|This article is about Damon Salvatore from the TV Series. You may be looking for Damon Salvatore from the novels.|
|“||Look, what happened to Enzo is gonna haunt you and her for the rest of your lives. But the you standing with me right now, the you that's gonna marry Caroline Forbes tomorrow, the you that I have known for almost 200 years, you didn't do it. Evil, nasty, Ripper Stefan did it, and you are not him. You hear me?||”|
Damon Salvatore is one of the two main male protagonists of The Vampire Diaries. Damon was a 178-year-old vampire and distant descendant of Silas. Since his younger brother, Stefan Salvatore, injected him with the Cure, he is now human. He was a major antagonist in the first part of Season One. He was born in 1839 and lived in the colonial town of Mystic Falls with his brother Stefan, his father, Giuseppe Salvatore, and also with his mother Lillian Salvatore until her death in 1858. He became a vampire in 1864. At the time of his return to Mystic Falls, Damon and Stefan hadn't seen each other in fifteen years due to their bitter and violent relationship.
In the 1950s, Damon was captured and tortured by the Augustine society, led by the Whitmore family, who experimented on vampires for a "bigger purpose". During his five years of captivity, he met another prisoner, Enzo, with whom he became best friends. Eventually, the plan the two made failed at a critical moment and, thinking that Enzo "died" because of him, Damon turned off his humanity to suppress the guilt and sadness. He sought revenge, an act of hunting down every member over generations that left one alive to carry on the family name until he finally killed the last descendant in the Whitmore family, which ended with Aaron Whitmore's death.
Damon's sole purpose in coming back to Mystic Falls was to free his sire Katherine Pierce from a tomb she was never in. Damon deeply loved her after 145 years. After realizing that Katherine never loved him, his love for her faded as his friendship and love for Elena, Katherine's descendant and doppelgänger, grew. Due to her impact on him and the strengthening relationship with his brother, they began working together to protect Elena, along with her friends and family. He lived with his brother Stefan, girlfriend Elena (when she wasn't away at college), and her brother Jeremy Gilbert (after Elena burned their house down) in the Salvatore Boarding House.
In Season Three, Damon filled the role as a deuteragonist in the first half of the season due to Stefan falling prey to Klaus.
Throughout the series, his bond with Elena continuously grew and they eventually fell in love with each other. Shortly after her death and subsequent transition into a vampire, Elena's feelings for Damon were heightened which made her admit her love for him and they started a romantic relationship in Season Four. The relationship was complicated when they realized that, due to the fact that it was Damon's blood that turned Elena, she was sire-bonded to him, so nobody was sure whether Elena's feelings for Damon were real or because of the sire bond, but most of the people they knew insisted that, once the sire bond was broken, Elena would return to Stefan. When Jeremy died, Elena turned off her emotions; after she turned them back on, the sire bond was broken and Elena revealed that her feelings for Damon were real and she was still in love with him.
In Season Five, he discovered Enzo's undead status and they became friends once again. However, once "Elena" broke up with him, he put an end to his diabolical plan against the Whitmore family and was then injected with a dangerous compound by Wes Maxfield, causing him to become the only Augustine Vampire in existence. This injection caused him to crave vampire blood and he would not be able to stop feeding until he had killed. He was later cured, thanks to Enzo, Stefan, and Caroline's actions. Due to the Other Side collapsing, Damon gave up his life to save his loved ones and this caused Elena, Stefan, and Alaric much grief.
