Jersey’s Frank: Sinatra at 100

How a strong-willed mom, a few lucky breaks and some (shall we say) influential friends turned a skinny kid from Hoboken into an international legend.

Photo by Corbis

Natalina “Dolly” Garaventa, not yet 17, and Antonino Martino “Marty” Sinatra, older by two years, ran away from their Hoboken homes—but didn’t go far. They eloped to Jersey City, two miles away, and were married on Valentine’s Day 1913. Both had emigrated from Italy as children—Dolly from the north, near Genoa, and Marty from Sicily in the South.

He was a bantamweight boxer, fighting as Marty O’Brien. It was common for Italian boxers to take Irish ring names, in order to appeal to a wider audience. Sinatra family lore has it that diminutive, blue-eyed Dolly, less than 5 feet tall and weighing 90 pounds, once hid her strawberry-blonde tresses under a boy’s hat to sneak into an arena and watch Marty fight her older brother. Women weren’t allowed, but rules never stopped Dolly. The fight ended in a draw, though Marty would soon meet his match. How Dolly and Marty met is unknown, but for 56 years, as long as he and Dolly were together (he died in 1969), it would be Dolly over the mild-mannered Marty by a knockout.

Their first marital domicile was at 415 Monroe Street, in the Italian section of Hoboken’s west side. The four-story building had two cold-water flats on each floor, both sharing a bathroom at the end of the hall. It was in that apartment, on December 12, 1915, that Francis Albert Sinatra endured the first trauma of his life—his birth.

Dolly’s small frame would have made the delivery of any size baby difficult but the women attending her as she lay on the kitchen table soon realized the task was beyond their skills and sent for a doctor. Rosa Garaventa, Dolly’s mother, was there to assist her daughter through the ordeal.

By the time the doctor wrested the 13½-pound baby through the birth canal, using pincer-like forceps with such force that the boy’s left ear was torn, his neck disfigured and his eardrum punctured, it appeared to all—all but Rosa Garaventa—that the child was stillborn. Putting the bloody, seemingly lifeless baby aside, the doctor gave full attention to Dolly, whose survival was in doubt. Rosa saw to the child, holding its still form under the tap until, finally, the cold water brought him around. The baby let out a cry. Frank Sinatra, later known as the Voice,  had just given his first vocal performance to a small but appreciative audience.

The familiar Sinatra backstory—that of a tough, scrappy kid struggling to overcome poverty—was a press agent’s fabrication. As Anthony De Palma Jr. wrote in 1982 in New Jersey Monthly, “Sinatra and his publicity machine milked Hoboken for every drop of pathos the American public would buy. They presented him as a poor kid from the slums of Hoboken, a kid who was just like everyone else in those post-Depression early war years. His was the American success story all those young people, whose own futures had been swiped by another stinking war, dreamed about for themselves.”

In reality, the Sinatras were relatively well-off, thanks to Dolly’s fierce ambition. She became a midwife and performed abortions as a sideline. In her view, she was providing a service to the Italian-immigrant community, where a moment’s indiscretion could ruin a young girl’s reputation. Dolly also put her skill with Italian dialects to work helping paisans navigate the courts and City Hall bureaucracy. In the process, she gained notice in Hoboken political circles. In time, she built a following among Italian-Americans and was able to reliably deliver 600 votes  in every election to the local Democratic machine.

In 1927, with Marty out of work, Dolly demanded the politicians she helped elect hire her husband as a Hoboken fireman. When told by the mayor’s top deputy that there were no openings, she responded in typical Dolly fashion, “Make an opening!”

They made the opening. Shortly thereafter, Marty and Dolly opened a bar, Marty O’Brien’s, at 333 Jefferson Street, where Frankie, as his parents called the young teen, first sang to an audience for nickels and dimes. The lettering on the saloon’s window read: “M.O.B ASSN. of ALL NATIONS.” It was a Prohibition-era ploy to avoid openly advertising liquor sales. M.O.B stood for Marty O’Brien, but was strangely prophetic of Frank Sinatra’s future links to a different kind of mob.

By his own admission, Frank Sinatra was an indifferent student. “In my crowd,” he once said, “school was very uninteresting, and homework was something we never bothered with. The few times we attended class, we were rowdy.”  Arthur Stover, Sinatra’s principal at A.J. Demarest High School in Hoboken, agreed. “Frankie showed no real talent for anything,” Stover later recalled. Teacher Macy Hagerty remembered Frank as “a lazy boy” with “absolutely no ambition at all when it came to school.”  But it took a friend from those early years, Tony Consiglio, to relate the incident that ended Sinatra’s formal education—a story that only came to light in 2012 in Consiglio’s book about growing up with Sinatra.

“Frank got kicked out of school because of pigeons,” Consiglio wrote. “He and three other kids bought pigeons for 25 cents apiece, put them under their jackets, and went to see a school play called Cleopatra. During the most serious part of the play, Frank and his pals opened their jackets and the pigeons went flying. They flew all over the auditorium while kids ducked and screamed. That was the end of the play and the end of high school for Frank.”

