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.

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.

Tony Accardo have taken the reins of the criminal empire built by their mentor Al Capone. Thanks to Sam Giancana's takeover of the policy racket, the gangsters are now making millions. With so much money coming in, Accardo knows they need a place to hide it. They find their answer in a growing city where gambling is now legal: Las Vegas. However, the New York mafia is already there, led by criminal mastermind Meyer Lansky.

The story of America's most notorious gangster, Al Capone, starts on the streets of Brooklyn. In 1913, at the age of 14, Capone starts running errands for local gangsters - just one of many immigrants struggling to survive. One day, young Al Capone gets caught in a police raid. He quickly grabs what money he can, evades police, and runs to the headquarters of mob boss Johnny Torrio. Torrio rewards Capone for his quick-thinking. When Torrio recognizes Capone's intelligence and drive, he takes him under his wing.

In less than two years, Al Capone has risen from a humble bookkeeper to second-in-command of Johnny Torrio's criminal empire in Chicago. The empire is worth the modern-day equivalent of $35 million. Capone purchases a home for his family and moves them from New York to Chicago. Torrio and Capone expand their empire from Chicago's South Side to the North Side, which is controlled by Chicago's second largest gang, the Irish. Violence erupts as ruthless Irish gang leader Dean O'Banion protects his territory and bootlegging business from Torrio and Capone.

After the murder of his brother Frank, Al Capone is out for revenge against William Dever and the Chicago police. He plots to kill every undercover cop that was in Cicero on the day of Frank’s death. Before he can set his plan in motion, however, Johnny Torrio returns from Italy and reclaims his control of their criminal empire. Torrio forbids Capone from killing cops, fearing it would spark an all-out war. Despite Capone’s personal loss, Torrio returns to a booming business that’s raking in $10 million a month. However, as Torrio and Capone’s empire grows, it becomes harder to keep smaller factions under control. After a small group of Italian mobsters attacks one of Dean O’Banion’s distilleries, O’Banion blames Torrio and decides to end their business partnership. He announces his retirement to Torrio and offers Torrio an opportunity to buy him out. Torrio meets O’Banion at the Seine Brewery on May 19, 1924, with the buyout money. Chicago police raid the brewery and arrest Torrio while letting O’Banion walk free: O’Banion had set the whole thing up. With prior convictions, Torrio serves a mandatory prison sentence but is first released on bail. He vows to kill O’Banion as payback and gives Capone his blessing to kill O’Banion. Capone spends months planning the hit. Capone knows that catching O’Banion off guard is nearly impossible, so he places an order with O’Banion’s flower shop for nearly $20,000 worth of flowers, knowing that O’Banion personally oversees his biggest arrangements. On November 10, 1924, O’Banion works in his shop preparing the flower delivery. Two of Capone’s men enter the shop and fatally gun O’Banion down. Four days later, Chicago’s most powerful Irish gangster is laid to rest in one of the most lavish funerals Chicago has ever seen. More than two dozen cars are required to transport floral arrangements as a crowd of 10,000 mourns the death of the infamous gangster. Torrio and Capone attend the funeral, infuriating O’Banion’s top lieutenants, Hymie Weiss and Bugs Moran. Chaos breaks out as smaller gangs through the city begin a turf war. It’s the beginning of an era of bloodshed in Chicago known as the Beer Wars. Over 300 people are murdered at a rate of 75 to 100 murders a year.