You bring up alot of interesting points for your list I might not agree with it but atleast you are a little more civil with your ideas.
Odd words for a civil conversation! Looks like you have had some bad encounter.
So here is my list it is a little different than yours.
1. Madara- obviously even the 4th Hokage knew he was too powerful. And anyone that can completely control the 9-tailed demon fox i mean come on naruto can't even do that yet.(Sasuke can somewhat but he couldn't completely control it like Madara yet)
2. Minato- Yeah I know he's dead but he fought and sealed the 9-tails into his own son and was a genius.
2. Naruto- yeah i put him as tied with his dad for now. Even Minato couldn't use Sage mode the way Naruto could. And eventually Naruto will learn Flying Thunder God jutsu. He completed his dad's jutsu as well the Rasen-Shuriken which we have all seen totally owned pain.
3. Nagato- Rinnegan enough said. Well actually he could have been the strongest i think if he had not went through all the crap he did because of Hanzo and Danzou. And if he had more time to train.
4. Jiraiya- he fought pain alone and took out some of his bodies even though they came back. Pain pretty much destroyed the whole village before Naruto got there. He destroyed more of pain's bodies than anyone by himself besides Naruto.
5. Itachi- yeah may have been able to beat J-man but we are not certain i mean he did run away. Look at what he did to Kakashi. He could have fought him without killing him but he didn't becasue he wasn't sure about fighting J-man. Sasuke could not have beaten him if he were not already sick and dying. And he planned for Sasuke to take his eyes anyway to fight Madara. Even though Madara is using Sasuke right now. this overall list
Comparing any shinobi with others doesn't do much good. Temari beat Shikamaru, Shikamaru won against Hidan. Doesn't mean that Temari had any chance against Hidan.
Nagato: Strongest Shinobi. It's too bad that he never got a chance to use his power to full potential. Rinnegan was amazing and Nagato was a talented. I doubt Madara would even ever challange him in real battle.
Madara: Most cunning and coniving. Madara's real power is manipulating others. He attacks from behind and rather fight in gurrilla style.
Orochimaru: Evil intellectual. His thirst for power went beyond Madara's.
Itachi: Losing him to politics was the greatest loss for Konoha. His fighting skills combined with his sheer will power and intellect would have made him a great successor to hokage position some day.
Minato: A great talent and genius shinobi. Acheived quite a lot in a very short time though he didn't have any special blood line ability as far as we know. He caged the Kyuubi and succeeded in chasing off Madara for a second time.
Some may argue that he didn't beat Madara as he said that Madara countered his every move to fight with Kyuubi. But my POV is that he did seal Madara's weapon, thus Madara+ Kyuubi < Minato.
If Madara had any other thing up his arm besides Kyuubi, he would have profitted by Minato's death. Instead he had to retreat again to gather some other pawns. War was not over but, that particular battle was won by Minato. And Minato also managed to think a future strategy to deal with Madara, at the same time fighting with kyuubi.
Jiraiya: Greatest sensei in his time- he inspired his pupils to great things in his own way- Minato, Naruto, Nagato... extraordinary students.
Jiraiya probably would have beaten Pain if he realised sooner what was he up to. Jiraiya was taken by surprise. Nagato probably would not have been able to use shinera Tensi ( his personal favourite defence and offence in Konoha) in Amegakure- his weakness= Jiraiya's power. i don't mean to say Jairaiya was more powerful than Nagato or not- In Naruto verse it's just a matter of having a lucky day.
Also I see many argue that Itachi lied when he said he won't be able to defeat Jiraiya. Itachi had said that at the best it would be a draw- both parites Itachi+Kisame and Jiraiya all three dying. It's a mere speculation that Itachi lied- Itachi never lied about skill level of any shinobi any time. He gave analasis quite neutrally and as a matter of fact. He would have just told Kisame that they didn't need a full scale fight anyway as he said him after their encounter with Kakashi and others. He woould have told Jiraiya that he was leaving.
Let's face it Jiraiya had not even started- he had just summonned toad belly and Itachi had to use Ametseasu to escape it. It use to damage his eye- why would he use if he could escape at less than that? Ametsrasu was sealed by Jiraiya.
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Maybe Itachi was wrong and would have won. but, one can never be sure- only speculate at best.
Same goes for every other comparison too.
Naruto is no doubt going to turn out to be the strongest in his own way- he has something more than fighting skills. A will power and a positive infulence over others... Sasuke is better skilled at fighting - because he is able to be more focussed and think faster than Naruto. Still the path he chose limited his accomplishments. Naruto uses more than his fighting skills in a battle. As I read somewhere at theis forum itself- Nagato was defeated by a book.
Sasuke would end up the best general out there, but the king would be Naruto. Sasuke doesn't show much people's skills , does he?
