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I don't think Itachi can beat madara probably there will be a challenging battle between Itachi and Kabuto but against Madara no chance. Itachi maybe a skill and genius ninja but Madara have alot of unknown hidden skills and knowledge almost about any forbbiden jutsu.

Well interesting topic, well i think Kabuto is a genius and he wouldn't take any risks to revive the sage of the six path. Probably he'll learn from Itachi and prepared for the worst. I guess both of them were surprised, because Itachi did it for Naruto to protect him from Sasuke, so Kabuto...