Did Kakashi eventually surpass Itachi, Jiraiya, Tsunade, and Orochimaru? 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?



Note:- Before posting any answer to the question please read most (if not all) of the answers that's already posted below.
Taijutsu

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.

Ninjutsu

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.

Chakra

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.

Genjutsu

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.

Based on this, we can say that overall, Kakashi hasn't surpassed the other 4. He's just pretty much on the same level, or a bit under the other 4.