It was the month before the final Chunin exams, and his new teacher was drunk off his ass.

Somehow, someway, the conversation had gone to the regret Jiraiya had not killing Orochimaru when his betrayal was first known. How he could have saved a lot of lives by killing the damn snake when he had the chance, instead of giving into compassion and hope that his friend might change if given the chance.

"(Hic) I shoulda killed him then. He had always looked down on me for not bein' from a clan and being the deadlast. Always with the fan girls who wanted him, and he didn't even see them. (Hic)."

Naruto had been dragging Jiraiya back to his house with liberal use of clones. It was better than leaving the drunken toad in the forest where he could get eaten.

However something about what Jiraiya said about killing Orochimaru when he first showed his true colors struck a chord with him.

He got the feeling that Jiraiya was a lot like him in many ways. Always trying to be noticed, being ignored by his crush, having to deal with a prick of a teammate who wouldn't give him the time of day that came from a prominent clan.

"If you could go back and do it over, what would you do?" asked Naruto, shifting the drunken sage a bit.

"I don't know. (Hic) But if I had known then what he would become, I would have killed him that day," said Jiraiya in a slur.

"So Orochimaru is your Sasuke to me?" he said.

"(Hic!) Close enough...the similarities are (Hic) too disturbing to think about."

Naruto dumped the sage onto his moth-eaten couch, where the man finally passed out.

Something about the odd conversation bothered Naruto greatly.

Sasuke was a bit too much like the bastard snake, if what Jiraiya said was true. Jiraiya's biggest regret was not killing his former best friend when he had the chance, before Orochimaru became an even bigger threat to everything he loved. What would he do if Sasuke did the same?

Two months later, after the Invasion...

Naruto's mind went back to that night Jiraiya had gotten drunk and mentioned his regrets in not killing the snake. His mind flashed to the look in Sasuke's eyes, at how cold they were.

Sasuke cared nothing for Konoha. In fact sometimes Naruto would swear the boy would enjoy it if the village were to burn.

One by one, the team split off to deal with the Sound 4. Even with the assistance of Gaara and his siblings, it looked to be close.

Suddenly the barrel containing Sasuke broke apart, and he dashed to the Valley of the End. Naruto followed him without hesitating.


Sasuke sneered at him, his curse mark clearly active. His Sharingan was active, but despite that, Naruto could only see hate and rage.

Sasuke wasn't going back willingly. He fully planned to kill his brother, no matter what it took.

Once again, Naruto's mind flashed back to that conversation he had with Jiraiya. How his biggest regret was never killing Orochimaru when he had that chance.

And so, Naruto made up his mind. He would give Sasuke one chance to come back, hopefully of his own free will. If not...well, he wasn't going to let this become his biggest regret.

Rasengan clashed with Chidori. The tainted curse mark energy collided with that of the malevolent Kyuubi chakra.

Finally, Naruto had Sasuke pinned.

"I am giving you one last chance, bastard. Either you give up this poisonous dream or else."

"Or else what? What can a weak Konoha shinobi do to the great Uchiha clan? You don't have the courage to kill me!" sneered Sasuke.

Naruto's mind flashed to Jiraiya's face. How he spoke of Orochimaru's betrayal. How hurt the man had become because someone he thought of as his friend had turned into a monster because had never stopped him

"There are many kinds of courage, Uchiha Sasuke. One of them happens to be knowing when you have to let go of the past and what could have been. I will not allow you to become my biggest regret in life. Goodbye, my former comrade," said Naruto quietly.

Naruto formed a single Rasengan with his remaining demonic chakra, and shoved it into Sasuke's chest. The look of shock was something that would haunt him until the end of time.

By the time Kakashi got to Naruto, the boy was crying silently.

"Naruto...what have you done?"

"I did what Jiraiya should have done years ago. Stopped a problem from growing out of control because of weakness," said Naruto.

Naruto bore the hate filled eyes of the village with practiced ease. Sakura was the worst though.

"He was your best friend! How could you kill him!" she demanded, tears falling from her eyes.

"He wasn't my friend! Open your eyes, you fucking bitch! Sasuke didn't give a damn about this village, or about you! All he every cared about was killing Itachi! He didn't care about who he hurt if it meant killing his fucking brother! He made his choice to leave the village and go to Orochimaru!" snapped Naruto.

