Itachi left Konoha at midday, his weasel ANBU mask covering his face. Anyone that had opened a Bingo book would know that he was the only Konoha ANBU operative with such a mask, and even if the reward on his head would make most men weep, not a lot of people were foolish enough to engage him in battle.
The elder Uchiha had been displeased with his foolish little brother's actions. After Hatake had left the hospital, assigning Naruto to guard Sasuke while the younger Uchiha recovered his sight, the three had discussed the last known location of Sakura Haruno. They had been in one of the valleys that lead straight to Three Wolves Mountains, and the cave the pink haired woman had found had been a few kilometers East of where they had been ambushed. To Itachi it was clear that her quick thinking had undoubtedly saved his Otouto's life.
What annoyed Itachi was the fact that Sasuke, in fear of losing his two comrades, had abused his Sharingan, and to add insult to injury, Fugaku had clearly reprimanded his youngest son for not having left his comrades to die in order to obtain the Mangekyou Sharingan. Good thing the Hokage had appeared at that moment, or the Uchiha patriarch would probably have been tackled by a very irate looking Naruto.
Whatever the means to obtain power; Fugaku was a heartless tyrant. Itachi had obtained his own Kaleidoscope Copy Wheel after Shisui's, his best friend and cousin, death. At the time, he had been no older than 13 summers. As the Uchiha heir, Itachi had been told about the coup the Uchiha clan was preparing against Konoha. After turning to the Third for help, the other Clan heads of the village had shown their support to the young Itachi in order to find common ground with the Uchiha Clan, making them step down from their rebellion. Unfortunately, one of the Council members, Danzo, had been the one supporting this rebellion in the shadows. Not pleased with the peace treaties signed between the clans, Danzo decided to kill off the Uchiha heir, and attacked Itachi and Shisui on one of the clan's training grounds. That day, Danzo died, but so did Shisui.
Itachi still remembered the panic and fear crawling over his body as he rushed his wounded cousin to the hospital. Shisui's wounds had been too severe, and the young Uchiha had died during the night. The searing pain Itachi had felt that night while gaining the Mangekyou Sharingan still lingered on the edge of his mind, as if it had never left. It was not the kind of pain he wanted his Otouto to experience, but after Tsunade's examination, one thing was sure; with the desperate situation Sasuke had been in, his Mangekyou had started to manifest, but that had been too much strain on his eyes, almost leaving him blind.
Itachi shook those gloomy thoughts from his mind, concentrating on the mission at hand. The night had fallen over the plains he was currently running by. If he kept this fast pace, he would be able to reach the valley in a little more than a day, but he would have to take a break at some point. Even if this was supposed to be a recon mission, the Hokage had made it clear that he was to bring Sakura Haruno back, and Itachi didn't find the idea of infiltrating a base full of undead shinobi, with only half of his chakra reserves, a very appealing one.
His mind wandered to the Kunoichi that his brother saw as an older sister, and smirked inwardly. He could still remember his little brother's comments about the pink haired girl that had been on his team. She had been a shy one, and had held a crush for his little brother that had kept her grounded to Sasuke, stopping her from finding her own strength. Of course, she was the brains of their little trio, a quick learner, and had remarkable chakra control, but stayed in the shadows of the two boys who's only motivation were to best the other.
When Naruto had left the village, his little brother had become very moody and easily irritable. Sakura had also been sad that her energetic teammate had left them in order to train, but she had stayed optimistic and had tried to cheer his Otouto up.
Itachi still remembered the day that Sakura had appeared on their training grounds, bringing him and his little brother a bento each. At first Sasuke had ignored her, his Sharingan concentrating on the genjutsu Itachi had been teaching him. When the pinkette had walked into the illusion and dispelled it almost instantly, Itachi had been surprised. Then again, with her perfect chakra control, it should have been obvious that Sakura was a genjutsu type.
Sasuke, on the other hand, had seen his weak teammate dispel the genjutsu effortlessly with no Sharingan or bloodline limit. The younger Uchiha had been trying to learn how to detect and dispel the attack since that morning, and she had just came up and cleared it in a matter of seconds. It was then that the youngest Uchiha heir had snapped at her, saying how she was just a weak and bothersome annoyance, how she had nothing to do on their team and should just disappear.
Itachi could still remember the shocked expression on her face, while her body started shaking from Sasuke's degrading words. Her green jade eyes had gone wide before starting to shimmer, tears ready to fall. She disappeared before the tears could roll down her cheeks, and Sasuke just turned back towards him to continue with his training.
As the days turned into weeks, Sakura didn't come back to the compound, but his little brother showed no signs of caring. Itachi rarely got irritated with his younger brother, but this time he couldn't help but feel annoyed at how the young Sakura Haruno had been treated. So he sought her out.
Of course, she probably never knew that he had looked for her, but for over a week he had observed her from the shadows. Apparently she had asked the Godaime Hokage to take her in as an apprentice, and seeing how hard she worked, more determined than Itachi had ever seen her, the elder Uchiha could only smile at her resolve. After that, Itachi had brought his foolish Otouto to one of the training grounds Tsunade and Sakura were currently at. As Sasuke saw Sakura being flung across the field by Tsunade's fearsome strength, the younger Uchiha could only watch as his once feeble teammate got up from the splintered debris of a tree and dashed back towards the Hokage, dodging most of the hits before being thrown back into the nearest tree as if she was a ragdoll.
Itachi had then pointed out to Sasuke how unfair it had been for him to take out his frustration on Sakura, just because his teammate had left them to train. After all, Naruto was also her friend.
A few days later, Itachi learned that, after seeing Sakura work so hard in order to prove his little brother wrong, Sasuke had apologized to her before going to Kakashi Hatake and asking him for a special training.
Years passed, but even if Itachi was busy with ANBU missions, he still tried keeping tabs on his little brother. Sasuke and Sakura had become close now that Naruto was not here, and Team 7 had gained a new member, Sai. Sasuke and Sai didn't get along at all, but it was Sakura that held the team together and kept the two shinobis in check.
When Naruto came back four years later, him and Sasuke had sparred near the Uchiha compound to see who was strongest. When their fight had started to get out of control and the two boys had accidently destroyed a portion of Mikoto's zen garden, it was Sakura that had literally pummeled the two idiots into the ground, before apologizing to his mother for the rash actions of her two teammates.
A week later, when Team 7 had been invited over by Mikoto for dinner, Sasuke had surprised them all by asking Sakura for a spar. Itachi had been curious when his little brother had practically demanded that Sakura sparred with him that very night, something he had never done. Of course, Naruto had opened his big mouth and asked Sakura for a rematch after the hit he had taken in Mikoto's garden. Itachi had followed Team 7 to one of the training grounds that the Copy-nin favored, and had thoroughly enjoyed seeing the frightened look on his Otouto's face when Sakura had, with a single kick, destroyed the training field and sent Naruto flying, literally, over Konoha. But not as much as he had enjoyed seeing the small pink haired medic send Sasuke through several trees with a single hit, probably making his little brother regret each and every single insult he had ever thrown her way when they were kids.
After that, she had healed them both, but it was clear that the two boys were now very weary of their female teammate's temper, and would never doubt her strength again. Then again, Itachi had seen her potential since day one, and could only admire her strength.