Bayonne Boy: Frank Sinatra

Pick Yourself Up and Get Back In The Race

Jeff Cunningham
3 min readSep 5, 2022


I’ve been a puppet, a pauper, a pirate, a poet
A pawn and a king
I’ve been up and down and over and out
And I know one thing
Each time I find myself
Flat on my face
I pick myself up and get
Back in the race

Frank Sinatra (Photo: Crime Museum)

1938 may have been a very good year, but not for Frank Sinatra. Three decades before releasing That’s Life, the 23-year-old fell flat on his face.

He had been in occasional brawls but until that evening never spent a night in jail. Now he was in real trouble, the kind spelled w-o-m-a-n. As he would later sing, he picked himself up and got back in the race, but at that moment, he had to worry about making bail. The blue-eyed wonder spent the night in a filthy New Jersey cell charged with a violation, hold onto your seats, seducing a married woman. I already know you’re thinking, “not a question.”

The charge was accurate. Sexuality was a morality test in those days, not a multiple-choice exam. In voyeuristic detail of a Russian KGB agent, the FBI reported breathlessly that, “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 contrary and in violation of the revised statute of 1937.”

Fortunately for Sinatra, the description of a ‘single female of good repute’ turned out to be fake news. The small technical detail the constable neglected was that she was married. As a result, a false promise of matrimony was not justifiable cause even for the charge of seduction. It wasn’t double jeopardy that got him off the hook but double matrimony. Sinatra was released the following day. It was not recorded whether he sang like a canary.

Sinatra may be remembered for many things, including womanizing, but his official bio often leaves his most attractive hallmark blank. While performing in New York in the late 40s, he hoofed it up to Harlem and caught a show he had heard about by the Will Maston Trio. To those who’ve never heard of Mr. Maston, the band’s lead singer was a young man named Sammy Davis Jr. Frank could not believe his ears and waited for Sammy to finish. He asked him to attend his next performance.

The following week, no Sammy. Frank returned to Harlem to see the Maston Trio again and asked why. Sammy replied, “I was there, but they wouldn’t let me in.” Sinatra rushes out of the theater he was performing and tears up his contract in front of the manager. He never performed there again. When Sammy wasn’t refused a date at the Copacabana, Frank stopped performing there. Once Sammy was not permitted to stay at a Las Vegas hotel. Frank gave him his room. He paid Sammy’s medical bills after a car accident left Sammy blind in one eye. When asked why he did these things, Sinatra replied, “He’s my brother.”


Whenever Sinatra hosted a party, he would give his favorite toast, “May you live to be 100, and may the last voice you hear be mine.”

Although he didn’t make it to that ripe old age, we still hear his voice. He was the very definition of ‘beyond the normal order.’ Even though Sinatra died at age 82 from a heart attack at Cedars-Sinai Medical Center in Los Angeles on May 14, 1998, my wife and I listen to him every day from 3–5 p.m. during our reading hour. We never bought his records while he was alive, yet his legacy has grown more prominent. As CNBC reported, Sinatra’s oeuvre’ comes to 1,400 recordings, 31 gold, nine platinum, three double-platinum, and one triple-platinum, including over 150 million albums worldwide and 60 films.

In 2007, “Sinatra’s children (Nancy, Frank Jr., and Tina) and the family’s attorney and Warner Music Group founded Frank Sinatra Enterprises” to manage the Sinatra business. His daughter, Tina, said, “we do well, and we are profitable, but we don’t just do it for the money.” She added that her father gets more than a million streams a week.

His voice may yet be the last we hear.