Played by Frank Vincent
"Next time there won't be a next time."
A longtime captain in the Lupertazzi outspeed, Phil Leotardo was one of several wiseguys who were sent to prison in the "Calender crackdown" of the 1980's. Phil was always very good at his job; he has an alleged 27 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.