In Season Six, Damon and Bonnie were trapped in a 1994 Prison World, which Damon initially believed was his own personal hell, as they were continually reliving a day from his history that Damon believed was the worst thing he ever did. Bonnie was convinced her grandmother sent them there and that there was a way out. They worked together to find a way back to Mystic Falls. They also formed an alliance to take down Kai. During this time, he was able to form a healthy friendship with Bonnie, and they were able to move on from their past and become friends. When Bonnie had a chance to send him home, leaving herself alone with Kai, she did so. Damon initially believed Bonnie was killed in the process, but when he realized she was still alive, he became determined to find a way to bring her back. After returning home, he learned that Elena had Alaric compel away all her memories of their relationship and he attempted to win her back. Damon soon learned of Liz's sickness and, soon after, she passed away in the hospital in front of him, leaving him devastated. He was soon reunited with Bonnie who made it out of the prison world and showed him a video of a mysterious lady, who turned out to be Damon's mother. Bonnie had managed to escape the 1994 prison world by going to Nova Scotia and regaining her magic through Qetsiyah's calcified blood in Silas' tombstone. She also picked up the Cure for vampirism and gave it to him, who in turned gave it to Elena. He expressed the desire to take the Cure with her too and become human. At the end of the season, Kai placed Elena under a sleeping curse and tied the spell to Bonnie's life, which was supposed to keep the now human Elena in a mystical coma until Bonnie died; until then Elena would remain asleep. Damon was devastated by this and said a difficult goodbye to Elena as they locked her in a coffin while his best friend, Bonnie, lived out her remaining days.
As of Season Eight's I Was Feeling Epic, Bonnie managed to break the spell, allowing Elena to wake up, while not killing herself in the process due to the spell, and Damon being able to reunite with her. In the final flash forward, the newly human Damon married Elena Gilbert and they lived a long and happy life together before passing away and finding peace.
His best friends are Elena Gilbert, Alaric Saltzman and Bonnie Bennett. He was close friends with Elizabeth Forbes until her death. His friendship with his sister-in-law, Caroline Forbes, has improved during the last season and they now consider themselves as close friends. Damon was also best friends with Enzo from the time he first met him, until the latter was killed by Stefan, despite the two occasionally being at odds.
Damon Salvatore was born on June 18, 1839, to Giuseppe and Lillian Salvatore in what would eventually become the town of Mystic Falls, Virginia. He is the oldest and firstborn child of Giuseppe and Lillian. During his human years, Damon was seen and described to be rebellious, carefree, emotional, independent, troubled, insecure, misunderstood, principled, impulsive, competitive, and irresponsible and seemed to lack a general sense of direction. People of the town of Mystic Falls even described Damon to be irresponsible and cowardly, including his own father Giuseppe. The reason for this is because Damon rebelled against the town's and his own father's wish, by leaving the Confederacy on his own terms during the time of the Civil War after an inspiring conversation with Oscar, one of the Heretics that his mother sent to look after her sons.In his human years, when it came to love, Damon was always seen to be the chaser and the pursuer, the opposite of Stefan, who appeared to be harder to get and challenging with women, especially in regards to Katherine. Damon during his human years also displayed womanizing tendencies. Damon and his father, Giuseppe, never got along or had a good, close relationship and Giuseppe frequently expressed extreme disappointment and resentment in the elder Salvatore. Despite his very strained relationship with Giuseppe during his human life, Damon was very close to his younger brother Stefan and they shared a very close relationship and bond. Damon described Stefan as his best friend or companion and the person who trusted the most. However, the brothers eventually became strained after Katherine Pierce came into their lives and both brothers started to compete fiercely for Katherine's affections, with both of the brothers not being aware of Katherine playing them against one another. He was turned into a vampire in 1864, when he was 25 years old after he drank Katherine Pierce's blood willingly and was shot by his father, Giuseppe, after attempting to save Katherine from being buried burned in Fell's Church.
When he was 12 years old, his father was very abusive towards him, burning him with a cigarette at a thanksgiving dinner. In his father's eyes, it was a lesson for his elder son, as he thought that Damon had stolen his money. Damon, over 150 years later, learned that it was his mother who stole Giuseppe's money in order to run from her abusive husband and that she planned on taking Stefan and Damon with her, but the plan failed, as Giuseppe found out about it.At the age of 17, in late May 1858, his mother died of consumption (he later learns in 2013 this was not the case). Damon had promised Stefan that he would write his mother's eulogy and say it at his mother's funeral. Just before the funeral, Damon comes to Stefan and helps him get dressed. Stefan says that their father told him not to cry. Damon replies that he is a child and that if he feels the need to cry that he is allowed. Saying all of this, Damon doesn't even go to the funeral. Instead, he got wasted, returned to his younger brother who was angry with him for not showing up.
