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Itachi
Gaara/Sasuke/Nagato
Obito
Watching your family die is one thing, and being forced to kill them is another. Itachi suffered more.
Gaara/Sasuke/Nagato
Obito
You mean the last two. Tsunde's ***** ass ain't up for candidacy. It's Gaara and Sasuke for sure.
Gaara has gone a majority of his life being unable to sleep. Going without sleep for just a few weeks can have a disastrous effect on a person, doing so for years, please, we'd all be insane in the first few months, dead after the first year.
Sasuke was tortured by being forced to see his entire family be murdered at the age of seven. That kind of psychological damage is bounds ahead just seeing one family die as a teenager, or losing one person you love.
Edit: Nagato too, forget he was surrounded by war, poverty and death since birth.
Watching your family die is one thing, and being forced to kill them is another. Itachi suffered more.