Chapter 1Monroe Street

Foreword

I could name the photograph before I could name the charge.

Everybody can. A young man in a jacket and tie, straight on and then in profile, photographed the way a county photographs anybody it processes in a given week. It has been on shirts and posters and record sleeves and the walls of bars that wanted a particular atmosphere for most of my life. I had looked at it for years without once wondering what was behind it.

When I did wonder, the answer took about a minute to find and has never improved on that minute. In November 1938, in Bergen County, a married woman swore out a complaint. The charge is reported as seduction. It was amended to something else, and the matter was dismissed. Every clause in those sentences reaches me through writers who had it from other writers. The court records for that month exist, and so far as I can establish almost nobody has read them.

So the most widely reproduced image of one of the most photographed men of the century is an administrative by-product of a proceeding that failed. The picture travels perfectly. The paper behind it has been in a drawer for close to ninety years. I went looking for the book that had gone and read the file, did not find one, and started this instead.

The second thing that stopped me was arithmetic anybody could have done at any point in the last quarter century. The Federal Bureau of Investigation watched this man from the war until the nineteen-eighties. Something close to fifty years of informant reports, wiretap summaries, association memoranda and index cards, and out of all of it not one charge. He died on May 14, 1998. The dossier was released on December 9 of that year, and the New York Times reported it under a headline calling the contents tidbits, old and new. Kitty Kelley's unauthorized biography, where a very large share of what the public believes about him begins, had been published in 1986, twelve years earlier. Two journalists, Tom and Phil Kuntz, annotated the released documents in 2000, and the volume they made has been substantially unused since.

Verdict, then evidence, then nothing. And when I tried to check the simplest available fact about that release — how big it was — I found two page counts in circulation that do not agree with one another, apparently describing different quantities, printed side by side by people who had not noticed. No page count appears in this book.

There is one page in that file I have not got past, and it decided the shape of everything after it. In 1943 an Army physician examining him for induction found the left eardrum perforated — an injury inflicted by forceps on the day he was born — and classified him 4-F. That is the public reason he did not go to the war, and nothing I have read contradicts it. The examination made a second finding. It recorded that he was not acceptable material from a psychiatric viewpoint, and that finding was kept out of his classification, on the stated grounds that telling him would cause him emotional upset.

Read that arrangement slowly, because there are two decisions in it. Somebody assessed him and wrote it down. Then somebody decided he was not sturdy enough to be shown what had been written, on the authority of the very finding being withheld. He lived fifty-five more years without knowing the sentence existed.

The argument of this book is that the two things everybody knows about Frank Sinatra — that the mob made him, and that America eventually made him a monument — are one fact seen from opposite ends. Both were assembled out of proximity: who he flew with, who slept in a chalet on his property, whose name sat next to his in somebody's address book, which room he was standing near when something good or bad occurred. Nevada took his gaming license in 1963 without charging him with anything, on the evidence of a guest, and gave it back in 1981 with no new finding about anything, on the evidence of a letter from a President and two well-liked actors. Nothing underneath had changed in eighteen years. Only the names had. The same government that could not build a case against him in five decades gave him the Presidential Medal of Freedom in 1985 and the Congressional Gold Medal in 1997, on material of precisely the quality that had been failing against him the whole time, which is to say hardly any. The suspicion and the sainthood came off one machine. That is a position, and the people who have worked this subject hardest disagree with it in both directions.

I should say what this book is not, because two versions of the man are available off the shelf and I refuse both.

It is not a prosecution. The two most famous scenes in his life were written by a novelist. The pistol in Tommy Dorsey's mouth and the horse's head that got him a part in a picture are both Mario Puzo's, and they entered the record from the fiction rather than the other way around, because a scene can be pictured and a transaction cannot. The suitcase of cash in Havana, which holds up the entire criminal reading of his early career, rests on informant statements taken later, from people with reasons to be useful and never tested by cross-examination. I do not assert it. Eight of these twenty-two chapters deal with the file and the men in it, and that is as much room as the evidence earns; a book that gave the Bureau more space than the recordings would have conceded the Bureau's own account of what mattered about him.

It is also not a defense. The absence of a charge is not a certificate of good character, and I have not once written it as one. He sought these men out. He enjoyed them and was flattered by them, he held nine percent of a Las Vegas hotel and better than half of a lodge at Lake Tahoe, and in 1963 he surrendered a state license rather than answer for a guest. Those were choices made by an adult with other options. The consoling version in which a man who came up in rooms owned by such men was guilty of geography and nothing else does not survive the calendar, and neither does the version in which he desegregated the Las Vegas Strip.

