So...How did Itachi plan on getting Kakashi, Kurenai and Asuma out of this?

USSJ Future Trunks

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We know now that Itachi never wished to hurt anyone in Konoha
he beat up 3 uchiha police. thats malicious intent on hurting people and then doing so

And if he didn't care about them, he would have just killed Kakashi when he had the chance.
or he doesnt want to get his hands dirty and waste chakra

He had to keep up the act of being evil after all.
he wasnt acting when savagely mindraping kakashi and sasuke. even kisame noted itachi was acting merciless

Also itachi needed the Akatsuki to believe him and leaf to portray him as the ultimate bad guy so sasuke could look like a hero
he isnt portraying himself as anything. he IS a bad guy. so is sasuke. they ahve no reason to worship a traitor just cos he killed another traitor.

Itachi was meant to be a bad guy/psycho maniac genocidal killer in Part I.
and still is

Itachi doesn't like to fight
for absolutely no reason he made deidara fight him so deidara could be forced into akatsuki servitude. had he not said anythign diedara would leave and be fair game to be killed as a terrorist who might hurt konoha one day. for absolutley no reason he challenged sasuke to a torture session when he could just finger genjutsu him and leave him.

That was necessary to show kisame that he is still in Akatsuki, if he was to walk away after hearing that Kakashi knows about them, Kisame would be suspicious about him, so i think he was ready to sacrifice them at the moment.
kisame is itachis friend and wouldnt rat him out to tobi or anything. even if he flat out told kisame the truth kisame would just laugh and continue being his partner. even if itachi said "i intend to kill you". kisame already wanted to fight him upon meeting him
 

EliteKakashi

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itachi sensed gai coming so he told kisame to that because itachi knew gai was going to save them also he did to keep kisame thinking he was a spy/trader
Not only was Itachi surprised by Gai coming, Gai's speed is incredible, so him surprising Itachi is more than believable. Him sensing Gai coming would be a pretty big ass cop-out.
 

USSJ Future Trunks

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itachi sensed gai coming so he told kisame to that because itachi knew gai was going to save them
thats too much of a gamble. and why waste his breath saying anything if he knew gai was coming? why specifically order kisame to murder them? kisame could have just shot a giant shark bullet for all he knows

he did to keep kisame thinking he was a spy/trader
he hadnt betrayed anything regarding akatsuki even after 7 years of being a member. he wouldnt start then. hes the worlds worst spy and kisame wouldnt even care if he was or not.
 

nj tandi

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Either he was sure help would come,and took a gamble(he didn't care about them that much,sacrifices have to made) or he needed to look like a true member of Akatsuki and after having killed his clan,three joining shouldn't be too much.
 

Lrrrrr

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Asuma and Kurenai still had their eyes closed, even AFTER Gai arrived. They were done for at that moment.



That's possible, I guess, considering Itachi knew Naruto was in Jiraiya's care at that point.
I'm sure they'd open their eyes if he was coming at them, and was close enough to be able to strike. They just wouldn't look at Itachi's eyes. Since Kisame was the only one of the two attacking them.
 

Frikid

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at that time, we didn't knew he wasn't evil...

kishi wanted to show him as a villain first, so it would not be a big deal even if he kills someone
 

raju22

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kisame is itachis friend and wouldnt rat him out to tobi or anything. even if he flat out told kisame the truth kisame would just laugh and continue being his partner. even if itachi said "i intend to kill you". kisame already wanted to fight him upon meeting him

Kisame is nobody's friend, he is loyal to the organization because of Tobi, he killed his own comrades many times to serve his country, the moment he finds out that Itachi is not with Akatsuki, he will consider him as traitor and enemy, he gave his own life to serve and protect Akatsuki.
 

Kinimaster

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His plan was really good, he just went to Konoha to remember Danzo and the village he is still around after the Third died to prevent any action against Sasuke, and at the same time making Kisame think they were under Akatsuki orders to capture the Kyubi, nonetheless Kakashi was unwise or careless enough to mention their organization's name and plans in front of Kisame, therefore making Itachi to make that command, or Kisame would get suspicious and tell Akatsuki that Itachi's allegiance isnt that reliable to the organization. I really think Itachi thought(with sadness or resignation) after Kakashi's words that he messed up and should become a sacrifice to protect his cover otherwise all his plan could of went down the drain. I dont know if he actually with his perceptive skills knew Gai was coming, but he surely took that opportunity to tell a excuse to leave, he never really wanted to "kill" anyone despite having the upper hand with autority. Itachi is a complex mysterious guy but remember he doesnt have that battle thirst nor murder intentions(ironic is that he murdered his whole clan, but everyone knows he got in the corner). Gai appearing was the best thing that could happen to Itachi, i mean Gai really thought that without looking to his eyes he is ok lol, not knowing Itachi has Amaterasu and could cast genjutsu with his finger.
 

irishboy9780

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Like others have said it was probally just a small hole in the plot that was overrlooked. Itachi was likely one of the first villians kishi had in mind but after creating the akatsuki, he likely thought it would be a better alternative to make him good and open new paths in the story to prolong it. I'm assuming that he just didn't notice this when he went back and looked.

Even if thats not the case Itachi already killed his entire clan, he wasnt going to let 3 leaf ninja ruin his chance at staying in the akatsuki and keeping tobi in check. So ya he was likely going to sacrifice those 3 if need be in order to keep a far greater evil from attacking the village.
 

Gooner4life

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Here's your explanation, Itachi is just like Danzo in that he will do anything to protect Sasuke and the leaf. Sasuke tsukuyomi'd his brother and left him hospitalized, did he know that Tsunade would come back to save him? He most likely didn't because Jiraiya wasn't sure, that example and this example prove this.
 
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