Board Thread:Versus Debates/@comment-26958911-20151010214426/@comment-26537507-20151012131301

You say 'imperfect' as if that doesn't already put him leagues ahead of the average shinobi. The only things Itachi has that can win this fight are: Totsuka Blade and Tsukuyomi.

To use Tsukuyomi he needs to get close, which would benefit Jiraiya thanks to his wide variety of ninjutsu and his mastery of frog kata. He would also have to deal with any of the toads Jiraiya can summon and would be at risk from the Toad Confrontation Chant.

To use the Totsuka Blade he needs to use Susanoo, which is his best chance for survival. The Yata Mirror can deflect any ninjutsu and the Totsuka Blade can deal with the toad summons but multiple attackers could overwhelm him. He's also still at risk from the sound genjutsu.

Itachi can win but he would be pushed to his limits. Jiraiya winning is more likely IMO.