Tony Accardo receives a phone call from Joseph P. Kennedy, asking the mob kingpins to use their pull with the Illinois union vote to help his son, John F. Kennedy, win the upcoming presidential election. In return, he offers to put an end to his son Robert F. Kennedy's investigation into Giancana and the Outfit. As election day nears, Kennedy's fight against Richard Nixon tightens, turning Illinois into a key battleground. Giancana delivers the union votes. After a close race, Kennedy is declared the victor. Just weeks after Kennedy takes office, his brother Robert is named Attorney General. To the Chicago mob's surprise, when Robert takes office as the new U.S. Attorney General in 1961, he makes his top priority going after organized crime ó and one of his primary targets is the Outfit. Weeks after, John F. Kennedy is shot and killed in Dallas. After his brother is assassinated, Robert steps down from his post as Attorney General and the investigation into organized crime is virtually dropped. The government begins an investigation into the assassination, with rumors already circulating that the mafia could have been involved.

After becoming the most powerful mob boss in the country, Al Capone now finds himself locked up in America's newest and harshest maximum security prison: Alcatraz. Prohibition has recently been repealed and one of the Outfit's most important sources of income dries up. With Capone cut off from all communication, his most trusted men, Frank Nitti, Tony Accardo and Paul Ricca, must keep his organization from collapsing. With Americans flocking to theaters by the thousands, the movie business is raking in millions of dollars a month. To take advantage of Hollywood, Nitti recruits Willy Bioff. Acardo breaks into a new racket in Chicago: slot machines. With help from Ricca, Accardo builds a network of slots in Chicago bars, earning up to $20,000 a year. By the end of 1939, the Outfit is bringing in more money than ever before... But new problems start to appear.

This featured documentary delves into the tangled web of politics, show business, and organized crime in post-World War II America. It traces the unlikely connections between President John F. Kennedy, iconic singer Frank Sinatra, and notorious mobsters, revealing a saga of mutual assistance amidst corruption and betrayal. The film highlights the complex interplay of fame, money, and power, illustrating how these forces helped these figures rise to prominence in a chaotic and corrupt American landscape, ultimately leading to personal and political tragedies.
The documentary paints a vivid picture of Kennedy and Sinatra's ascent, influenced by their ties with the mafia. Kennedy, groomed for power from birth, and Sinatra, rising from humble beginnings, both relied on mafia connections for their successes. As Kennedy's political career and Sinatra's entertainment stature grew, so did their dependence on the underworld. The film culminates in the portrayal of Sinatra's deep involvement in Kennedy's 1960 presidential campaign and the subsequent betrayal of the mafia by the Kennedy administration, suggesting that this complex network of relationships may have played a role in Kennedy's assassination. This provocative tale is a stark reminder of the dark intersection of fame, power, and crime.

Dive into the gripping world of organized crime with the enthralling documentary series focusing on John Gotti, a name synonymous with the Gambino crime family. In this second installment, viewers are transported into the shadowy corners of mob life, exploring the brutal enforcement of mafia rules and the dire consequences of betrayal. Highlighting a chilling assignment carried out in Florida, the documentary captures the ruthlessness embedded within the mafia's code, where personal lives intertwine dangerously with business, leading to violent outcomes.
The episode also provides a fascinating look into the pivotal legal battles that defined Gotti's reign as a mafia boss. Witness the intense courtroom drama involving Diane Giacalone, the tenacious assistant U.S. Attorney, who took on Gotti and his associates in a high-stakes trial. Despite her efforts, the complexities of prosecuting organized crime come to the forefront, showcasing the challenges faced by law enforcement in penetrating the secretive and loyal underworld. This documentary is a must-watch for those intrigued by true crime and the intricate dance of cunning and law that shapes the world of organized crime.

The last installment of the series features a revealing first-person account that delves into the complexities of Gotti's mentorship and the stark realities of gang life. From a determined youth facing rejection from his father to his bold declaration to work for Gotti, witness the tumultuous ascent of Sammy ‘The Bull’ Gravano within the criminal underworld.
The narrative captures a pivotal confrontation, where Gotti chillingly outlines the dark path ahead, juxtaposed against the awe-inspiring backdrop of the Justice Department in Washington D.C., a symbol of the relentless pursuit that future gangsters will inevitably face. This episode doesn’t just recount events; it places you at the heart of an ongoing battle against organized crime, providing an intimate look at Gotti’s life, from his rise to power to his ultimate indictment and the intense legal battles that followed. Dive into a gripping exploration of loyalty, power, and the consequences of a life in the mafia.