Woobie / Bleach

• Nemu Kurotsuchi, the daughter/creation of ruthless and sadistic Mad Scientist Mayuri Kurotsuchi, who abuses and humiliates in the Soul Society Arc. He's been toned down since his first appearance and hasn't beaten her since the Soul Society Arc, but he's still apathetic about her safety. To make matters worse, look what the Syazel Aporro Granz does to her...
• Orihime has lived alone since her brother died, had to suffer bullying throughout her school years and suffers from major self-esteem issues. Not to mention the whole reason she lived with her brother in the first place was because her parents were such abusive assholes that an eighteen-year-old boy took off with his three-year-old sister to raise her by himself. Her problems are only magnified after she not only has problems with the Barrier Warrior powers she was bestowed and specially with her Heroic Self-Deprecation, is forced into a Sadistic Choice by an Omnicidal Maniac's servant and taken into a Crapsack World. Things only got worse from there, and it took her quite a bit to get better.
• Ichigo tries to play the Stoic Woobie, but epically fails. For the longest time, he blamed himself for his mother's death, and became a Determinator who wouldn't let anything hurt his family or friends. Oh, and he Used to Be a Sweet Kid. He reached the point of a woobie. Just look at what Tsukishima's done to him! And Ginjou's revelations to Ichigo only made things much worse. It took a massive intervention to get him back to a functional state.
  • It gets even worse as the new enemy Vandenreich a group of Naziesque Quincies are keeping him in a cell of energy and are forcing him to listen to the screams of the Soul Society as the new enemy is tearing them all apart.
• Momo Hinamori, the sweet and gentle lieutenant whose obsession over her captain (Aizen) not only was groomed carefully by him, and eventually led to her near-death and coma. Her lack of briefing on the matter led her to believe that the one responsible (Aizen again) was thoroughly innocent for a long while, and right as she had managed to start getting over with it and return to the battlefield, Aizen tricks others into stabbing her. Eventually, she got a new captain and this new captain has been really kind to her that she became a lot more stable. Then the Vandenreich invasion happened and it looks like she could pull herself together, but unknown to her, her best friend Hitsugaya has been zombified and fighting for the enemy's side. Really, it's one disaster after another for Momo.
• Poor Hanataro, who just gets dragged around by the more powerful shinigami to help them out when they're about to fall over.
• Arisawa Tatsuki, Ichigo's childhood friend who is forced to attack her best friend Orihime by Numb Chandelier, is the only survivor among her karate teammates who were killed by Yammy's Gonzui, is coldly dismissed by Ichigo after she confronts him over Inoue's disappearance and his spiritual activities, and being chased by Aizen when his spiritual pressure alone could crush her in his Hogyoku state. The poor girl has gone through a lot.
• Abandoned in a hellhole by her sister, Rukia lost all her friends to death except Renji, who she loses when the Kuchiki Clan adopt her. Isolated by both her new high social rank and an adopted brother she thinks hates her, she latches on to her mentor Kaien. When Kaien is possessed by a Hollow, she's forced to kill him and cannot forgive herself. She's later sentenced to execution for illegally giving her power to Kaien's lookalike, Ichigo. She's emotionally tortured by Gin due to a fake promise of freedom and has her soul ripped open by Aizen to obtain the Hougyoku that Urahara had secretly hidden inside without her permission.