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- Vua Rapuung, a Yuuzhan Vong warrior who fell in love with a Yandere bioengineer. When this was about to come to light, she denied it and discredited him by making his body reject his implants, considered a sign of divine disfavor in the Vong's death cult.
- Ben Skywalker, who is remarkably aloof about working for an SS-like organization, until, of course, his mother is killed and his father and Jacen are openly in conflict. That, and the implication of having emotional fragility after violent events.
- X-Wing Series:
- Tycho Celchu's extremely unfortunate backstory—pilot for the Empire who had been talking to his entire family on Alderaan when it was destroyed and initially thought it was normal comm breakdown—combined with his near-breaking in a secret prison and his incredible patience when he's believed to be an Imperial double agent and comes under heavy suspicion, particularly being framed for Corran's apparent death, is probably a good percentage of the reason why he ended up being far more popular than his creator ever imagined.
- Quietly lampshaded in Starfighters of Adumar. By that point, while Tycho's not as tragic as he used to be, having picked up the pieces and made a new life, he still looks sad, and his history is there to see.
- Poor Lara Notsil. A former Imperial Intelligence agent who, after infiltrating the Wraiths, ends up realizing her leaders are morally bankrupt while at the same time coming to love her cover identity and want to stay in that life thanks to The Power of Trust. Then her identity is exposed... causing the last surviving member of a squadron her espionage had helped kill, who had been falling in love with her, to try to kill her in turn. Couple this with her Intelligence training having completely messed up her head and ruined her life so she has no idea who she is or how to be happy, and she's a prime source of Woobie material. It's only the fact she manages to survive her final battle and escape to a new identity, where she eventually reunites with Donos and they marry and have kids that saves her story from having a complete Downer Ending.Lara: There was never a time I saw a file labeled "How to Destroy Talon Squadron" and thought to myself, "Oh, that's what I want to do." To me it was just data about occupied territories and interplanetary borders. Then I infiltrated Wraith Squadron, just a ploy to make myself more valuable to prospective employers, and things started happening. All the furniture that made up the way I'd thought and felt about things all my life started coming loose in my head. Nowadays it slides around and breaks into pieces and I have no idea what parts of it are real and what aren't. It hurts, and a lot of the time I don't know who I am anymore. But I know what I have to do. Whoever I am, I'm staying here, like a vibroblade right next to Zsinj's vitals, and when the right time comes I'm going to stab him deep. That'll probably be the last thing I do. I don't have any friends here, except one droid, and I don't have any where you are, or anywhere else in the galaxy, so when I'm gone there isn't going to be anyone to remember me kindly. So I was just sort of hoping you wouldn't hate me anymore. I really can't stand thinking that's the only way I'll be remembered. I wish I'd been someone else. To give you that chance you wanted.
- Donos himself counts as well, first due to the loss of said squadron, then his Heroic BSoD when he loses his droid Shiner who had been the last Talon in his mind, who as long as he lived would keep him from being a complete failure. His squadmate Falynn Sandskimmer falls for him while helping him recover from this loss, but by the time he realizes and is in a state to even consider returning her feelings, she's died bringing down the Implacable. Then he falls for Lara, and it all goes downhill from there. He does finally manage to put his sanity and life together again, and finds her in her new identity so they can start a family and a shipping company together on Corellia.
- You really have to feel at least a little sorry for Lorana Jinzler, a young Jedi from Outbound Flight. She's got a domineering Master with no confidence in her, and so she has little confidence in herself and not much say in what she does and where she goes. A man confronts her and turns out to be the brother she never knew, angrily telling her that the parents who never knew her loved her more than they loved him. She wants peace and acceptance and to get along, but her Master is totally blind to that, starts all kinds of conflicts, and eventually indirectly dooms Outbound Flight despite her efforts. Lorana steals a hand-holding with a Chiss syndic as they sacrifice themselves to save all the survivors. No one ever knows what she did, and the survivors she died to save curse her name for decades.