"What about all we went through together?!" she demanded, unwilling to look at the truth.

"Wake up and face reality Sakura! I refused to allow Sasuke become my biggest regret in life! He wouldn't rest until he had his revenge!" said Naruto coldly, doing something he should have done years ago.

He bitch slapped the girl, shutting her harridan voice once and for all.

"You asked me to bring Sasuke back! You never said he had to be alive!" said Naruto coldly.

Sakura was in shock at the way he twisted her words against her.

"How could you?! You know how I felt about Sasuke!"

"You and the entire fucking village! Bloodlines die out all the fucking time, yet the other villages don't cry as much as they did for the goddamn Uchiha! The entire village turned him into a traitor with how they coddled him, all because of some damn bloodline! It's like you don't care about the fact he willingly betrayed the village and his team!"

"He was being manipulated!"

"No he wasn't! When has he ever said a kind word to us? When has he ever bothered to socialize with anyone in the entire village, except when we forced him to? Sasuke didn't care about the village, and he didn't care about us! I did what any shinobi would have done, and took out a traitor!" snarled Naruto.

What the two didn't notice was that they were being overheard by quite a few ANBU and loyal shinobi. Many of whom agreed with Naruto.

Yes, Sasuke was the last of a noble clan, but he had willingly gone to Orochimaru. And many were aware of the fact that he was displaying signs of treason for months leading up to this point. The fact Naruto had taken the initiative and killed him before he could become an actual threat to the village had only endeared him to the upper level shinobi, even if his friends were having difficultly understanding his decision.

Naruto gave up his argument, leaving a broken Sakura behind in anger.

Naruto ate his ramen atop the Fourth Hokage's head, which was one of the few places he could get any peace these days.

Tsunade had saved his ass from the council, as had a majority of the shinobi half, most vocally Tsume Inuzuka, Kiba's mother.

Naruto had done only what he knew needed to be done. And Tsunade knew all too well the sting of betrayal, since she had been Orochimaru's teammate as well.

When Sakura's mother demanded shrilly why he had killed Sasuke in cold blood, Naruto had looked her dead in the eye and told her bluntly that he didn't want Sasuke's survival to be his biggest regret in life.

Tsunade, having spent many a drunken night hearing this same thing from Jiraiya before, had realized what had prompted his decision.

And then Naruto looked at the council and asked why they were so upset about the death of a single bloodline when they had many bloodlines in the village, notably looking directly at Hiashi when he said it.

Hiashi had taken the hint and also asked why they had put so much emphasis on the Uchiha when the clan was clearly unstable.

Even though the Uchiha helped to found Konoha, there was little denying the fact that the clan was a loose cannon, and that bloodlines died off every day. The loss of another couldn't be that hard a blow.

In the end, Naruto was cleared of wrongdoing as Sasuke had clearly been ready to betray the village without hesitation or any help from Orochimaru, who simply gave him a place to go to. The end result was that quite a few civilians had been giving him evil looks and he had ignored them with ease.

Naruto looked up from his ramen, noting someone was behind him.

"Whoever you are, come out now! If you're here to bitch about the traitor, please note I have no issues with punting you off the damn mountain!" said Naruto flatly.

It was Jiraiya.

"Kid, I heard about what you did," he said.

"I had to. All I could think about was the look you had when you said how you should have killed the snake when you had the chance, before he became a bigger threat."

Jiraiya sat down next to Naruto. He brought out a single sake bottle.

"I'm not blaming you Naruto. It was pretty obvious what road Sasuke was heading down, and there is no happy ending waiting for him. At least he was killed by someone who cared about him rather than Orochimaru. Even if it means that there are no loyal Uchiha in the village, at least you took out someone who could have become an even bigger threat if given half a chance. From what I read about his psyche reports, it was only a matter of time before he betrayed the village," said Jiraiya, taking a drink.

He handed Naruto a cup, and wasn't surprised the boy actually drank it instead of handing it back.

"I couldn't let him betray the village. I don't think he even saw me as his friend. All I saw was rage and anger."

