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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.
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. 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 on June 8, 1940, and their son, Franklin Wayne Sinatra, known as Frank Sinatra, Jr., was born on January 10, 1944. Both of these children were born at the Margaret Hague Hospital in Jersey City.
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. A third child, Christina Sinatra, known as "Tina", was born on June 20, 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.
Gardner's power in Hollywood helped Sinatra get cast in From Here to Eternity (1953), 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. At the time, Sinatra was enjoying a wave of renewed popularity 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. 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.
On July 11, 1976, Sinatra married Barbara Blakeley Marx (formerly married to Zeppo Marx, the straight man in the Marx brothers' act), 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.
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 the writer James Bacon on a 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 fall of 1961 (around the same time he saw Juliet Prowse).
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. 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 legally changed her last name 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.
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A biography of Frank Sinatra titled Frank: The Voice by James Kaplan, alleged that 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.
Also James Kaplan assumed that Frank Sinatra had links to Charles Fischetti, a notorious Chicago mobster, and with Charles's brother Joseph who ran the Fontainebleau Hotel complex in Miami and arranged work for Sinatra. Charles Fischetti 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. Columnist Robert Ruark claimed that Sinatra was also in Havana during a "notorious Mafia conclave" at the Hotel Nacional in February 1947. 
Sinatra had a relationship with mafia don Sam Giancana, who helped the Kennedys with the primary in West Virginia in 1960. In biography of Frank Sinatra titled The Rough Guide to Frank Sinatra Chris Ingham claimed that after the Cal-Neva incident in the summer of 1963, the relationship between Giancana and Sinatra cooled. . According to Sinatra: the Untold Story by Michael Munn, Sinatra subsequently colluded with the government to help to bring Giancana down. 
In a biography on her father entitled Frank Sinatra: An American Legend, Nancy Sinatra claimed that "the FBI files indicated that my father had been investigated endlessly for 30 years. (The early FBI files have him listed as a "Communist" because he appeared at a rally with Mrs. Eleanor Roosevelt and because he sang "The House I Live In"). The files disclosed that there was no evidence of Mafia membership, Mafia affiliation or going business with the Mafia. The FBI files also showed that the stories about Sinatra and members of the Mafia had come out originally as rumors printed in newspaper articles - rumors that were reported as rumors but were subsequently reported over and over until they were accepted as "facts."