Damon Salvatore's character evolution through the people he hurt looking at this poster, I realized Damon has directly or indirectly hurt almost every single one of them. he killed some, nearly killed others, manipulated them, betrayed them or caused them unimaginable pain but what's interesting is that, over time, many of these same people became people Damon genuinely cared about Bonnie Damon spent a long time treating Bonnie like an obstacle, constantly clashing with her she's a witch, we know how much damage witches caused...but after being trapped together in the Prison World, their relationship completely changed. He became one of the people who would do almost anything to get Bonnie home Caroline Damon's treatment of Caroline in Season 1 was one of the darkest examples of his early behavior. he compelled her, fed on her and used her for his own purposes, leaving her terrified and traumatized. Years later, their relationship became surprisingly civil, and Damon genuinely cared about Caroline and her family Matt Damon never had much patience for Matt, but he crossed a major line when he snapped Matt's neck in front of Elena to force her humanity back on. Matt survived because of the Gilbert ring, but Damon deliberately used him as a means to an end Damon eventually came to see Matt as someone worth protecting rather than simply another human standing in his way Tyler Damon repeatedly put Tyler in danger and eventually killed him in Season 8 after Tyler confronted him about what he had become(his fault tho, Damon and Enzo were protecting them from Cade) Jeremy Damon snapped Jeremy's neck in Season 2, knowing Elena would be devastated by it. Jeremy survived because of his Gilbert ring, but Damon had deliberately crossed a line to get what he wanted. over time, Damon became protective of Jeremy and helped keep him alive when the supernatural world kept coming for him Alaric Damon once stabbed Alaric with a stake during a confrontation, only for Alaric's Gilbert ring to bring him back Somehow, the two went from enemies(trying to kill each other) to one of the funniest and most genuine friendships in the series. Enzo St. Johh (my Goat) Damon left Enzo to die in the Augustine facility, a decision that haunted their relationship for years. He also killed Maggie, the woman Enzo loved, further deepening the resentment between them. Despite everything between them, Damon came to see Enzo as a brother (imo) Elena Damon hurt Elena in ways that are impossible to ignore. he killed Jeremy right in front of her, repeatedly put the people she loved in danger, and even compelled her to forget their relationship because he couldn't handle losing her But Damon also loved Elena deeply and repeatedly risked his life for her and the people she loved. Stefan Damon's relationship with Stefan is probably the clearest example of his destructive side. He spent years blaming Stefan for his misery, killed Lexi But underneath all of it, Damon never stopped loving his brother, and eventually became someone who would sacrifice himself for Stefan. That's what makes Damon such a complicated character of the list of terrible things he's done is LONG. but so is the list of people he eventually learned to love, protect and sacrifice for.