In the Naruto manga, Kakashi Hatake has been acknowledged by both Jiraiya and Tsunade to be one of Konoha's most powerful shinobi. But Kakashi himself had confessed that Orochimaru was on a completely different level from him, who in turn openly acknowleged that Itachi Uchiha was more powerful than him. Obito Uchiha was noted to be more powerful than any other Uchiha except Madara Uchiha, whom Kakashi defeated.
My question is, at the time when Kakashi defeated Obito, had he surpassed all of Tsunade, Jiraya, Orochimaru and Itachi? Is there any reference in the manga itself from which a definite answer can be given, either in the affirmative or in the negative?
Jiraiya got the Frog Kumite, Tsunade has brutal strength, so it is clear here that in terms of Taijutsu, Kakashi is not as strong as those two. As for Orochimaru and Itachi, they don't use taijutsu much so it can be said that Kakashi could be on the same level or better.
Kakashi is the renowned Copy Ninja, the one who has copied over 1.000 jutsus. In term of Jutsu knowledge, it can be said he is on par with Orochimaru if not greater. Tsunade is not that great in ninjutsu other that ninjutsu for healing purposes. Jiraiya has great ninjutsus but if we talk about the jutsu element, Kakashi can perform 4 basic elements (Katon: Goukaku, Suiton: Suiryuudan, Doton: Doryuuheki, Raiton: Raikiri). He was also able to learn Rasengan, which was rated as an A rank jutsu. Meaning that it is very hard to learn. Itachi, being an Uchiha, would be able to copy jutsu the same way Kakashi did. So they can be said on the same level. However, it is not known whether Itachi can use 4 elements like Kakashi did. Itachi for sure can use fire jutsus as demonstrated during his fight against Sasuke. Kakashi learned to use Susano'o after Obito transferred his remaining chakra to him upon his death. So here, Kakashi can be said has surpassed the other 4 in this.
Kakashi is very well known as having a low reserves of chakra. He commented that Naruto has about 4 times of his. And considering that Naruto-Sasuke-Sakura was like the new Sannin of Konoha, it can be said that Jiraiya has about the same or greater level of chakra than Naruto. Orochimaru as we know is a chakra monster, same with Tsunade. Itachi is pretty much on the same level as Kakashi in term of chakra reserves, except that being an Uchiha, he gets less strain than Kakashi in using the Sharingan.
Kakashi is better in Genjutsu than Jiraiya, except of course, when Jiraiya used the help of Fukasaku and his wife (the frog sennins) to cast sound genjutsu. He should be better than Tsunade and Orochimaru too since he has the Sharingan. He, however, is far weaker than Itachi.
Kakashi can't spam his Kamui abilities so even if he could use it against pain, he probably only use it 1-2 times till he gets drained. Also, Kakashi is no where near the Sannins level. Unless you count Kakashi with the boosted power ups from Obito which I really don't give because he had the power for only 1-2 chapters ._. Itachi slays Kakashi, how much more proof you need to believe this ?! Orochimaru slays Kakashi... Kakashi fears the man as seen on many episodes. Tsunade & Kakashi is the only reasonable fight seeing that tsunade is a medic ninja that has great strength & power. But even then Kakashi would have his hands full. Kamui spams is a bad reason for Kakashi to get the edge. Kakashi is my favorite character but this is too easy. & yes, Hokage Kakashi still loses. Hokage Kakashi is the weakest Kakashi since he has no sharingan & he probably can't use the jutsus he copied due to that. & you guys bring up the 1000 Jutsus he's copied yet we don't know what the jutsus are. Kakashi loses.
If we were to have a direct match between Jiraiya and Kakashi, Kakashi would be defeated. How? Well, Jiraiya faced pain in his full glory in Amegakure, i.e. the opponent's territory, while Kakashi could not defeat just one of Pain's Paths when Konoha was attacked.
Now comes up Orochimaru. During Search for Tsunade arc, we see a hell of a battle -- Tsunade and Jiraiya vs. Orochimaru, still Orochimaru was able to escape in the end. Thus, Kakashi can't defeat Orochimaru either.
Now it's time for Itachi. In the very first days of Itachi's first premier in the series, Kakashi fought him and had to be admitted to the hospital for a very long time. Even in the Shippuden version, Itachi is just too powerful to be taken down.
You must note that Kakashi did NOT defeat Obito. I say this because Obito knew about Madara's seal (chapter 675) and wanted to undo it to become the Ten-Tails Jinchuuriki. Also, he wasn't even trying to kill Kakashi. So he LET Kakashi STAB HIM IN THE CHEST. We all know that he could use his Rinnegan (because he used Edo Tensei) but he didn't use it in his fight with Kakashi. Kakashi couldn't even survive two Paths of Pain and Obito can use all of them and also Izanagi. Kakashi himself accepted that Orochimaru and Jiraiya (because Jiraiya fought all Six Paths of Pain BY HIMSELF) are better than him. I don't know about Tsunade, but Kakashi would be easily defeated by Jiraiya or Orochimaru.
