- If anything, The Clone Wars has retroactively made Anakin Skywalker into a large woobie due to the events that happen to him over the course of the installment. During the Mortis arc, he is confronted by the truths of his destiny, emotionally manipulated by the Son, forced to duel Ahsoka, and Mind Raped into turning to the Dark Side. Later on during the Deception arc, he witnesses Obi-Wan's faked death, not helped by the fact that the Jedi Council deliberately kept him in the dark about it. Then in "The Wrong Jedi", Anakin does everything he can to help Ahsoka, but is powerless to clear her good name until it's very nearly too late and still loses his beloved Padawan when she leaves the Jedi Order, which results in him being left with one less Morality Pet. In the sixth season, it gets even worse, as Fives dies in "Orders" at the hands of Commander Fox. During the Clovis arc, his relationship with Padme is damaged by the presence of Rush Clovis. If there's anyone in the Star Wars canon who needs a hug, it's Anakin.
- The three Jedi younglings introduced during the Trandosha arc, who had been relentlessly hunted by the Trandoshans to the point where they had all crossed the Despair Event Horizon by the time Ahsoka arrived. Special mention goes to Kalifa, who struggles to keep the other two younglings safe and is the only one who doesn't get off Wasskah alive.
- Waxer's death scene sets him up as, arguably, the biggest woobie out of all the clone troopers during the Umbara arc.
- Fives. Apart from experiencing everything the other clone troopers have, he was almost executed by his own brothers and, before the Umbara arc, he had to cope with being the sole survivor of the Domino Squad. It only gets worse for him during the Order 66 arc, where he discovers the inhibitor chips implanted into every clone and eventually gets killed for it.
- The Father. After spending God knows how long keeping his children in check (and having to live with the fact that they, as he says, could tear apart the fabric of the universe), his only reward is to be dying by the time the Jedi arrive on Mortis, as well as nearly being murdered by his own son, watching his daughter sacrifice herself to save him, and having to arrange his son's death before dying of a self-inflicted stab wound.The Father: And now, I die, my heart broken...
- The Daughter, despite the fact that she was given the least characterization of the three Force-wielders. She's the embodiment of all that's good about the Force and is the very epitome of selfless. She then uses the power that could be used to save herself and sacrifices her life to save Ahsokas own.
- Although she is usually an Iron Woobie, Ahsoka becomes a flat-out woobie in "The Wrong Jedi", having been accused of a terrorist attack at the Jedi Temple, being forced to go on the run, the Jedi Council throwing her over to the Senate Court without a fair trial (not to mention that the Republic court wouldn't have helped either with Tarkin being more than happy to sentence her to death), and worst of all, seeing her best friend Barriss revealing herself as the true mastermind being the attacks. Even though Anakin barely clears her name at the last second, she becomes disillusioned with the Jedi Order that she ultimately decides to leave. As she walks away, she sheds a Single Tear, leaving behind Anakin, the Jedi Order and the only people she considered a family.
- Duchess Satine. She has had some of her closest friends either betray her or die in addition to being almost helpless to stop the corruption and terrorism that threatens her homeworld, nearly assassinated, framed for murder, tortured, and led to believe that Obi-Wan, with whom she's been in love for years, had been killed. It's only the last item on that list that's provoked an openly emotional response, with Satine breaking down in uncontrollable tears. By that point, it's hard to blame her for crying. And in season five, she is helpless to stop Darth Maul from sowing chaos on Mandalore and equally helpless to prevent Pre Vizsla from using the chaos to conquer Mandalore along with throwing Satine herself into prison. To compound this suffering further, Vizsla is then killed by Maul and Almec pins Vizsla's murder on Satine in order to near-unanimously turn Satine's people against her while her world is left to be ruled by a sadistic monster. And finally, in "The Lawless", she is brutally murdered by Darth Maul, who uses her death to torture Obi-Wan.
- Rush Clovis in "The Rise of Clovis" and "Crisis at the Heart". Given a chance to do good by taking a chance to lead the Banking Clan, but his taking the position was just to turn him into an Unwitting Pawn of Dooku and Sidious, ends up bringing the war to Scipio and he watches everything fall apart around him. In the end, he sacrifices himself (possibly out of guilt for his actions) to save Padmé's life, and to pour more salt in the wound, he gets scapegoated for the corruption in the Banking Clan and control of the banks falls into the hands of Palpatine.
Woobie / Star Wars: The Clone Wars