|“||I sense hostility, and that's fine. All emotions are valid and welcome here. But, it's the truth. She just wanted to know you were happy, Damon. She loved you.||”|
Oscar's story is not very known, he was a member of the Gemini Coven who was banished because he was a siphoner. Later he met Lillian Salvatore, a vampire who later turned him into a hybrid; half-witch half-vampire.
Oscar had been sent by Lily to make sure how Damon was and met him in a bar in Gettysburg. He told Damon to follow his heart and it is revealed that when Damon backed out of the battle, Oscar had actually saved his life.
Oscar and the Heretics traveled from England, back to America on a ship. Lily found a friend, who was dying of consumption. Lily took pity on him and turned him into a vampire intending him to be a new member of the family. Just before docking, Lily and the Heretics drained and killed everyone on the ship. On the docks, they were confronted by the Gemini Coven and were sent to the prison world, where they were cursed to relive that same day, over and over again.
After spending many years in the prison worlds, they eventually began to run low on blood. They had already drained every butcher on foot. The Heretics made a sacrifice and let themselves desiccate so that their leader, Lily could live on.
Throughout The Vampire Diaries Series
In A Bird in a Gilded Cage, While on the search for his mother, Damon came to the prison world with Elena, Bonnie and the leader of the Gemini Coven, Kai. Damon and Elena found Lily and explained how long she had been stuck there and what had happened. While about to leave the Prison World, Lily reveals to her son that she will go and get the others, the Heretics. They venture to where the Heretics have desiccated. Lily attempts to use the remainder of the blood to revive them but Damon knocks the blood out of her hands and smashes on the floor. Just before that, she had managed to give Malcolm enough blood that he would later attack Kai (as he was left in the prison world) and feed of of him.
In I'd Leave My Happy Home For You, Kai feeds the other Heretics, reviving them and they continue to feed them until he finds a way for them to get out. While Kai is making dinner, the Heretics are outside. Kai alerts them that their dinner is ready by ringing a bell. They all emerge from the trees and head towards the house. Kai informs them that they are getting out.
In I'm Thinking Of You All The While, Oscar escaped the 1903 prison world but was trapped with his fellow Heretics in a container (which was cloaked with magic) until the death of Kai, which uncloaked the container, making it possible for Lily to find them. Not long after, Lily comes wondering in, calling the names of her "family". They all come wandering around the corner. Lily looks relieved and runs up to them and gives then a hug with a tear in her eye.
In Day One of Twenty-Two Thousand, Give or Take, Oscar is performing an 'errand' for Lily, one she is not willing to share with the other Heretics.
In Never Let Me Go, Oscar is still away doing Lily's errand while he misses Malcolm's funeral.
In Age of Innocence, Damon tracks his cell phone to Myrtle Beach and goes there with Alaric & Bonnie. They find him as he's living under the radar from Lily as he wants freedom from her since she keeps the rest of the Heretics on a short leash. He agrees to siphon Bonnie's visions and becomes aware that the Phoenix Stone is within their possession. He manages to steal it from Alaric and escapes, but however Damon catches him. Oscar gives a warning about the stone but Damon states that he does not care about the stone, as he intends to exchange Oscar for Elena. Oscar later gets into a fight with Damon, Bonnie and Alaric and managed to overwhelm them but is defeated. At a room in the Whitmore Medical Center, Oscar finds himself strapped to a gunnery being drugged with vervain dripping from a IV as Valerie finds him and asks Oscar if he found Julian yet to which Oscar responded that he found Julian months ago. Oscar intended to bargain Julian in exchange for his freedom from Lily. Valerie then apologized to Oscar and then kills him as she knows what Julian is capable of.
In I Carry Your Heart With Me, he's the first one resurrected with the Phoenix Stone, but experienced memory loss as he couldn't recall Valerie being his killer or being in Myrtle Beach. He goes on an Ripper Serial Killer Rage as a result of heightened hunger. Damon saves Lily from him recommend a detox and an intervention to her on how deal with Oscar. A little while later Damon has just set the victims of Oscar's Halloween tour bus massacre on fire to hide the evidence before returning to talk to Lily as she tells him he will have Elena's casket in his possession as he brought Oscar back who's back at Salvatore Boarding House recovering.
In Live Through This, it is revealed that Oscar had not been resurrected, but another had been placed in his body instead. This person showed to be aggressive and before he could do any damage to Bonnie or Enzo, Enzo stakes Oscar's body and kills the spirit.
Oscar is laid-back, friendly and desires for freedom. Unlike the other members of the Heretics, he isn't prone to violence and murder, but will use magic and fight back when the situation is necessary.
Oscar looks to be an Asian male in his late 30's to early 40's, with medium length black hair and brown eyes.
Powers and Abilities
Oscar was originally born a Siphoner, a witch with no personal power, meaning that he could only practice magic by siphoning it from another source. However, after becoming a vampire, he retained his siphoning abilities, allowing him to function as a witch-vampire hybrid. As such, he possessed all the standard powers and abilities of a witch, non-original vampire hybrid.
Oscar had the typical weaknesses of a non-original witch-vampire hybrid.
- A Bird in a Gilded Cage
- I Never Could Love Like That (Flashback)
- I'd Leave My Happy Home For You
- I'm Thinking Of You All The While
- Day One of Twenty-Two Thousand, Give or Take (Mentioned)
- Never Let Me Go (Mentioned)
- Age of Innocence (Death)
- I Carry Your Heart With Me (Corpse/Resurrected/Physically only)
- Live Through This (Physically only/Possessed by Unknown Spirit/Death)
- Best Served Cold (Mentioned)
- Mommie Dearest (Mentioned)
- Hold Me, Thrill Me, Kiss Me, Kill Me (Mentioned)
- Postcards from the Edge (Indirectly Mentioned)
- This Woman's Work (Indirectly Mentioned)
- Moonlight on the Bayou (Mentioned)
- Somebody That I Used to Know (Indirectly Mentioned)
- Oscar is an English name and means "divine spear" or "God's spear".
- He is described as "an Asian male in his 30s, is described as a laid back stoner who's been living the high life off the grid for months…but his zen lifestyle comes to a screeching halt when a spell destroys his memories and turns him feral. 
- Oscar was sent by Lily to make sure how Damon was and met him in a bar in Gettysburg.
- He was human when he met Damon.
- He is the only member of the Heretics to have been killed by another Heretic.