Why Frank Sinatra Went to Jail: Seduction, Adultery & a $500 Bond

Why Did Frank Sinatra Go to Jail?

Frank Sinatra went to jail because he was arrested for seduction in Bergen County, New Jersey, on November 26, 1938. The complaint said he had slept with a woman after promising to marry her. The turning point came when she proved to be already married, which voided the charge, and a reported adultery charge that followed was dropped too. He spent less than 16 hours behind bars, according to ReMIND Magazine, and the mugshot became famous.

Quick facts

• Arrest date: November 26, 1938
• Place: Bergen County, New Jersey
• First charge: Seduction
• Second charge: Adultery, as reported by ReMIND Magazine and Showbiz Cheat Sheet
• Alleged dates: November 2 and 9, 1938, in the Borough of Lodi
• Time in jail: Less than 16 hours
• Bond: $500
• Outcome: Charges dropped, fingerprint sheet stamped “dismissed”

Early Life

Sinatra was born on December 12, 1915, at 415 Monroe Street, a tenement in Hoboken, New Jersey. He was the only child of Italian immigrants, Dolly and Marty Sinatra. A. J. Demarest High School expelled him for rowdiness after 47 days, and he never graduated.

Work followed, first delivering for the Jersey Observer newspaper and later riveting at the Tietjen and Lang shipyard. He also sang in local social clubs and, unpaid, on radio stations such as WAAT. Speaking at a University of Nevada, Las Vegas, commencement in May 1976, he credited “the school of hard knocks” for his education.

In the summer of 1934 he met Nancy Barbato in Long Branch, New Jersey, while working as a lifeguard. In 1935 his mother talked a singing group, the 3 Flashes, into taking him on. Baritone Fred Tamburro said he hung around them “like we were gods or something,” and admitted they wanted his car.

The group became the Hoboken Four and won first prize on the Major Bowes Amateur Hour with 40,000 votes. The prize was a six-month contract for stage and radio work across the country. Even so, ReMIND Magazine places the 1938 arrest years before his first movie or his first single.

The Seduction Charge

In the 1930s a man could be arrested for seduction. Lauren Novak of ReMIND Magazine describes it as a charge usually brought against a man who slept with a woman through a lie or a false promise. Alice Stone of Showbiz Cheat Sheet calls it trickery, gives a false pledge of marriage as her example, and notes that it is no longer a crime.

Ben Branch of Silodrome quoted the wording of the case in May 2018, drawing on FBI reports. It alleged that on November 2 and 9, 1938, in the Borough of Lodi, Sinatra had sex with the complainant after promising marriage. It described her as “a single female of good repute” and said he had broken the revised statute of 1937.

Novak writes that the accuser was reportedly an ex-girlfriend who said he had promised marriage and then ended the relationship. Stone also calls her an ex-girlfriend, one unhappy that the romance was over. ReMIND, Cheat Sheet and Silodrome do not name her.

The same three disagree slightly on his age. Novak and Stone say he was 23. Branch says he was a little short of 23, which fits his December 12 birthday.

Jail, Bond and the Adultery Charge

The case changed once the woman’s own marriage came to light. Novak writes that it canceled the seduction charge, and Stone says it left the charge null and void. Branch agrees that she was already married and reports that the charges were dismissed once this was established.

The published versions part ways on what came next. Novak and Stone both say New Jersey then charged Sinatra with adultery, and both say that charge was later dropped. Branch does not mention adultery in his Silodrome piece. He reports only that the fingerprint sheet carries the stamp “dismissed.”

The $500 is also told two ways. Novak says the adultery charge was dropped after Sinatra paid a $500 bond. Stone attaches the same sum to the seduction charge and says he never had to pay anything over the adultery charge. Both put his total time in jail at less than 16 hours.