The vervain weakened Damon to the point where he was not able to fight Kai off. When Damon continued to fight back, Kai smashed the entire shelf of bourbon, splashing it on Damon, and told him that he had no idea which bottle he would drink, so he put vervain in all of them. After a few comments here and there, Damon lost his patience and attacked Kai, who managed to calm him down and trick him into drinking some bourbon laced with vervain. In Welcome to Paradise, after watching Damon Salvatore and Bonnie Bennett in the Prison World for some time, Kai made his presence known to them at Bell's Market in the otherworldly-Mystic Falls, when Damon encountered him after having a fight with Bonnie. He realized that it was part of his punishment, a safeguard by the Gemini Coven to make sure that Kai didn't end his eternal imprisonment early. In the Prison World, Kai tried to kill himself several times, each unsuccessful. However, she had relinquished her magic, and the coven harnessed the power of a solar eclipse to trap him in a purgatory dimension for his crimes, which kept him trapped in a snapshot of the day that he was imprisoned. He stabbed Jo with a hunting knife to get her out of the way as he went after their siblings, but Jo managed to cloak the twins to protect them, promising to merge with him so long as Liv and Luke could live. Realizing this, on May 9, 1994, he decided to kill his siblings and merge with Jo. Due to this, Joshua and his wife kept having children until another pair of twins was born: Liv and Luke. However, Joshua knew that Kai would win the merge given his powers, and knew that Kai could not lead the coven. As twins of the Gemini Coven, Kai and Jo were expected to merge. As a siphoner, he was shunned by his family, even revealing to Caroline that he wasn't allowed to touch anyone. Malachai was born in Portland, Oregon in 1972 as the eldest son of Joshua Parker and twin brother of Jo. Kai's family in the newspaper on May 10, 1994, after he massacred them 2 Throughout The Vampire Diaries Series.Kai was a member of the Parker Family, and the last leader of the Gemini Coven. He was decapitated for a second time by Alaric Saltzman after he attempted to betray the Necromancer and destroy the Prison World. A decade later, he was given the key to his escape by Josie, information about the Malivore portal, and worked with the Necromancer, targeting the Salvatore Boarding School. After he failed, he was banished and imprisoned in another Prison World by Bonnie, Lizzie, and Josie. With the deal struck, he attempted to once again kill the last remaining Gemini witches, his nieces Lizzie and Josie Saltzman. After he escaped Hell, he bargained with Arcadius to remain in the living world by giving him Elena's coffin. His reign was short-lived when he was killed by Damon and found himself in Hell. Freed, he sought revenge on his family that led him to Merging with his brother, Lucas, and assuming control over his family's coven. He was trapped within a Prison World by his father and coven in 1994 until his eventual escape after meeting Damon Salvatore and Bonnie Bennett. When his nature as a siphoner was revealed in adolescence, his family began to treat him poorly and referred to him as an 'abomination,' which, among other factors, led to him growing up to be a sociopath and murdering most of his younger siblings. He was the son of Joshua Parker and his unnamed wife, the twin brother of Josette, and the older brother of Olivia, Lucas, Joey, and three other unnamed siblings.

In the third episode of the sixth season of The Vampire Diaries as well as the main antagonist. Malachai 'Kai' Parker was a siphoner- vampire hybrid that first appeared

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