Jiraiya poured him another cup. Better to get the kid drunk so he could let it out with someone who knew exactly what he was going through than to keep it all in.

"It seems he was your Orochimaru. Take solace in the fact that he has probably gone to see his parents now," said Jiraiya.

Realizing that he was about out of sake, he had one of the toads bring a barrel of Gamabunta's secret stash. Three cups of that, and Naruto started to talk a bit more. He let out all the pain he had been feeling, all the glares, everything.

And when he finally passed out drunk, Jiraiya took him to his parent's house, which was so heavily sealed that it would take quite a bit of time for anyone to try and kill the kid. More than enough time for him to make anyone reconsider the idea.

A wise move, considering Naruto's apartment was burned down that night, in hopes it would kill him.

Orochimaru was beyond pissed. He had finally gotten a report on what happened to Sasuke and his Sound 4.

Sasuke and a good portion of those he sent to retrieve him were dead. Only Tayuya had survived, and that because Tsunade had accidentally discovered she was of the Uzumaki clan.

Finding out she still had family left had given all the opening Tsunade needed. Chances were Tayuya would join, if only to be near her kin.

But what really pissed him off was the fact that the Kyuubi container was the one responsible for the death of the Uchiha. And he had died by a Rasengan to the heart. Sasuke remains were burned beyond recognition and buried. To add insult to injury, Jiraiya had the remains placed in a specially sealed container to keep him from bringing the boy back from the dead.

It seemed that the student had learned from his teacher's mistake.

Itachi, when he learned of his brother's death, immediately went to learn the specifics of what actually happened. Even if it meant dealing with Sasori and Kakuzu.

Between their information networks, he learned the truth of what had happened.

Sasuke had attempted to go to Orochimaru, and a team of Konoha shinobi, all rookies, had gone after him. Many had suffered severe injuries and miraculously there hadn't been any deaths. Suna had assisted them at the last second, since the children of the previous Kazekage had been in the area at the time.

Orochimaru lost his Five best shinobi pawns, and Sasuke's teammate Naruto had killed his former comrade to prevent him from joining up with the Sannin.

According to Sasori, the Kyuubi container's only words on the matter was that he didn't want Sasuke's survival to join Orochimaru to be his biggest regret in life. Of course the puppet master had known what the boy meant by those words.

It wasn't a big secret that Jiraiya's biggest regret was that he hadn't killed Orochimaru when he first betrayed the village. Or that Naruto was now his apprentice.

Itachi, once he had the information he needed, closed his eyes in regret.

He had hoped Sasuke would kill him and restore the honor of the Uchiha. He had thought keeping Danzo from getting his claws on his brother would keep him safe.

While Naruto had ended his brother's life, he had also prevented Sasuke from making the biggest mistake he had ever could. Itachi had defeated Orochimaru and kept the Sharingan from him, but he had gone after Sasuke instead.

And unlike him, Sasuke had agreed to it. Above all else, Orochimaru could not have the Sharingan. It was bad enough he had to kill the clan, but allowing that snake to get the bloodline was a disaster.

Next time he saw Naruto, he was going to get a quiet thank you for preventing that from happening.

Tsunade had a massive headache, and she fully blamed the Uchiha clan. This had nothing to do with the rivalry that had started with Madara Uchiha and her grandfather. Oh no, this had to do with Naruto's decision to kill Sasuke rather than let him join Orochimaru.

While she fully supported the boy's actions, quite a few didn't. Most of the civilians had worshiped the ground the spoiled brat had walked on, and seeing their reaction to his death pissed her off beyond belief.

It seemed that the story Naruto had told Jiraiya after the man got him drunk off his ass was true, the civilians would like nothing more than to see the boy dead for doing his duty.

About the only good thing that she could see coming out of this mess was the fact she fully planned to release the knowledge Naruto was the son of the Fourth Hokage and the Princess of Whirlpool. She had learned that Sarutobi had kept it hidden in hopes to protect him from Iwa, but with the way things were going it was more likely that the very people he was trying to protect would kill him first.

And Naruto had displayed the true Will of Fire whenever tested. She saw no reason to keep his true heritage from him any longer than she had to.

She could only hope that his friends would forgive him for killing the Uchiha brat. Even if the boy had deserved it.