Jack Massarone is a recurring character portrayed by Robert Desiderio. He is the owner of Massarone Bros. Construction General Contractors & Engineers and an associate of the DiMeo crime family.
Sometimes referred to as "Black" Jack Massarone. The DiMeo crime family had an interest in Massarone's construction company. In 2000, Jack was the unwitting victim of a shakedown - black protesters caused work to cease at one of his sites by picketing because they thought his joint fitters' employment policies were racist. Jack was under Junior Soprano's protection initially but when Junior was arrested and his crew were decimated by the DiMeo civil war, Jack was without any support and unable to get a line to Junior in prison. Instead he paid now DiMeo boss Tony Soprano to intervene on his behalf and Tony organized a gang of mob associates to break up the protest. Tony had actually orchestrated the protest through his contact Reverend James, Jr. Massarone Construction was later involved in Soprano construction schemes like the Esplanade project and HUD scam.
In 2004, Jack had become a federal informant and wore a wire concealed in a baseball cap to several meetings with Tony. Tony realized something was wrong when he was tipped off by DiMeo soldier Patsy Parisi that one of his meetings with Massarone was staked-out by the FBI. Raising Tony's suspicions further was the fact that Massarone gave him a framed picture of the Rat Pack at that meeting. Tony wasn't sure if his suspicions were correct and planned another meeting with Jack Massarone to "feel him out." Soprano was unable to confirm his suspicions but Massarone sealed his fate when during the meeting he asked if Tony had lost weight, something that he had never dared ask before. This small slip up was enough for Tony to order Jack's death. Jack was murdered and found in the trunk of his car with a golf club cover stuffed in his mouth - a message that his killers knew he was talking to the FBI.