To all the millions of Naruto fans around the world, I know this subject is simultaneously old hat and yet still this character's journey is the second most famous one in the show. I believe most polls consider Kakashi the number 1 beloved character, and Itachi as a close second. I’ll confess for the most part of the first series I wasn't on board with the Itachi fangirl train. It had me baffled how the character who kills the entire Uchiha clan and is labeled as an S rank criminal of the Leaf Village could be so loved by all anime fans. Still, I knew what the show was capable of when I saw Gaara’s redemption arc, so I was eager to see what was going on with Itachi that made him so widely respected. My sister and I are now 11 seasons into Shippuden and Itachis’ story arc finished a little while ago. I can finally say–I understand.

The brilliance of the set-up in the first series:

In Naruto the first series, we see very little of Itachi. Mostly we’re afflicted with the presence of his younger brother, Sasuke. I’m not Sasuke’s biggest fan, but for the sake of examining this story I’ll try to limit my jabs at him. In the first series we have every reason to sympathize with Sasuke and hate his elder brother. Sasuke’s entire clan was murdered by his elder brother and it seemingly came out of nowhere. Itachi kills everyone in the clan except his youngest brother whom he tells to “run and cling to his wretched life.” The show writers set things up for the viewer to see Itachi as a monster, and Sasuke as the Batman type character with the simple tragic past. Perception is everything in this. Because the devil of the story is in the details but the viewer only sees the details which the writer wants us to.

• We meet Sasuke first and we hear him say he has to kill the one who murdered his family and restore his clan. Automatically, the viewer believes the character he speaks of to be a purely a monster.

• In the first series we see very little of Itachi’s life except for what Sasuke remembers. 

• Sasuke is living for revenge and stuck at a moment of trauma from when he was a child so all he remembers is his final moments with Itachi, when his brother was killing the clan.

The key to the viewer being led emotionally is the way in which all these events are portrayed, and the eyes through which we are seeing them. Undoubtedly, the slaughter of the entire Uchiha clan was a horrific event that never should have happened. But because the viewer is so surprised by the trauma of it, and so busy sympathizing with Sasuke and his revenge, we don’t stop to ask all the logical questions which were gradually posed by my sister and I:

• What made Itachi kill his entire clan? He tells Sasuke it was “to test the limits of his abilities,” but that answer is completely weak if the viewer stops to think about it. Is Itachi suddenly some power hungry world conquering character? He never acts like one.

• Why did Itachi let Sasuke live? If he really was a purely evil psychopath who was mad enough to kill his whole clan, why spare his little brother? It’s so oddly specific but the viewer would be too busy hating him to consider that.

• If Itachi is purely evil, why does he never seem happy or vindictive in his actions? Most other villains in the show will laugh over you as they kill you or go on and on how they’re more powerful etc. Every time Itachi is seen the only thing in his expression is brokenness. In the first series he encounters Sasuke who throws insults and accusations at him, once again screaming that he lives to destroy him. Itachi doesn't defend himself or verbally attack Sasuke, he simply turns away like a person who doesn't feel anything at all. And once again, though he harms Sasuke when attacked he doesn’t kill him–even though it would be incredibly easy. The voice actor for Itachi—Crispin Freeman—noticed this in the first script reading of that scene. He wondered where Itachi’s head was and why he felt the need to hurt his brother so much, but never kill him. Freeman reasoned there had to be more to Itachi than was being shown. Audiences at the time insisted Itachi was just a purely psychotic villain but the actor persisted against that theory.

All of these were subtle hints there was much more going on with this character’s story. None of it is really uncovered, though, until Shippuden.

Sasuke finally gets his revenge–end of story. So we thought:

Itachi tells Sasuke in their final battle that his reality is entirely different because of what he’s seen. And that Sasuke’s only seen what Itachi has chosen to reveal to him. Sasuke (being dumb as a rock like always) does not stop to think or consider what his brother is telling but presses on to end his life. 

• They fight and eventually Itachi dies, but he has a million chances to kill his little brother–once again–he doesn't take them but keeps allowing Sasuke to recover and come at him again.

•  Any sane person who wasn't full of themselves would be wondering why one of the most powerful characters in the series (Itachi) who supposedly hates you, is letting you live over and over again until you get the upper hand.

•  Itachi dies of illness during the battle (which Sasuke was unaware he had), and his final action is to lightly press two fingers at the top of his little brother’s head. A show of affection he’d done to Sasuke all through their childhood but hasn't done for years.

