3. Itachi Uchiha vs Orochimaru

Since the time Orochimaru lived in Konoha, he had observed Itachi’s training—a young boy who deliberately allowed himself to be attacked by multiple kunai. However, Itachi skillfully deflected the kunai with his shuriken, and his agile movements ensured that none of the kunai struck him. Orochimaru was astonished by Itachi’s brilliance and greatly admired the power of his Sharingan.

It’s no wonder that when they were in the same organization, Akatsuki, Orochimaru warmly welcomed Itachi and continued to monitor his activities. Orochimaru became obsessed with Itachi and didn’t hesitate to express his desire to make Itachi his Akatsuki partner, which irritated Juzo, Itachi’s current partner. After Juzo’s death, Orochimaru even offered to replace him as Itachi’s partner, causing Sasori, Orochimaru’s former partner, to feel disrespected.

One day, as Orochimaru ascended the stairs, he crossed paths with Itachi, who was descending from the opposite direction. As they passed each other, Orochimaru attacked from behind, wrapping Itachi in his snake coils, immobilizing him. Orochimaru then revealed his intention to make Itachi his new vessel so that he could achieve immortality.

However, the situation changed in an instant—Itachi was now standing right in front of Orochimaru. Using Kanashibari no Jutsu (Paralysis Jutsu), Itachi trapped Orochimaru in a Genjutsu. Orochimaru tried to perform hand seals to break free, but Itachi swiftly severed one of Orochimaru’s hands.

Orochimaru was even more awestruck by the power of the Sharingan. Itachi calmly told Orochimaru that any jutsu he used would be futile against his Sharingan. After utterly humiliating Orochimaru, the legendary Sannin of Konoha, Itachi confessed his confusion—he wasn’t sure whether to kill Orochimaru or simply let him live. Luckily for Orochimaru, Itachi allowed Kabuto to rescue and take him away.

But it didn’t end there—Itachi defeated Orochimaru not just once, but twice.

When Sasuke ran out of chakra during his battle against Itachi, Orochimaru’s chakra, sealed within Sasuke’s body, was automatically released. This caused a giant white eight-headed serpent to emerge from the curse mark on Sasuke’s neck.

Orochimaru then emerged from the mouth of the massive serpent, ready to fight Itachi. He pulled the Kusanagi sword from his mouth and thanked Itachi, claiming that Sasuke running out of chakra was the perfect opportunity he had waited for. Orochimaru intended to take over Sasuke’s body.

Without wasting any time, Itachi summoned Susanoo and stabbed Orochimaru with the Totsuka Blade. At first, Orochimaru laughed at Itachi’s attempt to defeat him with a simple sword stab. However, his confidence turned into panic when he realized that the blade piercing his body was the Totsuka Blade. Orochimaru was stunned—he had spent years searching for this legendary sealing sword, only to discover that Itachi possessed it.

As a result, Orochimaru, pierced by the Totsuka Blade, was instantly sealed and trapped in an eternal Genjutsu.