Itachi vs Pain: The Ultimate Showdown in Naruto Shippuden

Time of India

13-05-2025

The most talked about match-up in Naruto is probably
Itachi vs Pain
. After all, both of these characters have similar feats. Both of them have defeated a Sannin, both have a Great Visual Jutsu, and both of them are a part of the Akatsuki.
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While Pain was Naruto's mid-series fight, Itachi was Sasuke's mid-series fight. And both of them could have defeated our heroes in a 1v1 if they wanted to. So, if these 2 top-tier characters were to fight each other, who would win? Let's break it down.
Pain vs Itachi: Power vs Strategy
If it were all about power, Pain would win easily. Shinra Tensei can level a village, and Chibaku Tensei could trap even a tailed beast. The
Six Paths of Pain
offer insane versatility, making it nearly impossible to surprise him in battle.
Itachi, on the other hand the kind of guy who doesn't need to out-power you — he can outplay you. But if it were just power vs strategy, Pain's overwhelming power would come out on top.
Feats
Both of these characters have some unbelievable feats. Pain took down Jiraiya with low difficulty. He destroyed the Hidden Leaf Village and fought Six-Tails Naruto. Itachi, on the other hand, humiliated Kakashi in Genjutsu. He shut down Orochimaru (twice and pretty easily).
And most importantly, he planned an entire death match with Sasuke while dying from illness, and still won!
Ninjutsu
Itachi's Amaterasu is a nightmare for most opponents, but not Pain. The Deva Path can repel it with Shinra Tensei, and the Preta Path can just simply absorb it. That's two simple counters right there. Some even argue that Preta Path might even absorb parts of Susano'o, since it's a chakra construct—but that's still debatable.
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Genjutsu
Itachi's biggest wild card is his Genjutsu. Tsukuyomi can break a person mentally in less than a second! But here's the problem — it only affects the mind of one person, and the Six Paths of Pain are essentially puppets with shared vision but separate chakra systems.
So even when Itachi lands Tsukuyomi on one path, it won't break the whole network. And once he uses Tsukuyomi, he won't have the stamina to cast it again mid-fight.
That leaves his standard Genjutsu, which is still deadly, but less effective against Pain's unique body.
Final verdict: Itachi vs Pain – who wins?
Based on the points mentioned above, Pain wins 9 times out of 10. He is just way too powerful to face. Even someone as strong as Itachi will not be able to defeat him alone without some help. Things would change, however, if Itachi figures out the trick behind the Six Paths. Someone as clever and tactical as Itachi will give a strong fight to Pain if he knew the secret.
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