Usually at a distance, although sometimes close enough to eavesdrop, I followed Frank Sinatra at midnight after the fight into the dawn of the next day.

I began as part of the audience in the Sands’s lounge watching his routine with Dean Martin and Joey Bishop, and then I took a taxi to pursue him and his friends to the Sahara, where, for more than an hour, they sat at a crowded table in the clubroom drinking and bantering, while at the same time Sinatra was being roasted in friendly fashion onstage by his pal the comedian Don Rickles. Finally, at close to four in the morning, he left the Sahara and headed back to the Sands with his retinue in tow, some of them carrying their glasses of whiskey with them, sipping along the sidewalk and in the cars, all of them dwelling casually and cheerfully in their chosen time zones.

Sinatra was apparently hungry, and so at the Sands he headed toward the dining room and sat at a large table in the corner that had been reserved for him and his guests. In front of the table, for added privacy, was a white wooden trellis that I saw as my line of demarcation, a spot beyond which I should not trespass; and so I sat alone at a small table close by, surrounded by dozens of other dining gamblers and tourists, and adjoining the casino floor that was vibrant with spinning roulette wheels and clamorous crapshooters.

From left, Don Rickles, Buddy Lester, George Sidney, Sinatra, Jack Entratter, and Dean Martin have lunch at the Sands Hotel and Casino, in Las Vegas, 1960.

With my beer and hamburger in front of me, and while reviewing the notes I had scribbled earlier on my trimmed slices of shirtboard, I noticed that Jim Mahoney was greeting me with a wave from Sinatra’s table. I waved back with a smile, guessing correctly that our exchange was not meant as an invitation to join him and the others. They included Dean Martin, Joey Bishop, and Jilly Rizzo; Jack Entratter with his girlfriend, Lari Laine; Leo Durocher with a date named Betty; Harold Gibbons, a high-ranking official with the Teamsters union; and a few more I could not identify.

Sinatra with his bodyguard Ed Pucci at the Sands, 1965.

Actually, I did not mind sitting alone. At least I was being permitted to follow Sinatra and his people around Las Vegas, as I had done the previous week at the NBC taping in Burbank. And while there had been no clear concession on the part of Sinatra or his representatives, we seemed to have reached a kind of détente: As long as I did not bother Sinatra, Sinatra would not bother me. I remembered being told by the actor Richard Bakalyan, whom Sinatra had initially ridiculed and then cultivated: “Frank never says ‘I’m wrong’ or ‘I’m sorry,’ but he shows it in other ways.” Maybe this explained why I was presently allowed to walk in the shadow of the man who had earlier tried to banish me with his pronouncement: “No dice.” Or maybe Hayes’s threatening letter was now a factor in my favor. I would never know.

Except for the few words exchanged with Sinatra a week before at the NBC taping, after I had complimented him on his CBS interview with Cronkite, we had not spoken. He also said not a word to me during our time in Las Vegas, nor did he even look at me directly; and yet, again, he appeared not to mind my presence in the crowd that regularly encircled him, such as when he briefly left the dining room to play blackjack and I was able to observe and overhear his exchange with the dealer.

In the notes later typed in my room at the Sands before going to bed at sometime after five—I was now living Sinatra hours—here is what I wrote:

Martin and Sinatra at the Sands, 1960.

“… resting his shot glass on the blackjack table, facing the dealer, Sinatra stood a bit back from the table, not leaning against it. He reached under his tuxedo jacket into his trouser pocket and came up with a thick but clean wad of bills. Gently he peeled off a $100 bill and placed it on the green-felt table. The dealer dealt him two cards. Sinatra called for a third card, overbid, lost the hundred.

“Without a change of expression, Sinatra put down a second $100 bill. He lost that. Then he put down a third and lost that. Then he placed two $100 bills on the table and lost those. Finally, putting his sixth $100 bill on the table, and losing it, Sinatra moved away from the table, nodding to the man, and announcing, ‘Good dealer.’

“The crowd that had gathered around him now opened up to let him through. But a woman stepped in front of him, handing him a piece of paper to autograph. He signed it and then he said, ‘Thank you.’”

Continuing, I also described Sinatra and his people having dinner:

Sinatra works the room at the Sands, 1965.

“The table was about the same size as the one reserved for Sinatra whenever he is at Jilly’s in New York; and the people seated around this table in Las Vegas were many of the same people who are often seen with Sinatra at Jilly’s or at a restaurant in California, or in Italy, or in New Jersey, or wherever Sinatra happens to be. When Sinatra sits to dine, his trusted friends are close; and no matter where he is, no matter how elegant the place may be, there is something of the neighborhood showing because Sinatra, no matter how far he has come, is still something of the boy from the neighborhood—only now he can take his neighborhood with him.”

While there had been no clear concession on the part of Sinatra or his representatives, we seemed to have reached a kind of détente: As long as I did not bother Sinatra, Sinatra would not bother me.

