I really didn't want the debate to be dragged out any longer then it has but I want to throw out a fact and hopefully leave it there. These "Naruto vs Jiraiya" debates have been going on for so long and most of the evidence has been provided through simple means, "Naruto beat Pain while Jiraiya lost". I don't disagree that Naruto is much stronger than before but it still doesn't mean that he has surpassed his master (not saying he won't but even with the Rikudo mode I think he has a little left to go while in comparison with Jiraiya).
Now as for the fact I mentioned it is nothing more then
this. Here we clearly see Pain, despite his massive ego and god complex, praising Jiraiya and admitting that if Jiraiya had known his secret he would of lost. If this isn't substantial enough then we can move on to the battle aspects, and if we observe the battles closely there are many things to take into account, and firstly it would be battleground and scenario.
Naruto knew there were six pain's and fought all six from the beginning in a wide open area while in sage mode already (not to mention three gigantic toads along with ma and pa). Jiraiya on the other hand fought in a tight, enclosed space only believing there to be one Pain and holding his own with just one toad and unable to use most jutsu's at that time due to the summoning. Once he was in sage mode two more Pain's appeared further confusing Jiraiya yet he didn't let it phase him and as we all know after a while with a nice collaboration from ma and pa he defeated the three pain's while sustaining no/minor injuries. The part which really brought him to his defeat was him being unaware of Pain's resurrection ability which eventually led to him losing his arm and his life.
Just from these facts alone it's more than safe to say that if Naruto was in Jiraiya's situation then he would of lost while facing only the first Pain. Also if Jiraiya's information had never made it to konoha then, again, it would be safe to say Naruto would of lost due to lack of knowledge. There are much more aspects I would like to point out but I think this is more then enough to conclude that you can't judge Jiraiya's strength based on this battle. In real battle I believe Jiraiya would of beat Naruto in no time with his justu arsenal and experience, and I still believe him and Itachi were the two strongest characters ever shown