- Death Star:
- Poor Tenn Graneet: The guy spends the first half of the novel as a carousing badass in love with BFGs and More Dakka whose main ambition is to pull the trigger on the biggest BFG he can get his hands on. Then he gets transferred to the Death Star and get ordered to blow up Alderaan. It doesn't end particularly well.
- The Alderaanian contractors on the Death Star. Bad enough that The Empire chooses their home planet to demonstrate its destructive power, but they're on the kriffing station that did it. And then that sergeant comes in and gloats about it. Talk to the Fist, sithspawn!
- Scout, poor kid. She's a Jedi Padawan who is the epitome of Weak, but Skilled, having little Force ability but ridiculously determined to make up for it by perfecting all other skills. She lives in fear of being washed out of the Padawan ranks and sent to labor in the less-glorious Agricultural Corps; she was ecstatic when a Master picked her as Padawan... and then that Master died early in the Clone Wars. Scout tried harder, tricking her way into winning a tournament of unattached Padawans, and ended up with a reluctant new Master... who only finally accepted her in the moments before he died. She gets some happiness in the last book of the Republic Commando series, when she becomes the unexpected guest of Kal Skirata and his Mandalorian clan.
- "Happiness". Mandalorians, as written by that author, are universally deeply anti-Jedi, and Jedi universally either get proven wrong by them constantly, or don't even protest the vitriol that's chucked at them, tucking their chins and accepting that they're inferior morally, philosophically, and so on. Scout is described as looking and acting very similarly to Etain, a young Jedi who fell in with them and quickly learned her place, that she should never question them, and that they're all smarter than her and should be able to govern her life and body. Scout goes from an assertive girl who Master Yoda says has impressive spirit and determination, and isn't to be underestimated, to someone the Jedi think are useless.
Scout: Oh, thanks, but I'm a Jedi. I can still be a Jedi, can't I? It's all I ever wanted to be.Mij Gilamar (Mandalorian): Of course you can.
- Except that's not what happened. Etain was treated as an equal by them for most of the story. Kal Skirata even almost went to blows with Walon over insulting the women his Clones fell in love with, and treated Etain throughout like a surrogate daughter, hating himself for screwing up with her and never getting the chance to make things right. Throughout the story, the two Jedi with them are fully aware and determined to help the Mandos in their quest to free some of the clones, because they truly want to help them, and are never talked down to. In fact, they warn Bardin to calm it down, because they worry him going native will cause other Mandalorians to attack him for being a wannabe and taking their culture. In fact, the main characters discuss killing Death Watch traitors more then killing Jedi. Scout herself is allowed to keep being a Jedi, by the Mandalorian that basically adopts her.
- Jacen. Sure, he turned out to be a horrible, evil Sith tyrant similar to his grandfather, but he did it because he genuinely thought it was the only way to save the galaxy—and his daughter. Really, the only thing his lives for in the end is his daughter. He nearly obliterates Aurra Sing when she tries to kill poor Allana, and, when he finds out about the deadly virus bioengineered to kill Allana and his lover, Tenel Ka, instead of defending himself from his sister's killing blow, he screams a warning to them through the Force, becoming his old Jedi self the instant before he dies.
- For that matter, Allana. She lost her father to the dark side and she almost never gets to see her mother owing to the fact that Allana is supposed to have died in the virus attack, covering up for the fact that Jacen was her father; Tenel Ka had to give Allana up to the Solos to preserve the illusion, yet she manages not to go insane.
- The Jensaarai of I, Jedi. Coerced into helping a Pirate queen pull her mooks' choobies out of the conflagration (or else their Protectorate will be annihilated), and the Saarai-Kaar herself has lost her (evil, but she didn't know it) mentor to a Jedi team and her son to Darth Vader.
- Choices of One:
- Ferrouz, when Mara gets to him and finds out his reasons for offering the Rebels sanctuary.
