Jack Massarone is portrayed by Robert Desiderio. He is the owner of Massarone Construction, 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 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.