Frank Sinatra’s Involvement In Criminal Activity

Sinatra was considered a hero by many during World War II. However, he was not the usual hero that dressed in uniform and fought for his country during the war; instead, he stayed home and performed to large crowds. Although he caught the attention of most people because of his voice and style, he caught the attention of a much more intimidating group of people because of his inability to serve in the war. In 1944, the Federal Investigation Agency began an investigation on Frank Sinatra that would last until his death. This sudden interest by the FBI was due to the rumor that Sinatra had paid a $40,000 bribe to a doctor to declare him unfit to serve in the war and therefore avoid being drafted. It had been said that Sinatra could not serve due to a punctured eardrum. Upon further investigation by the FBI, the allegations were released, and no evidence was found against Sinatra’s claim to a failed physical. Although this claim against Frank Sinatra was proven to be false, it did not withdraw the FBI’s suspicions from his life.

Sinatra had been exposed to politics from a very young age, having grown up with a very political household. The singer was a very openly Democratic supporter and became extremely involved in politics once he became successful. Being the son of two immigrants, Sinatra had experienced and seen racism first-hand; motivating him to become an active supporter of civil rights. Sinatra would repeatedly oppose discrimination of any kind in very public manners, which led him to receive a lot of backlash and criticism from many public figures and news sources. He was charged multiple times of being a communist by political leaders, reputable news sources, and even by FBI informants. This new label of being communist triggered further FBI investigations, but never stopped Sinatra from standing up for what he believed.

After having received so many backlashes for his political involvement, Sinatra had fallen into a downward spiral in his career. On top of being labeled a communist, Sinatra also faced accusations of mafia involvement. It all began with his support for John F. Kennedy’s presidential campaign in 1960. Sinatra had devoted his time to help JFK get elected that year, which established the so-called “Hollywood-Washington connection”. This connection was the beginning of the relationship between politicians and celebrities, for the benefits of celebrities to be considered serious and for politicians to be seen with the famous. Although this relationship sprouted from a genuine friendship, there was still an impression of suspicious activity behind it.

Frank Sinatra’s influence in helping JFK get elected had to do a little bit more than just with publicity. Sinatra had introduced JFK to his former lover, Judith Campbell; which also became JFK’s lover. However, the introductions did not end there. Sinatra also introduced Campbell to the Chicago mob boss, Sam Giancana; effectively the former president and mob boss shared a common love interest for a time. Giancana and his associates became involved in the presidential campaign as well, due to Sinatra’s influence. It was crucial for Kennedy’s campaign to win the vote of Illinois, which is where Giancana played his role in the campaign. In exchange for his influence in the voting, the mob boss expected the Kennedy administration to go easy on Mob activity. However, after winning the election, JFK faced a lot of criticism for his friendship with Sinatra, which was known to have ties with mafia leaders. The former president cut all connections with Sinatra to avoid further accusations, and in response, Sinatra publicly embraced the Republican Party.

After Sinatra’s death in 1998, all of the files kept on Frank Sinatra’s life by the FBI were released. These reports followed Frank Sinatra’s every move from his first incident in 1944, all the way up to his death. The FBI had taken great interest in Sinatra’s friendships and affiliations with Mob bosses and their associates. Sinatra had always been very open about his friendships with mafia members, he had been photographed several times hanging out with these despised men, but one thing Sinatra never failed to do was deny any association with the mob itself.

The files that kept a record of Sinatra’s connections for over four decades did reveal multiple ties to Mafioso friends, however. There are accounts of presents from the Chicago mobster, Charles Fischetti, and evidence of pressure from mob members, on Sinatra’s behalf, to release him from a contract. The documents also include reports on Sinatra’s friendships with other mobsters including Carlo Gambino, a Sicilian-American mobster; and “Lucky” Luciano, an influential Italian-born mobster. There are also accounts of testimonies against Sinatra saying that he was a close friend of Raymond Patriarca, the godfather of New England.

There is no denying that Frank Sinatra had many friendships within the American mafia and that he cherished those relationships. Becoming one of the most influential entertainers of the twentieth century, it is predictable that Sinatra had many unusual connections. Although his ties with the mafia are quite unexpected, it does not take away from who is as a person and performer. Sinatra is known for his capability to deliver songs in a way that adds meaning to every lyric and melody he sings; he is known for his revolutionary success as a singer and actor. He was a person that portrayed vulnerability and honesty like no other and a person that was not afraid to stand up for civil rights. Sinatra definitely made mistakes throughout his career and although being friends with mob members is not the most appealing for such a public figure, there is not one piece of evidence in all his four decades of investigation under the FBI that says he was involved in any criminal activity. 

16 December 2021
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