Board Thread:Versus Debates/@comment-9782468-20150308163348/@comment-17623-20150325134324

NeedleJizo wrote: Kurama wasn't able to gather energy for Naruto until the Fourth Shinobi World War. At the levels they were when the fought Pain, I think Jiraiya would win. Pain said the only reason he won was because Jiraiya didn't know about the Six Paths. Naruto, with information on that and time to prepare, still lost in a one-on-one engagement.

You can't pick a time when they fought the same villain because they did not fight that guy at the same time. Gotta pick a time when they both were at their prime, so basically when Jiriaya died for him and the end of the war for Naruto.

I'm not knocking Jiraiya's experience with using Sage Mode, but that experience still wouldn't help much unless he had a plot token that would specifically answer the amount of stupid a Tailed Beast Sage Mode.

(And as a side, what Pain was referring to was knowing that 1) Pain had multiple bodies and 2) the real Pain was somewhere else. Had Jiraiya knew fighting the Six Paths were pointless he would have went after Nagato and that is why he would have won. Naruto knew about the real body, but still went on to fight and destroy 5 out of the 6 paths before getting overwhelmed by the last one.)