A word on method. The evidence here is, first, the recordings — roughly fourteen hundred commercial sides made across six decades by a man who could not read a note of music, cut live with the orchestra in the room because he refused to assemble a performance out of pieces afterward. That archive is the only one in this story no institution issued him, and the only evidence in it a reader can test personally, in the time it takes to play it. Everything else is published: dated documents, contemporaneous reporting, court and committee records where printed, and a small shelf of books, named on the page wherever they carry a claim. I conducted no interviews. There is not a line of lyric anywhere in this book; I describe what a performance does and print nothing but titles.

More important is what I did not do. I did not pull the Bergen County docket, sit with the dossier page by page, or go into the Gaming Commission minutes at Carson City, the regulator's own oral history, the printed record of the 1972 hearing, or the New Jersey commission's file at Trenton. The Capitol session logs and take sheets are somebody's property, which is why no take count appears here. The columns that destroyed him in 1944 and again in 1947 are on microfilm and I have not turned the reels. Where an account rests on the family, I say it is the family's; where it rests on one unauthorized book and forty years of repetition, I say that.

When the record is contested I have given both versions and graded them in the prose rather than in a note: not in dispute, disputed and left disputed, asserted by others and not asserted here. When it simply stops — which happens constantly, and most often where everyone is most confident — I have written a sentence saying so instead of closing the gap with something that sounds like knowledge. And I print no sales figure for any record he ever made, because every total in circulation originates in a press release.

He wrote no memoir, and he came out of a place where explaining yourself to officials was the mistake. What survives is the paper other people made about him, most of which he was never shown, and the noise he made himself, all of which anybody can still hear. I have graded the first and listened to the second, and where they disagree I have said so and left them disagreeing.

Nothing was ever proved. That is not the same as nothing having happened, and it was never going to be enough, because a country does not require a proof about a man. It only requires something it can repeat.

Chapter 1 · Monroe Street

Hoboken sits on the west bank of the Hudson with Manhattan on the far shore, and everything in it was built for the water. Piers, ferry slips, rail sidings, warehouses, coal yards, ships' chandlers, saloons, and behind them the tenement blocks that housed the men who worked all of it. A port town has one industry, and the industry is arrival: cargo off a ship and onto a train, and people off a ship and into a room. Italians came into Hoboken late, and found the work on the docks, the police force, the fire companies, the magistrates' benches and the Democratic organization already held by people who had arrived before them. Nothing there was allocated by application. Work on the piers came through a hiring boss. A city job came through a ward leader. A liquor license came through the men who issued liquor licenses, and a fight came through whoever controlled the card. Every job came through somebody. The question that organized daily life in that town was never what a man could do. It was who would say his name.

The other fact about the place is the one visible from any upstairs window on a clear day, which is that the money was on the opposite bank. Hoboken faced Manhattan across the river and was tied to it by ferries, and a great many of the people who lived on the Hoboken side worked, drank, spent or wanted to be on the other one. That is a particular condition to be raised in: a town whose principal export is people, situated close enough to the thing everybody wants that you can watch its lights go on. The men who stayed loaded ships. The men who left crossed the water.

On Monroe Street, on December 12, 1915, in that town, Natalina Garaventa gave birth to a son. The delivery was done with forceps and it went badly. Obstetric forceps are a hinged metal instrument that closes around a child's skull, and they are used when a birth has stopped and the alternative to force is losing the mother, the child, or both; a doctor reaching for them has already decided that damage is the better of the available outcomes. The instrument tore the left side of the child's face and tore his neck, and it perforated his left eardrum, which never closed again. He did not breathe. He was set aside while the room worked on his mother, and his grandmother carried him to the sink and held him under the cold tap until he cried. The figure the family gave for his weight was thirteen and a half pounds.

It is worth stopping on that paragraph before the book goes any further, because the way it reaches us is the way most of this life reaches us. There is no delivery record in front of this writer. There is a story, told by the people who were in the flat or who heard it from the people who were, repeated to interviewers long afterward when the child had become famous, and then set down in books. The weight is the family's number and it is the number every account uses. So is the tap. So is the being laid aside.

One element of it was later checked by somebody with no stake in the story. In 1943, an Army physician examining him for induction found the left eardrum perforated. That is on the record because a government put it there, in the course of deciding what to do with him, and not because a family put it there in the course of explaining him. The rest of it — the pounds, the sink, the cold water — has no such second source and is never going to acquire one.

