Frank Sinatra had many close relationships throughout his life. He was married four times, and had at least six other notable relationships in between. Sinatra had three verified children, as well as one who claimed to be Sinatra's child but whose parenthood had not been verified and one potentially his but of uncertain parentage.
- 1 Marriages
- 2 Relationships
- 3 Children
- 4 Personality
- 5 Cal Neva Lodge
- 6 Alleged organized-crime links
- 7 References
- 8 External links
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, Francis 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 move to Hollywood, Los Angeles, California, Sinatra errantly strayed from his marriage into extra-marital affairs, the first known 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."
Kelley claims that Sinatra had first seen photographs of  Sinatra took responsibility for Gardner's business affairs long after the split, and was still dealing with her finances in 1976. When she fell into financial difficulty in later years, Sinatra paid $50,000 towards her medical bills. 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 film career.
Sinatra married 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. In an interview for the November 2013 issue of Vanity Fair, Farrow said that she and Sinatra "never really split up" and answered "possibly" when asked if her son Ronan might be Sinatra's.
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 had numerous extra-marital affairs, the first of which was with blonde starlet Alora Gooding from October 1940 while in Hollywood, his "first big love away from home" according to Nick Sevano. Next followed Rita Maritt, a 16-year-old Long Island debutante, the daughter of an oil baron, and Mary Lou Watts, a wealthy socialite. Gossip magazines published details of affairs with the likes of Lana Turner and Marilyn Maxwell.
Summers and Swan claimed that Turner had gushed of a "very serious affair" between the two, and that they had only faked splitting up their relationship to oblige to MGM's concerns. Turner later denied the claims in her 1992 autobiography, saying that "the closest things to dates Frank and I enjoyed were a few box lunches at MGM".
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 was very close to Lauren Bacall. According to Kelley, her husband Humphrey Bogart believed that Sinatra was in love with Bacall and failed to attend the Sands on Bacall's 32nd birthday out of jealousy, though the two men were on good terms. Sinatra and Bacall were frequently seen together in public throughout 1957, and on March 11, 1958 they reportedly became engaged, though Sinatra denied intending to marry her.
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 Marilyn Monroe in 1954 (while he was still married to Ava Gardner. although some sources say that Sinatra and Monroe first met several years earlier) 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 the apartment of another woman, 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. The radio program This American Life interviewed one of the kidnappers, Barry Keenan, in the 2002 episode "Plan B".
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.
In his spare time, Sinatra enjoyed listening to classical music, and would attend concerts when he could. He also liked opera, particularly Luciano Pavarotti, and told himself, "I'm just a wop baritone. This guy can really sing". In return, music critic Henry Pleasants said that he had rarely interviewed an opera singer who did not have a collection of Sinatra’s recordings. Jo-Caroll Dennison commented that Sinatra had "great inner strength", and that his energy and drive was "enormous".  A workaholic, he reportedly only slept for four hours a night on average. Rojek considers him to have been an "overtly sexual performer, caressing the microphone and standing in a suggestive manner". Impeccable with his dress and cleanliness, while with the Tommy Dorsey band he developed the nickname "Lady Macbeth", because of frequent showering and switching his outfits. He enjoyed golf, and would often play with golf champion Ken Venturi at the course in Palm Springs, where he lived.
Throughout his life, Sinatra had mood swings and bouts of mild to severe depression, admitting to an interviewer in the 1950s that "I have an over-acute capacity for sadness as well as elation". Avoiding solitude and unglamorous surroundings at all costs, he struggled with the conflicting need "to get away from it all, but not too far away." Anthony Quinn once stated that he had a "cruel streak in his personality", but that he still loved him as he was "what all men are and not one man in a million ever is". Sinatra's mood swings often developed into violence, directed at people he felt had crossed him, particularly journalists who gave him scathing reviews, publicists and photographers. He received negative press for fights with Lee Mortimer in 1947, photographer Eddie Schisser in Houston in 1950, and Judy Garland's publicist Jim Byron in 1954, whom he reportedly referred to as a "fucking parasite". Yet Sinatra was known for his generosity, particularly after his comeback. When Lee J. Cobb nearly died from a heart attack in June 1955, Sinatra flooded him with "books, flowers, delicacies", paid his hospital bills, and visited him daily, telling him that his finest acting was yet to come. In another instance, after a heated argument with manager Bobby Burns, rather than apologize, Sinatra bought him a brand new Cadillac.
In a 1963 interview with 
Cal Neva Lodge
In 1960, Sinatra bought a share in the Joe E. Lewis, Lucille Ball, Lena Horne, Juliet Prowse, the McGuire Sisters and others. By 1962 he reportedly held a 50% share in the hotel. Sinatra's gambling license was temporarily stripped by the Nevada Gaming Control Board in 1963 after mobster Sam Giancana was spotted on the premises. Due to ongoing pressure from the FBI and Nevada Gaming Commission and mobster control of casinos, and trouble with the Mafia, Sinatra agreed to give up his share in Cal Neva and the Sands.
Sinatra became the stereotype of the "tough working-class Italian American", something which he embraced. Sinatra commented that if it hadn't been for his interest in music he'd "probably have ended in a life of crime". Kelley claims that Eddie Fisher once remarked that Sinatra "wanted to be a hood" and had once told him that "I'd rather be a don of the Mafia than president of the United States". However, Peter Lawford had said that Sinatra only referred to them as the "boys" or "the Outfit", rather than the "Mafia".
