The Casanova, 1938

Getty Images

The arrest had sent a shiver down America’s spine, and horrified Frank Sinatra’s fans. To understand the circumstances that led to Old Blue Eyes being taken into custody in New Jersey in 1938, we must delve a little deeper into his character. Frank Sinatra was born in New York in 1915, and was the son of Italian immigrants. Little Frank had a happy childhood, although rivalries between gangs of immigrant children often came to insults and blows. From a young age, Frank dreamed of conquering America, and especially its women. American women were beautiful; whether they were from New York or they spoke with a southern drawl, American women were the stuff of dreams. His desire led to him playing hooky; being at school bored him, and felt like a prison. He thirsted for freedom, and adventure. He practiced the art of seduction on every girl who crossed his path. He was not yet possessed of the charm we now know him for, being still a frail, pock-faced teen. Still, he was learning that charm and self-assurance could take a guy a long way. Frank didn’t scare easy, and made seduction his way of life. Rejection or mockery did not dissuade him. When he went back to high school to avoid the principal’s wrath, he took these habits with him. He wanted to be in the spotlight, and any way of getting noticed was fair game. He was eventually expelled for “general rowdiness”, a sentence that he could not help feeling proud of. To Frank, “general rowdiness” sounded like showmanship. Either way, he had left his mark. Everyone would remember his prowess as a troublemaker, and an incorrigible charmer.

Frank’s next move was to join a band: “The Hoboken Four”. Finally he had found musicians who recognized his value; finally he was on center stage. Frank didn’t care that he monopolized the crowd’s attention and left the other group members in his shadow. He’d never been one to share the spotlight. His womanizing was dialed up another notch now that he could tell people he was a singer. Ladies were not indifferent to his Italian charm and bad-boy looks; they pushed to the front of the crowd to meet his stormy gaze, in hopes of getting a wink or a smile. Frank took full advantage of his success, and every night after the show he’d disappear with an admirer. Tonight, the Hoboken Four were playing at the Rustic Cabin. All the local girls were out to see the young singer, and many of them ran in high-society circles. They devoured Frank with their eyes, his deep voice stirring their emotions. His confidence made them weak at the knees. One fan in particular caught Frank Sinatra’s gaze. The Hoboken Four had the whole room jumping, but Frank Sinatra kept his eyes on Evelyn. She was pretty, and he wanted her.

A few hours had gone by, and Evelyn had fallen asleep. Frank was getting dressed. He kissed her and slipped quietly out of the apartment. He was well-used to this kind of nocturnal prowling. As he left the building, two police officers stopped him and slapped handcuffs on him. “What did I do? I kill someone or something?” growled Frank Sinatra. “What’s the charge, officers?” he cried, trying to free himself. Frank Sinatra was dumbfounded. He had done nothing wrong. The officers brought him back to the station.

                  “Sit down, and hold this sign,” ordered one of the cops.

                  “Can you tell me why I’m being arrested?” Frank asked, calmly this time.

                  “You’re under arrest for seduction of a woman of good repute. You have the right to an attorney. Name?”

                  “Sinatra. Frank Sinatra!”

Alan Alfredo Geday