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Disclaimer II: I don't care if you only follow some obscure timeline of Naruto releases. I am mostly up-to-date on the manga scanlations and will freely use whatever kind of spoiler I want. You have been warned. Ignore this at your own peril.
Disclaimer III: As usual, I will blithely disregard anything from PTS unless I happen to like it. Canon whores, please leave, for I do not want the likes of you to read this or to comment on it.
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Failing Dreams
I.) Namikaze Minato always dreamed about holding his son, about teaching his son to be a man in his father's image, about teaching his son how to fight and about having a family all for himself. As he completes his work and activates the grand seal array and feels his life-force being sucked out by Death itself, he weeps for opportunities lost.
II.) Hatake Sakumo dreamed of justice, of being allowed to do the right thing in a world full of betrayal and murder. The world, unfortunately, does not share his dream, and it is the knowledge that even the best intentions and grandest dreams of justice are nothing in the face of pragmatism that drives him to commit suicide.
III.) Hyuuga Hizashi, more than anything else, dreamed of being free, of forsaking Konoha and the Hyuuga forever, of raising his child to be free of the hatred that has always run in the veins of the guardian-slaves of the Branch House. And then, just a week before he would have fled - during the week that his brother would have been on guard duty on the great wall surrounding their village, 'mysteriously' missing Hizashi's escape - the traitor-diplomat ruins their plans forever.
IV.) Orochimaru, once upon a time, wanted to become Hokage. Not for his personal gain, not to fulfil some twisted scheme of terrible evil, but because he was the best, and their village needed just that. But Sarutobi proved to be healthy and cunning, and survived the Second War, and after that Jiraiya taught that miserable blond-haired upstart to surpass all limits. It was at that point - when Orochimaru met the man who would later become the Fourth Hokage - that he realized his inability to be a good person..
V.) Jiraiya had a simple dream - that of a family. The surrogate father, their jonin instructor and later their best friend, Sarutobi Sandaime-sama. The surrogate sister, Tsunade, kin to two Konoha's Finest and the biggest brat of a girl any man could ever hope to meet. The surrogate introvert brother, Orochimaru, one of the few in Konoha who truly understand Jiraiya's struggle between loneliness, power and blood ties. And then the sister falls in love and suffers heartbreak for it, the brother becomes an abomination and a traitor and the father grows old and weary. It is little wonder the Toad Sage has such an intimate relationship with things that help him forget.
VI.) Uzumaki Kushina dies screaming her defiance into the uncaring wind. She will never again see the man that made the sun shine, the moon rise and the stars sparkle for her, the man who would hold off an army one moment and make tea for her the next, the man who promised her the impossible and had done it to prove that he was a man of his word. She will never again see their child, their beautiful baby boy - how little he looks like her, she thinks - because the man who did the impossible for her is now doing the impossible to her. Then the chakra of the Fox burns her from within, and all is silent again.
Relief
VII.) Mitarashi Anko, with all her heart and soul, appreciates what Uchiha Sasuke has done. No, not that he has betrayed Konoha and nearly killed those out to save him - she will be the first to ram a knife into his heart for that, believe it - but instead the boy has done what she could not. The death of Orochimaru marks the transformation from suicidal psychopath to only-just-marginally-not-well-adjusted member of a society that trains its children how to kill efficiently.
VIII.) The death of the Third Hokage is a day of both joy and sorrow for Sarutobi Asuma. Finally, he can stop being The Third's Son and start being Sarutobi Asuma. When he discusses this with the lady of his life, she smacks him on the head and tells him to stop being an idiot. He has always been Sarutobi Asuma - he has always been the only one seizing himself up against his father.
IX.) Maito Gai has, for his entire life, suffered from crushing self-esteem problems. It wasn't until he met a boy with problems that eclipsed his own by a magnitude that no words can sufficiently describe it that Gai faced himself and decided that from this day on, he would live as an example to all who would believe in the magnificent Green Beast of Konoha. By all accounts, he has succeeded.
X.) Hatake Kakashi has more inner demons than anyone else in Konoha (including Uzumaki Naruto, Kakashi thinks. That boy has one inner demon). He hates the village, he hates the system, he hates it all so much that he would gleefully tear it down with his own hands. But he has learned from his father, from his teacher and from bloody, hard-earned experience. He obeys his orders, he completes his missions, he becomes a celebrated hero of the village for committing crimes so atrocious that the records are sealed forever. He kills without mercy, hesitation or compassion and fully expects the same to be done to him at any moment. But when he meets his latest team of soon-to-be failures, Hatake Kakashi realizes that within these boys lies the future. Misogyny makes him disregard the girl. But for the first time in years, Kakashi knows hope again, and it will not be disappointed.
