Unlike his grandfather and even to a lesser extent his father, Vanno did not grow up in a Spartan, almost barracks like environment. Old Anzori Cholokosh was well-to-do, and liked to show off his success; notably by spoiling his wives, mistresses and children, both legitimate and illegitimate. Vanno, as one of the "heirs apparent" (the third son of Anzori's first wife) was raised almost as if he were the member of the nobility. This was a source of friction between Anzori and his father, Zviad Cholokosh, who was a conservative, traditionalist member of the Cherskiians, and was greatly put out at his son's indulgence and lack of urgency towards furthering the cause of a hamazin revolution in the homeland. As tensions mounted between father and grandfather, Vanno found himself a pawn, sent to a hamazin "boot camp" in the deserts up north to learn the arts of death and assassination.
Vanno found that he was exceedingly talented at this career, and rose quickly to the top of his class. When he returned to Porto Liure, he disappointed both his father and his grandfather; he did not become indoctrinated in the hamazin revolution movement, and he in fact stepped away from being inducted into the Mafia. Vanno became a free agent, hiring his services out on an independent basis. It didn't take too long before his reputation in the underworld of Porto Liure was secure, and contracts both there and abroad came in steadily. Vanno spent a few years traveling frequently and amassing a significant amount of cash, which he cleverly invested and hid, keeping as always a low profile.
While away on an assignment in Terrasa, old Anzori and Zviad both were killed in a hit by a rival gang. Vanno's elder brother, Anzori Jr., became the new head of the syndicate in Porto Liure. After a brutal purge of both the incompetent and untrustworthy in his own organization, he turned his attention on his rivals. When Vanno returned, he joined his brothers at their request, but he would only work with them under contract. Junior's anger at his refusal to help in the revenge that he felt his father and grandfather deserved, as well as his inability to bring Vanno under his thumb as a part of his organization, was a thorn in his side that eventually led to a major split between them. After demanding that Vanno make himself available for syndicate business when called on, the two brothers fought. Vanno stormed out of the manor, killing a guard or two on his way out, and has not spoken to his brother since.
Although he has been back to Porto Liure many times, usually on assignment, he keeps a low profile whenever he travels there. He has since set up his headquarters in Terrasa itself, the largest city in the region, and the one with the briskest business. Although he still travels frequently, he finds that he can find more than enough work in Terrasa itself that he doesn't need to.
Mechanics: The D&D option has a tailor made class for assassins; the assassin class, published in the d20 Freeport Companion. Pathfinder also has an obvious choice; Vanno would be a rogue with the poisoner archetype. In the d20 Past variant, he's actually a Fast hero and a Gunslinger... although for many assignments, his trusty bow and arrow is a preferable weapon to a gun, as it fires silently and the arrows can be poisoned for maximum efficiency.