Frank Sinatra had many close relationships throughout his life. He was married four times, and had many other notable relationships before, after and during these marriages.
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Frank Sinatra met Nancy Barbato when he was nineteen, and they were married on February 4, 1939, in Jersey City, New Jersey, Barbato's home town.[1] Their wedding was held at Our Lady of Sorrows Church at 93 Clerk Street, after which the newlyweds resided in an apartment house at 137 Bergen Avenue. Their first child, their elder daughter Nancy Sinatra, was born in June 1940, and their son, Frank Sinatra, Jr., was born in January 1944. Both of these children were born at the Margaret Hague Hospital in Jersey City.[2]
Following their moving to Hollywood, Los Angeles, California, Sinatra errantly strayed from his marriage into extra-marital affairs with Marilyn Maxwell. These affairs also became public knowledge and caused great embarrassment to Nancy Barbato Sinatra, who considered calling off their marriage then and had an abortion when she became pregnant in 1946.[3] A third child, Tina Sinatra was born in 1948.
Nancy Barbato Sinatra and Frank Sinatra announced their separation on Valentine's Day, February 14, 1950, with Frank's additional extra-marital affair with Ava Gardner compounding his transgressions and becoming public knowledge once again. After originally just seeking a legal separation, Frank and Nancy Sinatra decided some months later to file for divorce, and this divorce became legally final on October 29, 1951. Frank Sinatra's affair and relationship with Gardner had become more and more serious, and she later became his second wife.
Sinatra later expressed regrets at having married Nancy saying "What I had mistaken for love," he ruefully stated later, "was only the warm friendship Nancy had brought me."
Sinatra first met Ava Gardner in 1944, but saw her only sporadically until late 1949, when they began their relationship. Their relationship was tempestuous, and coincided with the collapse of Sinatra's professional career, as Gardner's blossomed.
They married on November 7, 1951, ten days after Sinatra's divorce from Barbato became final. Both were frequently made jealous by the other's extramarital affairs, and Gardner had an abortion.[4]
Gardner's power in Hollywood helped Sinatra get cast in From Here to Eternity (1953),[5] and his subsequent Academy Award for Best Supporting Actor helped revitalize Sinatra's professional career. They separated in October 1953 and divorced in 1957.
Sinatra married the actress, Mia Farrow on July 19, 1966, when she was 21 and he was 50. He proposed at Loveladies beach in Long Beach Island New Jersey. (Coincidentally, Sinatra was enjoying a wave of renewed popularity at the time, as the song "Strangers in the Night" returned him to the top of the Billboard charts only seventeen days later. They met on the set of Sinatra's film, Von Ryan's Express.[6] She agreed to appear in his 1968 film, The Detective, but when she reneged as her filming schedule for Rosemary's Baby overran, Sinatra served her divorce papers in front of the cast and crew.[7]
On July 11, 1976, Sinatra married Barbara Blakeley Marx (formerly married to Zeppo Marx, the straight man in the Marx brothers' act[8]), who converted to Catholicism to marry him. She remained his wife until his death, although her relations with Sinatra's children were consistently portrayed as stormy, something Nancy Sinatra confirmed when she publicly claimed that Barbara had not bothered to call Frank's children even when the end was near, although they were close by, and the children missed the opportunity to be at their father's bedside when he died.[9]
Sinatra and Judy Garland remained good friends up until her death in 1969, but on only two occasions were the two legendary singers romantically involved. The first was in 1949, when Garland was recovering from a nervous breakdown and the two went on a romantic rendezvous in the Hamptons (Garland was still married to director Vincente Minnelli). The second was during one of Garland's many separations from her third husband Sid Luft in 1955. Sinatra had just come off his messy separation from Ava Gardner and was spotted in Garland's company until Luft found out.
Sinatra proposed to Lauren Bacall, shortly after her husband Humphrey Bogart died in 1957, but reneged when word of their relationship became public. They split a little over a year later.
Sinatra was also engaged to South African-born actress and dancer Juliet Prowse for a short while from fall 1961 to early 1962, before Sinatra broke the engagement late that year because Prowse refused to give up her career. The two first met on the set of the 1960 film Can-Can.
Sinatra met the actress Marilyn Monroe in 1954 (while he was still married to Ava Gardner) and was a friend of Monroe's second husband Joe DiMaggio, and after DiMaggio and Monroe divorced, he joined his friend DiMaggio and another man named James Bacon on a "Wrong Door Raid" set up by DiMaggio himself in pursuit of his ex-wife (Monroe) and her lover Hal Schafer, and instead of raiding their apartment, they raided another woman's apartment, whose name was Florence Kotz. In summer of 1961, Sinatra saw Monroe again and began an affair with her, and Monroe talked about marrying Sinatra, but Sinatra broke off the affair in September 1961.
Sinatra was romantically involved with Angie Dickinson off and on for ten years from around 1954 to 1964. "We had an incredible 'like' for each other" and "a very comfortable relationship", stated Dickinson in 1999, adding that if they'd had "a burning love affair" then the romance might not have lasted as long. The two remained friends until Sinatra's 1998 death.
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.[10] 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.[10] 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 legally changed her last name to Sinatra in 2000.[11] Awarded $100,000 by the Sinatra estate in 2002,[11] elements of her story concerning her mother's trip to Cuba with Sinatra have been disputed.[12]
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.[13]
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 personally linked to Moretti;[14] 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 and marijuana.
He had associations with and did favors 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 and 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 giving the famed mobster a gold cigarette case engraved "To my dear pal Charlie, from his friend Frank" the next year. Sinatra was also in Havana during a "notorious Mafia conclave" at the Hotel Nacional in February 1947.[14]
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,[15] 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 emotional weak display Sinatra would not imply as a part of his personality.
In June 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.