As a young man, Damon joined the Confederate Army on his father's order, to defend the South during the American Civil War. However, Damon secretly hated everything the South stood for and had been planning to desert for some time before his squad joined the army at Gettysburg. The only thing stopping Damon was fear of Giuseppe's disapproval. Eventually, he met a man named Oscar who convinced him to follow his own beliefs rather than his father's. That night, Damon deserted while his squad was decimated during the following battle.
It is uncertain how or when Damon found out that Katherine was a vampire, but unlike Stefan, he did not fear or reject her and willingly drank her blood. She once demonstrated to him one of her tricks for securing victims, which was lying in the middle of a road to stop any travelers that may come to pass. Though he showed an initial hesitance, Damon even kissed her while a victim's blood still stained her lips.
Damon wanted to give up his human life and spend eternity with Katherine, and he begged Stefan to keep the secret from their father, who was a member of the Founder's Council and a vampire-hater. When Stefan inadvertently revealed that Katherine was a vampire, she was taken away by the townspeople. Their father was furious and scolded Damon for trying to conceal her secret and protect her. Damon was furious with Stefan, but Stefan agreed to work with him to rescue her. In the midst of their daring plan, they were both shot and killed by Giuseppe, who was ashamed of his sons for sympathizing with and loving a vampire. They both died with Katherine's blood in their systems, but Damon awakened first and witnessed the burning of Fell's Church, where the townspeople had imprisoned the vampires, including Katherine.When Stefan awoke the next morning, Damon told him that Katherine's death meant his reason for living was gone, and he wouldn't complete his transition into a vampire. Later that day, when Stefan returned after being unable to resist feeding on his own father, and inadvertently completing the transition, he forced Damon to drink from a young woman's neck, causing Damon to also complete his transition. He promised Stefan an eternity of misery, not for making him turn but for the fact that Katherine had turned Stefan as well, instead of just Damon. At some point Damon received a daylight ring from Emily Bennett. She told Damon that she had spared the vampires in the church, which Damon kept secret from Stefan until 145 years later when he would be able to free Katherine from the church.
Damon saw Stefan in 1912 for the first time in 48 years since they transitioned; both had returned to Mystic Falls for their nephew's funeral. After initial hesitation, Damon agreed to have a drink with Stefan and catch up. When he was feeding on a human alone, the vampire Sage found him and commented on his lack of enjoyment for the feed. Damon seemed content to feed just enough to survive, but Sage encouraged him to enjoy it, to take pleasure in being a vampire. Once he was persuaded, he tried to get Stefan to enjoy the feed and talked him into feeding on human blood again. Stefan fed so hard on his victim that he tore her head off, shocking both brothers. Furious with Damon for making him drink human blood, he ran off and Damon did not pursue him.
Damon was living in New Orleans with a vampire he had turned named Charlotte. Damon soon noticed a pattern of strange behavior from the woman, in that every order he gave her, even seemingly innocuous ones, she followed with frightening enthusiasm. He sought guidance from the witch Valerie LaMarche to break the sire bond between him and Charlotte, and the witch told him she needed a human sacrifice of 12 people to do the spell. Damon killed the 12 people, but could not find Val to perform the spell he needed. He ended up ordering Charlotte to count every brick on every building in New Orleans and meet him at the corner of Bourbon and Dumaine. He left New Orleans soon after.Stefan and Lexi found Damon while he was in New Orleans. At Lexi's insistence, Stefan sought to make peace with his brother before shipping out to the North African front of the war. After an initial hesitance, Damon seemed happy to reunite with his brother after thirty years apart, and the two spent the evening talking. Damon even suggested he might join Stefan and leave for war with him, but Lexi made it clear she did not approve of the idea. Her concerns seemed warranted especially after Charlotte brought a bleeding victim to the bar where they were talking and Stefan started to lose it at the sight and smell of human blood. Later, Damon was all ready to ship out with Stefan when Lexi talked him out of it, citing his profligate lifestyle and how Damon's behavior would not be good for Stefan's rehabilitation. Realizing she might be right, Damon decided not to go and he left the train station without explaining to Stefan.
