Phil Leotardo was a capo with in the lupertazzi crime family who served twenty years in prison. When new jersey mob boss Tony Soprano learned Phil had cheated his father's mistress out of money he was furious which led him to drive Phil off the road though later compensated him by having Phil's car repaired free of charge at Angie Bonphnseiro's body shop. Phil took full advantage of this trying to wire as much work possible out of the deal. During the power struggle between Johnny Sack and Little Carmine Lupertazzi for control of the family Phil sided with John along with his brother and Joey peeps Phil murdered loan shark Lorraine Calluzo for directing her payments to little Carmine instead of John. Little Carmine's men Angelo Garepe and Rusty Millio Contracted Soprano's cousin Tony Blundetto and had him kill Joey peeps. In retaliation for Angelo's involvement in Joey's death Phil and Billy murdered him coldly ignoring his pleas to be spared. When Blundetto learned of this he was furious as Angelo was a good friend of his and he sought vengeance by killing Billy leaving Phil grief stricken. Soprano initially protected Blundetto and refused to give him up. Due to his knowledge of Phil's plans to torture Blundetto Soprano ultimately chose to murder his own cousin in order to give him a painless death. Though Phil resented Soprano for robbing him of vengeance they would have to work closely together after John's arrest which made Phil the family's acting boss. Phil was contemptuous of Tony's best Earner Vito Spatfore who fled in fear for his life when he was discovered to be a homosexual especially because Vito was married to his cousin Marie making Phil see the situation as an embarrassment to his family. Phil wished to murder Vito and tried asking Marie if she knew of her husband's whereabouts, lying that he only wanted to get Vito help and also harassed Soprano over his attempts to find Vito. Phil planned a high-jacking With Soprano and they both agreed to cut John out of the profits. When Vito returned Soprano was initially tempted to give him a pass because of his earning capabilities but decided that would cause too much trouble and privately arranged for Vito to be Killed by Carlo Gervasi. However before this could be carried out Phil had his men Fat Dom and Gerry Torciano beat Vito to death frustrating Soprano as he saw it as a sign of disrespect to take out one of his captains without permission. When Silvio Dante and Carlo Gervasi murdered Fat Dom after he made jokes over Vito and Carlo being in a relationship it heightened tension between the families after an unsuccessful attempt by Little Carmine to broker peace between the families Phil's underboss Butch Deconcini seemingly talked him into targeting someone inside Soprano's inner circle however soon after this Phil suffered a heart attack (something Soprano was ecstatic over). When Phil was visited by Soprano in hospital, Soprano told him about his own feelings of fear and regret after his near-death experience which was effective as it moved Phil to tears and convinced him to forgo his vengeance in the interest of business. In keeping with the sentiment Soprano had offered him Phil wanted to spend more time with his family wishing to step down as boss and have Torciano succeed him however When Torciano was killed by Doc Santoro in a bid for power Phil believed it was due to the softer approach he'd ben taking to life and decided to abandon it. After getting back in the game Phil had Santoro Killed which thus reestablished his authority. While Soprano tried to compromise over an asbestos removal project Phil rejected these offers when Soprano's daughter Meadow was sexually harassed by one of Phil's men, Coco Soprano responded by viciously assaulting Coco. Phil then declared War on Soprano putting hits out on Soprano Silvio and Soprano's brother in law Bobby Baccala which led to Bobby's death and Silvio's hospitalization. When Phil seemed disappointed with him Butch became worried, meeting with Soprano and agreed to call a ceasefire on the war which led to Phil's death at the hands of Soprano soldier Walden Belifore which Soprano arranged knowing no retaliation would be carried out.