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Many characters qualify at some point in the story, they are, after all, mostly teenagers thrown in amidst of a war between forces they neither comprehend nor were ever warned about, in a world where creatures that hunt by mortal despair, grief and destruction are always looking for new victims. The show really may as well have been called "WBY" instead.

Spoilers up to the end of Volume 6 are unmarked. Proceed with caution. You Have Been Warned.

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    Iron Woobie 
  • Ruby Rose began as just a Woobie, but transitioned into this ever since the end of Volume 3. Despite all the events mentioned below, she goes off with the remainder of team JNPR to go after Cinder themselves, and Jaune makes clear that Ruby is a source of inspiration and bravery for team RNJR, as in the worst possible situation, and after having lost so many people she loved, she still finds the strength to fight:
    • In "PvP" she found out that the people from Haven Academy that she'd considered friends have been manipulating her and her team all along, and watches a close friend gruesomely dismember Penny in the tournament, thanks to said fake friends. Considering that all her life, she'd never been lied to in such a manner, this must be rather difficult for her to handle.
    • Things only get worse for her in "End of the Beginning" wherein she sees her sister's condition, witnesses the death of Pyrrha at Cinder's hands, and after being stuck in a coma for a few days awakens to find out that her team has disbanded in her absence. In Volume 4 Episode 2, it's revealed she has nightmares of Pyrrha's voice, hinting that she may have Survivor Guilt. This is further emphasized by when she goes to check on Jaune one night, and sees her friend broken by her failure to save Pyrrha.
    • Once Qrow intervenes in RNJR's battle with Tyrian, she forces her way into a battle that's far beyond her level, despite being told repeatedly to keep her distance. Bear in mind, this warning came from her own uncle who, presumably, knows her capabilities better than anyone. This results in Qrow's semblance kicking in, and Qrow getting stabbed and possibly fatally poisoned.
  • Nora Valkyrie spent her childhood as an orphan Street Urchin, often having to steal food from the garbage in order to feed at all, being bullied by other kids, she was alone when the Nuckelavee attacked the village, being stuck below a house until Ren saves her, she then goes on to survive with him by her side, deciding to suppress her feelings for him. Way later, she faces the death of her good friend Pyrrha, and to find answers, she agrees to leave everything behind and go with Ren, Jaune and Ruby to Haven, at which point, she has to face with the Nuckelavee again, in a battle that almost costs Ren's life due to his own Unstoppable Rage, until she has to snap him back to sanity. Despite having a hard life and her still-unexplained Mysterious Past, she keeps her cheerfulness, bravery and keeps the spirits high in her team.
  • Ozpin has... had a rough existence. He was originally a hero who rescued a lonely girl named Salem, trapped in a tower. The two fell in love, but he soon fell ill and died. His lover tried to bring him back by asking the gods to revive him, but her method of doing so soured things. The God of Light asked him to bring the next group of humanity together, but he would not be able stop reincarnating until he did. On top of that, he reunited with the woman he loved and began to act as the new gods of the world, and started a family. However, he eventually began to realize that the woman he loved had changed. He tried to leave with their children one night, but he was caught. His wife attacked and killed him (and it's highly unlikely their young daughters survived the fight). He spent many incarnations drowning in alcohol his sorrows and trying to avoid thinking about it, but eventually he came back to the quest he was given and continued to work toward bringing humanity together, becoming the king of Vale and forming the academies to ensure they could fight back against the creatures of Grimm. However, the knowledge that Salem couldn't be destroyed weighs heavily on him, and his cycle of reincarnation has largely taken a toll on his ability to believe in people, due to how many times he's been betrayed. Nevertheless, he insists on encouraging others to believe in humanity and hasn't stopped trying his best to keep the world safe from Salem.

    Stoic Woobie 
  • Lie Ren. Despite being very calm and polite most of the time, his backstory is easily among the most traumatizing of the main characters: during one night, a devastatingly powerful Grimm invaded his village; during said invasion, his mother died before his eyes and his father died attempting to give him time to survive; the trauma awoke his Semblance in time for him to save himself and Nora, which leaves them as the two sole survivors of the entire village. Making matters worse, Episode 10 makes it clear that the same Grimm that killed his father and destroyed his village is back and just a few meters ahead of him.