- Sorro retroactively becomes one when it's discovered that he's only working for who he is because his family was kidnapped and threatened.
- Mara Jade, at the end, waiting for the Hand of Judgment to come back, and missing them. Despite the fact that she basically conscripted them and never told them her first name, she trusts them and is unhappy when they don't come back. It's an unfamiliar feeling. There are two constants in her life—the Emperor, who she could never miss because he's always there, and people like Vader, who she could take or leave. It really illustrates how she really does have no other friends or allies—when she later tells Luke that he destroyed her life, she wasn't exaggerating.
- Thrawn of all people shows a hint of this when Car'das asks why Thrawn picked him. Thrawn lets his icy stoic exterior crack slightly into a sad smile. "Because you're the only one I trust."Car'das stared at him, some of his own self-pity fading away into a fresh pool of shame. Thrawn had left everything: his home, his people, his prestige, his life. He'd dedicated himself to protecting the civilized parts of the galaxy against pirates, warlords, and distant, nameless nightmares that Car'das could barely even imagine.
And yet, in the end, all that work and sacrifice had come down to this. The greatest military mind of the age, with only a single, solitary, worthless man whom he could trust.
- Car'das himself, as he spends much of the mission wondering why he's there and considering himself worthless, only along because he has nothing better to do and it's something to do other than think about dying.
- In Luke Skywalker and the Shadows of Mindor, the Book-Ends, taking place after the main story, have Luke hiring a private investigator to build a case that he's committed war crimes, then later finding that the investigator had decided to write a swashbuckling holothriller script based on the events instead. The whole time there's the sense that he's on the brink of despair, as when he describes his 'best trick'.Skywalker lifted his face from his hands, and his eyes were dark. Wounded. Haunted by shadows. "My best trick is to do one thing—to make one small move, even a simple choice— and kill thousands of people. Thousands."
- In the Clone Wars Gambit novels, Obi-Wan is even more of a woobie than he is in the films. In Wild Space, he spends several days on a Sith planet getting tortured by a Sith device with the ability to dredge up his worst memories and make him experience them all over again as if it were the first time. In addition to getting really badly injured physically, he has to repeatedly experience the death of Qui-Gon, Xanatos drowning in acid, the grisly torture of a man called Tayvor Mandirly, the battle of Geonosis, Anakin losing his arm and a multitude of other traumatic memories. Add to that the incessant murmur of die Jedi, die Jedi, die Jedi, die and it's a wonder that he managed to stay sane.
- And then there's Stealth and Siege, which basically amount to two entire books of Obi-Wan getting seriously injured and mentally exhausted, but retaining his status as both a Messianic Archetype and a Deadpan Snarker. He gets a few hugs from Taria, but she's going to die very soon. And knowing what lies in his future... The poor man is in serious need of a hug, not that he'd ever admit it.
- Zayne Carrick from Knights of the Old Republic is the woobie for the first 2 years of the comic's main story: he's framed for murder, forced to learn that his friends never believed in him, is thrown in prison, and towards the end his girlfriend tries to kill him twice. After proving his innocence to said girlfriend and getting a real lead in clearing his name, his luck slowly picks up until he earns his happy ending after the Vindication arc.
- The Dark Times comics, which take place right after Revenge of the Sith, regularly put characters through the wringer, but minor character Crys Taanzer probably takes the cake. Poor woman's life since her appearance in the comic has been nothing but Tear Jerkers, Hope Spots, and dog shootings (yes, both kinds). It culminates with her being infected by Raghoul Plague, and her captain being forced to shoot her dead before she finishes transforming into a mindless murder machine. Poor woman definitely deserved a lot more hugs.
- The planet Orvax IV is a woobie factory. Especially for those who are sold, or whose loved ones have been sold, to Dezono Qua.