Well, about Itachi, we all saw Itachi defeated Kakashi with his genjutsu in the original Naruto series when Itachi didn't even use Susanoo (his Susanoo had the Totsuka blade which could seal literally anything) or Amaterasu. Also, Kakashi, without Obito's Sharingan, is nothing in front of any of the above mentioned since Obito's eye allowed him to see his opponent's moves (he would've been defeated by Zabuza if he didn't have Obito's eye). Kakashi also agreed that the Chidori would've remained as an incomplete jutsu if he hadn't got Obito's Sharingan. It would also feel like you are cheating when only Kakashi's abilities are unknown and not Jiraiya's. One can escape from Kamui with good speed (as Minato did). Also, Kakashi exhausts almost all of his chakra if he uses Kamui twice and Jiraiya won't let him do that. Even if Kakashi uses Kamui on Jiraiya and Jiraiya got teleported into another dimension, he could easily summon himself back to Mount Myouboku by summoning one of the toads and then summon himself back to the real world. This would make Kakashi's Kamui useless and also would exhaust his chakra.
This question is not even that complicated a much as you guys make it seems...So let's break down and compare the skills of the four to Kakashi's skills...i be starting from the weakest to the strongest.
First, the weaker of the four would obviously be Tsunade...Taijutsu, well in this department Kakashi outclasses Tsunade by a long shot...Strength, Tsunade would make Kakashi look like childs, Offensive capabilities Kakashi takes this aswell, Ninjutsu, Kakashi has more than her and with both Mangekyou Sharingan kakashi would stomp her completely...So its pretty much Kakashi is stronger.
The second weakest I would say is Orochimaru...Orochimaru is on a different level when it comes to Taijutsu, Ninjutsu, and Genjutsu...Plus its impossible to killed the without sealing him...Remember his fight with the naruto's four tails...he got cut in two about a hundred (not literally) but he just shed his skin and he's good as knew...Sasuke tried to kill him, Itachi tried to kill him...crying out loud the entire Narutoverse tried to kill him...and he's still alive to date...he's impossible to kill...the dude has impure world resurrection, immortality to a huge extent, eight head serpent jutsu, a million and one jutsu, large chakra reserve.
Third weakest of the four would be Itachi...just like how Orochimaru wasnt debatable this is the same...Itachi wins...Itachi has Izanami, Susanoo'o (Sword of Totsuka and Yata Mirror), Amateratsu, Tsukuyoumi...so there is no chance of winning.
Last Jiraiya...I just got one word for you sage mode...the man can summon a million and one toad to fight along side him...he has sage mode...that sealing justsu that can seal away anything (the one he use to seal Itachi's black flames), he has a wide range of jutsu aswell.
So from my observation of reading every single manga and watching all anime episode (Cannon and filler)...i can completely say the Kakashi is stronger than Tsunade with or without both Mangekyou...However the other three is just out of his league, they all have jutsu's and abilities that makes him look like child's play
In my opinion, Kakashi did surpass them all, momentarily that is. I don't see Jiraiya, Orochimaru and Tsunade taking on Kakashi with his double Mangekyō Sharingan (Complete Body Susanoo, plus both variants of Kamui).
Itachi, on the other hand, just might have a chance against him. Since Itachi's Susanoo is equipped with Totsuka Blade and Yata Mirror, which was stated to be essentially invincible by Zetsu, he might have a chance against Kakashi's Susanoo.
In the anime, Itachi is certainly one of the most powerful shinobi. It has been observed that Kakashi was defeated by Itachi by the Tsukuyomi. This is one of the strongest jutsu that he could use. But as has been remarked earlier, Sharingan user can't protect himself from a Genjutsu cast by Mangekyo Sharingan. To remain immune, the opponent should at least use Mangekyo Sharingan (other than the method that Jiraiya said to Naruto, which applies mostly to the people with an immense amount of Chakra). Kakashi was seemingly unaware of his Mangekyo Sharingan at the time he fought Itachi, so he failed to defeat Itachi.
It should also be noted that the Amaterasu would have no effect on Kakashi, because he could simply warp away the flame or move into the Kamui dimension. As for the Tsukuyomi, Kakashi's Susanoo would perfectly counter it.
Besides, as Sakurai Tomoki noted in his answer, Kakashi can perform all 5 basic elements, which is a feat Itachi is not known to have. In this aspect, Kakashi is also ahead of Itachi. Itachi also noted that fighting Kakashi alone was dangerous with a high chance of injuries.
While comparing between Jiraiya and Kakashi, it should be noted that in the anime, Kakashi was in a developing stage, meaning that his power was increasing whereas Jiraiya's power showed no notable development.
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