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Originally Posted by Lexander
Lets look at this scenario:
There is a room with something you need but there is a guy that will fight you if you try to go in. You know if you fight him you will beat him and get acces to the room ... but ... during the fight you will be badly injured. You also know that at some point the guy will leave to eat dinner so you can go in without all the commotion. So would you be patient and wait ... or would you just charge the guy beat him up but loose an arm or something.
Let's say you choose to be patient and wait for the guy to leave ... does that automatically mean that you are scared of the guy?
If there was no way to avoid a 1v1 match between Itachi and Jiraiya(like 3rd vs Oro) do you honestly think Itachi would try to run or be afraid of Jiraiya?
I don't get this ... does Itachi really come off as a coward to you people?
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At least finish the scenario:
When the guy leaves for dinner you enter and grab the thing you are after. Then as you turn to leave, the guy is back and blocking your exit. He says he is going to kill you. He then lunges at you. What do you do? You drop the thing you already had in your grasp, and blow a hole in the wall so you can run away.
As for Itachi's killer mange sharingan, as Gai already said all you have to do is look away from his eyes and it won't be able to work on you. I'm sure there are several jutsu out there that can counter it too, whoever decides not to look away... staying behind a summon and out of the sharingan's range could be one way.
For most powerful ninja I'd go for Orochimaru. He wanted a kage body, so he killed one to get it. He's the only ninja we know to have killed not one, but two kages. He can summon kages/giant snakes to do his work for him. It took the godofdeath-sealing technique to stop him, last time that technique had to be used it was against kyuubi. He created the curse seal and has eyes which can freeze a ninja on the spot. He's near impossible to kill too. If you gave him something worth fighting for(if sasuke's sharingan/body was at risk) and Oro went all out with all his jutsu... that's gonna leave a mark.
But the facts say Sarutobi knew all the jutsu in Konoha and was the most powerful in his prime so I'll go with Sarutobi 1vs1, but Oro for larger scale destruction(like destroying a city).