Itachi in his prime is Madara level I mean, wasn't Madara kind of afraid of fight Itachi? That's canon. Its like taking away Itachis main power. The only thing orochimaru has that might stand a chance is Edo Tensei. Then again , it seems he has not mastered it as when he edoed Hashirama and Tobirama , Old Hiruzen was able to take them on!! We all know thats impossible.
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Itachi , also known as the Clan Killer, is one of the Uchiha clan's finest ninjas ever in Naruto. Ever since Itachi was a kid, he excelled at everything, be it Ninjutsu, or Taijutsu. One of the youngest Uchiha ever to awaken the Sharingan, Itachi made sure to take his skills to the pinnacle and being the pacifist that he was, his goal was to bring about peace. At the mere age of 7, Itachi had the wisdom of a Kage, making him one of the smartest characters in the entire series. To surpass such a shinobi would prove to be an arduous task for anyone, yet there are few who have achieved this feat. Here are five Naruto characters stronger than Itachi and five who are weaker. Updated July 30th, by Josh Davison: Itachi Uchiha was often floated as the true most powerful character in the entire Naruto saga.
Itachi is the older brother of Sasuke Uchiha and is responsible for killing all the members of their clan, sparing only his younger brother Sasuke. He appears working as a terrorist from the organization Akatsuki and serves as the biggest threat to his brother. During the second part of the manga, Itachi becomes involved in terrorist attacks to ninjas possessing tailed-beast creatures until facing Sasuke in a one-on-one battle. Although Itachi perishes during the final duel, it is later revealed Itachi had a secret reason for assassinating the Uchiha clan. Itachi has appeared once in an original video animation of Naruto , and is a playable character in most of the video games from the series. Itachi's character has been popular with readers of the manga,  and has been positively received by critics. His appearance as an antagonist has been praised by several writers, although some have considered his initial appearance to be unsurprising. The gradual revelations of his past and its impact on the story has also received positive reception,   and his fights were noted to be "one of the best" in the series. When Itachi Uchiha is first mentioned by Sasuke Uchiha in the manga , Masashi Kishimoto had not planned out the character's backstory.
With a life-ambition to learn all of the world's secrets, Orochimaru seeks immortality so that he might live all of the lives necessary to accomplish his task. After being caught red-handed performing unethical experiments on his fellow citizens for the sake of this immortality, Orochimaru defected from Konoha rather than be persecuted for his ambitions, and for many years sought the village's destruction in order to take revenge and demonstrate what he had learned. After several apparent deaths in the pursuit of his goals, Orochimaru realises his approach is flawed through Kabuto Yakushi , his former associate, and begins monitoring the choices and actions of his former apprentice, Sasuke Uchiha. Orochimaru was once an orphan who became a pupil of Hiruzen Sarutobi alongside Jiraiya and Tsunade. Compared to the more laid back Jiraiya, Orochimaru stood out as a genius — his talents, knowledge, and determination were considered by Hiruzen to be that of a prodigy seen only once in a generation. His sadistic attitude was presumably due to the death of his parents. At some point after losing them, Orochimaru found a white snake near his parents' grave, with Hiruzen's explanation of it representing fortune and rebirth inspiring Orochimaru to study kinjutsu and obtain knowledge of all techniques. Orochimaru performed various experiments on his prisoners, some being fellow Konoha shinobi he kidnapped.