AND had the help of the first two Hokage [who Jiraiya is stronger than, especially since Sarutobi was too old to keep up].  Orochimaru WAS the strongest of the three of them once upon a time, but Jiraiya is stronger based on showings. "

Fights in part 1 aren't exactly that special compared to part 2. 3rd Hokage even said Orochimaru was the most powerful of the 3 sannins and that he surpassed himself as well. Orochimaru was very confident in the sannin fight against both Tsunade and Jiraya despite being handicapped. Jiraiya is stronger, but Oro is more versatile and is virtually immortal. He'll kill Jiraiya before Jiraiya kills him. If he can at all. "

The only time Sarutobi said that to my recollection was in a flashback and he was considering who his successor as Hokage would be, even so, the Third's opinion only goes so far.  Orochimaru wasn't the only person handicapped in that match. Jiraiya was heavily drugged by Tsunade if memory serves and he had Kabuto fighting off Tsunade [who was still afraid of blood].  If we're going by stats I'm pretty sure Jiraiya was shown to be the strongest in the databook, only behind Itachi by a tad.  The fight isn't to the death, I didn't see that in the rules and I'm pretty sure that Orochimaru can be harmed and hurt...even knocked out. Even if Jiraiya COULDN'T kill him, I'm pretty sure that he could very much seal him away.  "

" @Ego said:

" @SlimJ87D said:

" @Susanoo said:

" @Cosmic_Falcon said:

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

Oro's kuzanagi sword can grown to a very long length in the fight against 4 tailed Naruto. He can cut through Jiraiya. He's most likely on par with Jiraiya in the speed department when he's a sage. He also has crazy regenerative ablities, is virtually immortal, and alot of powerful techniques. Jiraiya has Ma and Pa for genjutsu but Oro can strike them before that happens.  Basically,  Strength: Jiraiya obviously Durability: Orochimaru for obvious reasons. Speed: Tie Techniques: Both have different kinds of jutsus but I'd probably go with Jiraiya for tax consuming jutsus but can spam it while Oro has the special unique ones that can enable him the victory.  We have already seen that manda > Gamabunta. Oro has better summons outside of Ma and Pa which owns all snakes, Oro has the Kuzanagi sword, has jutsu's that involve moving in the ground without digging, can regurgitate himself, 8 headed Yamato snake, and reanimation. "

But in sage mode, Jiraiya is far stronger in speed and strength.  
 
He also has better summons IMO. 
 

@Ego

 said: 

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

 This is not true at all. Jiraiya didn't know who pain was, anything about his technique or what would happen. Naruto would NOT have beaten them if Jiraiya did not fight him first and pass on all the intel about the bodies. It was that battle that let Pa Toad tell Naruto about each and every single enemy.   Pain also commented that the fight could have been a lot different if Jiraiya knew about his abilities.    "

no jiraya was winning but they keep comming back to life. and he was eye balling the girl and lost distraction and started to run off. "

He did not lose because he got distracted for the last time. He lost because he didn't know anything about the technique or that one of the bodies could revive the other ones. Or even which one or most importantly WHERE nagato really was.  "

@Ego said:

"the only thing that made orochi "more powerful than the 2 other sanjins" was becuase of his immortality jutsu and his preptime genius. "

 
That's why he was more powerful then them. Knowledge of the jutsu's and his immortality and his genius. 
 
 
Jiraiya with Ma and Pa while in Hermit mode is just too much for Orochimaru. Not to mention Ma and Pa can also access sage mode, remember when Pa lifted that huge giant statue with one arm while explaining sage mode to Naruto? Yeah, Orochimaru is fighting against 3 people with extreme strength and speed (although i haven't too much speed from ma and pa, but they are attached to Jiraiya.)  
 
Also Ma and Pa can keep his Hermit mode at a constant flux so he doesn't have a handicap like Naruto. All of his techniques are also amped, his Rasengans are giant Rasengans along with all his techniques.

