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Frank Sinatra was a true icon of the entertainment industry and one of the most successful singers of the 20th century. But out of the spotlight, the man dubbed Ol’ Blue Eyes had a rather colorful private life. And thanks to the star’s apparent associations with dangerous organized crime figures, a long shadow has been cast over his legacy. So, is there any truth to the shocking rumors that dogged Sinatra even before his death?

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Indeed, some of the gossip surrounding the singer stands in marked contrast to the enduring vision of him as a slick, expensive-suit-wearing crooner. And Sinatra’s music was arguably the soundtrack to an era. In his 1940s and 1950s heyday, he released countless hit singles and chart-topping albums as well as scooping an Academy Award.

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Famously, Sinatra was also the unofficial leader of the “Rat Pack.” Alongside Sammy Davis Jr., Peter Lawford, Joey Bishop and Dean Martin, he bossed Las Vegas’ nightlife scene in the 1960s. And the star’s public image ultimately became that of someone living life to the full. Men wanted to be him, and women wanted to be with him.

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However, rumors of various kinds would always surround Sinatra. While the singer officially has three kids from four marriages, his reported philandering means that other potential children have cropped up over the years. In fact, three of the women who claim to have had extramarital relationships with Sinatra have said that he is the biological father to their offspring.

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A resident of Sedona, Arizona, named Julie has maintained that she is Sinatra’s daughter, for instance, and she even changed her legal surname to that of her alleged father in 2000. Julie has said that her mother, a Las Vegas hostess named Dorothy Bunocelli, engaged in a seven-year affair with Sinatra in the 1940s. And, apparently, Dorothy finally told her the truth of her parentage a few years before the mom passed away.

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Then there was an Australian woman named Deana, who has also gone under the last name of Sinatra. Her mother was the German actress Eva Bartok, who reportedly had an affair with Sinatra while he was married to Ava Gardner. And Deana asserts that she and her mother made efforts to meet Sinatra in person, including sending him a letter when she was 15 years old.

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Unfortunately, though, Deana received a response saying that Sinatra wasn’t open to bringing another child into his family. And not only was she deeply hurt by this reply, but those words also apparently altered her perception of the star. “I don’t think he was a man of high morals and values. That’s my feeling from where I stand,” Deana told Australian morning TV show Studio 10 in 2015.

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Pulitzer Prize-winning investigative journalist Ronan Farrow has also long been rumored to be another illegitimate child of Sinatra. Indeed, in 2013 his mother, actress Mia Farrow, told Vanity Fair that it was “possible” Sinatra was her son’s father rather than writer and director Woody Allen.

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Furthermore, during Farrow’s November 2019 appearance on Real Time with Bill Maher, the host was bold enough to question his guest’s parentage. In a seeming reference to the writer’s reporting on the Harvey Weinstein scandal, Maher even quipped, “There’s no one more #MeToo-y than Frank Sinatra.” And while Farrow wouldn’t be drawn into the conversation, he did previously joke in a 2013 tweet, “Listen, we’re all ‘possibly’ Frank Sinatra’s son.”

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On top of the claims of affairs and illegitimate children, however, there have also been negative stories about Sinatra’s personality. It’s been said, for example, that he had a hair-trigger temper. His fourth wife, Barbara, has also noted the “Jekyll-and-Hyde aspect to Frank,” while Mia Farrow once called him a “24-carat manic depressive.”

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Over the years, it’s additionally been reported that Sinatra was prone to hurling things at loved ones and friends during arguments. Yes, apparently, the singer once threw a glass pitcher of water at drummer Buddy Rich’s head. Sinatra had previously accused Rich of making errors in his drum solo – a complaint to which the musician had responded with name-calling. And by all accounts, the pitcher only just missed its intended target.

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Furthermore, it’s alleged that Sinatra once threw a heavy telephone at businessman Frederick R. Weisman in the Beverly Hills Hotel, with this assault reportedly fracturing Weisman’s skull. The star’s second wife, Ava Gardner, also suggested that a long crack in the porcelain of one of their bathroom sinks had been his handiwork. According to Gardner, Sinatra had previously heaved a champagne bottle at her, but the missile had ultimately damaged the basin instead.

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And in her book Lady Blue Eyes: My Life With Frank Sinatra, Barbara wrote about a frightening incident that she claimed to have had once experienced. After Sinatra’s team had lost a game of charades, the singer had allegedly picked up the brass clock that Barbara had been using to time-keep. His former wife went on to write, “I think [Frank] wanted to hit me with it. He threw it against the front door, and it broke into a thousand pieces.”

