He got radicalised and began to disassociate from reality. He learned to not value life because he was genuinely put in denial that he was even in the true world. In Kishi's own words, Rin is a metaphor.
It's not all about how much you lost, Obito's fall from grace is tragic.
Oh for sure, didn't put it in my top 5. Probably not Top 10 but there's a lot more to it than just losing the only person special to him.
Tragic backstories aren't a competition and not everybody processes grief the same way. Obito ended up the way he did under Madara's radicalisation. Basically orchestrating his issues and indoctrinating him into a cult :')
Oh for sure, didn't put it in my top 5. Probably not Top 10 but there's a lot more to it than just losing the only person special to him.
Tragic backstories aren't a competition and not everybody processes grief the same way. Obito ended up the way he did under Madara's radicalisation. Basically orchestrating his issues and indoctrinating him into a cult :')
#1 Itachi
Sasuke (probably haku too)
kakashi/madara/nagato
neji
gaara
Naruto
Naruto lost his parents before he even knew them so that alone eliminates him from top 3 then puts him below all the others simply due to the fact that his tragic story has a silver lining to it which was that they died as heroes who sacrificed themselves for hope and potentially that naruto will speak to his parents again when the time comes. his "demonized" childhood is exaggerated, kids in his age group didn't like him because he was an immature dumbass not exactly because of the kyuubi. so the illusion that naruto's is the worst is due to hiruzen being such a crap hokage in handling naruto's development and environment.
Gaara is the same case just without the romanticizing sacrifice of his parents and that he was much more demonized and physically threatened rather than verbally by his own village. however, again despite his siblings fearing him they still cared for him regardless. it couldn't had been that traumatizing if he was easily willing to be kaze of that village rather than resent it.
Neji shouldn't really need to be explained why he's above naruto and gaara. the guy was essentially a slave to his own clan and that his father died as a scape offering of a crime that his uncle committed even thou that said crime was to protect his child hinata from a village that was KNOWN for kidnapping little girls such as kushina (lol yet people still trash talk taka sasuke for returning the favor :lol)
No idea where to put kakashi tbh. his past is honestly normal for any shinobi in war so he'd probably tie with nagato and madara thou I'd probably put him and nagato above madara since those two were forced into killing their comrade. anyway there above naruto/gaara/neji because the only thing worst than death is having to suffer constant deaths in war which orochi briefed about when he said that nagato was better off being mercy killed than to live in such a harsh environments of war which is true because 20th century veterans say the samething for orphans and soldiers.
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Sasuke past can arguably be the most tragic due to his innocents being rape in a single fateful night, then traumatizing since he probably never witness a death, so I can't even imagine the immeasure of the consquences effect to someone's mind. but honestly I'd put him 2nd on the list simply due to the fact that despite his horrendous lost of his clan he was still able and could've continued a new life with team 7 which he admits from his own words even towards sakura which clearly isn't something sasuke would do unless he meant it.
Now imagine losing your parents, being demonized and having to suffer through it the rest of your life like itachi. reason I put itachi above sasuke is simply because it's one thing to see your parents die and another thing to be killed by you. then the burden of having to live with that as long as you live is just un-measurable unless experienced. also sasuke suffered the event but there was no need for him to feel responsible for anything unlike itachi. it sucks I have to downplay sasuke like that but it's true. I see folks here try to make itachi "mindless" but clearly have short sighted view because if he were then he would've sided with his clan because it's easier to follow your emotions than to be able to turn your back and mentally endure where as sasuke is ironically the opposite of that which danzo called him out on and inevitably became a blood lusted mindless killer during the climax of the kage summit with no deeper purpose other than to kill unlike itachi.