"Next time there won't be a next time."
A longtime captain in the Lupertazzi family, Phil Leotardo was one of several wiseguys who were sent to prison in the "Mafia crackdown" of the 1980's. Phil was always very good at his job; he has an alleged twenty-seven hits to his credit and can literally scare the piss out of people. When he was released from prison, he didn't waste any time getting back on the payroll.
But the "thing" Phil returned to has seen a lot of changes while he was away, and it's about to go through some more. Shortly after Phil rejoined the Lupertazzi organization, Carmine Sr. suffered a fatal stroke before naming his successor. Phil chose to throw in his lot with Johnny Sack, Carmine's second in command, instead of the old don's son, Little Carmine. It proved to be a wise choice. But when Tony B. retaliated against Phil's younger brother, Billy, for killing Angelo Garepe, it set off a near-war between the New York and New Jersey organizations - despite assurances that Tony B. was acting on his own. Phil wanted his revenge: he planned to torture Tony B. before taking him out himself. When Tony Soprano wouldn't let him, a lot of animosity was left between them.
The bad blood between Tony and Phil continued with the tense truce that developed with Johnny Sack's incarceration. Constantly pushing and tweaking Tony, Leotardo has never showed him the respect he deserved as a boss. But just as the insults between the two began escalating to murder and arson, Phil suffered a heart attack, prompting Tony to make a bedside plea for peace.
played by Frank Vincent