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The Mob’s Crooner? Frank Sinatra and the Underworld
It was rumored that Frank Sinatra’s criminal connections had played a role in his rise and professional success. Just how much truth is there to the iconic scene in The Godfather?
THE SOUNDTRACK TO THE 20TH CENTURY
Frank Sinatra was born to Italian parents in 1915, and dropped out of school when he was sixteen to pursue his dream of becoming a singer. He eventually found himself in a group called the Hoboken Four, which won the grand prize at a radio show’s contest for bands: a six-month contract for stage and radio work. Sinatra was soon made the group’s frontman, but they disbanded shortly thereafter due to personal conflicts.
The Hoboken Four’s dissolution left Frank working at a New Jersey roadhouse as a waiter and singer, but his career eventually got back on the right track thanks to the help of Harry James and Tommy Dorsey. By the mid-1940s he was already a popular and widely-recognized performer. Even though his star waned a little toward the end of the decade, his performance in the 1954 movie From Here to Eternity earned him an Oscar for Best Supporting Actor.
The Academy Award marked the beginning of Sinatra’s most prolific and successful years. It was during this time that he won his first Grammy – and then five more. He first announced his retirement and played a farewell concert in 1971 but would still go on to release several albums and make live appearances. In 1994 he received the Legend Award at the Grammys, and one year later he withdrew from the public eye. He died in 1998.
From the beginning, the Sinatra family lived in a neighborhood and operated businesses that made it likely that they would come into contact with organized crime. Sinatra’s grandfather Francesco was born back in Sicily, in Lercara Friddi, some 25 kilometers from the notorious town of Corleone. He lived on the same street as Salvatore Luciano, who later became a famous member of the American underworld as Lucky Luciano. Francesco immigrated to the US in 1900 with his wife and children.
Frank Sinatra’s father, Anthony (anglicized from Antonio) Sinatra initially studied to be a shoemaker, before becoming a chauffeur and a prizefighter under the name Marty O’Brien. He had multiple run-ins with the law (his criminal record included accepting stolen goods, among other things) but walked away scot-free each time. Anthony eloped with his wife, Dolly, because her parents did not approve of her marriage to the illiterate man. They settled in Hoboken, New Jersey, and opened a small bar in 1917 – just three years before the beginning of Prohibition in 1920, which – unsurprisingly – had a major effect on business. Anthony took to bootlegging with the help of a local criminal, Waxey Gordon, who knew Lucky Luciano well. As a port, Hoboken became an important center of alcohol smuggling, and eventually the brothers of Anthony and Dolly also got involved in the booming business. The family thus got to live in relative comfort and even managed to avoid the most adverse effects of the Great Depression. In fact, Frank’s mother could even afford to buy her son a new car in the 1930s.
Frank Sinatra would also sing at the family bar, where several members of the criminal underworld were regular clients. The singer never denied meeting mobsters but insisted that had done so strictly as a performer and never got involved in “business”.
WAKING UP NEXT TO THE HEAD OF A RACEHORSE
Most people have probably seen the iconic scene from The Godfather where the titular Don sends the head of a racehorse to a Hollywood director to get him to cast struggling singer Johnny Fontaine in a movie. It is easy to see the parallels between the scene and the real-life story of Eli Wallach, who turned down his part in From Here to Eternity in 1954, only to have it (and the Oscar) go to Sinatra.
However, the reality is much more simple than the myth that surrounds it. Eli Wallach actually turned down the role because he chose to appear in a Broadway production instead. And even though Sinatra did indeed lobby for the part, he ended up getting it for two main reasons: First, his wife at the time, well-connected actress Ava Gardner, left no stone unturned to secure the role for her husband; and second, Sinatra was at a point in his career where he needed the job badly and would have taken it for next to nothing.
But such rumors would nonetheless go hand-in-hand with Sinatra’s successes. Early on in his career he was contractually tied to Tommy Dorsey’s big band, and when he wanted out the bandleader understandably resisted – until he suddenly changed his mind. Sinatra would deny the story, but Dorsey claimed that he was once visited by Willie Moretti and two of his thugs, and the gangster told the musician – while playing with his gun – that he was glad to hear Frank had been released from his contract. Dorsey took the hint and let Sinatra go.
