In the first half of the program, George Knapp welcomed author Bill Friedman, who recounted inside stories about the organized crime origins of the Las Vegas Strip. According to him, Prohibition era gangs were responsible for a whopping eighty percent of the gambling resorts built on the Vegas Strip from 1946 to 1966. He explained that these gangs gained entry to Vegas because, following Prohibition, they spread out across America and created "incredibly elegant, high end casinos" which were fronted by hotels and restaurants throughout the country. Since they had shown such expertise in running casinos, the leaders of these gangs were seen as the ideal people to be granted licenses by the state of Nevada to build on the Strip as long as they had only previously been involved in gambling and prohibition activities and not violent crime.

Over the course of his appearance, Friedman detailed how his research was informed from a lifetime of association with the most powerful players in Vegas' casino industry and organized crime subculture, which began after he got a job as a blackjack dealer while still in college. Fascinated by the characters he worked alongside, Rogers befriended many of them and developed a level of access to these legendary gangsters which was so remarkable that the FBI ultimately tasked him with documenting the history of organized crime rather than serve in the Vietnam War. Over the ensuing years, more players in Vegas' early history confided in him because they were upset at being branded as criminals, due to their Prohibition-era activities, despite operating legitimate gambling establishments on the Strip and, thus, wanted the true story of Sin City's founding to be told.

--------------------------------

In the latter half, investigative journalist Toby Rogers (book link) shared the untold story of mafia legend Silvio Eboli, a Genovese mob scion who developed an ongoing organized crime operation which involves the sale of marijuana throughout the New York metropolitan area. He revealed that the impetus behind his work actually came from Eboli, himself, who personally asked him to write about his rise to power in the NYC marijuana trade. As such, Rogers was allowed to shadow the crime boss and was granted unprecedented access to the inner workings of his operation. His connection to Eboli became so deep, Rogers said, that "every day I was with him, I thought maybe it was my last," since the mobster could have, at any time, decided to scrap the project and have him eliminated because he knew too much or he could have wound up as collateral damage in a turf war over the drug trade.

Regarding the evolution of Eboli's marijuana business, Rogers recalled how he started as a mule bringing the drugs from Jamaica to America in the late 1980's. However, after NYC mayor Rudy Giuliani cracked down on drug dealers in the city's parks, home delivery of the marijuana began to rise in popularity. As this newfound industry began burgeoning, 9/11 happened, which created chaos amongst the various players in the trade and allowed Eboli to step in and use his criminal connections as well as his personal charisma to take over the world of marijuana home delivery throughout the region. Over time, Rogers said, Eboli developed a system which boasts a significant monopoly over downtown New York and generates massive profit, serving high powered clients including famous names in the entertainment and sports world.