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tobi wins. itachi has only susonoo to protect him from getting warped and as soon as thats gone he is srcewed. tobi just has to play wacka mole till itachi runs out of gas.
As far as I know, Tobi had the best chances to kill Itachi but didn't for few reasons. He was using Itachi to mold Sasuke into an evil, vengeful man. Tobi most likely wanted Sasuke for a long time, especially before JIraiya vs. Pain or real Itachi vs. Sasuke. By letting Itachi die by Sasuke's hand, Tobi awoke the chance for Sasuke to unlock Mangekyo and make it impossible for Itachi to stop Sasuke in any shape or form.
One reason why Tobi may have been scared of Itachi was because Itachi had information. No one but Itachi and few Akatsuki knew Tobi was really Madara, and as Tobi himself said, he was being cautious until he sent Sasuke to the Summit. It doesn't necessarily mean Tobi was scared of Itachi's power, he could have been scared of Itachi's knowledge as well. Despite what Tsunade says, Tobi is not immortal, and if secrets leaked out then Akatsuki would have had a hard time moving and Tobi's secrets may have been uncovered. Maybe Itachi was powerful and could have taken on Tobi or tie with him, but it can also be due to knowledge Itachi had on Tobi.
Also, why would Itachi leave Tobi alone for Sasuke to kill? Itachi was dying, so whether or not he killed Tobi had no effect apart from possibly rob Sasuke his chance at revenge and better image. Itachi knew the power Tobi had, how he could bend people to his will and the power his eyes still possessed, there is no way Itachi would have risked Sasuke meeting Tobi if he could. I mean, Itachi even implanted an Amaterasu in Sasuke to make sure Tobi never tells Sasuke the truth. If Itachi could have taken Tobi on, he would have while keeping himself as Sasuke's last opponent.
As far as I can see, Itachi would either tie with Tobi or lose to him, there hasn't been any evidence to show he'd beat Tobi although Itachi is the toughest and awesomest motherfucker ever (counting even Minato, Nagato, Kakashi, and Jiraiya). It took Minato Hiraishin to even hurt Tobi, and even then Tobi walked away. Konan needed prep time and tons of explosion, but Tobi escaped that, albeit with his Izanagi. Itachi probably wouldn't know about Izanagi since Tobi would have no need to use it in front of him.
It's a difficult one this one. If the two don't know each other, madara doesn't know about itachi's genjutsu skill, nor the fact that he has the mangekyou. On the other hand, itachi will probably figure out pretty soon in the fight that madara has his intangibillity and his teleport + sucking abillity, just like minato did. If itachi is smart enough and goes in with a clone to figure out abillities like kakashi does. He has a good chance of winning if his chakra allows it.
But in my eyes this match is probably a stalemate. I mean, I don't see madara having the power to kill itachi, (other than the sucking ability) which I doubt he can catch itachi with. On the other hand, I'm not really sure if itachi can figure out the timelimit on madara's intangibility jutsu. If he figures it out and has the chakra to deal with it, he obviously wins imo.
We'd probably never see minato use clones, since they have no use to him in terms of guaranteeing his survival. Pretty much nothing can touch him, so he can't die from a physical attack this doesn't go for the rest of the shinobi other than naruto and raikage. The only ones that can touch them at their fastest is minato. Minato can always test your abillities with the use of hiraishin.
Last edited by scandalous'; July 17, 2011 at 07:11 PM.
IMO Madara's 3 tomoe sharingans power and his skill at breaking genjutsu with his 3 tomoe sharingan would both have to exceed Itachi's skill at creating genjutsu and his power.