America, 1960. Joe Kennedy’s plan to take the White House takes a fateful turn when he uses the friendship between his son Jack and Frank Sinatra as a means to elicit a favor from Chicago Mafia boss Sam Giancana. The Chicago mob controls the West Virginia Coal Miner’s Union and their vote in that state’s primary in favor of JFK would seal the Democratic nomination - for which Joe offers future protection from government prosecution.
Sinatra and his Rat Pack (Dean Martin and Sammy Davis) campaign tirelessly for Frank’s pal Jack - who 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’s manipulation of America’s labor union vote.
But favors turn into betrayal when newly appointed Attorney General (brother Bobby) declares war on organized crime with massive indictments and deportations nationwide. Meanwhile, FBI Director J. Edgar Hoover has all the key players under surveillance - including the President and his mistress, Marilyn Monroe as he compiles a thick file of damaging evidence to blackmail the new administration.
The story climaxes with the mysterious death of Marilyn in Los Angeles after her repeated calls to the White House and threat to go public with her presidential affair…then an elaborate plan is initiated by Mafia bosses Carlos Marcello, Santo Trafficante and Giancana to assassinate President Kennedy at a Democratic fundraiser at Chicago’s Blackstone hotel using an unsuspecting Cuban assassin - one year before Dallas.