    The Woobie 
  • Blake Belladonna. Where do we begin?
    • During Volume 1 she is revealed to be a Faunus, and was subjected to Fantastic Racism by Weiss, with the result being feeling isolated from her team. This was somewhat ironed out in the following episode.
    • In Episode 5 of Volume 2, the events going on outside of school seem to bear down the most heavily on Blake, making her haggard and snappish towards Sun and her teammates.
    • In "Mountain Glenn", she is shown to have a great deal of self-loathing because she sees herself as a coward who only runs away.
    • Then in "Heroes and Monsters", she's attacked and stabbed by Adam, a man she's implied to have had a romantic relationship with, who then slices Yang's arm off right in front of her when Yang tried to intervene. Word of God actually confirms that her relationship with Adam, the one person who took her in and cared for her as a fellow Faunus, was an abusive one.
    • After the fallout of Beacon's invasion, the rest of the main two teams are with friends/family (Ruby and Yang are together and with their dad, Weiss may be with her sister and father, who cares about her safety enough to have her taken back home, Ren, Nora, and Jaune have each other and Ruby with them), but Blake is completely alone, separated from the people she'd finally warmed up to after so long. So, she runs off back to Menagerie, where her parents live, but is followed by Sun Wukong, who has a crush on her. They manage to get along a bit. However, the White Fang have a presence there as well. And some of her interactions with Sun are rather abusive, which might be due to her past relationship with Adam.
  • Jaune.
    • He lost Pyrrha to Cinder and his other love interest Weiss left for Atlas to go back home, and to make matters worse, Pyrrha didn't complete his training with him. To make matters even worse he loses Pyrrha right after sharing his First Kiss with her and doesn't even get to see her before she dies. Then there's the song "Cold" that plays in the credits which clearly shows he's still hurting from Pyrrha's death even weeks/months later. On the lighter side, Ruby decided to join Team JNPR as a replacement huntress after Pyrrha's demise.
    • In Volume 4, he continues his training the only way possible: by listening to a recording of Pyrrha over and over, said recording also having her almost-confession. The face Jaune makes when he hears that confession can be interpreted in many ways, but none good. To make matters even worse for him, come Chapter 9, he has to separate from Ren and Nora for strategic (and Ren's emotional) reasons. The look on his face is a mixture of heartbreak and bottomless worry and the way he hugs Ren drives home how scared he is of losing his friend.
    • Volume 5 reveals during his battle with Cinder that he's become a Death Seeker who no longer values his own life, being content with the possibility of dying just to buy his teammates a little time.
  • Taiyang Xiao Long, Ruby and Yang's father, lost both his two wives (Yang's mother Raven and then Ruby's mother Summer) and then his two daughters. And to make matters worse, his brother-in-law and close friend Qrow has ditched him to look after Ruby.
    • Raven and Summer had both been on a Team with him when they were in the Academy and knew each other for many years. According to Yang, the loss of Summer had caused him to "shut down".
    • In the aftermath of the Battle for Beacon, his eldest daughter, the only link he likely has left to Raven, has lost an arm and is now going through her own bout of depression (with all the Fridge Horror about depression and Grimm that entails.) His youngest meanwhile had spent days in a coma after using unknown magic, and a few weeks later, has decided to go after the villain herself leaving only a note explaining what she's planning to do. As of Volume 4, he now has to deal with his daughter suffering from PTSD as well where he can only watch and wait while his youngest daughter and brother, two-thirds of his already shattered family, are being chased by the Grimm and Salem's own associates.
  • Qrow Branwen is an alcoholic loner, raised with his twin sister, Raven, by a Bandit Clan who named him after the crows they believe bring bad luck. His permanently-active Semblance brings misfortune to all, benefitting him in battle but forcing him to distance himself from loved ones to protect them. Sent by the tribe to Beacon Academy to learn how to murder Huntsmen, Professor Ozpin changes his life by being the first person to ever see past his curse and give him a place in life; abandoning his tribe to become Ozpin's most loyal follower in the Secret War against Salem damages his relationship with his sister, whose mistrust of Ozpin leads her to eventually make the opposite decision.
    • After the Battle of Beacon, Qrow struggles to cope with Ozpin's responsibilities and starts drinking more heavily. He tries to look after Team RNJR from a distance to protect them from his Semblance until they're attacked by Tyrian Callows, where his intervention gets him poisoned when he has to save Ruby from being killed by his own Semblance.
    • When Qrow seeks Professor Lionheart's help, he inadvertently reveals to Salem's forces the secret location of the Spring Maiden: his sister's tribe. Previously neutral, Raven is forced to side with Salem against Ozpin, leading to a betrayed Qrow disowning her completely.
    • And in Volume 6, his entire world collapses when the heroes learn the truth about Ozpin's past; his confrontation with him devastates both men for the rest of the Volume, forcing the students to take over as Ozpin disappears and Qrow descends into an ever-worsening spiral of drunken despair.
  • Weiss, though at points she's more of a Jerkass Woobie, had it rough both during childhood and during the different volumes' events.
    • What little we know about her background implies that her more hostile tendencies are the result of a very troubled childhood, and her expressions in "A Minor Hiccup" manage to convey quite a bit of pain. Her uncharacteristic rant in "Black and White" has her flat out say that watching family members go missing, or worse, be executed, is par for the course for a Schnee.
