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There has been many speculations that Itachi stands a remote chance of beating Obito, and I'm going to prove that false.
This is the scan most people use to say Itachi>Obito
And then we have this one
Itachi and Obito made a deal and cooperated with each other. We found out that Obito persuaded Itachi into joining Akatsuki. Reasons Obito considered the Leaf village off limit are
1. Obito knew how valuable Itachi is in helping the akatsuki out in hunting the bijuus.
2. Obito didn't want the secrets of akatsuki to be given to the villages. Itachi giving the info he gathered on akatsuki regarding the bijuu hunt would have made the hunt much harder, as villages would limit the freedom of their jinchurikis even further, and they would increase the security of their villages. Two akatsuki members aren't enough to take care of one of the major villages.
Obito played along with Itachi to keep the Akatsuki's secrets secure.
We also have this scan
But with what exactly? Nothing in Itachi's arsenal would work on Kamui, and even a surprise attack didn't work.
Also the lack of information makes it much harder for Itachi to bypass Kamui.
I'll later on the thread go on why Itachi can't bypass kamui
Now, let's analyze the techniques of the individuals
Itachi is known for his genjutsu prowess, but his genjutsu is useless against a full blooded Uchiha
Inb4: "Obito isn't related to Itachi by blood".
1. We all know all the Uchihas are coming from the same blood, the blood of Indra.
2. An expert mangekyo sharingan user like Obito would easily see through Itachi's Tsukuyomi by his normal 3 tomoe shringan.
Izanami is a technique that uses opponent's and caster's five senses
But you need to memorize the bodily sensations
Itachi took advantage of his edo body, and purposely took Kabuto's hit. In a battle that he is alive he has to take attacks on purpose to land izanami, or land an attack on Obito. Kamui easily prevents that, due to the lack of speed from Itachi.
Obito can also go for the one hit kill to avoid taking chances in Itachi using Izanami. Mukton branches can easily do so
In Obito's case, we have this
Feat of Obito controlling Yagura, a perfert jinchuriki, for many years is above any genjutsu feats shown by Itachi. Battle of Genjutsu is in Obito's favor.
Obito has stronger Ninjutsu feats
A juubi sized katon that can overwhelm any water or fire attacks from Itachi.
Itachi's fire style or water style can get rid of Obito's wood release, but it doesn't protect him from Obito piercing Itachi's body with it.
Obito's Kamui can easily avoid Amaterasu as sharingan can see Itachi's eye building up chakra to use Amaterasu. He also can see the blood that signals the coming of amaterasu
Also we have Obito canonically countering Amaterasu even when it hit as a surprise attack
Susanoo wouldn't add anything as everything is phased through or dodged, and it doesn't serve its defensive purposes either as Obito can go through Susanoo with Kamui.
Totsuka blade isn't helping Itachi here since it is too slow to pierce Obito, or bypass Kamui's activation speed.
Yata mirror won't be blocking Obito from phasing through it, since Obito's right eye Kamui isn't an offensive technique. Totsuka can't repel what isn't there.
Obito has the ability to remain intangible for 5 mintues straight
He simply can to tangible, and they resumes the intangibility to renew his 5 minutes.
Taijutsu
Itachi can outperform Obito in taijutsu, but Kamui makes it child's play for Obito, since he could stalemate four kage level shinobis. Itachi doesn't come close to that.
Tl;dr
I believe Obito wouldn't have any major problems if he had ever faced Itachi.
This is the scan most people use to say Itachi>Obito
You must be registered for see images
And then we have this one
You must be registered for see images
Itachi and Obito made a deal and cooperated with each other. We found out that Obito persuaded Itachi into joining Akatsuki. Reasons Obito considered the Leaf village off limit are
1. Obito knew how valuable Itachi is in helping the akatsuki out in hunting the bijuus.
2. Obito didn't want the secrets of akatsuki to be given to the villages. Itachi giving the info he gathered on akatsuki regarding the bijuu hunt would have made the hunt much harder, as villages would limit the freedom of their jinchurikis even further, and they would increase the security of their villages. Two akatsuki members aren't enough to take care of one of the major villages.
Obito played along with Itachi to keep the Akatsuki's secrets secure.
We also have this scan
You must be registered for see images
But with what exactly? Nothing in Itachi's arsenal would work on Kamui, and even a surprise attack didn't work.
Also the lack of information makes it much harder for Itachi to bypass Kamui.
I'll later on the thread go on why Itachi can't bypass kamui
Now, let's analyze the techniques of the individuals
Genjutsu
Itachi is known for his genjutsu prowess, but his genjutsu is useless against a full blooded Uchiha
You must be registered for see images
1. We all know all the Uchihas are coming from the same blood, the blood of Indra.
2. An expert mangekyo sharingan user like Obito would easily see through Itachi's Tsukuyomi by his normal 3 tomoe shringan.
Izanami is a technique that uses opponent's and caster's five senses
You must be registered for see images
You must be registered for see images
Itachi took advantage of his edo body, and purposely took Kabuto's hit. In a battle that he is alive he has to take attacks on purpose to land izanami, or land an attack on Obito. Kamui easily prevents that, due to the lack of speed from Itachi.
Obito can also go for the one hit kill to avoid taking chances in Itachi using Izanami. Mukton branches can easily do so
You must be registered for see images
In Obito's case, we have this
You must be registered for see images
You must be registered for see images
Ninjutsu
Obito has stronger Ninjutsu feats
A juubi sized katon that can overwhelm any water or fire attacks from Itachi.
You must be registered for see images
Obito's Kamui can easily avoid Amaterasu as sharingan can see Itachi's eye building up chakra to use Amaterasu. He also can see the blood that signals the coming of amaterasu
Also we have Obito canonically countering Amaterasu even when it hit as a surprise attack
You must be registered for see images
Susanoo wouldn't add anything as everything is phased through or dodged, and it doesn't serve its defensive purposes either as Obito can go through Susanoo with Kamui.
Totsuka blade isn't helping Itachi here since it is too slow to pierce Obito, or bypass Kamui's activation speed.
Yata mirror won't be blocking Obito from phasing through it, since Obito's right eye Kamui isn't an offensive technique. Totsuka can't repel what isn't there.
Obito has the ability to remain intangible for 5 mintues straight
You must be registered for see images
Taijutsu
Tl;dr
I believe Obito wouldn't have any major problems if he had ever faced Itachi.