- "So they go through labor, big deal. Try a prostate exam."
- ―Jack Massarone[src]
Jack Massarone is portrayed by Robert Desiderio. He is the owner of Massarone Bros. Construction General Contractors & Engineers, sometimes referred to as "Black" Jack Massarone. The Soprano crew 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. He paid 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 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, and later asked him if he had lost weight. 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 feds.
- Tony calls Jack by the nickname "Black" Jack Massarone.