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Though I believe that Sharingan Tobi might be slightly above Itachi due to his S/T techs, if Itachi would've known everything about him, he would've came up with a plan that would have better chances of getting through his S/T techniques.
If Itachi were to fight Tobi head on, I think Tobi would come out ontop. The reason why Minato managed to escape being warped in was because of his instantanious teleportation (FTG).
Itachi doesn't have this but he does have pretty good reflexes. The problem would be having a technique to avoid being warped. If Tobi warps behind him and begins to suck him in, I don't know any technique of his that could prevent him from being warped. Since Itachi's entire shape starts to deform as he's being sucked in, he would need something instantanious that doesn't really require movement. FTG or Shinra Tensei are examples along with Konan's paper bombs that she revealed as she was about to be sucked in.
(This is a maybe) If Itachi could manifest Susanoo at a distance from himself the moment he activates it, then Susanoo could attack Tobi if Tobi attempts to warp Itachi away. That's if Susanoo itself has good movement speed to counterattack Tobi before Itachi is warped away. Considering that Susanoo pierced Orochimaru in the middle of his words, it seems to be quick in movement. If it could only manifest with Itachi inside it when it's activated, then I don't know how it'll counter if Tobi just happens to warp inside and behind Itachi.
The situation Tobi was in when he had a talk with Sasuke though, he would've died if he had not had the S/T that cancelled or warped Amaterasu away. He admited that he would've died if Itachi had known his secret because Itachi would've probably looked for a different plan that would actually get through his S/T. Catching him offguard worked but Amaterasu might've not been the best solution.
Itachi probably didn't know that Amaterasu would be rendered useless so he had that as his booby-trap thinking that the flames would remain on him until he is burnt to ash.
He caught Tobi offguard just like Minato caught him offguard when he FTGed to the kunai that had just phased through Tobi followed by a Rasengan. Except, this time Tobi was caught offguard through Sasuke's sharingan. At first, he didn't seem to expect anything as he showed him his sharingan until Sasuke's turned into Itachi's and spawned Amaterasu on him.
This doesn't mean that Itachi automatically > Tobi but he did manage to nearly kill him. Though it was almost at the same sence as Konan. Konan had time to disguise 6 billion explosive tags as the ocean while Itachi had time to place his Amaterasu trap on Sasuke's eye. Itachi knows his own limits but his brain allows him to think ahead using a different approach.
If Itachi were to fight Tobi head on, I think Tobi would come out ontop. The reason why Minato managed to escape being warped in was because of his instantanious teleportation (FTG).
Itachi doesn't have this but he does have pretty good reflexes. The problem would be having a technique to avoid being warped. If Tobi warps behind him and begins to suck him in, I don't know any technique of his that could prevent him from being warped. Since Itachi's entire shape starts to deform as he's being sucked in, he would need something instantanious that doesn't really require movement. FTG or Shinra Tensei are examples along with Konan's paper bombs that she revealed as she was about to be sucked in.
(This is a maybe) If Itachi could manifest Susanoo at a distance from himself the moment he activates it, then Susanoo could attack Tobi if Tobi attempts to warp Itachi away. That's if Susanoo itself has good movement speed to counterattack Tobi before Itachi is warped away. Considering that Susanoo pierced Orochimaru in the middle of his words, it seems to be quick in movement. If it could only manifest with Itachi inside it when it's activated, then I don't know how it'll counter if Tobi just happens to warp inside and behind Itachi.
The situation Tobi was in when he had a talk with Sasuke though, he would've died if he had not had the S/T that cancelled or warped Amaterasu away. He admited that he would've died if Itachi had known his secret because Itachi would've probably looked for a different plan that would actually get through his S/T. Catching him offguard worked but Amaterasu might've not been the best solution.
Itachi probably didn't know that Amaterasu would be rendered useless so he had that as his booby-trap thinking that the flames would remain on him until he is burnt to ash.
He caught Tobi offguard just like Minato caught him offguard when he FTGed to the kunai that had just phased through Tobi followed by a Rasengan. Except, this time Tobi was caught offguard through Sasuke's sharingan. At first, he didn't seem to expect anything as he showed him his sharingan until Sasuke's turned into Itachi's and spawned Amaterasu on him.
This doesn't mean that Itachi automatically > Tobi but he did manage to nearly kill him. Though it was almost at the same sence as Konan. Konan had time to disguise 6 billion explosive tags as the ocean while Itachi had time to place his Amaterasu trap on Sasuke's eye. Itachi knows his own limits but his brain allows him to think ahead using a different approach.