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Add Danzo, Root (about half of Konoha's strong ninja work under the shadows), Tsunade, Shukaku, Chouza, Guy, Kakashi, and everybody else to the mix...at once. Or planned out- then Itachi will be overwhelmed.
I think Danzō and Kakashi are the only individuals who pose a real threat to Itachi out of this list. And since Itachi can control multiple people from a distance, he can complicate the attack on the village even more than Pain did. Instead of six foreign invaders, there would be many more *Leaf ninja* turning on one another. The chaos would be insane. And if Kabuto and Itachi thought Itachi could control even Kabuto, then practically nobody is off limits if he lands his strongest illusions. That means ninja with highly destructive jutsu like Gai could potentially wreck the village at Itachi whim if he tricked them into genjutsu (highly possible.)
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Here, Shikaku (who actually knows Itachi) thinks he could affect an entire war with an unknown genjutsu.
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Itachi also tell Nagato that he *could* change the tides of war with his genjutsu alone.
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And here Itachi/Kabuto imply just how strong a ninja he can control (albeit with his strongest jutsu.)