Frank Sinatra Arrest: How Many Times Was Frank Sinatra Arrested?

The iconic “mug shot” from 1938 is well known to many ardent Frank Sinatra admirers. On December 9, 1998, the FBI released a remarkable 1,300-page dossier containing the majority of Frank Sinatra’s personal records, which is when this scandalous photo was first made public. Along with the mugshot being made public, several alarming reports were also made available. The first was a document that purported to have information about connections to organized crime, and the second contained information about his devious escape from the military draught during World War II by claiming that he had a perforated eardrum and was mentally unstable.

Frank Sinatra Arrest

Frank Sinatra was the lone child of Italian immigrants Natalina Della (Garaventa) and Saverio Antonino Martino Sinatra, a Sicilian boxer, fireman, and pub owner. He was born Francis Albert Sinatra on December 12, 1915, in Hoboken, New Jersey. Early in his teens, Frank was dismissed from high school for “general rowdiness” after only 47 days of attendance, which gave rise to his reputation as a rebel. Then, in order to advance his singing career, he started playing in well-known social clubs like The Cat’s Meow and The Comedy Club and singing for free on the radio. He left school without receiving a diploma and worked odd jobs as a riveter and delivery boy.

The name of the first singing group Frank joined was “The Hoboken Four.”The others did not like it one bit when he rapidly became the center of attention. Frank was well-liked by women and was well-known for having late-night encounters with any girl he desired. He had an intimate meeting with a woman during one of their performances at a bar called “The Rustic Cabin,” which ultimately resulted in his imprisonment. On November 26, 1938, in Hackensack, New Jersey, Sinatra was detained on a “seduction”-related accusation. When it turned out that the woman in question was married, the allegations against him were dropped, and he was released after posting a $1,500 bond. He was taken into custody a second time on December 22, 1938, on suspicion of “adultery,” less than a month later.

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Once more, he was granted free after posting a $500 bond. Sinatra was incarcerated for a total of 16 hours but was never formally accused of adultery or seduction. In fact, in court in January 1939, all charges were dismissed. The tale goes that Sinatra’s reputation was damaged when an old flame said he had broken his engagement to marry her. This ex-girlfriend and Nancy Barbato, his betrothed and ultimately first wife, got into an argument. She eventually accused Sinatra of seduction and infidelity, and the events surrounding this “catfight” ultimately resulted in Sinatra’s incarceration.

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