Sasuke is clueless and needs another character–believed to be Madara Uchiha–to explain the history and lineage of his family name and his elder brother’s role in it. Sasuke foolishly believes that he actually beat his elder brother in a fight and Madara has to reveal to him that Itachi let him win, and every action of his elder brother’s his entire life has been for Sasuke’s benefit. In their final battle, Itachi had actually been dying of illness and basically killed himself. Insane, right? Not when you get the whole picture.

The side of the story we didn't see:

Sasuke naturally is hesitant to believe his older brother has loved him all this time. This is when Madara poses a question we all had watching this show: what was Itachi like as a brother before you saw him kill the clan? And then, of course, more extensive flashbacks are revealed. Sasuke had blocked out all good memories of his elder brother because of the tragedy of losing his family. But prior to the killing of the Uchiha clan, Sasuke recalls that Itachi was always a loving good brother. He protected him, played with him, taught him, and was a humble doting sibling. When pressed with this conundrum, Sasuke is forced to admit the two images of his brother don’t make sense together.

• His whole life Itachi was a humble kind brother who protected him from even the slightest danger.

• His last memory of Itachi is him killing their clan and treating him cruelly. 

The character believed to be Madara explains the life of his brother Itachi Uchiha.

The beginning of Itachi’s turmoil:

Itachi was always described as a very gifted, talented ninja in most of the flashbacks we saw in the first series. But aside from him carrying around his little brother on his back and playfully poking Sasuke in the head we don’t know much about his life. Itachi, similarly to now–never spoke about his own feelings, turmoil, desires or his pain. 

• It’s revealed in Shippuden that because of the attack of the demon (the nine tailed fox) fifteen years ago, Leaf village heads suspected the Uchiha clan. The suspicion wasn't entirely justified but it gained enough traction for the Hokage of the Leaf to put the Uchiha clan under close watch. 

• Itachi was a child during the first Shinobi war and witnessed far more violence and tragedy than anyone his age should have.

• When Itachi was old enough, he joined the Anbu black ops and was placed as a double agent spy in his own clan. He wasn't to tell his family or anyone he loved, even Sasuke. Itachi was most likely only a young teenager when the burden was put on him but as we see from Sasuke’s memories, he never spoke of it. 

• A rebellion grew amongst the Uchiha clan and they planned to revolt against the Hokage for distrusting and isolating them. This is all something Itachi knows, but his little brother Sasuke is shielded from. Itachi is distrusted and mistreated by some of his own clan because he won’t get behind their desires to revolt and kill the Hokage. As a child, Sasuke sees glimpses of the tension between Itachi and the rest of the clan but has no idea what it means. 

• Being in one of the Leaf Village’s most elite military factions and undercover among the Uchihas, Itachi is responsible for the actions of his clan and those above him want to ensure if they revolt he’ll be able to deal with them. Itachi continually begs for more time to pacify their growing rebellion, but the Uchiha’s won’t be reasoned with. The character is wedged between his clan (who’s forming a coup d’etat: violent rebellion and seizure of power from geovernment), and the Leaf village—who he’s sworn to protect.

• The Hokage still desired to reason with the Uchiha’s. Danzo Shimura, Itachi’s superior overseeing the potential rebellion/war between the Uchiha’s and the rest of the Leaf decides there are only two options: Itachi can support his clan in the coup against the Leaf. Danzo will have them all wiped out as punishment for rebellion. Or Itachi could accept the assignment of wiping out the Uchiha clan himself, and spare one life— his younger brother. 

Itachi chooses then, as he does for the remainder of the show–in his brother’s interest. Itachi wipes out his clan and in tears tells Sasuke to run and live. After accepting the mission, one of Itachi’s only requests (aside from letting Sasuke live), is that the world never knows the Uchiha’s were plotting war against the leaf. As far as anyone knows, Itachi killed them without reason or provocation. In doing so, he fulfills the role of a villain so that no shame will come to the Uchiha name and their honor is preserved. In this show (and in many Anime series’) I can’t stress enough how much honor seems to be the overwhelming moral compass. It was seemingly more important that the Uchiha’s die with honor, and an unblemished name than they live to go to war as traitors. Itachi’s own family don’t hate or question his actions before he kills them, they accept he’s performing his duty and simply ask he protect his younger brother. There’s all manner of problems I have with that moral logic, but it’s another argument in and of itself, so for now we’ll stick with the story.

