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.

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.

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

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 and wherever books are sold.

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