Philip "Phil" Leotardo, played by character actorFrank Vincent, is a fictional character on the HBO TV series The Sopranos. He was originally a Captain within the Lupertazzi Crime Family, but following the death of the original Boss, Carmine Lupertazzi, and the imprisonment of his successor Johnny Sack, Phil became the Boss of the Family. Phil was married to Patty Leotardo and was a second cousin of Marie Spatafore. Leotardo may be loosely based on Gambino crime family acting boss John "Jackie Nose" D'Amico.
A prominent member and longtime captain of the Lupertazzi Crime Family, Phil Leotardo was one of the wiseguys who was sent to prison during the "Mafia Crackdown of the 1980s" and, after serving 20 years, was released as part of the "Class of '04" at the beginning of season 5. Phil was always good at his job; he has an alleged 27 hits to his credit. He quickly rejoined the Lupertazzi Crime Family, of Brooklyn, New York, once he was released from prison.
Phil got into a financial dispute with Tony Soprano, and when he tried to duck Tony he was run off the road. Tony later compensated Phil for this by repairing Phil's car free of charge at the Bonpensiero body shop. Phil took full advantage of this and tried to wring as much work as possible out of the deal.
Following Carmine Sr.'s death, a power struggle between two factions ensued. One side was led by Carmine's underboss, Johnny Sack, while the other was ostensibly led by Carmine's 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.
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, 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. When she failed to comply Phil returned with his younger brother, Billy Leotardo, and Joe Peeps who killed Lorraine. When Peeps was later killed, Phil and Billy murdered Angelo Garepe in response. Phil coldly ignored Angelo's pleas to spare him because they knew each other. Acting only as Johnny's field marshal until that point, Phil became personally involved in the war when his brother Billy was murdered by Tony Blundetto, as revenge for the hit the Leotardos carried out on Angelo, who was Blundetto's friend.
Tony Soprano initially protected Blundetto against Phil. Phil stalked New Jersey looking for Blundetto hounding Christopher Moltisanti to his mother Joanne's home and badly beating Soprano associate Benny Fazio. When it became clear that Tony's men would not allow themselves to be imperiled for no good reason Tony was forced to act. Tony ultimately murdered his own cousin to save his family and give Blundetto a quick and painless death. Soprano did this because at an earlier meeting, Johnny Sack had made it clear that Phil would torture Blundetto if he got his hands on him.
Phil was, according to Johnny Sack, 'beside himself' that his opportunity for vengeance was stolen. However, at a meeting between the two bosses, Johnny and Tony made peace, but the moment was interrupted by Johnny's arrest by the FBI, while Tony escaped. With Johnny in Federal custody, Phil became acting boss of the Lupertazzi family, and on the surface was faithful in continuing the work of Johnny Sack. Even Tony Soprano commended his leadership skills.
Phil has worked closely with Tony and Vito Spatafore, the husband of his cousin, on the two family's joint construction efforts. Phil mediated the dispute over the sale of Barone sanitation passing messages back and forth between Tony and Johnny Sack. Phil also resolved a dispute over the beating of Hesh Rabkin's son-in-law Eli by offering generous compensation.
However, due to Phil's "old-school" mentality, he has developed contempt for formerly close friends who have displayed what he sees as "effeminate" qualities: particularly for Vito when his homosexuality was revealed, and even his own boss Johnny Sack for sobbing when forced to leave his daughter's wedding. At the wedding Phil also watched as Tony collapsed when asked to remove his shoes. Phil's homophobia is portrayed as excessive even by Mafia standards, reflecting a very personal obsession.
Distracted with all the duties of an acting boss Phil has made elderly Lupertazzi mobster Albie Cianfalone his consigliere. Phil also placed Gerry Torciano in charge of his old Brooklyn, NY territory. Gerry received his button soon after being given his new responsibilities and Phil gave a speech at a celebratory dinner held at Nuovo Vesuvio. Phil used the opportunity to expound on his feelings about Vito's homosexuality.
Phil visited Marie to try to find out if she knew where Vito was, when she pleaded for mercy for her husband he told her they just wanted to get Vito help. Phil has also harassed Tony about his efforts to find Vito.
Phil visited Tony at the Feast of St. Elzear and they planned a last minute hijacking together - Phil suggested they cut Johnny out of a share in the profits and Tony agreed. When Johnny was planning to give in to asset seizures to reduce his sentence he avoided using Phil to conduct any of his business. Once Johnny's allocution at his trial became public Phil again expressed his disappointment in the boss in front of his crew.
