Star Wars: The Clone Wars introduced fans to several new characters that would go on to be fan favorites, such as Ahsoka Tano. The show also reintroduced Legends characters like Asajj Ventress and Quinlan Vos, two mavericks who rebelled against the Sith Order and the Jedi Order during the Clone Wars.
During the Clone Wars, Vos and Ventress teamed up to assassinate Count Dooku. It was during this time that Ventress ended up turning the Jedi to the dark side.
Asajj Ventress and Quinlan Vos had very different upbringings apart from one thing: they were both raised and trained by Jedi Masters who died in battle. Both felt they could have prevented their masters' deaths.
Star Wars: Dark Disciple by Christie Golden dives into Vos's past through his conversations with Ventress. Vos, like most Jedi younglings, was housed and educated in the Jedi Temple on Coruscant. He eventually became the Padawan to Jedi Master Tholme, who died early during the Clone Wars. Vos wanted to go with his master but was assigned a different mission by the Jedi Council. He was enraged after hearing of his master's death and felt responsible for not being with him to prevent his fall. Little did Vos know that his master fell at the hands of his eventual lover, Asajj Ventress.
Like many Jedi Knights and Masters during the Clone Wars, Vos acted as a soldier and agent for missions as assigned by the Jedi Council. Although he was a maverick Jedi who rebelled against the Council, similar to Qui-Gon Jinn, Vos was also a capable Jedi Master with a special power. This Force ability, known as pscyhometry, allowed Vos to see the past of objects he touched through the Force. Because of his prowess and unique ability, the Jedi Council assigned Vos the special task of assassinating Count Dooku to end the Clone Wars.
Master Yoda told Vos to seek out Count Dooku's former dark side apprentice who he betrayed, the bounty hunter Asajj Ventress. By working together, Vos could use Ventress's personal knowledge of Dooku against him. Disguised as a bounty hunter, Vos eventually found Ventress and began working with her.
The two rogue hunters developed feelings for each other and Vos eventually told Ventress the truth: he was a Jedi tasked with killing Count Dooku. Ventress, to his surprise, already knew this, having noticed his inhuman speed and reflexes that only a Force-sensitive could have. In order to kill Count Dooku, Ventress took Vos to Dathomir, her home planet, to teach him the ways of the dark side.
Surrounded by the remains of her dead people who were slain by General Grievous, Ventress trained Vos in the teachings of the Nightsisters and their use of the dark side. Vos trained in aggressive lightsaber combat and learned to use his hatred when wielding the Force. The two also shared their pasts with one another, though Ventress kept the detail of her murdering Vos's master to herself. They eventually confessed their feelings and fell in love, with Vos deciding to leave the Jedi Order once the assassination was finished.
Ventress got word of Dooku's whereabouts, so the two lovers set out to finally kill him. They engaged Dooku in a duel but lost due to the intervention of General Grievous. Ventress managed to escape, but Vos was captured by Dooku.
Vos was then tortured in Dooku's palace. The Sith Lord wished to have a new apprentice and saw Quinlan as the perfect choice. Vos held out until Dooku gave him his master's lightsaber. Using his psychometry, Vos saw Tholme's death at the hands of his lover. His trust shattered, Vos fully embraced the dark side and became Count Dooku's new apprentice.
Ventress hired fellow bounty hunters Boba Fett, Bossk, Razzi, C-21, Highsinger, and Embo to rescue her captured love. She found Vos and attempted to free him, only for Vos to lash out at her and force her to leave without him. As Dooku's new servant, Vos became known as 'Admiral Enigma,' a deadly Separatist agent akin to Marvel's own Winter Soldier. Although Dooku completed Vos's transition to the dark side, it was Ventress who ushered him into darkness.
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