I'm not talking about just shiitty back stories alone, everyone in Narutos been screwed over in some way or another so no Nagato or Itachi or anything because they haven't been given a tough ride since.
I'm talking about the character Kishi just won't let have any peace. Which character's does he just treat the worst.
Kakashi. Father commit suicide, failed to keep his childhood promise, has to kill Rin, sensei is killed, own student goes rogue, has to kill Zabuza again which sends him into a rage, has to fight best friend and to deal with the war he inadvertently caused.
Tsunade. Loses literally everyone close to her. Little brother dies, lover Dan dies, wars, Orochimaru goes rogue, sensei dies, Jiraiya dies, has to teach Sakura, knocked into a coma by the Pain Invasion, conspired against by Danzo & the elders, wakes up into a war, beaten to death by Madara Uchiha.
Shikamaru. Loses sensei, almost murdered trying to save guy he doesn't like, has to deal with almost getting his friends killed, has to fight his corpse sensei, has his father killed.
Others are open for suggestions, just characters that Kishimoto keeps giving hard time after hard time.