Frank Sinatra's barkeep father and midwife mother had loose affiliations with organized crime that assisted Frank in his rise to stardom. John F Kennedy' father's bootlegging past cultivated criminal connections that helped him to run for President.

Kennedy wins the Presidency. Robert Kennedy, hellbent on cracking down on the Mafia, was appointed Attorney General. When Hoover discovers a love triangle, he tells the President to cut all ties with the Mafia, including Sinatra.