It's a strange thing, facing death with a smile. The very concept of death is viewed with such negativity and contempt that you'd think it'd be impossible for the divines to do it let alone regular mortals. Nevertheless, there are those strange exceptions who defy this trend. Souls who suffer from either being too brave, foolish, wise, or just too damn tired not to look at the end of their lives with anything less then a grin. For better or worse, Itachi Uchiha had been one of those people. Having been born in a time of turmoil for his home, he had learned very early on how the world was a dark and cruel place. And that simply living life, much less living a good one was gargantuan task that far too many took for granted. So he decided not long after his first battle that he would live his definition of what was a good life. The life of a protector. A guardian who looked after his family, his friends, their families and the place they all called home in Konoha. That was all the dream had ever been. Someone else could be leader. Someone else could be the best, the smartest, or the most powerful. Those titles meant nothing to him. As long as he could watch over those who were close to him and the people and place he called home, he would be happy. And yet, in spite of that worthy, selfless goal fate had decided he should instead be the opposite.

Despite being good hearted and wise enough to know when not to fight, Itachi had a natural ability for battle and killing that rivaled or surpassed any of the great warriors that had been born to the Elemental Nations. A gift that ,whether wanted or not, transformed him into one of the most feared men in Konoha. He rose through the shinobi ranks at an astonishing pace. Outclassing his comrades in everything he did. Weaponry, stealth, genjutsu, ninjutsu, taijutsu. Sure, there were some who could best him in a single area, but there was no one who could practice all of them to the level that he could. Eventually eclipsing his classmates completely and joining the elite of the elite. The ANBU BLACKOPS.

Yet, even after joining a notably dark and secretive organization such as the ANBU, Itachi had always tried to remain a cheerful person. Always greeting people with a light smile that most would simply overlook. Perhaps, seeing the worst humanity had to offer made him appreciate the good even more or perhaps he was simply a nice guy. Whatever the case was, those years with the Anbu ended up being the happiest years of his life. He was loved by the village, respected by his comrades, celebrated by his family, revered by his little brother, and perhaps the one thing he never really appreciated, it all felt simple and right. He was the good guy, the Uchiha were the good guys, Danzo, Hiruzen, Minato, and even Orochimaru for a while. All of them were allies everyone who served Konoha was good and those who stood against it were evil. Was that ever really the case? Deep down he knew the truth, but for those few years, he was perfectly fine with believing that it was.

Then things began to crack in his perfect world. He realized just how deep Danzo's schemes went, he realized the citizens of Konoha were turning on the Uchiha, he saw the Uchiha being backed into a corner and knew that they weren't going to stand it forever. It was then, he had personally asked to be taken out of the ANBU and serve directly under Sandaime, Hiruzen Sarutobi, and try to act as a mediator between the Konoha government's suspicion and the Uchiha's pride and rage. To try and save his idealistic world he had lived in for so long. For all his skills though, negotiating was not one of them. Soon enough his hopes for peace began to fade as his mediator role began to dissolve to him simply spying on his own clan for the Sandaime. And the normally decisive and quick thinking Itachi, found himself being torn apart between his loyalties. Who was he supposed to protect if he couldn't save both? His home or his family?

His stress began to get the better of him and eventually he confided in the only soul he really trusted more so then even his little brother, Shisui Uchiha, prominent member in the Uchiha police force and his oldest friend. Matching himself in almost category of skill and ever the optimist, he had hoped Shisui would be able to help quell the situation before it exploded into conflict. Shisui listened to everything Itachi told him with a relaxed eyes that occasionally flared up in surprise or anger and once he finished, decided on a solution. Together they decided that the best way to stop anything from happening, at least immediately was to cast a genjutsu Shisui possessed over the entire village and make them sort of forget their growing animosity for the Uchiha. A genjutsu so powerful yet so subtle on that scale would almost certainly kill him. But like Itachi, Shisui took that as a small price to pay for a lasting peace and would do it gladly. Just like that, there was a plan. A plan to turn things back to normal like it never happened. Naturally, it was too good to be true.

