Itachi Uchiha is the older brother of Sasuke Uchiha and one of the greatest Sharingan users in Naruto. He was considered a prodigy from a young age, and he developed Shinobi skills way beyond his years. Throughout the series, Itachi has performed both impressive and nefarious deeds. As a result, he is one of the most controversial yet beloved characters in all of anime.
Note: This article is subjective and solely reflects the author's opinion. It also contains spoilers for the Naruto series.
5 times Itachi made the right decision in Naruto
1) He accepted Shisui's Sharingan
After Danzo stole Shisui's left eye, Shisui knew that his demise was near and used all of his strength to escape the Anbu hunting him. He was able to narrowly escape and then met Itachi on a cliffside. Before committing suicide, Shisui gave his right eye to Itachi, so the immense power of Kotoamatsukami would not be wasted. Itachi was able to utilize this genjutsu later in the series, allowing for his bestfriend's death to not be in vain.
2) He revealed the truth about why he left Konoha to Sasuke
After Itachi died, he was reanimated by Kabuto. This allowed him to come back to life, albeit temporarily. He was able to fight alongside Sasuke to take down Kabuto after achieving Sage Mode. After the fight, he revealed to Sasuke the reason why he massacred the Uchiha Clan. This changed Sasuke's lifelong view of Itachi and made him love his brother again.
3) He programmed Sasuke's Sharingan to use Amaterasu one time
At the end of their final battle, Itachi performed his signature forehead tap on Sasuke. On the surface, it seemed to just be a comforting gesture, but Itachi took the opportunity to program Sasuke's Sharingan with a one-time Amaterasu use. The instant he saw Obito's Sharingan, the Amaterasu would activate and attack him.
4) He stopped Nagato from attacking Naruto and Killer Bee
Initially, when Itachi was reanimated by Kabuto, he was teamed up with Nagato Uzumaki. The pair was sent to fight Naruto and Killer Bee, and stop them from joining the war. However, neither Itachi nor Nagato wanted to fight them so they tried their best to make sure that Naruto and Killer Bee won. When Nagato was about to hit the pair of jinchurikis, Itachi used his Susanoo to protect them and dodge the attack, thus saving them.
5) He removed the Cursed Seal of Heaven from Sasuke's body
In a fight with Orochimaru, Itachi was able to use the Sword of Totsuka to remove the Cursed Seal of Heaven from Sasuke's body. Even though he had manipulated Sasuke for most of his life, he hated the fact that his younger brother had lost his free will to Orochimaru of all people. Itachi was also able to imprison Orochimaru with the Sword of Totsuka, incapacitating him temporarily.
5 ways Itachi messed up in Naruto
1) He massacred the entire Uchiha Clan
Perhaps one of the most gruesome crimes committed in all of Naruto, Itachi killed the entire Uchiha Clan besides Sasuke to prevent a cout d'etat. However, there were various ways that he could have prevented the Uchiha uprising without killing his fellow clansmen. Unfortunately, Danzo Shimura would definitely have made any alternatives to the massacre incredibly difficult to implement.
2) He assisted in hunting down the nine jinchuriki
As a member of the Akatsuki, one of Itachi's many tasks was hunting down the nine jinchuriki and extracting the Tailed Beast sealed within each of them. Extracting a Tailed Beast from a jinchuriki always results in the death of the jinchuriki. Itachi helped kill innocent people while in the Akatsuki just so he could go along with plans that he did not even believe in.
3) He psychologically tortured Sasuke in a genjutsu twice
After Itachi massacred the Uchiha Clan, he encountered Sasuke. Itachi proceeded to place his younger brother in a genjutsu using Tsukuyomi, that forced him to relieve the events of the massacre for hours upon hours. The second time Itachi placed Sasuke under a genjutsu was after Kisame and he failed to kidnap Naruto. Sasuke could be seen with a dazed expression as he is forced to relive the events of the massacre once again.
4) He made Kakashi fall into a coma
Itachi did something similar to Kakashi, but was even more brutal in his approach. He placed Kakashi under a genjutsu using Tsukuyomi, and stabbed him repeatedly with a katana for hours. Once the genjutsu wore off and Kakashi's mind returned to the real world, he fell into a coma and could not return to his Shinobi duties for about a week.
5) He encouraged Sasuke to kill Naruto
Throughout the original Naruto anime, Itachi was obsessed with getting Sasuke to hate him so that Sasuke could become stronger and defeat Itachi someday. One way Itachi did this was to encourage him to kill his closest friend, Naruto Uzumaki. Accomplishing this task would most likely have awakened Sasuke's Mangekyo Sharingan, thus granting him the ability to fight on equal footing with Itachi.