Excerpted fromFrank: The Voice,by James Kaplan, to be published in November by Doubleday; © 2010 by the author.

The voice was still developing in the spring of 1939—it would continue to develop for the next 50 years. It wasn’t as rich as it would be even five years later. But its DNA was there, the indefinable something composed of loneliness and need and infinite ambition and storytelling intelligence and intense musicality and Hoboken itself, the thing that made him entirely different from every other singer who had ever opened his mouth.

And Frank Sinatra had one more astounding thing at 23: a plan. He was going to knock over Bing Crosby. He knew it in the pit of his gut. But not even his new wife, Nancy, knew the true height of his hubris.

Frank had struggled and scrambled, at first, to gain even rudimentary success as a professional singer. He’d chased after Hoboken bands that didn’t particularly want him but saw uses for the Chrysler convertible and the musical arrangements his mother, Dolly, had bought him with her earnings as a midwife and abortionist. He’d sung for pennies in Irish and Italian social clubs and American Legion halls (and sometimes had pennies thrown into the megaphone he used for amplification). He’d sung for carfare, or less, on the radio. He’d foisted himself (with Dolly’s aid) on a vocal trio called the Three Flashes and, after the group surprised everyone by taking first place on Major Bowes’ Amateur Hour, set about overshadowing his partners.

With Dolly’s intercession once more (she had serious political juice in northern New Jersey), Frank had wangled his way into a singing-waiter job at a nightclub on the Palisades called the Rustic Cabin. Why? The Cabin had a telephone-wire hookup to the New York radio station WNEW, a station the kind of people Sinatra wanted to be heard by listened to—people such as the band singer Louise Tobin and her husband, the trumpeter and bandleader Harry James. It was Tobin who happened to catch Frank singing on WNEW one night in the spring of 1939 and thought enough of him that she woke up her husband and said, “Honey, you might want to hear this kid on the radio.” And it was James who decided soon thereafter, at the end of a long day of performing and traveling, to take a side trip to the Rustic Cabin.

He liked what he heard. “This very thin guy with swept-back greasy hair had been waiting tables,” James recalled many years later. “Suddenly he took off his apron and climbed onto the stage. He’d sung only eight bars of ‘Night and Day’ when I felt the hairs on the back of my neck rising. I knew he was destined to be a great vocalist.”

James offered him a contract on the spot: $75 a week. It was quite an offer, three times what Sinatra was currently making. What James neglected to say was that there were some weeks (he wasn’t especially good with money) when he didn’t have $75 to his name.

Since Harry had created Connie Haines that morning (that was the name he had conjured on the spot for his new girl singer, née Yvonne Marie Antoinette JaMais), he was feeling lucky. “Sinatra” was too Eye-talian, he said. How about Frankie Satin? It went nice with that nice smooth voice of his.

Just a moment before, Sinatra recalled in later years, he had been grasping James by the arm, incredulous at the offer, making sure his main chance didn’t get away. Now, as Connie Haines remembered sharply 67 years after that night, the singer’s eyes went cold. “Frank told Harry, ‘You want the singer, take the name,’ ” Haines said. “And walked away.”