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Sinatra’s extensive connections with the Mafia are potentially even more discomforting than his temper, however. And the associations appear to begin close to home, too. You see, Sinatra’s first wife, Nancy, was the cousin of John Barbato – a captain in the Genovese crime family. Famously, the Genoveses were one of the five clans that once controlled organized crime in New York and New Jersey.

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Consequently, Sinatra is said to have links to infamous Genovese underboss Willie Moretti. It’s said, for example, that Moretti helped Ol’ Blue Eyes during the early part of his career by booking gigs in New Jersey nightclubs. In exchange, the mobster simply wanted a cut of the singer’s payment. It’s even alleged that Moretti threatened to shoot bandleader Tommy Dorsey dead in 1941, as Dorsey was supposedly trying to hold Sinatra to a contract that he no longer wished to honor.

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In the 1940s, however, Sinatra decided to pursue an acting career. And he would go on to achieve huge success in the field, too. Perhaps owing to his stardom, Sinatra ultimately became great friends with cinematic royalty such as Cary Grant, while he famously wooed some of the most famous actresses of the day. Back then, though, a more sinister character was also floating around Hollywood circles, and ultimately the singer is said to have found himself in his thrall.

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In the late 1930s, New York gangster Benjamin “Bugsy” Siegel moved out to California to set up gambling and protection rackets. And thanks to his charm and charisma, he was soon embraced by Hollywood celebrities. But while Siegel was a real mobster who was known for his propensity for violence, that didn’t seem to put off some of the actors with whom he partied. Sinatra almost seemed to idolize the man, in fact.

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Jo-Carrol Dennison – who back then was the wife of actor Phil Silvers – has since spoke of her husband and Sinatra’s admiration of Siegel. “They would brag about Bugsy,” she said, “what he’d done and how many people he’d killed.” She also claimed that she’d always remember “the awe Frank had in his voice when he talked about him. He wanted to emulate Bugsy.”

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Willie Moretti and Bugsy Siegel were apparently far from Sinatra’s only links to the mob, however. You see, the Federal Bureau of Investigation (FBI) kept tabs on Sinatra for more than four decades. And the resulting file – which was made public following the star’s death in 1998 – contained a mammoth 1,275 pages of documents concerning his friendships with known Mafia personnel.

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Yes, throughout Sinatra’s career, there was a substantial amount of documented evidence of him interacting with known Mafia figures. His FBI file even had one heading that read, “Associations with criminals and hoodlums.” Yet while Sinatra admitted to knowing mobsters and was regularly photographed with organized crime personnel, he fiercely denied any true involvement with the mob.

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And in a 1965 interview with Walter Cronkite – which was later sold as a documentary titled “Sinatra: Off the Record” – the star explained away these supposed ties to the Mafia. In essence, he believed that they had simply come by way of his life as an entertainer. “In theatrical work, in nightclub work, in concerts. So, wherever I might be. In restaurants, you meet all kinds of people,” Sinatra said.

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Sinatra continued, “So… there’s really not much to be said about that. And I think the less [said] the better.” However, the FBI certainly believed that there may have been more to the claims than Sinatra would admit. Agents apparently even floated the idea of bugging Sinatra’s home, although FBI supremo J. Edgar Hoover ultimately decided against proceeding down that path.

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A mob-related controversy in 1947 didn’t exactly help dispel any rumors, either. In that year, Sinatra was snapped in Cuba while attending an event celebrating Lucky Luciano’s release from prison. And Luciano wasn’t simply a low-level hood. In fact, owing to his part in the formation of the Commission – the Cosa Nostra’s governing body – he has been called the father of modern organized crime in America.

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Unfortunately for Sinatra, then, he was pictured in two different spots with Luciano. One snap shows him with his arm around the crime boss’ shoulders on a hotel balcony, while another sees him apparently partying with Luciano in a Havana nightclub hotspot. And Sinatra was even photographed getting out of a plane while accompanied by Al Capone’s cousins Rocco and Joseph Fischetti. These two men were both known as big players in illegal gambling rackets.

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Yet Sinatra later excused his presence at the event as a misunderstanding. He reasoned that he didn’t know he would be attending what was effectively a Mafia conference; then, once he had realized the true nature of the attendees, it had been too late to back out. Still, Sinatra sang for the mobsters, and despite his subsequent protestations, witnesses claimed that he never seemed uncomfortable with the generosity shown by the criminals.

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Then, only three years later, Sinatra was experiencing a low point in his career, with the popularity of his records having dwindled drastically. And, interestingly, a 1950 note in the FBI file details contact from someone who was apparently close to the star. This person, whose name is redacted, reportedly said, “Sinatra feels he can do some good for his country under the direction of the FBI.”

