Disclaimer: I don't own Naruto.
Twelve Failures of Hatake Kakashi
1. When Kakashi was seven his father, Konoha's White Fang, committed seppuku with only his young son as a witness. Being told to hold the sword that had given his father the name White Fang above the man's head in case he should dishonor himself by showing pain as he disemboweled himself is a symbol of the greatest trust his father could ever place in him. It was also the hardest thing Kakashi has ever had to do, but his hands didn't waver.
Unfortunately, Kakashi listened to his father's comrades after the event, the ones he'd sacrificed his mission to save. They speak derisively of the weak man who abandoned the good of the village to save them, how his shame led to his eventual suicide. The White Fang should have left them to die, should have completed the mission they had been assigned. Kakashi fails to realize that they're wrong. That those who abandon the rules are trash, but those abandon their comrades are worse than trash. A rather (in Kakashi's mind) foolish and whiny child, later assigned to his team, knows this instinctively. Kakashi is convinced that Uchiha Obito is the greatest fool he has ever met. He is also disdainful of the female member of his team, Rin, who appears to have a major crush on him. He believes her a weakling more obsessed with love than the proper arts of a shinobi.
2. Despite being a shinobi genius, Kakashi fails to see an inherent flaw in the only technique he has ever created. Refusing to admit that anything he himself has created is a failure by its very nature, Kakashi attempts to use Chidori on an enemy Iwa nin. He never hits the man, and only the timely intervention of his sensei saves his teammate, Obito's, life. Minato forbids Kakashi from ever using the technique again, as the rapid movement required for the technique has him move too quickly to see any counterattack the enemy prepares.
3. In his blind, cold, utterly rational obsession with the rules of proper shinobi conduct Kakashi fails to immediately going after Rin when she is captured by an Iwa nin. Obito calls him worse than trash and goes after the girl medic. After several minutes Kakashi follows after, forced to admit he cannot sabotage the bridge by himself.
Only when he sees a distorted patch of tree and realizes that it is an Iwa nin about to kill Obito does he throw aside the rules and rush in headlong, losing an eye but temporarily averting a blow that would have killed Obito. In his desperation to save the both of them, Obito awakens his Sharingan and kills the nearly-invisible Iwa nin. Had Kakashi and Obito arrived at the same time, Kakashi would not have had to lose an eye to save Obito.
The blood loss from the eye slows him down enough that there is no way Kakashi can escape the landslide the final Iwa nin triggered after Kakashi and Obito had rescued Rin. Seeing his onrushing death by boulder, Kakashi can only stare. Obito selflessly runs back and throws Kakashi out of the way, and is crushed as a result. As his dying wish, he gives Kakashi his Sharingan eye.
4. When Iwa reinforcements show up, Kakashi fails to defend Rin from them. He throws a kunai, a gift from his sensei, at them before passing out. The Yondaime, who had placed a Hiraishin seal upon the kunai, immediately appears on the scene and shows the Iwa forces just why there is a "flee on sight" order attached to his entry in the Bingo Book. Rin survives, but barely.
5. Three days later, Kakashi's Sharingan shows him exactly the correct path to dodge the volley of kunai thrown at him by Iwa forces. Inexperienced with the new bloodline limit, he fails to remember that Rin was standing behind him, back to back. Her medical skills are nowhere near sufficient to save herself from the half dozen fatal puncture wounds, and it is only the intervention of the Yondaime yet again that saves Kakashi himself from following the girl to the grave.
6. When giving genin-hopefuls their true exam, Kakashi makes teamwork the focus. Not just because Obito stressed sticking together, but because he, a loner, failed to work with his other teammate, causing her death. He gives each and every one of them a failing grade, until the day the team he is testing contains Uchiha Sasuke, Obito's nephew. Compelled to do whatever he can to honor whatever fragment of Obito's memory that he can find, he constantly drops hints and gives the team endless second chances until he is eventually forced to tell them point blank that the point of the exercise is teamwork. The once cold-hearted shinobi failed to maintain his rationality and give the team a fair test.
7. Despite the fact that a blind man could see that Sasuke was nothing like Obito, Kakashi still favors him over the other two members of his team as a physical memory of the boy who became his best friend only after he was already gone. He failed to realize that, if he were to compare Sasuke to the members of the old Team Seven, Sasuke would not be the selfless Obito. He would be the cold-hearted, stubborn, arrogant genius, Kakashi.
8. He fails to realize that the true heir to Obito's legacy is Naruto, the boy who freezes at his first sign of real combat, the selfless boy who constantly seeks the approval of others, and the one who charged recklessly at an enemy more powerful than he could truly comprehend. Kakashi is convinced that Uzumaki Naruto is the greatest fool he has ever met.
9. He also fails to realize just how much Sakura is like Rin. She has amazing chakra control, practically limitless potential as a medic, a good understanding of genjutsu, but has a hopeless crush on the dark male figure of her team, completely ignoring the more outgoing boy who actively seeks her attention. He believes her a weakling obsessed with love instead of the proper arts of a shinobi.
10. When Naruto, slated to fight against the greatest genin of Konoha, Hyuuga Neji, asks Kakashi for help, Kakashi fails to be a real sensei, as always. Kakashi blows him off in favor of Obito's nephew.
11. Despite the fact that he knows that the one thing Naruto has sought his entire life is acknowledgement, Kakashi fails to ever congratulate the boy on anything he has ever done. Even defeating the genius Hyuuga prodigy, performing an S-Rank Summon, defeating one of the bijuu, and equalling the last Uchiha, is not enough for Kakashi to regard Naruto as more than what Sasuke called him: the dead last. Even after Naruto gives his all, even after he takes an arm through the chest, even after he goes through Hell to try and bring the other boy back, Kakashi still regards Naruto as the lesser of the two for failing. Despite the fact that Naruto pulled his final blow, merely scratching Sasuke's hitai-ate instead of destroying the boy with the Rasengan.
12. After waking up and realizing that he has failed, Naruto is inconsolable for days. Kakashi doesn't try; he is too busy mourning his failure to Obito's memory. He never realizes that he has indeed failed Obito's memory, not by not being there enough for Sasuke, but by not being there enough for Naruto.
Author's Notes:
Yes, I purposely used the exact same phrase to describe Kakashi's initial impressions of Obito-Naruto and Rin-Sakura, to emphasize just how blind the man with the all-seeing eye is. Obito isn't really Sasuke's uncle. There is no actual information on the death of Rin, or even precise confirmation that she is dead, beyond Kakashi saying that everyone precious to him is dead. Next character in the series...dunno. And it'll be awhile until I get around to writing the next character, as I'm trying to keep up with weekly updates for my other story, Overlay.