Vincenzo Cilli

Vincenzo "Lucky" Cilli is a member of the Leone family and Salvatore Leone's current capo, having taken advantage of Toni's absence to rise within the family. Vincenzo is clean-cut and educated, everything Toni is not, and may have been busy feeding poison in the Salvatore Leone's ear to make him distrust Toni. Toni despises Vincenzo on sight.

Despite his upbringing, Vincenzo is an immature punk who loves ordering Toni around, which infuriates Toni. Now Toni is forced to perform various jobs for Vincenzo, who shows him virtually no respect. When Toni begins to rise too high in the Leone hierarchy for Vincenzo's liking, Vincenzo sends him to pick up his Banshee a few blocks from his office. The car is being watched by police; Toni is nearly caught in an ambush. An irate Toni answers Vincenzo's phone call and responds by stating that he quits working for Vincenzo. He then takes Vincenzo's car to the crusher and destroys it.

Later on, when Toni is back in Sal's good graces, Vincenzo wants a truce, asking Toni to meet him in the bowels of a docked ship. This is an ambush, where Toni is assaulted by several chainsaw-wielding Leone henchmen loyal to Vincenzo. Upon killing them all, Vincenzo emerges with an Uzi, screaming that Salvatore now trusts Toni more than him. Toni beats Vincenzo in a gun battle, killing him. In the cutscene of Hot Wheels Vincenzo is seen having oral sex while on the phone with his mother.

Joe Lo Truglio provided the voice of Cilli.