The 1 v 1 s are debatable . But I can ' t see anything but a convincing win for team Akatsuki if it ' s 2 v 1 . Feats prove that one 2 v 1 with Jiraiya in Sage Mode against Itachi and Kisame , I ' d give the win to Jiraiya . This has been debunked in detail by Noodles in a post on character rant I believe . Genuinely don ' t know why kishi wrote that line . Jiraiya already had a multitude of advantages against pain and still lostJiraiya ' s only advantage was Pain not starting with all 6 out at the start . Had Pain done so and Jiraiya known the link at the start , he could ' ve just put them all in a Genjutsu or utilize clones with Sage Mode . I didn ' t say Jiraiya would win , I repeated Pain ' s own line where he says they would not have won . There ' s a difference .