10 Could: Itachi Uchiha 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 might not have been on the level of Madara and Sasuke, but he was certainly stronger than Pain.
Despite the power of the Rinnegan as well as the access to five different bodies, Nagato, aka Pain, would be no match for Madara Uchiha. Between Madara's own Rinnegan, his Mangekyo Sharingan, and the Susano'o, Madara has powers that Pain never quite reached.
His Tsukuyomi, Amaterasu, and Susano'o would deflect whatever attacks that Pain would unleash and ultimately pacify the Rinnegan user. Ultimately, Itachi could remove Nagato from existence or leave him in a vegetative state.
Hashirama, Tobirama, Minato, Kakashi and Naruto. These are the Hokage that can beat Pain individually. Let's get into it. As an Edo, he beat Edo Madara with the Rinnegan.
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.
Double Mangekyou Sharingan Kakashi would beat Pain without any issue. Kakashi would only need to use his Susanoo to fly out of range and then bombard them with his Kamui shuriken. Not even Chibaku Tensei could take Kakashi out because he could just use Kamui on its origin point to cancel it out.
Itachi would have surpassed Madara Uchiha if things were different for him. He learned every powerful Jutsu at a very young age and had a whole life to hone his skills and strength. However, he died too soon and his true potential never saw the light of day.
There is no denying that Itachi Uchiha ranks among the very strongest Uchiha clan members. Even when Itachi fought Sasuke, he did so while being almost blind, which just goes to show that his skills as a fighter were far beyond what people could comprehend.
As stated in the series, it seemed that Sasuke's Genjutsu abilities were indeed stronger than his older brother. Combine that with the powers he later gained through his Eternal Mangekyo Sharingan and Rinnegan, and it seems that Sasuke has him beat.
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.
Madara Uchiha
His only mistake was allowing Black Zetsu to influence his decisions, as his all-powerful form allowed the goddess Kaguya to possess and remodel his body in her image. Undoubtedly, Madara is the strongest Akatsuki member and the most powerful character in Naruto in a one-on-one fight.
During his lifetime there was only one character who could defeat Madara and that happened to be Hashirama. He was so powerful that later in life Madara went on to implant Hashirama's cells in his body to gain more powers which led to his Rinnegan awakening.
10 Could: Itachi Uchiha
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.
After completing his training with Orochimaru, Sasuke sought out Itachi and ultimately took him on in a tough battle. Throwing everything his way, Sasuke ultimately proved to be victorious as Itachi's fatal disease kicked in right in front of him.
Namely, Masahi Kishimoto has confirmed that Jiraiya is indeed stronger and all of that Itachi himself, who – on two separate occasions – admitted that Jiraiya was too strong, even from him, and that he would not be able to defeat him in a one-on-one fight.
As mentioned, he was extremely powerful in his teenage years, even before reaching his peak. Had it not been for his illness shortening his lifespan, Itachi would have grown to surpass the greatest of shinobi and would have totally redefined levels of power.
Itachi would probably lose to Goku in strict hand-to-hand combat, although he could hold his own for a while, but Itachi's true strength lies in his non-physical capabilities.
Originally Answered: What makes Itachi the so strong that he had to be killed by Kishimoto? Itachi's Susanoo wielded the Sword of Totsuka – an ethereal sword with the ability to seal any person it pierced into its gourd—hilt – and the Yata Mirror – a shield that was said to reflect any attack by changing its chakra ...
13 CAN'T BEAT: Itachi Uchiha
He is also a master of illusory genjutsu and would likely be able to keep Kakashi guessing until Itachi could make his winning stroke. Plus, Itachi's own Susano'o is immensely powerful and would certainly be a match for Kakashi's.
Is Kakashi better than Itachi? 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.
1) Madara Uchiha
This man was able to tame tailed beasts which really showcased his strength. As a child, Madara was able to awaken his Sharingan with one Tomoe in each eye. His mastery of the Sharingan and jutsu capabilities makes him far stronger than Kakashi.
No one, Nagato died on his own after resurrecting everyone killed by him when he attacked Konoha, as he was already in very weakened state.
This significance is accurately reflected in the series as the Deva Path is arguably the strongest out of the Six Paths of Pain, with powers comparable to a god's. The Deva Path has the power of attraction and repulsion at its core, with most of its abilities reflecting this concept.