So, this topic is basically a shoot question on how you think was Naruto greatest adversary or who you think was his greatest adversaries. Who do you think has pushed Naruto to his physical, emotional, and spiritual limit.
I believe Pain is a strong candidate because of his background and considering how much it took for Naurto just took bring him down. To lose Jiraya and his home village was his lowest of low points but getting the praise of the village as a hero was defiantly one of his higher points.
I like Orochimaru in there as well because of the mind games he played with Naruto and made him lose control, just by throwing around Sasuke's name. A fully healthy Orochimaru vs Naruto(before the god powers) would of been another great test for Naruto's character.
Lol. I would actually place Obito as well if they played up more of I ruined your whole life, you should want to kill me. I think if any one big missed oppurtunity in the war is the Naruto v. Obito personal dynamic, in terms of seeing Naurto push to a point of killer instinct.