" Jiraiya stomps them. "

" @Nefarious said:

" Jiraiya stomps them. "

This. "

" @iLLituracy said:

" @Susanoo said:

" @iLLituracy said:

" @Susanoo said:

" @iLLituracy said:

"I think Jiraiya punishes both Kakuzu and Orochimaru. "

With Orochimare willing to kill and not effin around? No. Orochimaru can win without Kakuzu. "

When does Orochimaru mess around other than his fight against Team 7 during the Chunin Exams. As far as I can tell he's very much tried in all of his fights and based on his showings against Sarutobi, where he almost lost his life AND had the help of the first two Hokage [who Jiraiya is stronger than, especially since Sarutobi was too old to keep up].  Orochimaru WAS the strongest of the three of them once upon a time, but Jiraiya is stronger based on showings. "

Fights in part 1 aren't exactly that special compared to part 2. 3rd Hokage even said Orochimaru was the most powerful of the 3 sannins and that he surpassed himself as well. Orochimaru was very confident in the sannin fight against both Tsunade and Jiraya despite being handicapped. Jiraiya is stronger, but Oro is more versatile and is virtually immortal. He'll kill Jiraiya before Jiraiya kills him. If he can at all. "

The only time Sarutobi said that to my recollection was in a flashback and he was considering who his successor as Hokage would be, even so, the Third's opinion only goes so far.  Orochimaru wasn't the only person handicapped in that match. Jiraiya was heavily drugged by Tsunade if memory serves and he had Kabuto fighting off Tsunade [who was still afraid of blood].  If we're going by stats I'm pretty sure Jiraiya was shown to be the strongest in the databook, only behind Itachi by a tad.  The fight isn't to the death, I didn't see that in the rules and I'm pretty sure that Orochimaru can be harmed and hurt...even knocked out. Even if Jiraiya COULDN'T kill him, I'm pretty sure that he could very much seal him away.  "

1. Orochimaru was a genius but evil.Being a genius helps alot in making someones decision. However, Oro was evil and no one knew. 2. Orochimaru couldn't use his hands nor his jutsus.His handicap is more severe than both of theirs. He was also tanking Tsunade's hits with minimal pain. Tsunade's hits are slightly stronger than Sage Jiraiya's from what I've seen.3. Oro has never been koed ever. Then again, most ninas haven't been. But Oro has durability exeeding Jiraiya's limits. "

But, Sage Mode Jiraiya will have trouble here...since Jiraiya has no forbidden technique(like Minato Namikaze and the Third Hokage do)  that will destroy Kakuzu for good. 

" @SlimJ87D said:

" @Ego said:

" @SlimJ87D said:

" @Susanoo said:

" @Cosmic_Falcon said:

"If both are fighting without handicaps, I would go with Jiriyia, the only thing Oro has going for him is that he's hard as hell to kill.  "

Oro's kuzanagi sword can grown to a very long length in the fight against 4 tailed Naruto. He can cut through Jiraiya. He's most likely on par with Jiraiya in the speed department when he's a sage. He also has crazy regenerative ablities, is virtually immortal, and alot of powerful techniques. Jiraiya has Ma and Pa for genjutsu but Oro can strike them before that happens.  Basically,  Strength: Jiraiya obviously Durability: Orochimaru for obvious reasons. Speed: Tie Techniques: Both have different kinds of jutsus but I'd probably go with Jiraiya for tax consuming jutsus but can spam it while Oro has the special unique ones that can enable him the victory.  We have already seen that manda > Gamabunta. Oro has better summons outside of Ma and Pa which owns all snakes, Oro has the Kuzanagi sword, has jutsu's that involve moving in the ground without digging, can regurgitate himself, 8 headed Yamato snake, and reanimation. "

But in sage mode, Jiraiya is far stronger in speed and strength.  
 
He also has better summons IMO. 
 