XI.) Tsunade, a month after taking up the hat of the Fifth Hokage, realizes that she no longer needs to drink herself into a stupor to sleep. No longer does she try and fail to save Dan in her dreams, but instead she sees herself helping the boy who is such an uncanny amalgam of both her lover and her brother. The boy has done the impossible - to pull off the Rasengan in but a week - fuelled with nothing beyond willpower and the drive to succeed to make her open her eyes and realize that as long as there is someone who tries hard enough, there is a future.
XII.) After over a decade of holding onto hatred, Umino Iruka is oddly content when he lets go of it at last. Once he actually starts talking to the Third about the boy, he realizes he has far too much in common with Uzumaki Naruto, and with that realization comes peace of mind. It is this, not duty, that makes him fight a superior foe for the sake of someone he hasn't exchanged words with beyond the absolutely necessary minimum as a teacher. And despite the wounds, the pain and the realization that one of his co-workers is a bloody traitor to the village, Iruka smiles when Naruto takes the first step on the path to greatness.
Fulfilment
XIII.) Despite the shock, the pain, the reeling mind, Hyuuga Neji sees one of his most private fantasies fulfilled after the Chuunin Exams: To see Hyuuga Hiashi kneel before him in apology. Some dreams are epic, some are petty, and Neji idly muses that this particular dream is an odd blend of both types.
XIV.) Chouji wanted to be thin, to fit the unrealistic ideals of beauty his very, very, very energetically loud blonde teammate espoused at any given opportunity. He got that - and more - when he took the third pill in his fight against Jirobou. He was so profoundly disturbed by the effect this had on the way people treated him that he locked himself in the Akimichi compound for three weeks and proceeded to put on all the lost weight again. Now, Chouji dreams of having enough self-confidence to be thin.
XV.) Haruno Sakura dreams of love, of romance, of companionship. She would never have expected to find all of it in the arms of another woman, but when she does, she can't bring herself to care about the scandal this causes. But no matter what forces are arrayed against her, the man she has learned to love (sadly, for him, as a brother) stands ever ready to defend her. Sakura knows what many refuse to accept: Uzumaki Naruto is just that awesome.
XVI.) Two years after losing what became known as the Battle at the Valley of the End, Uchiha Sasuke realizes that, confinement to the boundaries of the village or not, he has thought of the house he sleeps in as "home" for the first time. Passer-bys stare at the crying boy in the street for what seem to be hours, but the man that emerges from within the boy knows that he has a purpose in life beyond revenge. He vows that he will find out what it is before killing his brother.
XVII.) Aburame Shino has always accepted that he is a monster. When he is made the commander of Konoha's worst monsters, when the Sixth Hokage pronounces him to be the operative commander of the Konoha ANBU, Aburame Shino nods and smiles. This way, he will be able to keep those whose heart is not made of flint from having to hurt themselves by issuing orders that can only be called monstrous.
XVIII.) Hyuuga Hinata has always dreamed of proving herself in the eyes of her father, her sister and her cousin. When the Fourth Succession War starts and all of Konoha's shinobi are fighting for their lives and those of their countrymen, the legend of the mousy girl with the pale eyes taking command of a border fort and holding it against impossible odds until reinforcements could rearrive becomes a legend that few can rival.
XIX.) Inuzuka Kiba never really knew what he wanted. He became a shinobi since that is what all of his family had done, he cared for dogs because it felt natural to him and he lived hard and had fun where he could because he realized on some instinctual level that with a life like the one shinobi live, any moment not spent having fun is a moment he'd regret if he died young. Then he met Temari of the Sand Village, and for the first time in his like did Inuzuka Kiba know true fulfilment. For him, it is a simple four letter word: Love.
XX.) Uzumaki Naruto has always known what he wants to be: Hokage. He pursued that goal with unerring determination, shaking off blows to his ego, his mind and his body that would have killed lesser men than him a dozen times over in the process. He distinguishes himself as an epic hero from the get-go of his shinobi career, bringing down villains, toppling criminal organizations, assassinating evildoers, fighting his way into the Order of the Dragon of the Fire Country in the Fourth Succession War and charming princesses whereever he goes. It is no surprise when he is instated as the Sixth Hokage of Konoha. A few years later, after the birth of his second daughter, Naruto realizes that fulfilment is not just the goal, but the journey towards it, too.
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AN: Both the wife of one Uzumaki Naruto and the lover of one Haruno Sakura would be, if I were to write this, OCs. I do not believe in the religious matching up of canon characters.