Frank Sinatra’s mugshot from 1938 is a well-known image among his fans, but the story behind it is not as widely known.

On December 9, 1998, the FBI released a 1300-page document containing Sinatra’s personal file, which included his mugshot and reports of his rumored connections to organized crime as well as his clever dodge of the draft during World War II due to a perforated eardrum and apparent mental instability.

Francis Albert Sinatra, born on December 12, 1915 in Hoboken, New Jersey, was the only son of Italian immigrants.

His rebellious reputation began early in his adolescence when he was expelled from high school for “general rowdiness” after attending for only 47 days.

He found odd jobs as a delivery boy and riveter, until he began performing in popular social clubs and singing on the radio to boost his singing career.

The first singing group Frank joined was called “The Hoboken Four.” He quickly became the center of attention, which the other members did not appreciate one bit.

Frank was extremely popular with the ladies, known for his late-night rendezvous’ with any girl he wanted.

During one of their performances at a club, “The Rustic Cabin,” he had an intimate encounter with a woman, which led to his eventual arrest.

Sinatra was arrested on November 26, 1938, in Hackensack, NJ, on the charge of “seduction.”

He was released on a $1500 bond, and the charges were dropped once it was discovered that the woman in question was married.

Less than a month later on December 22, 1938, he was arrested a second time on an “adultery” charge. He was again released on bond, this time for only $500.

Sinatra spent a total of 16 hours in jail and was never formally charged with adultery or seduction. In fact, all charges were dropped in court in January 1939.

The official report of the FBI reads as follows:

”FRANK SINATRA, Arrest #42799, Bergen County Sheriff’s Office, Hackensack, New Jersey was arrested on November 26, 1938 charged with Seduction. Disposition was marked, ‘Dismissed.’ FRANK SINATRA, Arrest #42977, was arrested on December 22, 1938, charged with Adultery.”

“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.”

This was “contrary and in violation of the revised statute of 1937.”

As the story goes, an old girlfriend accused Sinatra of breaking his promise to marry her, which in turn tainted her good reputation.

This former girlfriend ended up in a fight with Nancy Barbato, his fiance and eventually his first wife.

The circumstances surround this “catfight” finally led to her accusations of seduction and adultery and Sinatra’s ultimate arrests.

Regardless of this black spot in his life, Nancy Barbato, followed through with her commitment and became Mrs. Frank Sinatra in 1939.

Early in their marriage Nancy worked as a secretary and Frank worked as a singing waiter.

Once they began having children, she stayed home and raised the family while Frank quickly built his career in both film and music, and starred in his first major motion picture in 1941.

During his 12 year marriage to Nancy, Frank’s career continued to soar, with him becoming one of the most popular and successful performers of his time.

Despite his earlier arrests, he went on to become a beloved and iconic figure in the entertainment industry.

He released a string of hit songs, starred in several films, and won multiple Grammy awards.

He was also a member of the legendary Rat Pack and performed at some of the most iconic venues and events in the world.

However, his personal life was often plagued with scandal and controversy. He was known for his womanizing ways, and had several high-profile affairs and marriages.

He also had a reputation for being temperamental and had several publicized feuds with other celebrities.

Despite these controversies, Frank Sinatra’s legacy continues to live on. He is remembered as one of the most iconic and influential performers of the 20th century.

His music is still celebrated and his films continue to be watched and loved by audiences around the world.

He was an artist who left an indelible mark on the entertainment industry, and his reputation as “The Voice” and “The Chairman of the Board” are still used to describe him today.