- "Because they're stupid, that's why. And jealous. They disrespected a proud Italian heritage, and named us after a ballet costume."
- ―Phil in the episode Stage 5 on his family's surname
Philip "Phil" Leotardo, portrayed by actor Frank Vincent, is a fictional character in The Sopranos. He was originally a captain within the Lupertazzi crime family, but following the death of the original boss, Carmine Lupertazzi, the imprisonment and death of his successor Johnny Sacramoni and a brief power struggle with would-be boss Faustino "Doc" Santoro, Phil became the boss of the family.
Phil was married to Patty Leotardo and was a second cousin of Marie Spatafore. Phil bears a resemblance to the last Shah of Iran, Mohammad Reza Pahlavi, leading to Tony Soprano and his family often referring to him as "The Shah". Phil expressed dislike for the nickname.
A prominent member and longtime captain of the Lupertazzi crime family, Phil Leotardo was one of the mafioso who were sent to prison during the "Mafia Crackdown of the 1980s" and, after serving 20 years, Phil was released as part of the "Class of '04" at the beginning of season 5. Phil frequently mentions that he did 20 years "without a peep" as a testament to his loyalty to the Cosa Nostra. Phil was always good at his job; he had 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 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.'s death, a power struggle between two factions ensued. 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. When she failed to comply, Phil returned with his younger brother, Billy Leotardo, and Joe Peeps and killed Lorraine and her lover Jason. 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 Leotardo brothers carried out on Angelo, who was Blundetto's close friend from their time together in prison.
Tony Soprano initially protected Blundetto against Phil. Phil stalked New Jersey looking for Blundetto, hounding Christopher Moltisanti, 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 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 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.
Distracted with all the duties of an acting boss Phil 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 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 allocation 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 supposed to meet up with Tony, Vito returned to his motel room, where Phil's soldiers Gerry Torciano and Dominic "Fat Dom" Gamiello were waiting. The two ambushed Vito by hitting him with pool cues when he walked in. Gerry and Dom duct tape his mouth, and then 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 eyes and tells him he is a disgrace. Fat Dom and Gerry Torciano proceed to beat Vito to death as Phil watches. After murdering him, they subsequently stick a pool cue up his rectum to signify their extreme disdain for Vito's homosexuality.
Phil soon returned to routine business, apparently not expecting a response from New Jersey. Not long after the murder, Fat Dom visited Satriale's where he proceeded make one too many jokes about Vito's murder and implies Carlo is homosexual. After he made a joke about Carlo and Vito having sexual relations, Silvio hit Dom in the back of the head with a DustBuster, and then restrained Fat Dom as he was stabbed to death by an enraged Carlo. Dom's body was quietly disposed of afterwards. 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.
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 his protégé Gerry Torciano in charge of the Lupertazzi crime family. Yet Phil did not strongly back Torciano as successor, and Lupertazzi underboss Doc Santoro soon made his own bid for power by having Torciano shot to death by a hired assassin.
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 Don 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. Tony viciously beats one of Phil's men, Coco, for drunkenly sexually harassing his daughter while she was on a date with Patrick Parisi. In response to this action, Phil refuses to meet with Tony and then launches a war against the DiMeo family. Phil orders 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 shot and killed while shopping at a model train store, and Silvio is shot multiple times and left in a coma doctors say he is unlikely to wake up from.
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. Walden shoots Phil once more in the chest to ensure he's dead. Leaving the grandchildren in her Ford Expedition, Leotardo's wife rushes to Phil's side in a panic. Unattended and still in drive with the engine running, the large SUV idles forward and a wheel rolls over and crushes Phil's skull, leading a witness to exclaim "Oh shit!" and another to vomit. Leotardo's murder was the 92nd and final murder on the series (excluding the suggested murder of Tony himself at the end of the episode).
Rank: Capo (appointed to Acting Boss immediately after the death of John Sacramoni. Later became the official boss after the murder of the following acting boss, Gerry Torciano)
Murders committed by Phil Leotardo
- Angelo Garepe: Killed by Phil in retaliation for the murder of Joe Peeps, he was ambushed by Phil and his brother Billy, and shot to death in the trunk of Phil's Lincoln Town Car.
- Lorraine Caluzzo : Phil ordered her death and was on lookout at her killing when she was shot and killed by Phil's brother Billy in the early power struggle between New York's families in Season 5 (they also killed Lorraine's boyfriend, Jason Evanina, for being a witness to the crime).
- Vito Spatafore: Ordered his death through Gerry Torciano and Dominic "Fat Dom" Gamiello, beating Vito to death in his motel room with pool cues as Phil sat on the end of Vito's bed and silently watched.
- Bobby Baccalieri : Ordered hits on the three top members of the DiMeo (Soprano) Crime Family, Bobby Baccalieri, Silvio Dante, and Tony Soprano, during the War of 2007. Two assailants shot Bobby multiple times in the head, chest, and torso in a model train store.
- Phil Leotardo's murder of Angelo Garepe referred back to the death of actor Frank Vincent's character, Billy Batts, in Goodfellas; both were beaten, thrown into a car trunk, and shot while pleading for their life.
- Phil Leotardo's murder of Vito referred back to the death of Nicky Santoro in Casino, where Frank Vincent watches Nicky being beaten to death.
- There is a recurring internet meme among fans of the show relating to Phil wanting a shinebox for his shoes. This is a reference to a scene in Goodfellas, where Frank Vincent's character Billy Batts repeatedly mocks Tommy DeVito about his childhood career as a shoeshine boy, eventually saying "Now go home and get your fucking shinebox." which results in Batts being beaten and murdered by Tommy and two of his friends.
- Phil believes that his family name, Leotardo, originally derives from the famous Italian name Leonardo. When Phil's grandfather came to America from Sicily, the immigration office at Ellis Island obliviously misspelled the name. Related to that, Phil idolizes Leonardo da Vinci as a great Italian.
- Phil's home is located at the intersection of Marlborough/Dorchester in Brooklyn. The street signs can be seen in "The Second Coming" episode, when Tony and Little Carmine attend Phil's residence to broker peace but are ultimately turned away. In reality, this house is located in northern Newark, New Jersey.
- Phil Leotardo's name is loosely based on Phil Leonetti, who was the underboss of the Philadelphia crime family.