@Ego

 said: 

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

 This is not true at all. Jiraiya didn't know who pain was, anything about his technique or what would happen. Naruto would NOT have beaten them if Jiraiya did not fight him first and pass on all the intel about the bodies. It was that battle that let Pa Toad tell Naruto about each and every single enemy.   Pain also commented that the fight could have been a lot different if Jiraiya knew about his abilities.    "

no jiraya was winning but they keep comming back to life. and he was eye balling the girl and lost distraction and started to run off. "

He did not lose because he got distracted for the last time. He lost because he didn't know anything about the technique or that one of the bodies could revive the other ones. Or even which one or most importantly WHERE nagato really was.  "

he knew their technques while fighting them he was analyising them, but he did not know that they can revive. i'm not talking about nagato, i'm talking about the pain 6. jiraya was beating them he even permenantly killed one of them before 3 of them revived themselves and ganged up on him. but he was focused on yahiko and most of all konan the girl. "

 1. Sorry, but I'm not sure how this has anything to do with what I said. No matter how smart Orochimaru is, Jiraiya would still work him because mentally he isn't that much of a slouch. 
2. The point is is that neither of them were at their finest. I don't see how anyone's handicap being worse would be a factor if neither could operate correctly. He wasn't tanking Tsunade's hits, either, To tank a hit is to take it without damage or harm. Tsunade was busting his ass. He might have still been smiling but he sustained injury. That's hardly the point, either. Jiraiya isn't going to engage him hand to hand in Sennin Mode, at all. 
3. Just because Oro has never been KOed doesn't mean he can't be. And to say his durability exceeds Jiraiya's limits is ludicrous. He's not durable, he has the ability to heal rapidly, but that's about it.

 
1. Oi 
2. In part 2 against the 4 tailed fox, he easily withstood a punch that sent him flying. I'll label that hit on par of Raikage and above any physical feats I've seen Jiraiya ever done.  
3. Orochimaru has never been koed by physcal means. A hit from 4 tailed Naruto and multiple hits from Tsunade. Also, Orochimaru hasn't been koed by 2 people thats stronger than Sage Jiraiya. So no.

well orichi could win becuase of his preptime genius and jiraya's half back tactics.
this is why the akasuki needed iatchi, becuase the pain 6 (aka six path of pain) can not beat orichi.
i doubt that the pain 6 could beat a well and healthy itachi.
and nagato is not really the most powerful akasuki nor is her the real leader... it's tobi aka kakashi's old friend obito

" @Ego: Jiraiya lost because he lacked knowledge on Pain. "

" @Ego: Jiraiya lost because he lacked knowledge on Pain. "

"

 1. Sorry, but I'm not sure how this has anything to do with what I said. No matter how smart Orochimaru is, Jiraiya would still work him because mentally he isn't that much of a slouch. 
2. The point is is that neither of them were at their finest. I don't see how anyone's handicap being worse would be a factor if neither could operate correctly. He wasn't tanking Tsunade's hits, either, To tank a hit is to take it without damage or harm. Tsunade was busting his ass. He might have still been smiling but he sustained injury. That's hardly the point, either. Jiraiya isn't going to engage him hand to hand in Sennin Mode, at all. 
3. Just because Oro has never been KOed doesn't mean he can't be. And to say his durability exceeds Jiraiya's limits is ludicrous. He's not durable, he has the ability to heal rapidly, but that's about it.

 
1. Oi 
2. In part 2 against the 4 tailed fox, he easily withstood a punch that sent him flying. I'll label that hit on par of Raikage and above any physical feats I've seen Jiraiya ever done.  
3. Orochimaru has never been koed by physcal means. A hit from 4 tailed Naruto and multiple hits from Tsunade. Also, Orochimaru hasn't been koed by 2 people thats stronger than Sage Jiraiya. So no.

"

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

" @Ego said:

" jiraya kids around too much though. and he thinks like a little pervert so his mind is obviously half ass focused on any battle. he would beaten the pain 6 if he weren't eye balling the girl. "

Then would you like to take this back? "

You're treating physical strength and durability (which Orochimaru clearly lacks, given how many times his body and his "indestructible" defenses have been torn up) as the absolute dictating factor.  It's not.
 