Meanwhile, according to another story about his Oscar-winning role, the head of Columbia Studios, Harry Cohn, was strongly against giving the part in From Here to Eternity to Frank Sinatra. However, when he received a call from well-known mobster Johnny Roselli he started singing a different tune. It should be noted, however, that the story of Roselli and Cohn’s “conversation” has been told about several other people as well, which leaves plenty of room for doubt, even if Sinatra is known to have helped Roselli join the very exclusive Friars Club in 1963.
FBI director J. Edgar Hoover was convinced that Sinatra had serious connections to the mob, and the Bureau amassed over 2500 pages of documents on the singer. He was put under surveillance in the early 1940s, and became especially closely monitored when his friendship with John Fitzgerald Kennedy became tighter. The singer and the future president first met at a Democratic Party rally in 1955, and bonded over their shared hobbies: They both enjoyed golf and the nightlife. Sinatra was even said to have “recruited” mistresses for JFK.
JFK’s father, Joseph, wanted to mobilize the mafia to help his son get elected, but in an effort to avoid the spotlight he chose to use Frank Sinatra’s connections instead of his own. The singer mediated between Sam Giancana and the future president’s father to convince the mobster that supporting JFK was a good investment. This relationship has been described in detail by the singer’s daughter Christina.
Kennedy’s presidential campaign was ultimately successful, but he and Sinatra quickly drifted apart afterwards. This was presumably due to the fact that the singer’s mob connections were widely known, and thus the president could not risk a political scandal. At one point Kennedy even refused an invitation from Sinatra at the request of a fellow singer, Bing Crosby, prompting Frank to smash the decorations he had carefully prepared for the visit in a rage.
This incident may have influenced his later decision to abandon his Democratic leanings, which had been instilled in him by his family and immediate environment, and switch his support to the Republicans. He backed Richard Nixon during the 1972 campaign (who in turn hosted the singer in the White House on several occasions), and later supported Ronald Reagan in 1980, after already proving to be a reliable ally during Reagan’s 1970 bid for Governor of California.
A PICTURE AND THE THOUSAND WORDS BEHIND IT
The best illustration of Sinatra’s presumed criminal connections is an image taken in Havana, featuring the singer and a group of Italian gangsters. In 1946 the authorities deported the recently released Lucky Luciano to Sicily, but he decided to go to Cuba instead. The US influence was very prominent in the country at the time, and as a result the American underworld got “exported” as well: Several members of the Italian mafia operated casinos and were able to find refuge in Cuba.
During the so-called Havana Conference, Luciano and his associates gathered at the Hotel Nacional to discuss the various points of contention between the different groups, such as the fate of the local casinos and operations related to heroin smuggling. From the outside the grand event resembled an upscale gala, and Frank Sinatra was also invited to perform. Moreover, several people who accompanied him to Havana were actual members of the mob and, for all practical purposes, served as his bodyguards during his stay in Cuba. When the media found out about Sinatra’s appearance at the conference, one paper ran the story with the headline “Shame, Sinatra.”
The allegations eventually cemented an image of the singer that would forever keep him dogged by rumors of his connections to organized crime. He dressed like a gangster, talked like one, was of Italian descent, and had grown up in an environment where he was bound to meet people involved in organized crime. It also did not help that he had a share in a casino in the sixties. And yet, FBI files released in 1998 revealed that the Bureau had never been able to prove anything more damning than personal relationships, and Sinatra himself had publicly denied having connections to the underworld on several occasions. It is thus safe to say that, even if he knew a few mobsters, it was primarily thanks to his involvement in show business, and he never became a member of any criminal group.
Frank Sinatra needs no introduction. One of the most successful singers of all time had a spectacular career, receiving countless awards and accolades. Yet a shadow continues to hang over his name, as throughout his life he was haunted by rumors that his criminal connections had played a role in his rise and professional success. Just how much truth is there to the iconic scene in The Godfather?
Did you know?
Frank Sinatra was mad about cars and passionately collected them.
Sinatra was arrested in 1938 for having an affair with a married woman.
The Empire State Building turned blue in 1995 for Frank Sinatra’s 80th birthday.