The books it comes down through are a small shelf. James Kaplan's two-volume life is the fullest modern account of the man. Nancy Sinatra published two family-authorized books about her father, indispensable for dates and photographs and neutral about nothing. Pete Hamill, a newspaperman who drank with him, wrote a short first-person essay that is the best available statement of the immigrant-generation case for the subject, and this book has to take that case seriously in order to be fair to it. Kitty Kelley's unauthorized His Way appeared in 1986; Sinatra sued to stop it and the suit was dropped; and a large share of what the public believes it knows about him begins there rather than in any archive. Anthony Summers and Robbyn Swan, working from documents rather than anecdote, produced the most systematic attempt anyone has made on the organized-crime material, which is a different subject from a delivery room and does not help here. J. Randy Taraborrelli's account is family-adjacent, interview-heavy, useful on the household, and sympathetic to it.

None of those books had a delivery record. That is not a complaint about them; it is the condition of the material. Hoboken is the phase of this life where the paper is thinnest and the anecdotes are densest, which is the reverse of the usual arrangement and worth flagging on the way in. A book whose argument concerns the difference between a story and a file has an obligation to say so at the start, in the first paragraph where the difference actually applies, and this is it. The scars and the ear are real. The pounds and the sink are a family's account of a night in 1915, and the honest way to carry them is as exactly that, and no further.

His mother was Genoese. Natalina Garaventa — Dolly, to everyone who dealt with her, which in that ward was most people — came from the north of Italy, and she married a Sicilian. By the reckoning of the neighborhood that was a mixed marriage. How the two of them met is not established by anything in front of this book, and the accounts that do exist were collected long afterward from people with reasons to shape them.

The distinction mattered inside the neighborhood and nowhere outside it. To a hiring boss on the piers, to a boxing commission, to a desk sergeant, to a census enumerator and eventually to a clerk typing an index card in Washington, Genoa and Sicily were the same entry. Italian was a category applied from outside, and like most categories applied from outside it was coarse, durable and impossible to argue with. His parents knew the difference. The paperwork did not. It is worth setting that down at the start rather than late, because the institution that would eventually take an interest in this child worked by category, and the category it filed him under was one neither of his parents would have recognized as a single thing.

What is established about Dolly is what she did for a living, and she did two things. The first was politics. She was a ward heeler for the Democratic organization in Hoboken's Third Ward, and the phrase that attaches to her is that she could deliver a precinct. That sentence is worth unpacking, because it is the load-bearing fact of the household. A ward heeler was not a candidate and did not hold office. A ward heeler was infrastructure. She knew who lived on which floor of which building, and which of them were registered, and which of them could be registered, and which of them would need the ballot explained in a language they could read. She got a man his naturalization papers. She got a family coal in February. She got a word to a magistrate when a boy was picked up, and she got a nephew onto a payroll, and every one of those transactions was an entry in a ledger that was never written down and that both parties remembered exactly. On election day the entries were called in. To deliver a precinct meant that the organization above her could be told a number before the polls opened and could rely on it afterward. In a ward where a great many voters had been born on the other side of an ocean, the person who could explain the ballot was, for practical purposes, the person who cast it.

The second thing she did was midwifery, in a neighborhood and a period when most children were born at home, and alongside it she did the other work that a woman with those skills was asked for and that the state had made a crime. She was arrested for it more than once. That is reported, and it is the kind of transaction that leaves paper in a county courthouse; this book has not read that paper, and the honest form of the sentence is that she performed abortions in a jurisdiction where doing so was an offense, that she was arrested for it on more than one occasion, and that the dockets behind those arrests have not been pulled here.

Put the two trades side by side and they are recognizably one trade. Both were services the official world declined to provide and the unofficial world required. Both ran on the same asset, which was knowing whom to telephone. And both were conducted in full view of a police department and a set of magistrates who were, in the other half of her working life, her clients and her creditors. An arrest, in that arrangement, was not a rupture. It was an operating cost, incurred in a business whose whole method was the management of official attention. Her son grew up in a house where the authorities were a recurring line item.

His father was Sicilian, and his father could not read. Antonino Martino Sinatra — Marty — was illiterate and asthmatic, and he made money in the one trade in America that was supposed to be open to a poor man with a strong back, which was fighting. He was a bantamweight. He fought under the name Marty O'Brien, because in that decade an Italian could not get a card.

That sentence deserves to be read slowly, because it contains the mechanism the rest of this book keeps running into. Boxing was licensed. Licensing is permission. Permission in that state, in those years, was administered by commissions and clubs and matchmakers and promoters who were not Italian, and the crowds who paid at the door had opinions about names. So an Italian fighter took an Irish one. It fooled nobody in the building — the men in the cheap seats knew exactly what they were looking at — and it was not intended to. It was a formality, like a union card or a stamped affidavit, a piece of paperwork carried in the mouth instead of the pocket. A nationality was a licensing category, it had a price, and Marty Sinatra rented one.

