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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's father's bootlegging past cultivated criminal connections that helped him to run for President.

Kennedy, Sinatra and the Mafia

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

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With his mafia wise guy links and access to entertainment industry star power, Frank Sinatra helps John F. Kennedy into the White House in 1960, but it all comes to a bitter end.