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.

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.

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.

Al Capone moves back to Chicago and takes over two floors of the city's finest hotel, the Lexington. With a thriving business and Chicago politicians in his back pocket, Capone soon reaches a level of celebrity normally reserved for athletes and entertainers. As Capone's profile grows, he begins to indulge in all that the Roaring '20s have to offer, including cocaine. While Capone enjoys his reign at the top of the Chicago underworld, Irish gangster Bugs Moran seeks to take him down as revenge for the deaths of his partners Dean O'Banion and Hymie Weiss. On March 7, 1928, Moran orders a hit on one of Capone's top associates, Jack McGurn, the man who took out Hymie Weiss. McGurn survives but Capone decides to retaliate by taking out Moran and as many of his men as possible - all at once. On February 14, 1929, Capone's men dress as law enforcement and raid the liquor buy. They order Moran's men to face the wall for handcuffing, but while their backs are turned, Capone's men shoot all of them. Firing 70 rounds of ammunition in less than 10 seconds, the assassins carry out the biggest gangland hit in American history that will come to be known as the St. Valentine's Day Massacre. Through a stroke of luck, Moran avoids the massacre, but knows he's been defeated.