Frank Sinatra (1915 – 1998) was known as a class act, and deservedly so. Among other things, he was a staunch opponent of racism at a time when that could damage a career. However, nobody is perfect, and that includes the legendary crooner. Not just the well-documented mob ties and short temper. As seen below, Ole Blue Eyes was once arrested for seduction and adultery – crimes that the authorities actually prosecuted in his era.
A Huge Cultural Icon

Frank Sinatra is not as famous today as he was back in his mid-twentieth century heyday. Nicknamed Ole Blue Eyes and Chairman of the Board (although he loathed the latter, Sinatra has captured the hearts of music lovers around the world. His records sold about 150 million copies, which puts him among history’s top artists by volume of sales. When he passed away in 1998, Sinatra was already established as a cultural icon, in the same league as an Elvis or Marilyn Monroe.
Sinatra had an abundance of self-respect. Early in his career, at a time of significant anti-Italian sentiment, bandleader Harry James recommended that he change his name because it was “too Italian”. He replied: “No way, baby. My name is Sinatra. Frank fucking Sinatra”. It is a good thing he kept the name: bobby-soxers, enthusiastic 1940s teenage female fans of pop music, loved it and him. Their passion for Ole Blue Eyes stayed strong for the rest of their and his life. While Sinatra was an all-around class act, he did have some edges – and not just his mob ties. As seen below, there was that time he was arrested for “seduction” of a reputable woman.
When Ole Blue Eyes Was Arrested for Seduction

Ole Blue Eyes 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. Back then, seduction was actually a criminal offense. An old girlfriend accused Sinatra 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 sexual intercourse with the said complainant, who was then and there a single female of good repute”.
Sinatra was arrested, booked for seduction, and released on a $1500 bond. The archaic charge was dismissed when 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 $500 bond. Eventually, that charge, too, was dismissed, and Ole Blue Eyes was free to go on with his seductive ways.

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Some Sources & Further Reading
Fuchs, Jeanne, and Prigozy, Ruth – Frank Sinatra: The Man, the Music, the Legend (2007)
Hamill, Pete – Why Sinatra Matters (1998)
