Frank Sinatra Was Tracked by the FBI for Over 40 Years

Frank Sinatra was a 20th century icon with a remarkable career in the show industry. With 50 years of appearing in iconic films and making award-winning songs; it is fair to give Sinatra a myth.

Sinatra’s career was one of a kind, but the FBI apparently found him suspicious and kept a file on him. It is reported that the FBI had been monitoring him for more than 40 years detailing his movements. The FBI file that emerged after his death sheds light on why the FBI thought Sinatra was an interested man.

Frank Sinatra standing for a picture in a chair
Frank Sinatra | Silver Screen / Getty Images Collection

Frank Sinatra’s legendary role

Sinatra was a musician and actress. His music career began in his early teens where he sang in local clubs. He later made records with Harry James and Tommy Dorsey before becoming a solo artist in the years 1943-1946.

He was unable to participate in World War II due to a brutal eardrum, and used the time to release singles. During this time he made his first film in 1943, appearing in the films Reveille by Beverley and Higher and Higher.

In the early 50s, he had a small lump in his career as he lost some film contracts. However, in 1953, he kicked back after winning an Oscar for being a supporting actor in the film From here to eternity. In the ’50s, his music was even better as this time he had a more mature voice attracting more fans.

Now to the 60s, where he was a founding member of the Rat Pack. The Rat Pack made iconic films such as Robin and the seven hoods and Eleventh of Ocean. In the 60s, the highlight of my musical career was the Grammy-winning award Strangers at night.

In the ’70s, Sinatra’s role was more about politics than the show business. He became involved with several political figures such as John F. Kennedy, Richard Nixon, and Ronald Reagan.

Famous mugshot, but what was the real crime?

Did you know that someone in their 30s could be arrested for a deceptive crime? At the age of 23, Sinatra suffered this, and his famous mug comes from this incident.

Apparently, a man could be arrested for making a reputable woman sleep with him. As for Sinatra, the allegations were dropped because that woman was married. However, his troubles did not last long as he was re-arrested, this time for an adultery charge.

For the second charge of adultery, a bond was established, he paid for it, and he was released. All these things happened when he was still young and he had not yet gained a reputation. Both incidents show Sinatra ‘s first interaction with the authority but are unrelated to why the FBI was monitoring Sinatra.

So why did the FBI track down Frank Sinatra for 40 years?

according to History, the FBI tracked Sinatra because of his connections to the mob. Sinatra was close to Sam Giancana, a famous leader in Chicago. Sinatra reportedly introduced Giancana and her lover to a Kennedy.

The FBI file also continued to monitor his ties with Anthony and Vito Giacalone, who were Detroit movers. Sam Ruffino, a retired FBI agent, says he gets Giacalone Sinatra from the airport several times a year. Ruffino still says Sinatra wasn’t worried about hanging out with hoodlums and killers.

Despite the large file the FBI kept on Sinatra; he was never charged with being involved in a move. Engaging with the mob also didn’t affect his friendship with the fans because they loved him.

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