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can consider Frank Sinatra one of the biggest celebrities of the 20th century, at least in the United States. A man with such a popular name was wanted not only by many women but also by the mafia. Celebrities in the early 20th century were very formal, meaning that they often established relationships with governmental bodies as well as important people from different parts of society. From this socialization, they not only acquire a vast amount of valuable knowledge but also the ability to create new valuable connections.

Avoiding the law

Frank started his career as a singer in 1935 in the hopes that one day he would become a star. Five years later in 1940, he became so famous that the whole of America wanted to hear his voice, with its clear and classy tones. It was also very helpful in raising the morale of the soldiers that were going to war in Europe. However, America needed men for war, and no matter how famous you are, you needed to hold a gun and go fight for your country.

Sam Giancana (Source: Wikimedia Commons)

Sinatra was at the highest peak of his career, he didn’t want to go to war and lose it all by getting killed. Therefore he offered a medic $40,000 (if we consider for inflation that would be $743,965.71 today) to give him a bad medical report, declaring that he was unfit to go to war. This is what attracted the attention of the FBI, as he seemed to be a person with a lot of influence.

However, they were not so interested in his ways of escaping enrollment, but more in his relationship with the mafia. Although Sinatra claimed that he never got involved with the mafia, the FBI has records of him meeting with Sam Giancana, a leader from the Chicago mafia.

Sinatra met Giancana in the early 1950s when he started singing at his club. Over the years, the two became well acquainted, but little did Sinatra know at the time that Giancana had big plans for him and even bigger plans for himself.

Playing a much bigger role

Sinatra became well acquainted with John F. Kennedy before his tenure as president as he loved his singing. In 1961, when Kennedy became the 35th President of the United States of America, Giancana wanted to meet Kennedy, so Sinatra introduced them. It is said that Kennedy and Giancana were working on a plan to assassinate Fidel Castro, however, these are just rumors.

Frank Sinatra and John F. Kennedy in the 1960s (Source: Biography)

However, Frank was not only in good relations with Sam Giancana but also with many other mobsters, such as Joseph and Charles Fischetti, known as the notorious Fischetti brothers from Chicago that were involved in illegal gambling. He was also involved with the mafia in Detroit. The FBI had reported meetings between Sinatra and Vito Giacalone, there was even a time when Anthony and Vito Giacalone took Sinatra from the airport. Sam Ruffino, a former FBI agent from that time, declared that he saw Sinatra and the Giacalone family spend a lot of time together.

The FBI watched Sinatra for over forty years, at one point even asking him if he wanted to become an interrogator, a request which Sinatra declined. There was nothing to hide for Sinatra as he appeared in many magazines and even in newspapers in photos with famous mobsters from the 1950s and 1960s. The FBI waited in the shadows for Sinatra to make a wrong move with his so-called friends. At one point, the FBI thought that Sinatra was collaborating with the communists in the Cold War.

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