Danzo had coveted Shisui's technique for some time and after learning of what he intended to do with it, acted on his urges. He crippled the Uchiha warrior and stole one half of his Sharingan. Destroying any chance of the plan being put into the action. Itachi's rage got the better of him and he briefly wondered if his family was right to rebel. But Shisui put those thoughts to rest, reminding him that even with his weakened, it was better than everyone else dying in a war. The wounds that Shisui suffered would ultimately prove fatal however, and to keep Itachi from possibly going to war on Danzo and Konoha itself, Shisui made him swear to find another way. That Konoha was built on the idea of finding one. And with those last words, he gave his friend his remaining eye and asked him to end his suffering. Granting him a power legendary among the Uchiha but ultimately leaving him to confront the inevitable alone.

The weeks that followed Shisui's death proved to be the worst Itachi had ever experienced. Riots were occurring against or for the Uchiha all the time and each time one occurred, things got more and more tense between them and Konoha. Itachi himself began to become an outcast in his own home. His father grew ever more distant, his mother acting like he wasn't even there. His former friends and comrades turning on him, growing suspicious of what had truly happened to Shisui. Saying that Itachi had killed him to grab power. All his loved ones had begun to turn their backs to him. All except one.

From the day he was born, Sasuke had always been one of the few shining lights in Itachi's life. He was HIS little brother. Someone he would always need to watch over and defend. He was kind, caring, energetic, youthful, and above all else genuinely soft hearted. As if he was too innocent and good to have been born into this world. He could do nothing wrong as far as Itachi was concerned. He was the one person who never turned on him or treated him differently, partly because he didn't quite understand why the others did and partly because he idolized Itachi. More than his father or any of the Kages, he was Sasuke's hero. Itachi never really knew how to react to such adulation but was nevertheless proud to be the center of it and strove to prove it whenever he could. And in those dark days, nothing meant more to him then simply spending time with his brother trying to forget about the incoming conflict.

Finally, the choice became unavoidable. The village stood at the edge of an abyss and the slightest thing would send it spiraling into all out war. He had to decide who he would ultimately side with. The Uchiha or Konoha. And the decision he made would ultimately shape the course of not only Konoha but perhaps the entire world.

He knew the Uchiha would never accept anything accept unconditional surrender if they went to war so the options dwindled down to a first strike mission. Before they would attempt to mobilize, they would be eliminated. Knowing the weight of what had to happened would've killed any other, he decided to do the task himself. He had only one condition for the Sandaime to meet if he was going to do this. Sasuke was to be spared. He would be looked out for by the entire village and hopefully be far away when this happened. Hiruzen accepted the agreement and reluctantly gave Itachi the permission to perform the task, informing him that no one could know that Konoha was responsible for what would occur. In essence he would become a fugitive wanted dead or alive by Konoha. Itachi took all of this with a simple nod and bow and when the night of the task came. Garbed in his Anbu uniform under the light of a full moon, he began what would ultimately be his last mission for Konoha.

By the night's end, every Uchiha save one had been slaughtered and the one who survived had been scared for life and set down a path of vengeance that would ultimately destroy any sense of childlike wonder or innocence he had. And as for Itachi, well he knew that their would be no redemption for what he had done. He had committed the ultimate sin, and to the rest of the world established himself as a powerful monster. With his dreams shattered, his loved ones dead and his home saved, all he could hope for now was a good death at the hands of his brother once he had found the strength to do so.

The eight years that followed came and went for Itachi with only a few things really leaving a mark on him. He joined an organization called the Akatsuki as a double agent, he drove out Orochimaru from the group, he met his little brother a few years to early and had to once again tear his soul apart as he brought Sasuke to his knees in front of his friend and to top it all off, fate had decided to punish him for his crime by giving him a disease that only seemed to weaken him as the years went on with strong coughing fits and frequent bouts of illness. Still though, despite all of that it was once again simple for Itachi. He was the bad guy working with other bad guys now and that was fine. He would play the role of villain until justice would one day get to him and that would the end of it. A simple fantasy that he always tried to believe in.