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The individual in question is also said to have put forth the idea of Sinatra “going anywhere the bureau desires and contacting any of the people from whom he might be able to obtain information.” This was a thinly veiled way of saying that Sinatra may be willing to snitch on his mob friends. However, FBI associate director Clyde Tolson wrote, “We want nothing to do with him” – and Hoover agreed.

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Sinatra’s career went on to recover in the 1950s, although his mob connections still seemed to run deep. For one, he was reportedly close friends with Chicago Mafia boss Sam Giancana. And in a 2000 interview with 60 Minutes, Sinatra’s daughter Tina alleged that, in 1960, her father had acted as a middleman between Giancana and then-Senator John F. Kennedy’s campaign for president.

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Apparently, Kennedy’s father, Joseph, felt that the Mafia could help deliver his son the labor union’s vote in the 1960 West Virginia primary. And Tina alleged that Joseph had subsequently approached her father because he knew of Sinatra’s connection to Giancana, whose outfit could strongarm the votes. She claimed, moreover, that it was considered better for JFK if his father didn’t approach the mob directly – which is exactly why Sinatra had been brought in.

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Fortunately, Giancana was all too happy to help out the Kennedys, according to Tina. Indeed, she said that he had told Sinatra, “It’s a couple of phone calls.” After JFK became president, however, his administration spearheaded a countrywide clampdown on the Mafia. And, reportedly, Giancana was furious, as he felt that the Kennedys – and Joseph in particular – owed him.

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This is where the alleged use of Sinatra as a liaison came in handy for the Kennedys. Tina claimed that Sinatra was able to calm Giancana down by reputedly saying, “No, I owe you. I asked for the favor.” He then made it up to his mob boss friend by playing two shows per night for eight consecutive days in Giancana’s Chicago club, the Villa Venice.

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However, Sinatra’s connection to Giancana would eventually cost him when, in 1963, the mobster was seen at the Lake Tahoe casino Cal-Neva Lodge. Sinatra owned the place, you see, having purchased it in 1960. And unfortunately for the singer, Giancana was on Nevada’s “List of Excluded Persons,” meaning he was banned from casinos in the state. Ultimately, then, Ol’ Blue Eyes lost his gaming license as a result.

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But Sinatra supposedly also had connections to other mobsters. Indeed, retired FBI agent Sam Ruffino talked about one of those apparent associations when speaking with author Scott M. Burnstein. According to Ruffino, as the FBI monitored Detroit Mafia figures Anthony and Vito Giacalone, the two were regularly spotted mingling with Sinatra.

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“It was like clockwork,” Ruffino said in 2018. “A few times a year, we’d trail the Giacalones to the airport to pick up Sinatra. They’d spend the weekend together socializing before and after his shows.” He also claimed that Sinatra and his mob pals would always be the last to leave any event. And, apparently, the singer himself was quite laissez-faire about the true nature of the men with whom he surrounded himself.

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Ruffino noted that Sinatra made no apologies for his associates, adding, “Those were his friends. The fact that they were known hoodlums and murderers didn’t matter to him.” He added that Sinatra “was going to hang around with who he wanted to hang around with.” After all, it didn’t make him a criminal by association.

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Meanwhile, the FBI file further revealed that the bureau was also very concerned about Sinatra’s alleged ties to communism. The singer publicly defended people who had been accused of being communists, for one, along with supporting anti-racism causes. Even so, this line of investigation similarly never led to prosecution of any kind.

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Plus, despite the fact that he was being constantly monitored by the FBI, Sinatra was able to turn to the bureau for help in 1963 when his son, Frank Sinatra Jr., was kidnapped. Agents subsequently advised Sinatra to pay the requested ransom, which would then enable them to trace the money to the culprits. And, fortunately, Frank Jr. was returned safely, with all three of his kidnappers eventually caught and then convicted.

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Yet Sinatra was fully aware that the FBI was keeping tabs on him. Indeed, in 1979 and 1980 he made official requests to take a look at the bureau’s file. And thanks to the Freedom of Information Act, Sinatra duly received those documents, meaning he was able to see exactly what the FBI was cataloging about his activities.

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Then, in 1998, The Washington Post writer Jeff Leen gave an insightful analysis of Sinatra’s curious relationship with the FBI. More specifically, he claimed that though the bureau’s interest in Sinatra had initially come as a result of “suspicion and contempt,” the relationship developed into a very odd co-dependency. In fact, Leen felt that the FBI needed Frank Sinatra and vice versa.

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Leen characterized Sinatra thus, “What every law enforcement agency needs to stay engaged and in business: a threat that must be tracked.” In turn, he wrote, “The FBI gave Sinatra what every celebrity needs: protection from lunatics and extortionists.” And although the bureau could never conclusively prove that Sinatra took part in any illegal activity, it took his “comings and goings among the criminal elite” very seriously indeed.

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