Philip " Phil " Leotardo is a highly respected captain in the New York City Mafia who eventually becomes boss of the powerful Lupertazzi crime family. After his release from prison following a year stretch in , he quickly comes into conflict with the DiMeo crime family and Tony Soprano. He serves as as the main antagonist of the The Sopranos's final season. His paternal grandfather immigrated to the United States from Sicily, and Phil claimed that officials at Ellis Island changed the family name from "Leonardo," which Phil perceives as a "disrespect" to his heritage and regrets as a besmirchment of his legacy.
He gained a fearful reputation as a ruthless enforcer, and had an estimated 27 hits to his name. Phil with Johnny Sack at Carmine Lupertazzi 's funeral. Phil is mentioned during a television segment Tony and Bobby watch about the release from prison after 20 years of several New York and New Jersey mobsters charged during the s crackdowns.
He is seen cheerfully entertaining mourners with jokes and conversations, but when Johnny goes to pay his respects to Little Carmine , the two begin arguing about Johnny's arrangement of Carmine Sr. This kicks off the start of their conflict, and the family is split between those supporting Little Carmine for the boss title and those supporting Johnny Sack, such as Phil and his brother Billy. Phil got into a financial dispute with Tony Soprano, and when he tried to duck Tony, he was forced off the road, crashing into a parked truck and injuring his neck bad enough requiring him to wear a neck brace around for a few weeks.
Tony later compensates Phil for this by repairing Phil's car free of charge at the Bonpensiero Bros. Body Shop. Phil took full advantage of this and tried to wring as much work as possible out of the deal. Following Carmine Sr. One side was led by Carmine's underboss, Johnny Sacramoni , while the other was ostensibly led by Carmine's only son and Miami Capo " Little Carmine " Lupertazzi, although it is likely that Consigliere Angelo Garepe and Capo Rusty Millio were the real power behind this faction, and Little Carmine, would be used as a "puppet" of sorts.
Phil became Johnny's right-hand man during the war, and carried out murders in order to weaken Little Carmine's resolve. Phil performed a mock execution of Lorraine Calluzzo , while she was tightly taped and gagged, shooting at her while holding a phone book in the path of the bullet, to persuade her to redirect her payments from Little Carmine to Johnny Sack.