In 1953, Joseph Salvatore lured Damon to Mystic Falls in order to hand him over to Dr. Whitmore. After Joseph injected Damon with vervain, Damon killed him, but Dr. Whitmore entered the room shortly after and injected Damon with another dose of vervain. When he woke up he was strapped to a table and Dr. Whitmore cut one of his eyes out, in order to experiment and study vampire healing abilities. Damon was brought to a cell and in the cell next to him was another vampire named Enzo. The two vampires bonded and it was Enzo's friendship that allowed Damon to hold on to his humanity. Dr. Whitmore continued to torture and perform experiments on him and he called him 21051.Every year Whitmore would show the rest of Augustine Damon and Enzo and demonstrate his research on the annual New Year's Party. Enzo then came up with a plan for one of the two would drink the other blood ration in order to build up his strength until the coming New Year's Eve. Damon was the lucky one and when the next New Year's Eve Party came he broke free from his chains and he slaughtered every member of Augustine while the building was set ablaze. Enzo was still trapped in his cage and Damon tried to free him, but the cage bars were soaked with vervain and couldn't get him out. Damon knew that if he was going to save himself he had to stop caring about Enzo so he turned his humanity switch off. Now not caring he left Enzo to burn alive. After finally being free from five years of torture, Damon kept the promise he made to Enzo to kill every member in the Whitmore family, but one and let that person have a family and kill them too but one and to the same thing again and again. Damon did exactly that and among the ones he killed were Aaron Whitmore's parents and Aaron was among the ones that he kept alive.
It had been two years since Damon escaped the Augustine cell, and he still had his humanity switched off. On November 8, 1960, during Election night, a lady asked Damon for an interview. She asked him questions related to the terrible fire at Whitmore House and then tried to attack him with a vervain injection, but Damon easily stopped her. When he found out that she was an Augustine member he ripped her head off. Decades later Damon finds out that the girl he killed was actually Enzo's one true love, Maggie James.
Damon lived in New York City during the '70s, where he maintained a wild life full of parties and feeding off of people. At the time, he still had his humanity switch off and he killed locals of New York; a soon to be fed upon victim asked if he was the Son of Sam, to which Damon replied, "Son of Giuseppe, but close enough". Damon was friends with Will, another vampire, who ran a bar and let Damon feed on the people there, while in exchange, Damon stole his victim's IDs for him.
Lexi had eventually found Damon and told him that she and Stefan had heard all about Damon's current life and that Stefan was worried for him. Lexi tried to help Damon get his humanity back, but Damon rejected her offer. However, Lexi was stubborn and she stuck with Damon for the following six months. She had gotten Damon to talk about Katherine Pierce, thinking that if he talked about her, his switch would flip on. Damon tricked Lexi into thinking that his humanity was back and the two had a night full of wild sex.The next morning, Lexi woke up on a roof because the sunlight was burning her skin. She tried to escape by opening the door to get into Billy's, but it was locked. Then she found out the truth: Damon had tricked her. Damon told her that it was his way of getting back at her for annoying him for the past six months. He ditched Lexi on the roof thereafter, leaving her trapped until nightfall. It was revealed in The Cell, that Damon turned off his humanity in the 1950s because he couldn't deal with the pain of leaving Enzo behind while escaping from the Augustine Society.
In April 1994 (after Kurt Cobain died), Damon with his humanity still off, showed up on Stefan's doorstep, wanting to make amends. Zach Salvatore, the owner of the house and their nephew, allowed Damon in on Stefan's promise that he would keep him in line. Zach had been living with Gail who was pregnant with his child. Stefan warned Damon to stay away from them, claiming that both of them were on vervain.
One day, at a party, Damon flirted with a young Liz Forbes. Stefan took a picture of Zach and Gail and noticed bite marks on Gail's wrist. He then confronted Damon about feeding on Gail and after Damon compelled Liz to forget ever meeting him, Damon breezily confessed that he swapped out Zach and Gail's vervain coffee for a little in-house feeding. An angry Stefan reminded Damon that they trusted them and then snapped his neck.
