#Sinatra100 – Sinatra’s FBI Files

By Matt Micucci

For decades, the FBI investigated on Frank Sinatra, especially for the rumours about his ties with Hollywood and Vegas mobsters and speculations about him being a Communist sympathizer.

Throughout his career as well as after his death, Sinatra had to defend his reputation as one of the greatest all around entertainers of all time from accusations of his involvement with the Hollywood and Vegas mob. Some of the spectualtions and rumours persist to this day.

For decades, the FBI, much like it did with other celebrities of the time from Charles Chaplin to John Lennon by way of Elvis Presley, spied, traced calls and investigated on Sinatra. The files of the investigation were released in 1998 shortly after his death. All but 25 of the 1,275 page dossier are now available for all to see, and as one glance at them reveal, all the rumours end up suffering from a fundamental lack of evidence.

The files begin with his famous mugshot following his arrest in North Carolina in 1938, after he was accused of seducing a married woman. The dispute was settled out of court. Another interesting early entry is one from 1943, where one can read that Sinatra paid off 40,000 dollars to a medic of the US army in order for him to deem him as physically unstable and prevent him from being able to be enlisted in the army and fight in the Second World War.

Two things, however, are of greater interest – his involvement with the mob, but also, his involvement with the Communist party.

In 1963, a particularly tough year for Sinatra in which he had to deal with the kidnapping of his son Frank jr. who at the time was embarking on a career following in his father’s footsteps, he lost his gaming license due to a snapshot (pictured above) that showed him in the company of the mob boss Sam Giancana in the Cal-Neva casino, of which Sinatra was a shareholder.

In reality, Sinatra had never officially “hosted” Giancana who showed up uninvited and asked to take a picture with him on account of him probably being, like millions of people around the world, a fan. Sinatra would never see him again following this incident. In 1963, according to his attorney at the time, Sinatra did not contest the complaint in the Giancana incident and later sold the resort because he was closing a deal with Jack Warner, the movie executive, who was opposed to involvement in gaming.

In 1971, his name was cited along those of mob bosses Aniello Dellacroce, Carlo Gambino and Giuseppe “Joe” Gallo for a suspected extorsion on a stockbroker. The subsequent trial never amounted to anything. He was even accused of being involved in a money laundering ring, and having ties with the infamous Lucky Luciano – however, the lack of evidence makes all these speculations inconclusive.

Sinatra himself never denied the existance of photograhs that portrayed him with mobsters, or playing at venues they owned and parties or events they organised. But he would also constantly reject the accusations from the House of Representatives’ Select Committee on Crime that claimed he might have been involved with their illegal activities, calling them on one occasion as “indecent and irresponsible”.

Along with his involvement with the mob, Sinatra was suspected of being a member of the Communist Party. There is no doubt that the film he made in 1945 called The House I Live In, in which a young Sinatra talks to a group of kids about all people being equal despite differences in race, color or creed, got him into trouble to begin with, and would later play an important role in supporting the idea that he may have been a Communist sympathizer, quite a scary fact that reveals the dangers of nationalist ideologies more than anything.

Ten years later, the Philadelphia FBI agents wrote “we have received reliable and confidential information that Sinatra, famous star of cinema and radio, is a member of the Communist Party.” Another memorandum from Detroit clearly shows that the FBI was seriouisly interested in verifying his belonging to the Communist Party of the state of Michigan, but the investigation never amounted to anything.

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