Here is the bottom line.  Itachi was intimidated by Jiraiya even when Kisame was with him.  Itachi and Kisame got worked in the short brawl they had with Jiraiya and were forced to flee.  Orochimaru has been worked by Itachi every single time, even when Itachi was on the brink of death.  I'm setting the standard with Itachi's views on Orochimaru and Jiraiya, which is the most current canon observation of their skills in comparison to each other.  Itachi was scared of Jiraiya, but not Orochimaru.  In fact, Itachi mocked Orochimaru.
 
That being said, Jiraiya is stronger than Orochimaru.  And that was before Sage Mode was even a thought in Kishimoto's head.  

"

You're treating physical strength and durability (which Orochimaru clearly lacks, given how many times his body and his "indestructible" defenses have been torn up) as the absolute dictating factor.  It's not.
 
Here is the bottom line.  Itachi was intimidated by Jiraiya even when Kisame was with him.  Itachi and Kisame got worked in the short brawl they had with Jiraiya and were forced to flee.  Orochimaru has been worked by Itachi every single time, even when Itachi was on the brink of death.  I'm setting the standard with Itachi's views on Orochimaru and Jiraiya, which is the most current canon observation of their skills in comparison to each other.  Itachi was scared of Jiraiya, but not Orochimaru.  In fact, Itachi mocked Orochimaru.
 
That being said, Jiraiya is stronger than Orochimaru.  And that was before Sage Mode was even a thought in Kishimoto's head.  

 I'm treating them what? I know. That's why I put him above sage Jiraiya in durability. Because of his healing factor and immortality.  Itachi would stomp Jiraiya easily with Amaterasu, Tsukoyomi, or Susanoo. Itachi was giving Jiraiya respect and doesn't want to suffer unnecessary battle wounds. In fact, Itachi could kill him judging from their showings and abilities. Itachi isn't evil. He's a master of deception. He was obviously lying to Kisame to save his hide and to save Jiraiya and himself the trouble.  I said why that didn't work. Itachi was lying. "

" You're treating physical strength and durability (which Orochimaru clearly lacks, given how many times his body and his "indestructible" defenses have been torn up) as the absolute dictating factor.  It's not. Here is the bottom line.  Itachi was intimidated by Jiraiya even when Kisame was with him.  Itachi and Kisame got worked in the short brawl they had with Jiraiya and were forced to flee.  Orochimaru has been worked by Itachi every single time, even when Itachi was on the brink of death.  I'm setting the standard with Itachi's views on Orochimaru and Jiraiya, which is the most current canon observation of their skills in comparison to each other.  Itachi was scared of Jiraiya, but not Orochimaru.  In fact, Itachi mocked Orochimaru.  That being said, Jiraiya is stronger than Orochimaru.  And that was before Sage Mode was even a thought in Kishimoto's head.   I'm treating them what? I know. That's why I put him above sage Jiraiya in durability. Because of his healing factor and immortality.  Itachi would stomp Jiraiya easily with Amaterasu, Tsukoyomi, or Susanoo. Itachi was giving Jiraiya respect and doesn't want to suffer unnecessary battle wounds. In fact, Itachi could kill him judging from their showings and abilities. Itachi isn't evil. He's a master of deception. He was obviously lying to Kisame to save his hide and to save Jiraiya and himself the trouble.  I said why that didn't work. Itachi was lying. "

Madara is not using Obito's body. Do you have proof of that?

" @Ego: I know. Madara is using Obitos body or it's actually Obito himself. "

" Madara is not using Obito's body. Do you have proof of that? "

I don't recall where Kishimoto ever stated that Itachi was lying.  In fact, Itachi is not a liar (and yes, I do understand that he isn't evil).  There is a fine difference between deception and outright lying.  Itachi ran with Kisame because he was intimidated.  He knew he wasn't going to be able to hand Jiraiya his ass, even with Kisame there.  Kishimoto hasn't stated otherwise, so you can't make the assumption that Itachi lied.
 
