Board Thread:Wiki Discussions and Support/@comment-24347194-20150211215621/@comment-25771935-20150214191117

Itachi has definitely proved to be one of the strongest characters of the series w/o being OP. He is shrewd, analytical and has excellent timing. All of his achievements as a shinobi as well as the battles he has fought more than prove that he could go toe to toe with the best.

I don't know if he could defeat Jiraiya but it would definitely be one of the best match ups that they could have and it would have shown both of them pushed to use their best. Makes me kind of sad that it didn't happen. I'd probably go with Itachi, but wouldn't be surprised if it went the other way.