That day finally came when an older battle hardened Sasuke faced him at the ancient Uchiha Temple. This was it. There was no going back from this. Sasuke wouldn't stop until he had killed him and he deserved to be faced with all the power Itachi could still muster. The battle they had shook the ground around them leveling the temple and scaring the very land itself. Itachi wanted to see everything his brother had learned. Every jutsu he had under his disposal and every trick he had under his sleeve. The sight of his brother's skill made Itachi prouder than almost anything else and decided to end things by giving Sasuke a glimpse at a technique he hadn't yet acquired. The Susanoo. And when Sasuke fully saw what such a technique could do, that was that. Itachi's strength had finally exhausted itself into oblivion and he collapsed right next to his brother. Dying with a smile on his face.

That was supposed to be the end of it. That was supposed to finally send him to hell with the worst demons and monsters ever to grace the planet and seal him there for eternity. But that wouldn't be enough however. He returned to life as Reanimated corpse bound to serve under a power mad villain named Kabuto along with his other Reanimated warriors. His first battle however, freed him of this predicament and now as a unbound undead warrior, he charged off towards Kabuto to put an end to his scheming and free the other souls he had forced back into servitude.

So he was to get one last chance to be the good guy huh? That worked just fine for him. Maybe he could actually live his dream one last time before truly dying. Fate proved kind to him that day as not only did he face Kabuto as the hero but did with the help of his brother. A sight he was sure he would never see again. Sasuke himself had figured out the truth about Itachi and had very mixed feeling about his brother. Wondering why he chose Konoha over the Uchiha but decided to help his brother defeat Kabuto before getting answers. And that battle despite being so much smaller in scale than his fight with Sasuke, might've actually been his proudest moment. Sasuke had grown into just as good of warrior as any of the legendary figures had been and his movement and technique were fashioned into all his own not taking queues from any of them.

Finally the battle finished with Kabuto subdued and him releasing the jutsu that held Itachi's soul and the souls of all those who were resurrected back to the afterlife. He was sad to see his brother clearly angry and confused and sad about his return to the grave but decided to end it on a note that would ultimately change Sasuke's path.

You see, ever since the death of his family, Sasuke's path had only growled darker and darker. To the point that his skills threatened to destroy everything Itachi had hoped to still protect. He blamed Konoha for their deaths and was hell bent on burning it and everyone who lived there to the ground. His chance meeting his his undead brother however began to crack that plan of action and by the time the battle with Kabuto had ended was now more confused about it then ever. He asked what Itachi wanted him to do. Itachi wanted to say protect Konoha. He wanted to say do as I and Shisui did and live for the greater good. Be a protector. But he loved his brother too much to tell him that and in truth he had often wondered if he himself had done the right thing. So he decided to give the one thing Sasuke needed more than anything else, reassurance.

"That's for you to decide Sasuke. But no matter what happens…" He grabbed the backs of his brother's head and pushed his own head forward until both made contact. Staring into his brother's tear filled eyes, he told him what would never be untrue. "I will always love you." He smiled, gratified he had gotten to say those last words as his body began to disappear in bright ray of light. Sasuke was too awestruck to say anything back as Itachi closed his eyes and took in one last breath as his body returned to the dust and his soul return back to hell.

So that was that. That was how the story of Itachi Uchiha came to an end….or at least it should've been. It seemed fate wasn't finished with him yet.

A brilliant flash of light dumped his body his body in a dark snow ridden Gotham city alleyway crashing down into an overflowing dumpster and scaring some poor hobo who looked to see what the hell just made that noise. His musings led him to said dumpster and widened his eyes when he saw the body of a naked young man lying in the dumpster. Now any self respecting Gotham hobo would've just left him there saying it was none of his business and do their best to forget what he saw. This particular hobo however felt that he couldn't very well leave a naked breathing man lying there in the cold snowy trash and so with a few grumbled curses he rolled the young man out of the trash. Unknowingly starting a chain reaction that would forever change the world around him.

A/N: Tada! I think we're good for the first one. So yeah, I finally worked up the courage to write a DCAU-Naruto Crossover. I know it was almost entirely a recap of stuff we've seen already but I think it was necessary. After all, I'd say dying causes someone to look back on their life and since Itachi's done it twice. Well you get the idea.

I also know some things about the backstory he has aren't exactly canon so just consider this a slight AU then. It's not like its that far off from the original anyway.

So what did you think? Good? Bad? Leave me a review and let me know. Special thanks to Afalstein for writing my inspiration for this work in Connectiong the Dots. If you haven't already, go read it