The CIA begins working with a rogue gallery of colorful characters as it attempts to "eliminate" Cuban leader Fidel Castro. Foremost among them is legendary mob fixer, "Handsome Johnny" Roselli.

The risqué private life of Chicago mob gangster and spy, Sam Giancana gets unwanted attention from the FBI and the press just as the CIA prepares its top-secret invasion of Cuba at the Bay of Pigs.

Facing political humiliation, the Kennedys double down on their plot against Castro. Meanwhile, things get personal for gangster spy Johnny Roselli and he decides to take matters into his own hands.