I have no doubt that Itachi, in his prime, could beat Jiraiya.  However, you do not have to be weaker than somebody to be intimidated by them.  Itachi was, in fact, intimidated by Jiraiya.  That is not a matter of opinio    n.  It's canon.
 
Orochimaru's "immortality" stemmed from being able to jump from body to body.  He's nowhere near truly immortal, and all healing factors have limits.  It is very much possible for Jiraiya to kill Orochimaru, even when taking into account the healing factor and false immortality.  You know, because Orochimaru also can't jump bodies without preparation.
 
So let's go back to what I was saying.  Itachi's assessment of Orochimaru is that he is weak enough to be mocked in every confrontation.  But Jiraiya was enough to intimidate him, even while Kisame was there.  That is before Jiraiya revealed Sage Mode.
 
Itachi, once again, mocks Orochimaru when he shunts boy-o out of Sasuke and seals him with Susanoo.  This is before Sage Mode is revealed.
 
And then we see Sage Mode, which amplifies Jiraiya's already considerable skills.  Skills that were enough to intimidate Itachi with Kisame present.  
 

" @chillinglyrics: 

I don't recall where Kishimoto ever stated that Itachi was lying.  In fact, Itachi is not a liar (and yes, I do understand that he isn't evil).  There is a fine difference between deception and outright lying.  Itachi ran with Kisame because he was intimidated.  He knew he wasn't going to be able to hand Jiraiya his ass, even with Kisame there.  Kishimoto hasn't stated otherwise, so you can't make the assumption that Itachi lied.
 
I have no doubt that Itachi, in his prime, could beat Jiraiya.  However, you do not have to be weaker than somebody to be intimidated by them.  Itachi was, in fact, intimidated by Jiraiya.  That is not a matter of opinio    n.  It's canon.
 
Orochimaru's "immortality" stemmed from being able to jump from body to body.  He's nowhere near truly immortal, and all healing factors have limits.  It is very much possible for Jiraiya to kill Orochimaru, even when taking into account the healing factor and false immortality.  You know, because Orochimaru also can't jump bodies without preparation.
 
So let's go back to what I was saying.  Itachi's assessment of Orochimaru is that he is weak enough to be mocked in every confrontation.  But Jiraiya was enough to intimidate him, even while Kisame was there.  That is before Jiraiya revealed Sage Mode.
 
Itachi, once again, mocks Orochimaru when he shunts boy-o out of Sasuke and seals him with Susanoo.  This is before Sage Mode is revealed.
 
And then we see Sage Mode, which amplifies Jiraiya's already considerable skills.  Skills that were enough to intimidate Itachi with Kisame present.  
 

Deception and lies are almost neck and neck. Tell me he wasn't lying to Madara or his father then. Or Sasuke even. For wanting the EMS.  Cannon? Naruto has twists and turns. Knowing Itachi, he was most likely paying respect to Jiraiya. Read the japanese version of Manga on that part btw. It's more cannon than the english one. Itachi did  not state that Jiraiya was more powerful in the japanese one, he said they would stalemate and suffer against unnecessary wounds.  However, he didn't die in the battle against the 2 other sannins and 4 tails. He took alot of hits and such. His healing factor has limits but it's not short. He will outlast Jiraiya in battle by killing him.  A>B>C logic doesn't work in Naruto actually. Sakura > Naruto for reasons being obvious, Naruto > Sasuke, and Sasuke > Sakura. And I can use others for this example. So no. Jiraiya also has no defence against Tsukoyomi btw. Or any MS techniques for that matter.   Skills that weren't seen on par with the techniques Orochimaru displayed in the sannin fight or the 4 tail fight. Orochimaru easily > base Jiraiya. "

Let's play it on your terms, then.
 
Itachi recognizes that, even with Kisame right there, he will fight Jiraiya to a stalemate and suffer wounds.  A stalemate means that both sides cannot claim victory, and Itachi has Kisame on his side.  Jiraiya had a beat-up Sasuke and a chakra-drained, untrained Naruto.  However, Itachi never recognizes Orochimaru as being able to come close to beating him, let alone reaching a stalemate with him.
 
