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American History

The Seedy Side of Frank Sinatra and other Beloved Historic Figures

frank sinatra

A Seedy Scandal at the Start of Sinatra’s Career

Frank Sinatra, circa 1957. Capitol Records

Frank Sinatra had a criminal rap sheet. Not a long one, to be sure, but he had one. In 1938, when he was 23-years-old, Sinatra was arrested in New Jersey for the seduction of a reputable woman. At the time, seduction was actually a criminal offense, and an old girlfriend accused him of breach of a promise to marry her and used that to get back at him. Per FBI reports: “On the second and ninth days of November 1938 at the Borough of Lodi … under the promise of marriage [Sinatra] did then and there have intercourse with the said complainant, who was then and there a single female of good repute“.

Seedy - Frank Sinatra mugshots
Frank Sinatra mugshots. Crime Museum

Sinatra was duly arrested and booked for seduction, and released on a $1,500 bond. The archaic charge was dismissed when it turned out that the supposedly single woman in question had actually been married when she got it on with him. Presumably, the fact that she had broken her marital vows meant that she was not “of good repute“, after all. However, that was not the end of Sinatra’s troubles. A month later, the charges were amended, and he was arrested again, this time for adultery. He was released on a bond of $500. Eventually, that charge, too, was dismissed, and Ole Blue Eyes was free to go on with his seductive ways.

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A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.

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