How Many Times Was Frank Sinatra Arrested?

Frank Sinatra, in addition to being an alluring ladies' man and one of the greatest singers in modern history, also had a criminal rap sheet, albeit a short one. Many have seen the celebrated artist's iconic mugshot from 1938, but few know the true story behind it. Sinatra was only 23 years old when he was arrested for "seduction" of a reputable woman. Yes, you read that correctly. It might sound silly, but at the time, the crime of seduction was a real thing, and Old Blue Eyes learned that the hard way. 

In the 30s, it was illegal to engage in sexual conduct with a woman of high-standing reputation, but oddly enough, the charges were dropped after authorities uncovered that the singer's girlfriend was in fact married to another man at the time of the encounter. However, that gave way to his second and last criminal charge: the crime of adultery (per Crime Museum). 

Seduction and Adultery

The original report after Sinatra's seduction charge read as follows: "On the second and ninth days of November 1938 at the Borough of Lodi" and "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" (via Showbiz CheatSheet). However, the "single" element was revised after police came to believe that the woman involved was married. In effect, the charge was revised, this time to adultery.

It's hard to believe that fickle and criminally impotent insubordinations like these were once against the law, but such was the case. Details ultimately began to fluctuate, and after determining that the woman in question was not actually married, the adultery charges were reverted back to seduction, only to be again dismissed. The following year, Frank married his then fiancee, Nancy, with whom he had three children (per Reference).