The Candidate (JFK) – The charismatic, playboy son of one of America’s most powerful (and ruthless) businessmen, born into American royalty and slotted for greatness. He almost reluctantly lets himself be guided to the White House, though he is drawn more to the glitz, glamor and carefree decadence of Hollywood.
The Singer (Frank Sinatra) – The singer/actor rose from the dirty, gangster streets of Hoboken to become Hollywood’s most powerful and influential performer. Despite his success, his ethnicity leaves him feeling shut out by the “white” west coast elite and he desperately looks to connect with the American hierarchy to finally establish his legitimacy.
The Gangster (Sam Giancana) – The son of poor Sicilian immigrants, natural progression leads him directly into the deadly world of the Chicago Outfit (mob). From his start as a murdering street thug, he quickly developed into a brilliant businessman/entrepreneur, spreading the reach of the Chicago Mafia’s gambling investments world-wide. He too is attracted to the glamor/celebrity world (and one actress in particular) despite warnings from his powerful gangster colleagues who wish to remain hidden from public view.
The Sex Symbol (Marilyn Monroe) – The iconic blonde bombshell whose intelligence and understanding of politics ran deeper than anyone imagined. She used her beauty and raw sex appeal to attract powerful men, but her steamy secret affair with JFK threatened to destroy his administration.
The Patriarch (Joseph Kennedy) – One of America’s most powerful and well connected businessmen who unapologetically clawed his way to the top. His driving ambition is to have his son elected president no matter the cost, financially or personally.
The G-Man (J. Edgar Hoover) – He outlasted seven U.S. Presidents and was arguably the most dangerous man in Washington. With secret (and often compromising) files on anyone who could possibly challenge him, he wielded his information to control the nation’s most powerful men.
Sensing JFK’s strong attraction to southern California’s glamour set, Sinatra quickly cements his relationship with the presidential candidate by introducing him to Hollywood’s biggest stars – as well as an endless cache of beautiful starlets. (including Marilyn Monroe).
At the behest of the controlling family patriarch Joe Kennedy, Sinatra asks a favor of his gangster pal Sam Giancana – The mob has firm control of the West Virginia Coal Miners Union and their vote in that state’s primary in favor of JFK would seal the Democratic nomination.
Leery of the father Joe Kennedy, Giancana is initially reluctant to help. But after Sinatra slyly introduces Sam to beautiful singer/actress Phyllis McGuire, Giancana is smitten and agrees to the favor. But Giancana has political dealings of his own: he is secretly recruited by the CIA to assassinate Cuban dictator Fidel Castro.
Sinatra and his Rat Pack (Dean Martin and Sammy Davis) campaign tirelessly for Frank’s pal Jack, and Sinatra enlists all his Hollywood connections to help the Kennedy campaign. Meanwhile more covertly, Giancana sends Atlantic City mobster “Skinny” D’Amato to West Virginia with a suitcase full of cash to be disbursed among union officials and local politicians.
JFK wins the nomination and ultimately the White House by the slimmest of margins over Richard Nixon, due in no small part to the vote rigging of the Cook County Democratic machine and the Chicago mob.
Despite pre-election assurances otherwise, the newly elected President’s Attorney General (brother Bobby) escalates his war on the Mafia with massive indictments and deportations nationwide. Sinatra is leaned on by Chicago to call off the Kennedy brothers but he is unsuccessful.
The President’s continued infatuation with Hollywood (and sex symbol Marilyn Monroe) has wife Jackie irate and brother Bobby worried – with J. Edgar Hoover ready to use compromising files and wiretaps to destroy the Kennedy administration. Robert convinces his president brother it’s finally time to cut ties with his famous California friends. Though reluctant, JFK cleans up his act and shuns his onetime pal Sinatra. Meanwhile, a drug induced Marilyn continues to pursue her president boyfriend with repeated phone calls to the White House until she dies mysteriously in her own bed.
Though Chicago mafia profits have soared to record levels under Giancana due to his gambling enterprises world-wide, his ultra-violent reign as boss as well as his well-publicized romance with singer McGuire draws the ire of his gangster colleagues. This, along with intensified anti-mafia efforts by Bobby Kennedy’s Justice Department has mobsters nationwide worried for their future survival. An elaborate plan is concocted in a Louisiana backwoods hunting cabin by the nation’s most powerful mafia bosses – Santo Trafficante, Carlos Marcello and Sam Giancana – to assassinate President Kennedy at a Democratic fundraiser at Chicago’s Blackstone hotel using an imported (and unsuspecting) Cuban assassin just one year before Dallas.