    • Volume 4 and the World of Remnant episode focusing on the Schnee Dust Company reveals that this was not always the case - the original owner of the Company actually cared for the people, but when Jacques married into the family, he transformed it into a monopoly that effectively ran everyone and everything into the ground in Jacques' desire for more money and power.
    • During Volume 4, when she's finally given a shot at independence, she's captured and held prisoner by bandits, threatened with the idea of being ransomed back to her father.
    • And then, during Volume 5, she's beaten down and nearly killed by Cinder.
  • Pyrrha Nikos. Her death is even considered the turning point towards the Darker and Edgier tone the series takes.
    • In "Fall" she's hit with knowledge that contradicts centuries of history. She is pressured by the headmasters, Ironwood, and Qrow to take what's left of the current Fall Maiden's Aura. The process would involve artificially forcing Amber's Aura into Pyrrha, and nobody knows what that will end up doing to Pyrrha, but they speculate that she may not be the same person. To see her abruptly thrown into the thick of things, and become so fearful of the headmasters she once respected and trusted is heartbreaking. The implications of this can be even more heartbreaking for her, among which are how she may be put on an even higher pedestal, isolating her even more from people, and how she may be another target of people who wanted the Maidens' powers. It really doesn't help when Jaune, the boy she loves, tells her to fulfill her destiny at any cost, not knowing what she's going through.
    • In her match against Penny, she ends up being tricked via Emerald's illusions into dismembering Penny in front of the whole world, subjecting her to the same fate as Yang. She's so horrified by what happened that she almost gets killed by a Nevermore. She decides to inherit the Fall Maiden's powers as things get progressively worse at Beacon however before she can receive the powers fully, Cinder kills Amber instead.
    • In the end, after a Now or Never Kiss with Jaune she has one Last Stand against Cinder that ends with her painful, fiery death.
  • Not even Yang Xiao Long is safe from Woobieness.
    • During the Vytal Festival Tournament, she's tricked into making herself look like an absolute monster on live television by Cinder and co., which gets Team RWBY disqualified from the tournament. Blake's initial hesitation to keep trusting her brings tears of pain to Yang's eyes, and Yang later loses her arm trying to save a wounded Blake from Adam, who has sworn to destroy everything Blake loves, starting with the approaching Yang.
    • Then, during the Time Skip between Volumes 3 and 4, Team RWBY is then forcibly disbanded when Weiss's father marches her home to Atlas and Blake runs away from Vale without a word to anyone, leaving Yang feeling betrayed and isolated. It hits hard that Yang stated early on that she would consider Beacon home - in the space of one night, Yang lost a home, nearly everyone she loves, her ability to fight and is left almost alone to pick up the pieces of her shattered life. The beginning of Volume 4 shows her struggling with life at home and flashbacks to Adam that are triggered by her dropping a glass on the floor indicate she's suffering from PTSD. Combined with her backstory of losing a parent, a history of being left behind by the people she cares about and the events in the woods, and Yang makes for perhaps the biggest Woobie in the entire series.
    • In Volume 5, not only Yang's PTSD is still there, as her remaining hand shakes whenever she gets agitated or upset, but it's made clear that of all the above, the thing that hit her hardest from the fall of Beacon was that Blake left without any explanation - she wanted to be there for Blake and needed Blake there for her, but Blake left.
  • Amber, the previous Fall Maiden, first appeared in "Fall" in a critical state, barely kept alive on life support. "Beginning of the End" shows how she came to be in her current predicament; one late evening, she happened to come across a crying child on the road, and offered said-child aid and comfort. Turns out the "child" was an illusion planted by three assailants intent on stealing her powers, an atrocious act never committed before. After a lengthy fight, one of the assailants critically wounds Amber with an arrow to the back, before the other two hold Amber down, allowing the remaining assailant to subject her to a torturous process to steal Amber's powers, which is only interrupted with the timely arrival of Qrow, but not without leaving Amber with a horrendous facial scar while rendering her into a coma. Since then, she's been in a state where she's unable to wake up, with her caregivers acknowledging that she will likely die soon. In "Heroes & Monsters", she is killed only after having woken up by the same assailant who put her into her predicament in the first place (with an arrow to the heart).
  • Oscar Pine. A small boy, living with his aunt on a dirt farm in bumblesquat nowhere, finds his mind invaded by the soul of an ancient, horrifyingly powerful man, suddenly has memories he didn't have before, loses all sense of privacy, and starts going insane before Ozpin gets the explanation through to him. A sense of moral obligation - and Ozpin's pestering - force him to abandon his aunt without warning, then charge through the rain to a train station, where he can't afford a ticket. He gets spooked by a member of Salem's group, then has to make his way to Mistral, all the while Ozpin floods his mind with knowledge of the ancient conflict between himself and Salem. By the time he finally meets Qrow and team RNJR, he's scared, alone, and confused. Luckily, he does gain some confidence later on, until Ozpin's manipulations are revealed to the heroes that is. Not only Oscar is now aware of how hopeless the quest he was drafted for is, but he is put between Ozpin and the bunch of huntsmen angry at him, suffering abuse due to someone else's mistakes.

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