By the mid-1980s, one of the most powerful illicit organizations was the Cuban mob. Known on both sides of the law as "the Corporation," the mob’s power stemmed from a criminal culture embedded in south Florida’s exile community. Journalist T. J. English joined guest host Richard Syrett to discuss an epic story of gangsters, drugs, violence, sex, and murder rooted in the streets, revealing how an entire generation of political exiles, refugees, racketeers, corrupt cops, and hit-men became caught up in an American saga of desperation and empire building. English stated that the story of American crime is, in part, "a result of the economic system that encourages it."

English spoke extensively on the dark career of Cuban American exile José Miguel Battle and his role in fighting with CIA-trained Cuban exiles during the ill-fated Bay of Pigs invasion in 1961. Battle remained in the US after the fiasco and began to build a criminal empire based on the illegal numbers racket (lottery) along the entire Eastern seaboard. He added that the Cuban mob also sponsored assassinations and other politically-motivated dirty tricks in support of the CIA, which promised Cuban exiles that they would eventually assassinate Fidel Castro. At its height, the numbers operation even counted certain police forces in New York and New Jersey among its co-conspirators. Battle was eventually caught and died in custody in 2007.

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James DiEugenio is one of the most respected researchers and writers on the political assassinations of the 1960s. He was included in the DVD extras for Oliver Stone’s 1991 film JFK, and Stone wrote an introduction for one of DiEugenio’s books. DiEugenio sharply criticized assassination skeptic Vincent Bugliosi and his book Reclaiming History, which concludes that Lee Harvey Oswald acted alone. Bugliosi is most famous for his prosecution of Charles Manson and his book about the case, Helter Skelter. DiEugenio believes that both of these books are deeply flawed, and that the real reason for the Manson trial was a coverup of "the association between the music industry and the black market for drugs in L.A. in the 1960s."

DiEugenio discussed a crucial part of the assassination testimony gathered in a lie detector test given to Oswald killer Jack Ruby. He claimed the technician conducting the report purposely changed the settings on the machine to be less sensitive to deception and that the session contained 70 questions, while a standard test has only 15. He also discussed various examples of what he believes is weak evidence for the so-called "magic bullet" that was used as primary evidence citing Oswald as the lone killer. Hollywood was a target of DiEugenio’s criticism as well, and he reserved more pointed comments for actor Tom Hanks and his participation in what DiEugenio considers inaccurate or even whitewashed versions of history in the films Parkland and The Post. He lamented that those in positions of power in the film industry are often involved in productions "which don’t even begin to tell us the truth."