- Poor Jorin Sol. A combination of bad circumstances served to utterly destroy the innocent and unassuming man. Jorin was a mathematician working for the Rebel Alliance who had almost nothing to do with the military aspect of the Rebellion, and was instrumental in devising a hyperspace jump algorithm that the rebel fleet used to meet up if they were attacked and had to flee. During a routine mission of diplomacy taken alongside Leia and Luke, Jorin was quickly caught up in a nasty course of events that led to him being turned over to Darth Vader by a traitor. Vader led Sol away for a private interrogation session, and afterwards turned him over to a group of Imperial specialists with orders to turn him into a sleeper agent. Over the course of several weeks, Jorin was tortured almost endlessly to break his will and make him more susceptible to brainwashing. They learned of the hyperspace algorithm and used it to set a trap for the rebels, allowing Sol to be rescued so as to put him in position to assassinate leaders if the chance arose. During the fleet battle that followed, Jorin broke through the mental conditioning long enough to tell the Rebels to make random jumps, lest they continually find Imperials waiting for them. Finally, he managed to fight through the brainwashing in order to initiate the rebel flagship's jump, at the cost of his own life when the badly damaged ship's bridge exploded.
- From the same series of comics is Deena Shan, a minor woobie who is, as her father told her, always in the wrong place at the wrong time. One of her first missions after joining the Alliance was to an unknown planet that happened to be infested by a vicious, man-eating plant creature—but she was with the Heroes, so she escaped unscathed. A little while later, Deena was included in a mission to rescue Jorin Sol (see above) and posed as an Imperial officer. During her stay at the base, she helped set a trap for the Imperials, but fell for the dashing young Imperial Captain Kale Roshuir... who soon lost his entire squad to said trap and quickly figured out that Deena was behind it. She barely escaped his vengeful wrath with the other rebels and became alcoholic. When undertaking an unauthorized mission with Luke Skywalker, she heard a door open behind her and turned to find Captain Roshuir flanked by a squad of stormtroopers. She and Luke narrowly escaped that situation, only to be sternly punished for disobeying orders.
- Prince Kaspar. He wanted to get married and do his planet a good turn. He met Leia, who promised to marry him (this was before she got together with Han), and helped arrange for the Rebels to have a base set up on his planet. Unfortunately, traitors within his palace alerted the Empire and killed both his parents. On his wedding day, his palace was bombed, his bride attacked (but escapes, obviously), and his mentor turned on him (and stated outright that he was responsible for the deaths of the king and queen). Kaspar was forced to shoot said mentor in the face—and the look on Kaspar's face implies that either he was so overcome with grief that he pulled the trigger in a fit of rage, or that he was horrified by the act he was committing. Within a matter of hours, his bride has fled the planet, his home is in shambles, and he now has to lead his people... who are no doubt going to be targeted by the Empire. The best part? He sends a message to Leia, who refuses to answer it (although she does admit she should be the one to blame for what's going to happen).
- Knights of the Old Republic:
- Zaalbar is a Woobie who is a hairy bipedal humanoid from the planet Kashyyyk. His brother betrays him, his father exiles him, he's sold into slavery, escapes to help out a little girl on a planet which hates aliens, gets captured again, swears the life debt that is the Wookiees' hat when rescued, and comes back to his homeworld only to find himself in prison while corporate scum ravage the planet.
- Even the player character, if you go Light Side, is something of this by the end; and the back-stories make almost everyone one of these:
- Mission Vao, street-smart teen, was brought to Taris at age 5 by her con artist brother, stowed away on a cargo ship—and then he left her there, to deal with the gangs and flesh-eating mutants by herself.
Worse, after you leave Taris, she doesn't even have a what little she had anymore. The Sith pretty much reduced Taris to rubble. When you meet her she's probably a bit overconfident. When Zaalbar is captured she panics and acts a few years younger than she is, but bounces back once you go after the Wookie. Once you escape Taris, though, she's very quiet. Playing light side you can really help her out both then and throughout the game, but Mission sure had it rough.