Damon woke up in the shed without his daylight ring. Stefan wanted to know what Damon was really doing there and Damon said he wanted to feel a connection to his humanity again. He tried to convince Stefan to go on a road trip with him. Instead, Stefan reminded Damon of all the times he had ruined his life and how he could not seem to help but do it. Damon got that there would be no road trip for them.On May 10, 1994, Stefan and Zach heard screams and rushed to the library to find bodies everywhere and Damon covered in blood, holding Gail hostage. He demanded his daylight ring back from Stefan, who returned it, realizing he would never be rid of Damon. Damon gave his own version of their past. Damon said, "In 1912, I showed you who you were, Stefan. In 1942 I gave you your freedom and in 1977 I almost killed your best friend because it should have been you there to help me. You owe me. It'll take you an eternity to pay me back.". Then he killed Gail by attacking her and left.
Throughout The Vampire Diaries Series
In Hello, Brother, the episode opens much like the first episode of season one with a couple chit chatting, driving through the fog when they have to swerve to avoid hitting Damon but they actually do hit Enzo. The couple sneak over to check on Enzo when Damon starts clapping from behind them, leaning against their car. Damon tells them it's a slow night as Enzo sits and pops his broken bones back into place. The two vampires drive the couple to an old slaughterhouse.
Damon and Enzo chat about how they are serfs, slaves or lackeys who are being mind controlled. And their job is to bring the worst of humanity to the slaughterhouse. Damon makes each of them tell him what the worst thing they have ever done was. The man is the winner so the woman gets a quick death by Enzo, feeding on her. He then takes he body to dispose of it while Damon takes the man into the main part of the slaughterhouse where many pieces of humans are hanging all around. Damon takes him to where they are standing over a grate. Below the grate is a pool of blood. Damon jabs a giant hook into the man's back; he screams out in pain. Damon pushes some buttons that lift the man up, open the grate and dips him down into the blood. The hook comes back up with only a small piece of the man remaining.
Later, Damon is kicked back in a lounge chair reading "Fifty Shades of Grey" by the bloody pool without the grate. Enzo asks Damon how many more bodies does that "thing" need?! Damon reminds him that it can hear him. Enzo asks Damon if he has any control of his own mind left. Damon tells him that he has flipped his humanity switch. Enzo yells at the bloody pool that has started to bubble "I'm sorry, did we wake you? When does this end"?! He wants to know how many more bodies until its full. Damon then kicks Enzo into the bloody pool. The monster grabs his face with clawed hands and pulls him back under. He is then released and able to climb out. Damon asks him if he got an answer.
Stefan finds the slaughterhouse where Damon sees him and says "hello brother". Damon starts mopping the floor and tells Stefan that he's doing daily chores. Stefan asks him what has a hold on him and what was in that vault? Damon says that it doesn't matter; only that he's been killing bad people. Damon tells Stefan to go home. Stefan observes out loud that Damon has flipped his switch and that he can help him flip it back. Damon tells him that he's seen how this ends and his humanity can't save him from it. He tells Stefan that he's talking about hell; he's seen it, tasted it, touched it. Stefan tells him that he's not making any sense. Damon replies with an "okay". Damon tells Stefan that he needs to go because "it" doesn't want him yet. Stefan says "not without you".
Bonnie finds her way to the slaughterhouse just as Damon says that Elena doesn't matter to him anymore. That he hasn't just flipped his switch, he's ripped it off the wall. Every bad decision he's ever made sealed his fate. His path and Elena's are not the same. He tells Stefan again to go but Stefan snaps a mop in two and stabs it through Damon's body, making him fall down. Bonnie approached and tells Stefan to get him in the car while she finds Enzo. When Stefan looks back Damon is gone and Enzo mouths the word "go" to Stefan, showing he still has his humanity. Enzo then fakes being emotionless toward Bonnie and they leave unharmed.
Damon and Enzo go to and art show where they confront and artist who painted entirely with blood. The artist whispers in Enzo's ear what he did with the victim that he got all the blood from for his art piece. As they leave with the artist, Damon tells Enzo that he might want to consider flipping his switch so "it" can't hurt those he cares about.
Damon and Enzo take their latest victim to feed the monster. When out of the bloody grate climbs a woman, who is singing to them without opening her mouth.