The logic still applies.
 
He took a lot of hits, sure.  But to say that he would outlast Jiraiya based off of that alone is false.  You're assuming he would even be capable of killing Jiraiya when the evidence so far dictates that Jiraiya, at the time, was an overall stronger and more skilled shinobi than Orochimaru.  That evidence, again, being Itachi.  Who, according to the official statistics, is only slightly more powerful than Jiraiya.
 
How are you trying to apply obvious showings of comedic action to this?  When Sakura strikes Naruto in the back of the head, that's for comedic effect.  It has no implication on her combat abilities, because we all know Naruto would work her in a fight.  So, Naruto logic is linear, actually.  Naruto > Sakura, Sasuke > Sakura, Naruto and Sasuke as of yet to be determined once again.
 
JIraiya can decide not to look Itachi in the eye, thus avoiding Tsukiyomi completely.  He can dodge Amaterasu.  And in Sage Mode, he could bust Susanoo up just like A broke the ribs of Sasuke's Susanoo.

" @Ego: When he was fighting Konan and she destroyed almost half of his mask, he showed two sharingan eyes. "

" Orochimaru is the most powerful out of the 3 sannins. He wins even without Kakuzu. "

So if both Kizame and Itachi they themselves estimate that both of them could go against Jiraiya and die, then that must mean that Jiraiya had a greater chance of defeating Itachi. Meaning that Oro was not stronger than Jiraiya. Specially since Oro was Itachi's b!tch. 

"Itachi is stronger than I am, that's why I pull myself out of that organization" - Orochimaru referring to Akatsuki

" @chillinglyrics: 

Let's play it on your terms, then.
 
Itachi recognizes that, even with Kisame right there, he will fight Jiraiya to a stalemate and suffer wounds.  A stalemate means that both sides cannot claim victory, and Itachi has Kisame on his side.  Jiraiya had a beat-up Sasuke and a chakra-drained, untrained Naruto.  However, Itachi never recognizes Orochimaru as being able to come close to beating him, let alone reaching a stalemate with him.
 
The logic still applies.
 
He took a lot of hits, sure.  But to say that he would outlast Jiraiya based off of that alone is false.  You're assuming he would even be capable of killing Jiraiya when the evidence so far dictates that Jiraiya, at the time, was an overall stronger and more skilled shinobi than Orochimaru.  That evidence, again, being Itachi.  Who, according to the official statistics, is only slightly more powerful than Jiraiya.
 
How are you trying to apply obvious showings of comedic action to this?  When Sakura strikes Naruto in the back of the head, that's for comedic effect.  It has no implication on her combat abilities, because we all know Naruto would work her in a fight.  So, Naruto logic is linear, actually.  Naruto > Sakura, Sasuke > Sakura, Naruto and Sasuke as of yet to be determined once again.
 
JIraiya can decide not to look Itachi in the eye, thus avoiding Tsukiyomi completely.  He can dodge Amaterasu.  And in Sage Mode, he could bust Susanoo up just like A broke the ribs of Sasuke's Susanoo.

   Even without Kisame, Itachi will stalemate Jiraiya. In the japanese cannon states this.  He will outlast Jiraiya because he'll kill Jiraiya. In a test of stamina, Jiraiya as he has the elder 2 toads and sage mode. Orochimaru is more intellegent, cunning, and more evil. And? Itachi in his prime defeated Orochimaru. Itachi fighting Sasuke can kill Jiraiya with Amaterasu.  I can so another as well.  Jiraiya hasn't shown to be fast enough to dodge amaterasu. I doubt Sage Jiraiya is on par with Raikage in terms of physical attributes.   Oro wins because of his techniques. "

" @Susanoo said:

" Orochimaru is the most powerful out of the 3 sannins. He wins even without Kakuzu. "

According to my calculations no
 
 They were close but a lot says that Jiraiya was the strongest between the two. 
 