He fought with asthma, which is to say he sold his lungs in a market where he had less of the merchandise than the men opposite him. Nothing in the record establishes what that cost him round by round, and no fight-by-fight account of his career is in front of this book. What can be said, flatly, is that the father earned by breathing under duress, and that the son's entire technical achievement would eventually be a matter of breath — not because the one caused the other, which nobody can show, but because it is a fact about the house and it is the sort of fact biographies usually convert into an explanation. This one will not.

There was a saloon on Jefferson Street with an Irish name over the door. What a saloon was in a town like that is not adequately conveyed by the word bar. A saloon cashed pay envelopes for men who had no bank and held mail for men with no fixed address. It was a hiring hall in the mornings, when the bosses came in and drank and pointed, and a clubhouse in the evenings, when the ward's business got done at the end of the counter or in the room behind it. The man behind the bar knew what everybody owed and to whom. And the name on the sign was Irish, which in Hoboken was not decoration. It was the same commercial instrument as the fighter's name: a thing that made a door easier to walk through, purchased for the purpose, and worth what it cost.

Later Marty Sinatra became a captain in the Hoboken Fire Department. Set that beside everything above and the shape of the family finances changes completely. A municipal appointment was the opposite of a purse and the opposite of a bar: a wage that came whether or not a crowd showed up, that did not depend on a matchmaker's opinion or a health inspector's mood, backed by a city. In a town like Hoboken those jobs were currency. It would be poor reporting to write that the ward leader in the kitchen got her husband his helmet. No appointment file has been read for this book, and no document in front of it links the two. What can be written, because everyone in that town would have understood it without being told, is that a fire department appointment and a woman who could deliver a precinct were not independent facts, and that the family contained both.

Which is the finding of this chapter, and it is small and it is the whole book in miniature. Here was a boy whose mother could produce votes and whose father had to borrow a nationality to earn a living. One parent's trade was persuading officials to act. The other parent's trade required officials not to notice. Between them they covered the entire available relationship between an Italian family and the American state in 1915, and neither half of it involved a piece of paper that said what it meant. The ledgers were memory. The name over the door was false and everyone knew it and it worked anyway. The most consequential transactions in that household — the coal, the word to the magistrate, the appointment — left either nothing behind or something that did not describe them.

What the child made of that is the question every biographer of this man answers and none of them can. There is no diary. He wrote no memoir, then or ever. The anecdotes of his boyhood were collected after he was famous, from people who knew they were talking about somebody famous, and they are shaped accordingly. This book will say when it does not know something, and it does not know this. What it can do is set down what he arrived with, because that part is physical and it lasted.

He arrived with a torn face, a torn neck, and a left eardrum that would never close. He never learned to read music, and he never would; the score stayed shut to him across a working life and roughly fourteen hundred commercial recordings. Everything he came to know about a melody, a lyric, an arrangement, a horn player's phrasing or the attack of a saxophone section, he took in through an auditory apparatus that had been damaged on the way into the world, and he gave it back through a throat and a set of lungs and nothing else. There was no instrument between him and the room. A pianist can put a piano between himself and an audience, and a horn player has a mechanical object to blame when the night goes wrong. A singer has a body. The body is the entire apparatus, it cannot be traded in, and it ages in public.

Nobody wrote down what music was in the flat on Monroe Street. There is no point pretending otherwise. The household inventory of songs and records and instruments and singing at the table is not recoverable now, and what circulates instead is recollection at long range, offered by people who already knew how the story came out and were being asked to explain it. What is recoverable is the shape of the equipment. One damaged ear, a throat, and no notation.

That is also where this book's evidence is, and it is worth saying plainly in the chapter where there is not yet any of it. The recordings are the one body of material in the whole subject that no institution issued him and no family curated. The votes are gone. The ledgers were memory. The dockets have not been read and the file, when it arrives, will have been assembled by people who were never in the room. The records are the exception: a reader who wants to test what the later chapters claim about the instrument — what the voice could do before the hemorrhage and what it could do afterward, what changed when the arranger changed — can go and check it, and does not have to take this writer's word or anybody else's. For a man who would spend six decades making a body of work out of listening and imitation, the damage recorded on Monroe Street is not a metaphor. It is a specification.

Natalina Garaventa was called Dolly. Antonino Martino Sinatra fought as Marty O'Brien and ended as a captain in the fire department. The child born to them on Monroe Street on December 12, 1915 was given both their countries and neither of their trades. He was raised where the transactions that mattered left no paper at all, which was the point of them and the local definition of safety.

He would spend close to half a century as the subject of an institution whose only product was paper — informants, wiretap summaries, index cards, an Army examiner's note he was never shown — and it never brought a charge against him. What that institution held was released in 1998, after he was dead, and it is where this book ends. It begins here, on a street where nothing was written down and everybody knew everything.