Itachi was able to fight against Naruto Uzumaki in his Nine-Tails Chakra Mode, something that Pain could never do. He was also able to incapacitate Nagato Uzumaki, and it is quite easy to see that he could definitely have taken on and defeated Pain in combat.
Itachi. Because Itachi. I think Itachi would win just because his visual prowess is one of the strongest in the Uchiha clan and he has the mind of a hokage. Plus, Nagato's weakness is genjutsu so Itachi has the upper hand.
Pain's Almighty Push is so strong that it literally destroyed an entire village. Given that he has the Rinnegan, he can use the Six Paths which has ridiculously high destructive powers. While Orochimaru is strong, he would lose to Pain given the difference in overall power levels and the jutsus.
Yes. Obito was afraid of Itachi. But it's not that Itachi was stronger than Obito. Up until Itachi was alive, Obito had Hashirama Cells, Kamui, Izanagi and some other common jutsus which were enough to defeat Itachi, if used wisely.
Itachi was tied for the highest stats in all of the databooks with Jiraiya. This makes sense, as Jiraiya is one of the few people whom Itachi seemed genuinely afraid to face in combat. He fled from Jiraiya, even though he had Kisame fighting alongside him.
But Jiraiya not only fought Pain alone in his territory but almost defeated him as well. However, in front of Itachi's Tsukuyomi and Amaterasu, his strength might not be enough. As a result, Jiraiya is a Naruto character who can never defeat Itachi.
As a fighter, Minato was deadly and capable of taking on both Nine-Tails and Obito Uchiha in a fight together. Pain, on the other hand, struggled to control the Nine-Tails with his power and ended up failing, which shows he was inferior to Minato in terms of skill and strength.
Despite his impressive achievements, there is no way Itachi can beat Obito in his most potent form. Obito Uchiha, in his strongest form, was the Ten Tail Jinchuriki. This means he had massive chakra reserves and endurance.
So in this scenario, Itachi would lose one Mangekyo, as he would have to replace it with a Rinnegan. Well, in theory, of course, Itachi could try to activate the Mangekyo on top of the Rinnegan, as Sasuke does, then his eyes would look something like Sasuke's with only three tamoe.
Even among the Akatsuki, nobody knew the true strength that Itachi possessed. His fighting prowess was phenomenal, and while Kisame was physically stronger, Itachi's Amaterasu and Tsukuyomi meant that it wouldn't take him long to subdue the former Kirigakure ninja.
Although some fans believe that Itachi is stronger than Madara Uchiha, there's hardly anything in the series that backs this claim up. Itachi may be powerful, but he definitely doesn't have even a fraction of Madara's godly powers.
7 COULD BEAT: Itachi Whose Genjutsu Would Fall Short
However, since Minato has absorbed half of the power and chakra of Kurama (in order to keep Naruto safe), it stands to reason he has many of the natural defenses against illusions that are inherent to a Jinchuriki.
While both Minato and Itachi have a superhuman battle sense and strategic mindset, Itachi has a severe advantage in this field. It is mainly because of his Sharingan. His Kekkei Genkai amplifies his analytical thinking in battle.
He then strikes them with precision, immobilizing them shortly. However, there's not much he can do to counter Six Paths of Pain. Pain was strong enough to defeat one of the three legendary Sannin, Jiraiya, and Neji is far weaker compared to him.
Pain killed Kakashi during his attack on the Hidden Leaf Village, but that was before a lot of training and the addition of the second Mangekyou Sharingan eye. With that enhanced power, Kakashi would be able to slay even the likes of Pain/Nagato.
Kirin struck at 1/1000th of a second once Sasuke's hand reached the end of its motion. That means Itachi had 1/1000th of a second to get Susanoo up or he would have died. Whether he tried to predict it or not, that is still impressive as that is faster than the speed of sound.
Yes buddy he can easily beat him. In their first encounter, Itachi was hesitant to fight Jiraiya even though he was with Kisame. If Itachi and Kisame chose to fight Jiraiya when Jiraiya came to save Naruto and Sasuke, who would've won?
If Shisui was his sibling he would definitely know since they were both living with the Uchiha and Shisui should only be around 4-8 years older than Itachi who is 9 years younger than Obito, hence they should also know each other...
What is means for Itachi is that when he was only just into his teenage years, he started undergoing an increase in stress that produced hormone imbalances that aged his skin prematurely and created the depressions.