In Sinatra's early days, mafia boss Willie Moretti helped him for kickbacks and was reported to have intervened in releasing him from his contract with Tommy Dorsey. Sinatra was present at the Mafia Havana Conference in 1946. When the press learned of Sinatra being in Havana with Lucky Luciano, one newspaper published the headline, "Shame, Sinatra". Kelley claims that Phyllis McGuire referred to Sam Giancana and Sinatra as the "best of friends", and would often play golf together in Nevada and visit each other.  She also quotes Jo-Carrol Silvers in saying that both Sinatra and her husband Phil Silvers "adored Bugsy Siegel so much", and would boast about him to friends and how many people he had killed. She also claimed that Silvers had told her that "like Bugsy, Frank had a Mafia Redneck mentality", with their shared love of high-living and grandiose plans in Las Vegas. Kelley claims that Sinatra and mobster Joseph Fischetti had been good friends from 1938 onward, and acted like "Sicilian brothers". She also states that Sinatra and Hank Sanicola were financial partners with Mickey Cohen, a West Coast mobster, in the gossip magazine Hollywood Night Life, which she claims that Sinatra funded $15,000 into to get back at Hollywood.
The  Their purported friendship finally came to an end in 1963 following the Nevada Gaming Commission's investigation into the casinos—according to Kelley, Giancana blamed Sinatra for the ordeal and was fuming at the abuse he had given to the commission's chairman, Ed Olsen.
The FBI's secret dossier on Sinatra was released in 1998 in response to Carlo Gambino, Sam Giancana, Lucky Luciano, and Joseph Fischetti, vehemently declaring that "any report that I fraternised with goons or racketeers is a vicious lie". When asked about his Mafia contacts in 1965 he stated that it was "due to a legitimate reason. We built a hotel together in Las Vegas". In January 1967 Sinatra stood before a Las Vegas grand jury investigating mobster influence in the casinos, and denied any financial exploits with Giancana. In his memoir, Dean & Me, Sinatra's associate Jerry Lewis said of the subject: "In the 1940s and '50s, before the Mob lost its hold on nightclubs and Vegas, it was literally impossible for an entertainer, any entertainer, not to deal with them."
- Kelley states that this was covered up by his representatives who told the press he had been admitted to hospital, suffering from "complete physical exhaustion, severe loss of weight, and a tremendous amount of emotional strain", and that he had simply had an accident with a broken glass.
- Sinatra always dressed immaculately, both in his professional and private life. He believed that as he was the best, he had to give his best to the audience, and would wear expensive custom-tailored tuxedos on stage as a sign of respect and to look important.
- The Rough Guide to Frank Sinatra, Chris Ingham, pg 9
- "Frank Sinatra's Jersey City Connection", CityofJerseyCity.org. Accessed June 30, 2008.
- Ingham, pg 10, as related in Tina Sinatra's memoir
- Kelley 1986, p. 155.
- Kelley 1986, p. 162.
- Kelley 1986, pp. 189-91.
- Kelley 1986, p. 202.
- Santopietro 2008, p. 133.
- Kelley 1986, p. 229.
- Kelley 1986, p. 239.
- Kelley 1986, p. 208.
- Kelley 1986, p. 230.
- Kelley 1986, p. 486.
- Santopietro 2008, p. 119.
- Ingham, pg41
- Ingham, p. 80
- Ingham, p. 81
- "Exclusive: Mia Farrow and Eight of Her Children Speak Out on Their Lives, Frank Sinatra, and the Scandals They've Endured". Vanity Fair. October 2 2013.
- Nash, Eric P. "Books in Brief: Nonfiction", The New York Times, February 18, 2001. Accessed January 7, 2008. "Sinatra's last wife, Barbara Marx, who had been married to Zeppo, the unfunny Marx brother, is depicted as the wicked stepmother, isolating the aging star from friends and family, persuading him to change his will and failing to notify the children in his last hours."
- Nancy Sinatra - Nancy Sinatra Blames Final Wife For Dad Frank'S Death
- Kelley 1986, pp. 62-3.
- Kelley 1986, pp. 63-4.
- Kelley 1986, p. 127.
- Summers & Swan 2010, p. 144.
- Summers & Swan 2010, p. 157.
- Kelley 1986, p. 265-68.
- Kelley 1986, p. 276.
- http://www.dougiethompson.com/frank-sinatra.htm Interview with Julie Sinatra
- Frank Sinatra - Sinatra Biographers Question New Lovechild Claims
- "Exclusive: Mia Farrow and Eight of Her Children Speak Out on Their Lives, Frank Sinatra, and the Scandals They've Endured". Vanity Fair. October 2 2013.
- Kelley 1986, p. 92.
- Kelley 1986, p. Introduction xii.
- Lees 1998, pp. 91-92.
- Summers & Swan 2010, p. 151.
- Santopietro 2008, p. 16.
- Rojek 2004, p. 31.
- Santopietro 2008, p. 53.
- Kelley 1986, p. 59.
- Sinatra 1986, p. 242.
- Sinatra & Coplon 2000, p. 47.
- Summers & Swan 2010, p. 218.
- Kaplan 2011, p. 485.
- Kelley 1986, p. 321-22.
- Kelley 1986, pp. 249-50.
- Kelley 1986, pp. 251-52.
- Kelley 1986, p. 53.
- Kelley 1986, p. 493.
- Kelley 1986, pp. 347-48, 355.
- Kelley 1986, p. 362.
- McNally 2015, p. 50.
- Kelley 1986, pp. 294-5.
- Sifakis 2005, p. 420.
- Sifakis 2005, p. 419.
- Lahr 2000, p. 63.
- Kelley 1986, p. 296.
- Kelley 1986, pp. 124-5.
- Kelley 1986, p. 135.
- Kelley 1986, p. 176.
- Kelley 1986, pp. 327-9.
- Kelley 1986, pp. 363-64.
- Kaplan 2011, pp. 446-7.
- McNally 2015, p. 49.
- Lewis & Kaplan 2005, p. 99.