In Today Will Be Different, Damon chats with a businessman about guns. Damon tells him that he is going to bring him to his buyer as she will find him irresistible. Damon takes him to meet Sybil who is swimming in a pool and she begins to sing to the man. The man starts walking down into the pool toward her. Sybil asks Damon if he enjoys this and Damon answers in a bored tone "I don't know. You're the psychic, you tell me". She tells him she needs Enzo to be like him: all in. She then drowns the man.
Later, Damon is catching a nap in a lawn chair and dreams of when he first met Elena. He watches himself like a spectator as he calls her "Katherine". Sybil then yells at him to wake up.
Damon and Enzo sit on a park bench while out on a hunt for Sybil when Damon suggests a game of twenty questions. Damon describes Enzo to a tee. Enzo tells him that that isn't how you play twenty questions but what Damon is tying to do is get Enzo to realize that while he is here, looking for Sarah Nelson aka Sarah Salvatore, he isn't having any fun. Enzo tells him he doesn't understand what the "boss lady" is up to; why she's pushing pause on her master plan. Damon tells him that her new priority is to give Enzo a spanking, to get him to flip his switch. Damon confesses that he's not so much afraid of Sybil as he is of the eternal damnation she showed them when she got into their heads. Enzo insists those were just mind games and none of it was real. Just then, Sarah Nelson walks toward them on the sidewalk. They pull her aside and down to the parking garage where she jabs Damon with a vervain dart.
Damon rushes up behind Caroline, who has been talking to her kids on the phone in the hallway of Sarah's apartment. Damon removes her daylight ring, throwing it down the sunlit hallway along with her phone which he smashes.
Damon jumps through Sarah's window where her and Stefan are talking. Damon grabs her, wrapping his arms around her head, with a murderous look on his face. Stefan pleads "Damon don't"! He quickly explains to Damon who she is but Damon thinks it's impossible. Stefan tells him that Sarah isn't on his list of sins; he didn't kill her in utero. Stefan tells him that letting her go is what Elena would want. Damon lets her go, telling her to run. As soon as Sarah opens the door to escape, Sybil is there blocking her way and she stabs Sarah in the abdomen. Stefan vamps over to Sybil and breaks her neck the goes to give Sarah his blood but just before he gets to Sarah, Sybil whispers in his ear "I'm a lot tougher than I look". She makes it so Stefan cannot move then she asks "So, who's Elena?"
Sybil reprimands Damon, as it he did not kill Sarah. She wants to know how he is disobeying her. It takes a shred of humanity to defy her. She reaches inside his mind and sees Elena. She sifts through every memory of Damon and Elena; she replace Elena with herself. Meanwhile, Sarah is still bleeding out on the floor and she dies. Damon is completely devoted to Sybil.
Back at the swimming pool, Damon is feeding off a victim's wrist while Sybil makes out with the victim who appears to be dead. Damon rushes over to Enzo and thrusts his hand into Enzo's chest, grabbing his heart. While Enzo is weak, Sybil gets a peak into his mind.
In You Decided That I Was Worth Saving, Damon and Sybil are bystanders at the Gilbert car accident on Wickery Bridge. It's revealed that he's reliving a past memory though Sybil has changed the memory so that Elena has died too. Altering his memory results in Damon telling Sybil that he had never met Elena.
Back at the hotel, Sybil is having trouble unlocking Enzo's mind. She encourages him to be more like Damon who looks quite content, sitting in a chair reading Fifty Shades Darker. Damon suggest they kill Enzo as he has a high tolerance for torture. Sybil says they are moving onto to Bonnie; Enzo assures her that Bonnie means nothing to him. Sybil asks Damon to kill Bonnie, which he has no problem with.
Damon interrupts Caroline's wedding dress shopping with Bonnie by killing the attendant and catching the practice bouquet toss. Caroline tells Bonnie to run and tries to attack him but Damon grabs Caroline around the throat as he realizes Stefan's getting married. He tells Caroline to consider this his R.S.V.P. and throws her across the room. He hunts Bonnie down but she fights back allowing Caroline time to stab a wooden pole deep through his stomach, pinning him into the adjacent wall, allowing time for the girls to flee.
