<Li> Recurring seasons: 5 </Li> <P> Lorenzo "Enzo" St. John is a vampire formerly under the imprisonment of the Augustine society, where he was Damon's cellmate in the 1950s . He and Damon later revive their friendship while he searches for his lost lover, Maggie . Enzo shuts off his humanity after Damon reveals that he was the one who killed Maggie and then killed himself by having Stefan rip his heart out . He was resurrected in the season finale . </P> <P> Enzo is a series regular in season six, helping Caroline discover a way to resurrect Damon and Bonnie . After they visit Stefan and learn that he had been lying about searching for a solution, Enzo kills Stefan's human girlfriend, Ivy . In response to this, Stefan later finds Enzo, incapacitates him, and turns him over to Tripp Cooke, a vampire hunter with a familial link to Mystic Falls . It is later revealed that Enzo had made Ivy drink his blood, and she became a vampire . Enzo won't reveal the names of other vampires, so Tripp plans to drive him and Damon into Mystic Falls to kill them, reuniting the two friends (in chains once again), who are narrowly saved by Stefan and Alaric . </P> <P> In season seven, out of love for Lily, Enzo allies himself with the Heretics . Eventually, he begins working for The Armory due to his interest in his past and later to learn his family's purposes . Enzo hides Bonnie from the Armory as they need her to open a mysterious vault . He gives her pills to mute her magic and the two fall in love . Enzo pursues Damon into a vault in the Armory when discolored and long - clawed hands grab his face and pull him backward . </P>

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