In the episode "Cold Stones", Phil played in the background for the majority of the episode, busy sorting out Johnny Sack's turning. Vito, who was back in New Jersey, met Tony and offered to buy his way back into the family. Tony refused, but didn't attempt to harm Vito. Phil and his associates later showed up to ask Tony Soprano about Vito Spatafore's whereabouts. Tony lied, delaying the inevitable.
Tony had arranged for Carlo Gervasi to execute Vito at the mall early in the morning on the pretense that Vito was supposedly meeting up with Tony, to straighten out the messy situation. The night before Vito was suppose to meet up with Tony, Vito returned to his hotel where Phil's soldiers Gerry Torciano and Dominic "Fat Dom" Gamielleo ambushed Vito with pool sticks when he walked in the door. After knocking him down on the floor, they duck tape his mouth shut. Phil ironically emerges from the closet. He slowly walks up to Vito who is being held by Gerry and Fat Dom and sits down on the bed. He looks Vito in the eye and says, "You're a fucking disgrace." And with that, Fat Dom and Gerry Torciano proceed to beat Vito to death with the pool sticks as Phil watches. After murdering him, they subsequently stick a pool stick up his rectum to signify their extreme disdain for homosexuality.
Phil soon returned to routine business, apparently not expecting a response from New Jersey. Yet not long after the murder, Fat Dom was murdered during a visit to Satriale's when he made one too many jokes at the expense of Vito and his former crime family, and the body quietly disposed of. Next, Leotardo himself received a shock from Tony Soprano's official response; while on a date with his Ukrainian housemaid, Leotardo approached one of his Brooklyn businesses, only to be blown off of his feet by a bomb planted in the wire room the building had housed.
After an unsuccessful attempt by Little Carmine Lupertazzi to broker peace between the families, Leotardo and his crew plotted revenge. Although Phil balked at the idea of killing Tony himself, captain Butch DeConcini seemingly persuaded him to target someone important to the DiMeo family. However, their planning was cut short when Phil suffered a late-night heart attack and was hospitalized during Christmas 2006. There, Tony paid him a visit, relating the fear and regret Tony had felt during his own near-death experience, and asking for peace in the interests of business. Tony's words seemed effective, even moving Phil to tears. As of 2007, a healed Phil expressed a wish to spend more time at home with his (blood) family, in keeping with the sentiment offered to him by Tony. He had decided to step down as boss and leave the Lupertazzi crime family with his protégé Gerry Torciano in charge. Yet Phil did not strongly back Torciano as successor, and Lupertazzi underboss Doc Santoro soon made his own bid for power by having Torciano murdered.
After deciding to get back in the game, Phil waited, working under Doc Santoro until the old man's arrogance got too much to handle. As Phil sat down to dinner with Doc to acknowledge him as boss, Doc humiliated Phil by literally taking food from his plate. Knowing that he had broad support, including Tony's, Phil ordered a hit on Santoro. Driven by Butch DeConcini, Phil's crew murdered Santoro and an associate outside a massage parlor, leaving him dead on the sidewalk. After the assassination, Phil was permanently elevated to Boss of the Lupertazzi Family, with Cianfalone cemented as Consigliere and DeConcini as Underboss.
Phil rejects Tony's offer of compromise on an asbestos removal project. After Tony viciously beats one of Phil's men, Coco, for threatening his daughter, Phil refuses to meet with Tony and then launches a war against the DiMeo family, ordering that New York is to "decapitate" New Jersey and do business with what's left, instructing that hits be made on Tony, Bobby, and Silvio Dante. Bobby is killed and Sil is wounded so badly that he falls into a coma.
In the Sopranos series finale, "Made in America," Butch DeConcini and Albie Cianfalone arrange a sit down with Tony and Paulie, where they express their dissatisfaction with Phil's leadership and agree to a ceasefire of the war. Butchie says he will not reveal the location of Phil, but then says "You do what you got to do." This following a recent phone conversation with Butchie and Phil, where Phil expressed great disappointment with Butchie and his inability to find Tony Soprano. Shortly thereafter, Leotardo is shown talking to his wife through a car window at a Raceway gas station when he is suddenly shot in the head by Walden Belfiore, a soldier in the Gervasi crew of the DiMeo crime family. Leaving the grandchildren in the van, Leotardo's wife rushes to Phil's side in a panic. Unattended and still idling, the SUV idles forward and a wheel rolls over and crushes Phil's skull, leading a witness to vomit.