Nearly everyone.
- Caroline. Her dad abandoned her, she and her mother don't get along, she is constantly finding it difficult to fit in with her friends and is constantly overshadowed by Elena, she is abused and discarded by Damon and her boyfriend neglects her. Really, Katherine making her a vampire in Brave New World was probably the best thing for her. Later she has to deal with her mother getting cancer and not even turning her into a vampire could cure it and when she eventually dies, Caroline is so distraught that she turns off her humanity for the first time after her funeral.
- Stefan. There is NOTHING he hasn't been through: love issues, blood addiction, family problems, loss of loved ones, emotional and psychological torture, etc. The show should be called "The Perpetually Abused Stefan Diaries".
- Matt as well. He is still has feelings for his ex-girlfriend despite her finding someone new. His mother and sister are immature wrecks who don't care how much they mess up his life, and he's left with far more responsibility than anyone his age should have to deal with, and doesn't even have health insurance.
- Jeremy is one of the biggest cases. Lets count the ways Life has utterly screwed him, shall We? He loses his parents, he is in love with a girl who strings him along and is ashamed to be with him, he gets picked on by teachers, his girlfriend is later murdered and he is mindwiped into forgetting. When things start looking up, he finds out about his past and how the people closest to him deceived him. Just before his next girlfriend is murdered by his uncle and revealed to have been using him which makes him attempt suicide. And that's just in the first season.
- Bonnie should get the award for this trope. In season one, her grandmother dies after over-exerting herself by doing a spell that Bonnie had to convince her to do. Later, she hooks up with Jeremy, only for him to cheat on her with his dead ex-girlfriend's ghost. Then Damon turns her mother into a vampire. Caroline and Elena can go episodes without acknowledging her existence until they need her magic and while the latter makes out with the very vampire that has caused her so much misery. She was made the anchor to the other side and endured pain every time a supernatural being died. Then she was imprisoned in an eternally repeating day with one of her least favorite people then left there with murderous psychopath until she was eventually left ENTIRELY ALONE and almost committed suicide. Worse, her supposed bestie Elena went out of her way to have Jeremy – the only person who wanted to rescue her – graduate from high school early for no reason and get into art school so he could "move on" when they were closer than they'd ever been to getting Bonnie back. And after escaping the prison world she endured her PTSD alone… This girl needs a drink.
- Culminated when Non-Humanity!Elena tried to kill Bonnie, all the while blaming Bonnie for her own faults. Taken into consideration, Bonnie's 'response' is quite expected. Of course, not long afterwards she dies anyway in the process of bringing Elena's brother Jeremy back to life, so yeah... And the first episode of the next season has Silas slit her father's throat in front of a brainwashed crowd, with Ghost!Bonnie there to see the horror.
- Rebekah is an original vampire who longs to be a normal human and clings to any sense of humanity she can find. Not only that, but she's used and betrayed on a regular basis; even by her own family. Her father, mother, and older brother have all attempted to kill her. Her mother actually took over her body at one point. She's stabbed in the back by a girl she begins to finally open up to. And to top it all off, Elena has murdered two of Rebekah's brothers: Finn and Kol. You don't get much more Woobie-ish than that!
- Elena. The SHOW seems to be about how many more times can life put her through the meat grinder. She can't seem to go a single day without herself or somebody she cares about being hurt, killed, or under threat by some supernatural being ever since the first episode, she has 2 boyfriends that endlessly fight over her that she's constantly conflicted about, she's too compassionate to just blow off anybody who's suffering so she ends up putting herself in even MORE trouble, and to top it all off she has serious loss and abandonment issues. Elena crosses into Woobie, Destroyer of Worlds territory once she becomes a vampire and turns her emotions off.
- Aaron in season five is a contender for the crown. In the space of nine episodes, he has seen two of his best friends murdered, found out that his only other friend is a vampire and a killer, his only remaining guardian is a sadist who has been lying to him for years and he has had almost every member of his entire family, including his parents and aunt, murdered by Damon for things They didn't even know about. It's no wonder the poor guy seems to have a perpetual rain cloud hanging over his head. And now he's dead.
- Amara, Silas's immortal love. Her only crime was falling for a man above her station who was supposed to love someone else, and as punishment for that she ends up tied to the afterlife, turned to stone, imprisoned for over two thousand years while her mind deteriorates, she feels the pain of every supernatural death over those years, and when she's finally woken she's Driven to Suicide. And she only manages to get her wish after watching the love of her life die.