A villain of complex motives:

Many anime fans will disagree with this assessment but I’m sorry, a character who slaughters his whole clan is a villain. Darth Vader is a beloved Star wars character but there’s no debate he’s an antagonist. Itachi is a tragic villain for certain, and even sympathetic—but his actions were unquestionably wrong. To be more specific, Itachi would be an anti-villain. Which is someone who has noble desires and intentions, but is willing to undertake heinous actions in order to achieve them. What makes the characters story so devastating is that both options Itachi was faced with were horrible. If he hadn’t killed his clan, Danzo would have ordered others to do it and none would be spared, or the Uchihas would have waged war against the leaf and even more would die. The complexities are what make this arc so good because it’s so difficult to find a clear “right” answer. My sister and I’s answer: DON’T kill the whole clan. Find out who’s involved in this rebellion against the leaf and protect or get out those who aren’t. Let the rest of them go to war and face the consequences of their actions. Maybe the character made an effort to do this? I don’t know because we aren’t done with Shippuden. And who knows, maybe Sasuke would still hate Itachi if he’d gotten him out of the village and let the clan go to war. Still, no circumstances condone Itachi’s actions. What makes Itachi unique as an anti-villain is that everything he did, every decision, did not benefit him but was made in the interest of something or someone precious to him. If Itachi’s fatal flaw could be pinned down, it would be his willingness to commit any kind of extreme action (no matter how horrendous it is to himself or others) in order to preserve what he cares for.

• Itachi accepts the mission to eliminate the Uchiha clan for the sake of the Leaf and the life of his little brother. This doesn't stop him from living tormented by guilt. Or accepting that he will one day pay for that crime with his life.

•  Itachi says cruel things to his brother before leaving the leaf and being branded as a criminal, though when Sasuke recalls the memory more clearly he recalls Itachi weeping as he left him. 

• Itachi wanted his brother to grow up strong enough to defeat him one day, so that Sasuke could be held as a hero in the future. Though, Itachi accepts he’ll live his life hated by the two things he cares for the most: the leaf village and his brother. 

•  Itachi’s sole purpose for living at that point is for Sasuke. Even in their final battle it’s revealed Itachi died giving Sasuke his mangekyou sharingan. Itachi was dying internally of illness by using and honing that ability so he could give it to Sasuke. And because Sasuke receives the power and defeats him, Itachi dies with a smile on his face, finally at peace. 

The reason the character’s story is so popular:

Already establishing that this guy is an Anti-villain who does terrible things, why aside from the brilliant story telling is he so liked and why is the relationship between him and Sasuke one of the most talked about? We all know that like many other forms of entertainment, the show is fiction. People who identify with Kakashi, Naruto or Itachi don’t do so because of the extreme tragedies and battles in their life. We don’t relate to Naruto because we have a nine tailed fox spirit in us. We relate and enjoy the stories because of the themes from them that ring true. The overwhelming theme of Itachi’s story—aside from the element of political corruption exposed in the Leaf and the Uchiha clan— is allegory for an elder sibling being forcibly immersed in horrendous circumstances to protect his younger brother and maintain family honor. The character crossed a sea of moral lines in doing so, but its the set up and unfolding of events that makes it into a good story. That seems to be the way Masashi Kishimoto (the creator of Naruto) was portraying the tale between the two brothers: a familial tragedy. Another clear theme in the story is that tragedies are often not black and white. Because Sasuke was so young and at a vulnerable age, his vision was narrow. All he saw growing up was that he was the victim and his brother was to blame. His final conversation with Itachi and later with Madara, shows him matters were far more complex. The leaf would have been the victims if the Uchiha’s had their way, Itachi was the victim in being planted as a spy in his own clan by a corrupt leader, the Uchiha’s were victims to Sasuke’s brother and Danzo. In other words, Sasuke viewed his life with himself as the primary victim of a tragedy when in reality, everyone was in tragic circumstances and had moral choices to make which affected the outcome—his own family included. What makes Itachi a well written character is he was forced to understand those shades of grey and moral corruption at a young age, but it was his desire Sasuke always be shielded from them. Itachi never wanted Sasuke to know about the Leaf’s involvement or about their clan’s desire for the coup, he let his little brother think he was the only villain in the story.

Did Kishimoto plan for Itachi to be as sympathetic a character like much of the fandom now sees him? I don’t believe there’s any question in Itachi’s mind that he became a condemnable villain for the sake of protecting his younger brother. But then Itachi does tell Sasuke, “I’ll always be there for you, even if it's just as an obstacle for you to overcome. Even if you hate me…that’s what big brother’s are for.”