Enzo and Sybil track him down and as Enzo removes the pole from Damon, Sybil is admiring herself in the mirror with a wedding dress held up to her. She says to Damon "So you got beat up by a girl." Damon explains that there were two girls which makes Enzo laugh. This makes him susceptible to Sybil's interrogation methods and she is finally able to see what Bonnie means to him. Since Damon doesn't fight her, she looks for Bonnie in his mind and finds their friendship. She replaces Bonnie with herself.
Damon calls Stefan from the high school and tells Stefan he needs a favor. He says that whatever desire he has to save him, he needs it right now. Stefan finds him sitting on a picnic table outside the high school. He tells Damon that if this is a trap he might as well spring it. Damon assures him that he just needs his help but can't tell him what he needs help with. He tells him that Sybil has LoJacked his brain and when he tries to form the words to tell Stefan it just comes out as "applesauce penguin." He opens the trunk of his car to reveal a knocked out and tied up Enzo.
Damon and Enzo are compelled to fight each other to the death when the clock strikes three. Damon brought Stefan as backup to help him kill Enzo. Damon and Enzo argue about their friendship. Stefan tells Damon that if Enzo can fight this, he should be able to also. Stefan tries to reason with him on all points. Enzo tells Stefan it isn't going to do any good because Sybil has been toying with his brain.
When the clock strikes three Damon and Enzo go for each other. Stefan puts himself in the middle, pushing them apart. They continuously push him out. Damon gets himself in a position where wooden handle is piercing through his back and Enzo is dangerously close to staking him. Damon calls to Stefan for help and Stefan throws Enzo off. Stefan is about to chop Enzo's head off with a shovel when Caroline stops him saying she promised Bonnie. Damon snaps her neck and Enzo snaps Stefan's. Enzo goes after Damon with a saw while Damon can almost reach Enzo's chest. They fall and Damon plunges his hand inside Enzo's chest. Bonnie enters and pleads with Damon not to do this. Sybil shows up behind her and tells her to choose which one to save. Bonnie chooses Enzo. Sybil tells Damon to remove his hand from Enzo's chest.
Sybil tells everyone that no one has asked her what she wants. Damon is an asset. Enzo is a burden. Sybil tells Bonnie that she chose wrong so she's going to have Damon kill Bonnie and then she will kill Enzo herself that way everyone can go on with their lives. Unless Enzo flips his humanity switch and pledges his loyalty to her. So Enzo flips his switch. Sybil asks her two loyal subject if they would mind if she were to take back her promise to spare Bonnie's life. Enzo replies coldly "No objections here". Bonnie runs.
Damon grabs Bonnie at her car but Ric runs him down. Damon recovers from being hit after a while and snaps his bones back into place. Stefan tells him it's over (they captured Sybil with the tuning fork). But Damon says his work is just getting started. Stefan asks, "What work"? Damon answers, "Applesauce penguins, brother."
As Damon is driving, he gets a loud ringing in his ear, Sybil is humming in her cell. She is in his memory of the 1994 prison world, eating pancakes. She has replaced Bonnie with herself. Sybil tells him he has too many people willing to fight for him still. True devotion to her is the only way to save him from that which he fears the most (hell).
Tyler Lockwood is driving along, only to find Damon playing his favorite game of laying in the road. He asks Damon if he is alright. Damon smiles lazily and gets up. Tyler tells him that his fight isn't with him as he turns around he draws a gun out of his jacket. He turns around only to find Damon right behind him. Damon grabs his arm with the gun in it and disarms him. Tyler tells him to do what he needs to do to get his life back so he's not the slave to some siren bitch. Tyler tells him that if he kills him he'll be the face that haunts him as the moment he gave up. Damon turns to leave him but gets a ringing in his ears and sees Sybil lay down on a mattress. He turns to Tyler. Then he sees Sybil again. His fangs come out and he heads toward Tyler, bites into his neck and drains him.
In An Eternity of Misery, Damon pulls up to a mechanic's shop in his Camaro. Damon interrupts a man who's welding and tells him he's looking for Peter Maxwell. The man introduces himself as Lou and tells Damon that Pete will be back soon. Damon tells Lou that Sybil wants Pete and they talk about women that "screw with your head." Lou tells Damon he's been married five times. Damon compels Lou to tell him the worst thing he's ever done. Lou confesses that he killed one of his wives and made it look like an accident. Damon pours gasoline all over him and tells him to get back to work. As soon as Lou fires up the welding torch he goes up in flames.
