Frank Sinatra Relationships
 Lauren Bacall
Sinatra proposed to Lauren Bacall, shortly after her husband Humphrey Bogart died in 1957, but reneged when word of their relationship became public .
Juliet Prowse
Sinatra was also engaged to South African actress Juliet Prowse for a short while, before Sinatra broke the engagement in late 1962.
Children
Sinatra had three children with his first wife, Nancy Barbato: Nancy Sinatra (born June 8, 1940), Frank Sinatra, Jr. (born January 10, 1944), and Christina Tina Sinatra (born June 20, 1948). Although Sinatra did not remain faithful to his wife, he was by many accounts a devoted father.
On December 8, 1963, Frank Sinatra, Jr. was kidnapped. Sinatra paid the kidnappers' $240,000 ransom demand (even offering $1,000,000 though the kidnappers bizarrely turned down this offer), and his son was released unharmed on December 10. Because the kidnappers demanded that Sinatra call them only from pay phones, Sinatra carried a roll of dimes with him throughout the ordeal, and this became a lifetime habit. The kidnappers were subsequently apprehended and convicted. A movie called Stealing Sinatra was made about the incident.
Julie Sinatra (born Julie Ann Maria Lyma on February 10, 1943) claims to be Sinatra's daughter through an unacknowledged affair that he had with a showgirl, Dorothy Bunocelli, in the 1940s. She changed her last name by deed poll to Sinatra in 2000. Awarded $100,000 by the Sinatra estate in 2002, elements of her story concerning her mother's trip to Cuba with Sinatra have been disputed.
Alleged organized crime links
Sinatra has been frequently linked to members of the Mafia and it has long been rumored that his career was aided behind the scenes by organized crime.
One of his uncles, Babe Gavarante, was a member of a Bergen County armed gang connected to the organization of Willie Moretti. Gavarante was convicted of murder in 1921 in connection with an armed robbery in which he had driven the getaway car. Sinatra was also allegedly personally linked to Willie Moretti — his first wife Nancy Barbato was a cousin of one of Moretti's senior henchmen and Sinatra sang at the daughter's wedding in 1948. According to testimony from Moretti, Sinatra received help from him in arranging performances in return for kickbacks.
He had associations with and did favours for Charles Fischetti, a notorious Chicago mobster dating back to 1946 (according to the FBI). Sinatra was also friends with Charles's brother Joseph who ran the Fontainebleau Hotel complex in Miami, who arranged work for him and introduced him to Charles Luciano in Havana. After Luciano's deportation to Italy, Sinatra visited him at least twice, singing at a 1946 Christmas Party and gifting the famed mobster with a gold cigarette case engraved To my dear pal Charlie, from his friend Frank the next year.
These visits were widely reported by the media and used as further evidence of Sinatra's ties to the mob, haunting him for the rest of his life. Among the allegations was the $2 million that Sinatra gave Luciano. As Joseph Doc Stacher later recalled of the Havana meeting, The Italians among us were all very proud of Frank. They always told me they had spent a lot of money helping him in his career ever since he was in Tommy Dorsey’s band. Lucky Luciano was very fond of Frank’s singing. Frankie flew into Havana with the Fischettis, with whom he was very friendly, but of course, our meeting had nothing to do with hearing him croon. Everyone brought envelopes of money for Luciano. But more important, they came to pay allegiance to him. The Havana allegations — while the basis of rumors for Sinatra's mob ties — have never been proved, and in his autobiography Luciano himself denied there was any criminal association.
Sinatra had a strong friendship with Sam Giancana, who always wore a sapphire friendship ring given to him by Sinatra. A number of alleged incidents have been noted where people who angered Sinatra had been threatened by Giancana's mob. Comedian Jackie Mason has alleged that after mocking Sinatra in his routine, he received threats and his hotel room was shot up in his presence. After he continued, he received death threats and was roughed up and his nose broken.
J. Edgar Hoover apparently suspected Sinatra over the years, and Sinatra's file at the FBI ended up at 2,403 pages, detailing allegations of extortion against Ronald Alpert for $100,000. Sinatra publicly rejected these accusations many times, and was never charged with any crimes in connection with them.
The character Johnny Fontane in the book and movie The Godfather is widely viewed as having been inspired by Frank Sinatra and his alleged connections. Indeed, Sinatra was furious with Godfather author Mario Puzo over the Fontane character and reportedly confronted Puzo in public with profane threats supposedly on the basis that Fontane is shown to cry in the film, an emasculating display Sinatra would have not ideally had implied as a part of his personality.
In June of 1985, soon after Sinatra received his Medal of Freedom, satirical cartoonist Garry Trudeau ran a series of Doonesbury strips resurrecting photos of Sinatra Doing It My Way, posing with known mafiosi many years earlier. Sinatra complained that the strip series was unfair, and pointed out that his mob associates gave him work when no one else would.
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