Board Thread:Versus Debates/@comment-26958911-20151010214426/@comment-26127155-20151018003057

Curse of Hatred wrote: The difference is that it would be a lot harder to hit a moving target, especially one with speed that's been enhanced by sage mode.

Fair call, It would be a lot harder for Itachi to hit jiraiya than it was for Orochimaru but is the speed enough? Itachi is not limited to only one strike of the Totsuka blade and at some point during the battle, Jiraiya would be distracted evading Itachi's other techniques such as his genjutsu, Ameterasu or yata matagama.

This is a very interesting match up as both characters have a very different approaches in fighting, while both being very good at analysing their opponents' abilities. Jiraiya's sage mode gives him a situational advantage as attacks from behind would be harder to achieve but Itachi has mastery of the sharingan which allows him to decipher his opponent's techniques very quickly as well as keeping up with Jiraiya's movements & diversions.