Originally Posted by Kraco
We have no idea how tough Pain is, though, so Jiraiya beating him wouldn't necessarily be that awesome. We have only heard nobody has beaten Pain before. That doesn't need to mean anything but that the man has chosen his opponents wisely in the past. Although never having lost is a weakness in itself.
Thus it would be more worthwhile if Pain slays Jiraiya and then comes after Naruto, because that would definitely put Naruto against a real, proven mofo as I doubt Jiraiya will go down without a fight.