For starters, at the time Trump’s mentor on issues of politics and business was Roy Cohn, a lawyer whose other clients included a passel of mobsters, among them the bosses of the Genovese and Gambino crime families. Cohn, who served as Senator Joseph McCarthy's chief witch hunter before going into private practice, operated out of a townhouse on East 68th Street where clients Anthony "Fat Tony" Salerno and Paul "Big Paul" Castellano were regular visitors. Besides getting advice on their legal problems, as a former secretary later recalled to Wayne Barrett in his 1992 book, “Trump: The Deals and the Downfall,” the visits by the mob titans to their lawyer's office allowed them to talk shop without having to worry about FBI bugs. Cohn told a reporter that Trump called him “fifteen to twenty times a day, asking what’s the status of this, what’s the status of that,” according to Barrett’s book.
Another reason the FBI might not have taken Trump’s professed ignorance at face value was that Trump had already brushed up against his share of wiseguys in New York's gritty construction business, without apparent concern. To help build his first big Manhattan project, the Grand Hyatt New York on East 42nd Street, Trump had chosen a notorious demolition company secretly owned in part, according to the FBI, by a top Philadelphia mobster who doubled as crime lord of Atlantic City. To pour concrete for the new hotel, Trump picked a firm run by a man named Biff Halloran who was convicted a few years later for his role in what prosecutors dubbed a mob-run cartel that jacked up construction prices throughout the city. For the carpentry contract, Trump settled on a Genovese family-controlled enterprise that was central to another mob price-fixing racket, as found by a subsequent federal probe.