The Seedy Side of Frank Sinatra and other Beloved Historic Figures

The Seedy Side of Frank Sinatra and other Beloved Historic Figures

Khalid Elhassan - October 7, 2022

The Seedy Side of Frank Sinatra and other Beloved Historic Figures
Frank Sinatra, circa 1957. Capitol Records

A Seedy Scandal at the Start of Sinatra’s Career

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“.

The Seedy Side of Frank Sinatra and other Beloved Historic Figures
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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