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Don't take me for a fool, I know the situation, but I've been watching the fight between Itachi and Sasuke, where he said something like this from the old times: "Come after me, when you will obtain the same eyes as mine, being the third to hold a MS."

He already had the Mangekyo Sharingan, so we can safely assume that he knew the story about his "elders", hence knowing not just about Madara, but Izuna and of course Shisui too. Obviously, he didn't know about Obito/Kakashi, but is this a plot hole, or did Itachi really not know that along with Madara and himself, two others already possessed that kind of Sharingan, making his statement false, since Sasuke would've been at least the fifth person?

(I've written Shisui for purpose in the title, but we don't just have to talk about him.)

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It is not a plot hole. And he isn't necessarily wrong. He just meant the third person alive. Of course he knew about Shisui, he had his eye. Of course he knew about Izuna and Madara too since he introduced their story to Sasuke. And he probably knew about other unnamed Uchihas too, if there were any, because as he said the Uchihas were killing their best friends for decades to achieve it. So I can't find any other logical explanation.

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  • I agree with this idea, Though based on how the story progressed, It probably was initially a plot hole, so it was made that there was only 3 alive with the mangekyo. As we learn later, sasuke was the 6th to unlock Mangekyo, though 7th if you count Kakashi., but at the time of saying that, excluding Kakashi (which is fair as he never used it until Deidara in Shippuden and its also not actually his eye), there were only 2 alive at the time, Itachi himself, and the guy he thinks is Madara.
    – Ryan
    Commented Mar 21, 2016 at 16:10
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I believe I understood your question a bit. I will try to elaborate on that.

If you check out the episode of the Nine Tails attacking the Leaf Village, you must have noticed different age groups of various characters. Kakashi, Gai, and Asuma were depicted as teenagers. There is even a clip where Itachi was holding the infant Sasuke on his lap, assuring him that he would always protect him. Itachi was around 10-11 years old. By this, I can conclude that Kakashi was an elder to Itachi.

In your question you stated that:-"Obviously, he[Itachi] didn't know about Obito/Kakashi",I would like to highlight something which could contradict with your statement. Itachi did know about Kakashi as he was a prodigy in his age. Getting Sharingan after Obito's death made him a source of attraction. By then, Obito was out of the picture completely [since everyone assumed him to be dead]. At the beginning of the Shippuuden episodes, Itachi called Kakashi, "Copy Ninja", while he fought against him. Now, coming to your question, Itachi couldn't figure out the man behind Tobi's mask. Because of his boastful nature and strong power, Obito made Itachi believe that he was Madara. Obito's calling himself Madara depicts his deceptional and boastful behavior.

With this, I can say that there is no plot hole anywhere.

EDIT

As debal said, both Kakashi and Itachi were in ANBU group.By this we can conclude that both knew each other.

EDIT II

To make it clearer we can list all current know Mangenkyo users and how they have or might have obtained it.

Itachi - It is thought he killed Shisui but did not. Very likely he witnessed Shisui's death. I can think of one scenario but it's just a speculation.

When Itachi saw Shisui for the last time, he had MS activated. I think Shisui used Kotoamatsukami on Itachi and made Itachi to kill Shisui. Itachi can't remember it, 'cause Shisui used Kotoamatsukami, so the victim isn't aware that they're being controlled. That way Itachi got his MS and Shisui wanted him to protect Konoha.

Shisui - Unknown. But seems unlikely he murdered anyone as he showed a great deal of self sacrifice do kill himself rather than have his eyes fall into the wrong hands.

Sasuke - Did kill Itachi and he witnessed his death.

Kakashi - Got his MS after killing Rin;although he came to know about his Mangekyou at later stages

Obito - Saw Kakashi killing Rin;which triggered his MS

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    both Kakashi and Itachi were part of the anbu and were bound to know about each other
    – debal
    Commented Apr 28, 2014 at 10:18
  • to be honest: May 31 to Jul 12:Itachi loses Uchiha Shisui and gains Mangekyō Sharingan;Jun 09 to Jul 21: Sasuke masters Great Fireball Technique';Next Day: Uchiha Massacre; so by this, I'd bet that Kakashi didn't know about Itachi's MS(since the shortness of the period), and if I recall well, when they fought each other, around the 80th episode of Naruto, Kakashi was quite speechless when he saw Itachi's sharingan.
    – Rinneg4n
    Commented Apr 28, 2014 at 12:43
  • oh and btw...I'm quite sure that even Kakashi didn't know about himself,that he holds a MS:))
    – Rinneg4n
    Commented Apr 28, 2014 at 12:47
  • @Rinneg4n i would like to ask you something......are u trying to tell me that Itachi killed shisui? If yes then i beleive u are wrong.... my updated answer would give you some idea
    – Jiraiya
    Commented Apr 29, 2014 at 5:48
  • is it ok if we can base this answer on the anime fillers? The fillers do mention about the life of Kakashi, Itachi and Shisui. And we can see they are all connected.
    – debal
    Commented Apr 29, 2014 at 6:01
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I myself think that the third person could have been Madara. Now Itachi had met Madara once or twice and Itachi was very wise. He paid attention to the things the others rarely did, said by the third Hokage when he was revived by Orochimaru. Also, he knew that Madara was the first one to awaken the Mangekyo Sharingan Izuna. He told that to Sasuke in Naruto Shippuden episode 136 or 137.

Note: now we know that masked man was Obito and the real Madara was dead but Itachi didn't at that time. Wise as Itachi was as a planner, Madara was better than him and Madara told Obito that he has to live with the alias 'Madara Uchiha'. As for the people who are saying he knew about Kakashi having the Mangekyo, Kakashi rarely showed his Sharingan. Itachi and Kakashi were also not that close to each other. If I remember correctly, he said you will be the third one alive to have it. Shisui and Izuna were dead and he didn't know about Kakashi's so it would have been Madara.

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This is false. What Itachi says because in The Itachi Story Arc we learn that Fugaku Uchiha, his father, possesses the mangekyou sharing and shows Itachi. Also Itachi tells Sasuke the story of the Izanami when he is reanimated and mentions the existence of many other Uchihas who possessed the mangekyou. Therefore, it must be a plot hole.

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