
I guess Itachi...
He defeated Orochimaru who always was better than Jiraiya...
And Jiraiya is weak against genjutsus... but still he is a Sannin.
So?
Itachi did say if ksame and him fought jiraiya in pretimeskip it wouldn't be without consequences. My guess is in the timeskip period itachi improved his sharingan and became much stronger than he were in pre timeskip. He also never used susanoo in pretimeskip, maybe he learned that during timeskip. I would say itachi mid diff
Jiraiya Low diff
Even though im the biggest Itachi fan on NB I can't deny the level of rape that J man will give him:|
Itachi wins Low-Mid diff
Username: Jiraiya lives :|