Orochimaru was about to be killed by Uchiha Itachi when he tried to posses Itachi to get the sharingan
 
When in Tanseku town (Whatever it's spelled) while trying to get Naruto for Akatsuki Kizame said, something along the lines, that he wouldn't be able to beat Jiraiya and that only Itachi could go toe to toe with him. But  Itachi clearly states that even with the help of Kizame the battle between Itachi and Jiraiya would be a double KO. They both would kill each other. (Something among those lines)
 

So if both Kizame and Itachi they themselves estimate that both of them could go against Jiraiya and die, then that must mean that Jiraiya had a greater chance of defeating Itachi. Meaning that Oro was not stronger than Jiraiya. Specially since Oro was Itachi's b!tch. 

 

"Itachi is stronger than I am, that's why I pull myself out of that organization" - Orochimaru referring to Akatsuki

  
In fact Jiraiya faced Itachi and Kizame and offer to wipe the floor with both of them, remember?
 

 
The big deal about Oro is that he was HARD to beat, not the most powerful but the hardest to beat due to his jutsus that were mostly about rebirth, genjutsu and restricted techniques.  Don't you remember he mostly escaped confrontation or had a few dogs with him in his fights?   He escaped from Itachi, he escaped from the battle against the Sanin (Don't blame him, though)  he escaped from the 3rd Hokage (When they first discovered he was doing experiments) He used Kinimaru (Spell check) and Kabuto to beat the Kazekage (He didn't do it on his own)  I'm not taking credit from him as that hes not a good opponent since he actually defended quite good against nine tails Naruto (Even if the only thing that saved him were his illegal techniques) but he is not the strongest between him and Jiraiya. He was just the slipperiest which shouldn't be a surprise since hes a snake..  Well, that's what I think anyway.. It makes a lot of sense I'd say. "

" @chillinglyrics: 

Let's play it on your terms, then.
 
Itachi recognizes that, even with Kisame right there, he will fight Jiraiya to a stalemate and suffer wounds.  A stalemate means that both sides cannot claim victory, and Itachi has Kisame on his side.  Jiraiya had a beat-up Sasuke and a chakra-drained, untrained Naruto.  However, Itachi never recognizes Orochimaru as being able to come close to beating him, let alone reaching a stalemate with him.
 
The logic still applies.
 
He took a lot of hits, sure.  But to say that he would outlast Jiraiya based off of that alone is false.  You're assuming he would even be capable of killing Jiraiya when the evidence so far dictates that Jiraiya, at the time, was an overall stronger and more skilled shinobi than Orochimaru.  That evidence, again, being Itachi.  Who, according to the official statistics, is only slightly more powerful than Jiraiya.
 
How are you trying to apply obvious showings of comedic action to this?  When Sakura strikes Naruto in the back of the head, that's for comedic effect.  It has no implication on her combat abilities, because we all know Naruto would work her in a fight.  So, Naruto logic is linear, actually.  Naruto > Sakura, Sasuke > Sakura, Naruto and Sasuke as of yet to be determined once again.
 
JIraiya can decide not to look Itachi in the eye, thus avoiding Tsukiyomi completely.  He can dodge Amaterasu.  And in Sage Mode, he could bust Susanoo up just like A broke the ribs of Sasuke's Susanoo.

   Even without Kisame, Itachi will stalemate Jiraiya. In the japanese cannon states this.  He will outlast Jiraiya because he'll kill Jiraiya. In a test of stamina, Jiraiya as he has the elder 2 toads and sage mode. Orochimaru is more intellegent, cunning, and more evil. And? Itachi in his prime defeated Orochimaru. Itachi fighting Sasuke can kill Jiraiya with Amaterasu.  I can so another as well.  Jiraiya hasn't shown to be fast enough to dodge amaterasu. I doubt Sage Jiraiya is on par with Raikage in terms of physical attributes.   Oro wins because of his techniques. "