Naruto’s Most Pivotal Itachi Scene From 21 Years Ago Nearly Stopped The Fourth Ninja War

Naruto fans rarely bring it up, but one quiet exchange published in Japan on May 9, 2005, may have been the biggest missed chance in the whole story. In chapter 257, Kakashi Hatake faced Itachi Uchiha’s body double and asked how badly his Mangekyo Sharingan eyes had deteriorated.

Itachi was visibly caught off guard, and Kakashi never pushed it further. Had he revealed what his own eye could really do, Itachi, who once teamed up with the masked “Madara,” might have cracked Tobi’s identity long before the Fourth Shinobi World War began, and maybe saved everyone a lot of pain.

How Kakashi’s Mangekyo Question Became Naruto’s Biggest Missed Hint

Kakashi and Itachi, as seen in Naruto Chapter 257 | Credits: Shueisha

It’s an easy scene to blink and miss. Chapter 257, titled “Kakashi’s EXP,” lands in the middle of the Kazekage Rescue Mission. Naruto, Sakura, Kakashi, and Chiyo are chasing the Akatsuki when Itachi steps into their path. Kakashi tells everyone not to meet his eyes. Chiyo points out that they outnumber him, but Kakashi says numbers won’t matter against a Mangekyo Sharingan. Then he turns to Itachi and asks how much his eyes have deteriorated. Itachi clearly didn’t see that coming. For a man who rarely lost his composure, that was a rare crack, and Kakashi was poking at the one weakness nobody expected a Konoha ninja to know about.

Kakashi had his reasons for sounding so sure. Back when Itachi and Kisame came to Konoha, Itachi trapped him in Tsukuyomi and left him laid up for days. He’d felt that power firsthand, and he also knew the Mangekyo can eat away at the user’s eyesight. By the end of his life, Itachi could only see blurs. In the anime, Kakashi even lifts his headband to flash his Sharingan, and Itachi looks stunned, wondering whether Kakashi has a Mangekyo of his own.

Here’s the catch, though. That wasn’t really Itachi. It was a body double, and once Naruto hit it with his Big Ball Rasengan in Chapter 260, the team realized they’d been fighting a decoy. Kisame had pulled the same trick on Team Guy. Kakashi wouldn’t use his own Mangekyo Sharingan until later in the arc, against Deidara, when he sent an explosion into another dimension and collapsed from exhaustion. Guy had to carry him back. By then, Itachi’s double was long gone, and the moment had passed. Kakashi never got to see what that Mangekyo reveal would have done to Itachi’s face, or to his plans.

One Look at Kakashi’s Eye Could Have Exposed Tobi Early

Now picture Itachi seeing that power up close. For years, he believed a masked stranger was the real Madara Uchiha. Before the Uchiha Clan Downfall, Itachi caught him sneaking around Konoha and offered a deal: he’d help the man take revenge on the Uchiha if the village was spared. The man agreed, and together they wiped out nearly the entire clan in a single night. Itachi had no idea who was really behind that mask.

It was Obito Uchiha, Kakashi’s old teammate. Kakashi’s Sharingan came from him, too. Obito, certain he was about to die, had Rin transplant his left Sharingan into Kakashi. Tobi could turn intangible or teleport, and later, Kakashi worked out that his Kamui and Tobi’s strange power share the same dimension. Itachi knew the Mangekyo better than almost anybody. Seeing that same kind of ability from a Konoha jonin’s borrowed Uchiha eye would have been a flashing red flag. He might have started asking who really gave Kakashi that eye, and the answer was sitting right there.

Itachi was also a longtime double agent for Konoha, so he’d have had every reason to warn the village. Instead, Tobi stayed hidden until Chapter 599, when his mask broke, and Kakashi and Guy stared at Obito in the middle of the Fourth Shinobi World War. By then, Tobi was deep into his Infinite Tsukuyomi plan, and the whole world was paying for it. Of course, Kakashi had no clue Obito was alive, and he hadn’t even used his Mangekyo yet. It’s a little wild that one of the series’ biggest secrets sat that close to the surface, behind a single question about Itachi’s eyes.

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