Board Thread:Versus Debates/@comment-26958911-20151010214426/@comment-26127155-20151020205436

The reason Itachi has a greater chance of breaking out of the toad chant genjutsu, compared to Jiraiya breaking out of Itachi's genjutsu is the based on their mastery (or the lack of) genjutsu. Jiraiya admitted that he is personally poor at genjutsu, while Itachi is at the other end of the spectrum being the greatest genjutsu user of that time. Itachi has been shown to reflect genjutsu from a genjutsu specialist, Kurenai and this opens a can of worms about if Itachi could reflect the toad chant genjutsu.

On the other hand, Jiraiya has never shown any impressive feats of escaping genjutsu (except for him teaching Naruto?) and his only genjutsu requires the use of Ma and Pa.

Jiraiya's genjutsu is more dynamic, but it also has a one time use policy. If Itachi either: stops the completion of the song, Kills Ma and/or Pa, escapes the range of the song, breaks out of the genjutsu, reflects the genjutsu back onto the users then the technique would become redundant.

In terms of Jiraiya's defences of the Toad stomach and the Lion's mane techniques, I am not sure how well either of them would take an Ameterasu, Yasaka Matagama or the Totsuka blade. The Toad stomach technique was shown to be instantly broken through with ameterasu and I don't think the Lion's mane technique would fair any better.