- Carth Onasi held his wife in his arms as she died in an attack on their home world led by his former mentor, then couldn't find his teenage son. During the course of the game, you can find his son on Korriban—as a member of the Sith.
- Jolee Bindo had to fight his own wife when she fell to the Dark Side, but couldn't do it, and has lived with the guilt of knowing she actually killed people after he let her live, ever since.
- Juhani. When she was a baby, the Mandalorians started a genocide of the Cathar, decimating her homeworld; her parents fled with her but were only able to get as far as Taris, the same human-dominated cityworld Mission hails from. All of her life, the only other Cathar she's ever known has been those two. The massive Fantastic Racism on Taris, and the stigma of being part of a species believed to be made entirely of violent warriors meant they had to live in the worst slums. Her father turned to stimulants and was shot by a human. Her mother broke inside after that, wasn't able to make enough money to feed herself and her daughter even after turning to a Loan Shark, and died of illness. Immediately after that the loan sharks, settling the debt, took her as a slave, bound her like a beast and treated her like one. She was almost bought by the man who killed her father, who had helped with the genocide on her homeworld. The Jedi came and saved her, and said she could become a Jedi too, but it wasn't over for her.
She made some friends at the Jedi Academy, but one of them ran away and joined the Sith when she couldn't return his feelings. Her Master goaded her into lashing out and allowed Juhani to believe that she'd killed her own Master; horrified, Juhani ran away to lurk in a meditation grove and tried to convince herself that now that there was no turning back, she had to embrace her darkness. The player character can convince her to stop and go back to the Academy, at which point she finds that it was all a lesson, to show her how easy it was to fall. Then, hastily promoted from Padawan to Knight, she is sent to join the player character, partly as a lesson to them about the Dark Side.
- Bastila; barely-trained Padawan with the weight of the whole war effort dumped on her shoulders before even finishing her training. Learns that her father, whom she missed terribly when she became a Jedi, has died without ever seeing him again. Reconciles with her mother only to learn mom has a terminal disease so she might never see her again. Has a direct mental link to an ex-Sith Lord exacerbating her existing problems with resisting The Dark Side. Probably scared stiff, and acting like an Ice Queen as a coping mechanism.
- The Jedi Exile would have to count. Followed Revan to war to stop the Mandalorians. Malak wanted to kill her. Was led to Malachor V for the final battle where it turns out those who were not loyal enough were to be killed. The pain of the deaths of her allies forced her to cut herself from the Force to survive. She returns to the Jedi only to be exiled. And this is just the backstory. Jump ten years and she is one of the last Jedi. Hunted by the Sith, bounty hunters and criminal organizations. Her mentor turns out to be using her for revenge. The allies she gathers hate each other. She is ultimately captured and forced to work for the crime boss hunting her. Her life is owned by a Mandalorian bounty hunter. One of the last remaining Jedi wanted her dead before she fell to the Dark Side. The remnants of the Jedi declare her too great a threat to be allowed to retain her new found Force sense and intend to sever it. And she still returns to Telos to save it from the Sith after all of that.
- Visas Marr as well. Feels her homeworld destroyed around her through the Force which damages her Force Sight in the process and is then taken by Darth Nihilus, the being responsible for the destruction of her homeworld, as his servant. Nihilus then crushes her spirit so utterly that by the time the gameplay starts she is begging him to kill her. When she fights the Exile the implication is that she wants to be killed by him/her. And to cap it all when she joins your crew she seems surprised and confused that the Exile would take the time to show some basic human decency and ask if she's alright.
- From The Force Unleashed, Starkiller, without a doubt.Juno's voice: Who are you?Starkiller: Juno, it's me!Juno's voice: You're a monster, a thing.Starkilller: [sounding like he's about to cry] Juno, please!Kota's voice: You're Vader's puppet. Just a body filled with the memories of a dead man.