Sinatra was 15 and happy to be done with school. He wanted to be a singer like Bing Crosby. Dolly and Marty tried to discourage him. They wanted him to get a regular job, but he lasted only a week or two at anything he tried, from bundling newspapers for the Jersey Journal to working in a shipyard. Finally, they gave in. Sinatra began singing at church-basement dances and social clubs, such as Cockeyed Henry’s in Hoboken. To get to his gigs, he and some friends bought an old Chrysler for $20. That was how he got involved with the Three Flashes, a local singing group.

Fred “Tamby” Tamburro was the trio’s leader; he and James “Skelly” Petrozelli were from Hoboken. The third member, Pat “Patty” Principe, lived in nearby West New York. Whenever the Flashes had a singing job, Frank offered a ride. When the trio auditioned for Major Edward Bowes’s Amateur Hour in New York, a radio program that was the American Idol of its day, Frank went along with them, hoping to score his own shot as a solo act.

READ MORE: Vote for your favorite Sinatra song in the Sinatra Song Bracket, presented by Hudson Whiskey.

Bowes liked the boys and put them together as a single act. The program card for the group’s September 8, 1935, debut listed them as Frank Sinatra and the 3 Flashes, but Bowes wrote above that entry the name that would become part of the Sinatra legend: Hoboken Four. They won the competition, and Bowes invited them to join his vaudeville touring group. Sinatra got the most attention on the tour, especially from females in the audience, prompting Tamburro and Petrozelli to physically batter the slender Sinatra. In a newspaper interview after Sinatra’s death in May 1998, Patty Principe described the fighting, which he attributed to jealousy.

“Sometimes it got pretty bad for Frank,” Principe said. “After all, he was a skinny little guy, and the two picking on him were older and bigger…and Frank couldn’t fight back.”  Sinatra, whom Bowes had pushed to the forefront as the lead singer, reached a point where he no longer tolerated the abuse. When he left, the act became the Hoboken Trio. Tamburro, Petrozelli and Principe quit the tour shortly thereafter. None would be successful in the entertainment business.

Part of Sinatra’s motive for quitting may have been Nancy Barbato, a cute 18-year-old he’d met when both were vacationing with their families in Long Branch. But before anything serious could develop, there was a living to be made. Back home in Hoboken, Sinatra took any gig he could get, paid or not. He sang for free on WAAT in Jersey City and WNEW in New York. He sang at the Hoboken Elk’s Club and the Cat’s Meow.

Hoboken’s Union Club, at Hudson and Sixth streets, was owned by Joseph Samperi, an Italian immigrant who rose from messenger boy to become a prominent and politically influential businessman. Dolly asked Samperi to give her son a steady singing job. Although he wasn’t overly impressed with the young man’s ability, Samperi couldn’t refuse her. “Frank was…sincere and anxious to do his best,” Samperi recalled in an interview years later. “Perhaps some would call him a perfectionist. He dressed well, always in a clean shirt, pressed suit and shined shoes. He made a good appearance, even though he was rather thin. He liked to sing, but his voice was not so appealing as it is today. It was good, but lacked the style [of the big bands].”

Sinatra quit the Union Club in the spring of 1938 when he was 22 to take a job as a singing waiter at the Rustic Cabin on Route 9W in Englewood Cliffs. The roadhouse, which no longer exists, looked exactly like its name implied: a structure of rough-hewn logs with white cement filling the chinks, situated along a desolate stretch of road feeding into the George Washington Bridge. It had one feature the Union Club lacked: a live hookup to a radio station, called a wire, that enabled its shows to be broadcast. Sinatra was in fine voice the night bandleader Harry James, looking for a male singer, showed up at the Rustic Cabin. “I felt the hairs on the back of my neck rising,” James recalled years later. “I knew he was destined to be a great vocalist.” James made Sinatra an offer that very night—the break Sinatra had been hoping for. But a bigger one lay ahead.

Tommy Dorsey, whose band was among the most popular in the nation, knocked on Sinatra’s door in December 1939. James graciously tore up Sinatra’s contract, allowing the singer to join Dorsey’s band. Sinatra’s departure from Dorsey, 2½ years later would be a different story. By then, Sinatra had become the country’s most popular band singer. Dorsey had an iron-clad contract, but with just five months left in the three-year deal, Sinatra grew restless. He couldn’t—or wouldn’t—wait to go out on his own. To gain his release, he recklessly assigned 43 percent of his future earnings to Dorsey and Dorsey’s agent.

For his first solo appearance, Sinatra played Newark’s huge Mosque Theater. The place was packed. That caught the attention of Robert Weitman, executive director of the prestigious Paramount Theater in New York’s Times Square. Sinatra made his Paramount debut on December 30, 1942, as an added attraction to the Benny Goodman Orchestra. The 3,600-seat theater was filled to standing room only. After the Goodman band finished its first set, the bandleader announced, “And now, Frank Sinatra.” The ensuing screams from the audience caught Goodman by surprise. He exclaimed, “What the hell was that?”  That…was Frank Sinatra and the birth of the bobby-soxers.

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