Peter Maxwell runs into Damon who has been waiting for him. Damon tells that he's the one who set Lou on fire. Damon asks Pete if he's ever met Sybil. Pete says that he hasn't so Damon compels him to tell the truth which confirms that he indeed hasn't. Pete thinks everything Damon is saying sounds crazy. Damon tells Pete that he has something Sybil wants. Pete tells Damon to take whatever it is and leave. Damon tells him that he doesn't exactly know what he's looking for but that it is a Maxwell family heirloom: he will know it when he sees it. Pete tells Damon that a couple years ago his grandmother died and left him a box of stuff that he never opened and that his son was looking for the box so maybe he had found it. Damon tells him to call his son.
Damon is playing on a pinball machine when Pete approaches with an ornament which Damon quickly dismisses as not being the heirloom. He accuses Pete of bringing him a bunch of junk when he notices Pete's watch and inquires about it. Pete tells him that his son gave it to him. Pete tosses the watch to Damon and Damon gets burned, as the leather on the watch must have been steeped in vervain. Damon realizes his compulsion hadn't worked on Pete. Damon accuses him of being on vervain but Pete denies it saying "I don't know what you're talking about." Damon tells him liars go straight to hell as he pierces Pete in the gut with a metal object. Just then Damon gets shot with a wooden bullet from behind. He turns around to see Matt Donovan who fires at him again. Damon falls flat on his back. While Damon is unconscious, Matt slits Damon's wrist and feeds his blood to Pete.
When Damon regains consciousness, he finds that Matt has chained him to a chair. Matt has a stake and Damon tells him that if he's trying to scare him it won't work as he has turned his emotions off. He tells Matt that all he senses from him is desperation. Matt confirms that yes, he is desperate and jabs Damon with the stake. Matt just wants to know why Damon tried to kill his father. Damon tells Matt that he didn't know Pete was his dad. Damon uses Tyler as leverage by telling Matt that if anything happens to him, Tyler dies. Matt tells him that he knows Damon isn't that stupid; Elena would never forgive him for that. Damon tells him that he and Elena are through and he's actually been seeing another woman. Damon goes on to tell Matt the exact details of how he "ripped into Tyler" and left him bleeding in the back of a green Mustang and where the location of the car is.
Damon is left alone, struggling against the chains. He knocks over a tall metal shelf and it falls right on top of him. He manages to free himself, snapping broken bones back into place. From the shelf he finds the heirloom he's been looking for: a mysterious iron-looking sphere about the size of a grapefruit. It appears to have the letter "M" stamped into it with a small X-like shape above the letter.
In What Are You?,I Was Feeling Epic,
- "You know, I used to miss being human. Now I can't think of anything more miserable on Earth."
- —Damon to Elena
Damon was originally a very free-spirited young man, who was best friends with his younger brother Stefan Salvatore, both of whom were instantly smitten with the vampire Katherine Pierce. He had a positive relationship with Stefan and he held his position as elder brother in high regard, being the one to teach Stefan how to fight when they were younger. As a human, Damon also held a sense of duty as he enrolled in the confederacy, however their father saw him as very irresponsible and reckless, proving he was very much a free spirit who did things on a whim, taking no mind to what people thought.Damon could be considered much the opposite to his brother in many regards. Whilst they both were respectful and polite, Damon had a dark side which came to play when he fell in love with Katherine, whilst initially terrified at the prospect, his love for Katherine and dependency for her affections made the choice easy and he willingly drank her blood and conspired with her to kill innocent humans, a trait which passed on to his vampire lifestyle. Damon was very naive as a human, he loved Katherine deeply and recklessly, regardless of the consequences and not caring that his father was ashamed of him. His carefree life fell apart when Stefan betrayed Damon by alluding to their father that Katherine was a vampire; information that resulted in Katherine being trapped and taken to a church to be burned, also doing whatever he could to get her back, even if it resulted in his death.