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.

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.

Sinatra’s breakout success made it clear he had to get out of the costly release deal he’d made with Dorsey, but Dorsey wouldn’t budge. Sinatra turned to friends for help—friends who would make the bandleader an offer he couldn’t refuse, or so it was rumored.

Willie Moretti was an underboss in the Luciano/Genovese crime family, one of New York’s Five Families, the ruling syndicate established by Lucky Luciano. In the early 1930s, Moretti moved to Hasbrouck Heights to oversee gambling and bootlegging operations in New Jersey. One of Moretti’s crew was a cousin of Nancy Barbato’s, whom Sinatra had married in 1939. Frank, Nancy and the first of their three children, Nancy Jr., moved to Hasbrouck Heights in 1942 and took up residence in a Cape Cod at 220 Lawrence Avenue, around the corner from Moretti’s home. Frank and Moretti were already acquainted.

In 1938 or 1939, Mafia boss Frank Costello telephoned Chico Scimone, a pianist he trusted, and asked for his help. “The amici from New Jersey had contacted [Costello] about a young fellow,” Scimone recalled. “They said he had a good voice and they wanted to test him.” Costello asked Scimone to play piano for this “young fellow,” who turned out to be Frank Sinatra. Costello’s request likely coincided with Sinatra’s Rustic Cabin job, before Harry James discovered him there. Scimone described the session as “a little audition” and remembered Moretti being in the room with Costello. Sinatra sang a few songs and left. Costello and Moretti then asked Scimone for his opinion of Sinatra’s ability. “It’s fine,” the pianist replied.

Costello and Moretti were regulars in the Riviera, an elegant nightclub and illegal casino atop the Palisades in Fort Lee, overlooking the George Washington Bridge and the Hudson River. The original structure burned down on Thanksgiving night in 1936, but the club reopened in spectacular fashion six months later. The new art-deco style Riviera featured a retractable roof, allowing patrons to dance under the stars.

There is no official record of Sinatra appearing at the Riviera at this stage of his career, but it seems he performed there at about the time he was singing at the Rustic Cabin. The “little audition” pianist Scimone spoke of was clearly a tryout for the Riviera. Jack Bruno, employed at the Riviera from the late 1930s until the club’s demise in 1953, kept a scrapbook of entertainers who appeared there. His daughter, Irene Bruno Orefice, learned from her father about a Sinatra gig at the Riviera in 1938 or 1939, when Frank was known as the Singing Waiter. Sinatra did not draw well, which may be the reason he wasn’t invited back until much later.

The audition establishes the close connection between Moretti and Sinatra and lends plausibility to media speculation that Sinatra asked Moretti to intervene on his behalf with Dorsey. Dan Lewis, an editor at the Bergen Evening Record, once asked his friend Moretti about the rumors of Sinatra getting Mob help to free himself from Dorsey’s grasp.

“Well, Dan” Moretti told Lewis, “let’s just say we took very good care of Sinatra.” Moretti didn’t elaborate. In October 1951, Moretti was gunned down, gangland-style, in a Cliffside Park restaurant.

Dorsey, in a Parade magazine interview shortly before his death in 1956, confirmed the rumors. “I was visited by Willie Moretti and a couple of his boys,” Dorsey said. “Willie fingered a gun and told me he was glad to hear that I was letting Frank out of our deal. I took the hint.”

After Sinatra went Hollywood, his press agents began referring to Hasbrouck Heights as his hometown. “Sinatra ran as far away from Hoboken as he could get,” De Palma wrote in his New Jersey Monthly article. “He moved to the desert and seemed to love it there. He built a baronial compound: houses, pools, garages, a helipad, all his own. The openness of the desert, the vast stretches of nothingness, were the antithesis of Hoboken, where every inch of land had been paved over and occupied by so many entire families per square foot.”

Even as her son tried to distance himself, Dolly Sinatra remained a force in Hoboken. In May 1947, she helped defeat Mayor Bernard McFeely, a 16-year incumbent she’d previously supported, and elect Fred DeSapio as the city’s first Italian-American mayor.  To give his declining city a boost, DeSapio decided to host a monthlong celebration, climaxing on October 30 with Sinatra Day, honoring Hoboken’s most famous son.

It was already a busy month for Sinatra, but he took that day off and joined his mother, father and Nancy on the steps of City Hall at 7 pm to accept a large wooden key to the city from DeSapio. Its inscription read, “To Frank Sinatra, from the Hearts of the Citizens of the City of Hoboken, New Jersey, ‘Sinatra Day,’ October 30, 1947.”

A huge throng witnessed the event—some estimates put the crowd at 20,000. They lined Washington Street, Hoboken’s main drag, to watch Sinatra take a triumphal ride in the open cab of a fire truck driven by his father. Sinatra abandoned the procession after 10 blocks to avoid a soaking rain. A planned outdoor ceremony and other festivities were hastily canceled, and Sinatra rushed off, overdue at a benefit at Madison Square Garden.

Five years later, on September 10, 1952, Sinatra returned to Hoboken to perform at a fire department dinner at the Union Club. Marty wanted to show off his son, who would just have time to sing a few numbers before heading back to the Riviera, where he was then performing. Tony Macagnano, Sinatra’s childhood friend, was at the Union Club that night.

When he “hit some clinkers,” Macagnano said, “people booed him and threw fruit and stuff, kidding around.” Paul Samperi, whose father, Joseph, owned the club, was present and gave a different account. In Samperi’s version, no one threw anything at Sinatra while he was singing—they simply didn’t give him the attention he thought was his due. In any event, Sinatra blanched at the insult and hurried offstage and out the back door. As he was leaving, he told Macagnano, “Tony, I’ll never come back and do another thing for the people of Hoboken as long as I live.”

Old Blue Eyes would keep that vow for the next 32 years. But then he did come back—to help a buddy, the President of the United States.

On July 26, 1984, a helicopter transported Sinatra and President Ronald Reagan from Newark Airport to Hoboken. Reagan, in the midst of his reelection campaign, had asked Sinatra to introduce him at the St. Ann’s Church feast, an Italian tradition that continues to this day. The Jersey Journal headline the next day read, “Reagan Wows Hoboken—Sinatra a bonus for the crowd.” Pushing 70, Sinatra was no longer the prodigal son returning to the city of his birth. He uttered a few words of praise for Reagan, then disappeared as quickly as he had from the Union Club dinner three decades earlier. He would make just one more public appearance in Hoboken, on May 23, 1985, to receive an honorary Doctor of Engineering degree from Stevens Institute of Technology.

Sinatra maintained a love-hate relationship with Hoboken for most of his life. He had benefited from his mother’s influence but shrank from her domineering ways, and while Dolly’s abortion business put food on the table and money in his pocket, it had also shamed him: As a teenager, he’d been barred from singing at a dance in the basement of Our Lady of Grace, Hoboken’s Irish Catholic church, because of his mother’s reputation.

Late in life, during a rare moment of self-reflection, Sinatra expressed his feelings toward Hoboken this way: “When I was there, I just wanted to get out,” he said. “It took me a long time to realize how much of it I took with me.”

Richard Muti is a former Bergen County assistant prosecutor and mayor of Ramsey, his hometown. His sixth book, Cent’Anni: The Sinatra Legend at 100, was published this fall by North Jersey Media Group. It is available at ShoptheRecord.com and wherever books are sold.

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