A few days after returning to Los Angeles I drove to the Paramount movie set and, while standing on the sidelines behind several stagehands and extras in the cast, I watched Frank Sinatra and his Italian co-star Virna Lisi, working together on Assault on a Queen. Sinatra was playing a deep-sea diver hired by some nefarious adventurers engaged in a failed attempt to hijack the Queen Mary during a transatlantic crossing. In the scene I saw, Sinatra and Ms. Lisi were adrift in a pool of thrashing water, struggling to climb into a flimsy float—a maneuver that the director, Jack Donohue, had to re-shoot a few times because Ms. Lisi seemed to have difficulty remembering her lines or pronouncing them properly.

Ordinarily, Sinatra might have shown signs of irritation due to the delays, but on this occasion he was uncharacteristically patient and did all he could to comfort Ms. Lisi.

In fact, he was lighthearted and charming to everyone on the set throughout the afternoon, no doubt still basking in the afterglow of the rave reviews received earlier in the day from his performance in Frank Sinatra: A Man and His Music, the hour-long special that NBC had broadcast the night before. Only after the director seemed to be unduly deliberative about inviting Sinatra and Ms. Lisi out of the water did the singer mildly complain to Donohue and the camera crew: “Let’s move it, fellows. It’s cold in this water, and I’ve just gotten over a cold.”

Sinatra and Raffaella Carrà on the set of the 1965 movie Von Ryan’s Express.

An hour later, having changed into dry clothes, Sinatra was standing outside his dressing room accepting congratulations for the NBC show from some of his friends, a group that included the actor Richard Conte, who portrayed a nautical mechanic in Assault on a Queen; and the comedian Steve Rossi, who, with his partner, Marty Allen, formed the Allen & Rossi comedy team, which was currently very popular on television and in nightclubs.

Sinatra at the Eden Roc hotel in Miami, 1965.

At one point, since I was standing behind Rossi, I drew Sinatra’s attention, and so I stepped forward to convey my own admiration for the NBC show. Sinatra smiled and conceded that the program had been excellent, adding, “I’m not that easily pleased.” I then expressed the hope that we might have some private time together before I returned to New York. I had already spent three weeks in Los Angeles.

“Oh, I’ve been so busy,” Sinatra said. Then, before turning toward his dressing room, he paused to suggest, “Maybe something can be arranged after I get back from Palm Springs on Monday.” Monday was only four days away, but I had doubts that a private one-on-one meeting with Frank Sinatra would ever happen. He had offered the same excuse about being busy during our brief exchange earlier in Burbank. I also recalled a comment made to me during a recent chat with a Warner Bros. photographer named Dave Sutton:

“In order to get to Sinatra the way you want, you have to be a friend. And if you’re going to be his friend, you’ll find you can’t write about him.”

After returning to my hotel from the Paramount movie lot, I updated Harold Hayes in a note I mailed on the following day:

Friday, November 26, 1965:

Dear Harold:

Yesterday I saw Frank Sinatra very briefly. He did not have time to talk—he never seems to have time … but perhaps we’re making progress … I may not get the piece we’d hoped for—the Real Frank Sinatra—but perhaps, by not getting it, and by getting rejected constantly and by seeing his flunkies protecting his flanks, we will be getting close to the truth about the man.

Sinatra and actress Virna Lisi, circa 1966.

When Frank Sinatra returned to Los Angeles on Monday afternoon to complete his final scenes for Assault on a Queen, I joined a hundred others on the sidelines of the Paramount studio, a gathering that included Jim Mahoney, Brad Dexter, Ed Pucci, Mickey Rudin, Al Silvani, the singer’s daughter Nancy, plus such celebrated fans of Sinatra as the six-foot-six Don Drysdale, the star pitcher for the Los Angeles Dodgers, and one of the nation’s leading professional golfers, Francis “Bo” Wininger.

Wininger had told me that although Sinatra did not spend much time on the course, he was capable of scoring in the low 80s, while Nancy Sinatra added that her father shied away from golf “because playing it took too long.” I had become personally acquainted with Nancy during our lunch a few days earlier, on Friday, being surprised and pleased that she accepted my invitation and even more surprised and pleased that Mahoney had not canceled it in advance, as he had done previously.

Mahoney also did not interfere with a meeting I arranged a day later with Brad Dexter, who invited me to join him at Sinatra Enterprises, where he served as the vice president, and, since his boss was out of town, Dexter took the liberty of occupying Sinatra’s large office—a glass-partitioned space of modern design festooned with bamboo palms and fig trees and dominated by a large tapered wooden desk shaped like the wings of an airplane. Behind it was a black leather chair with an orange-colored cushion into which Dexter made himself comfortable for the duration of our interview.

Sinatra with his daughters, Nancy (left) and Tina, and Martin outside Grauman’s Chinese Theatre, 1965.

As I sat across from him, he lamented that whatever fame he possessed was largely attributable to his having saved Sinatra’s life after the latter had partaken in a leisurely swim and got caught in a riptide in Hawaii. Sinatra had gone there in 1964 to direct and star in None but the Brave, a World War II movie in which Dexter played a tenacious Marine sergeant. All modesty aside, he cited it as one among dozens of outstanding roles he performed during his 20-year career as a talented if unheralded actor.

Indeed, shortly after we began talking, he suggested that if my planned article about Frank Sinatra did not work out, I might consider doing an Esquire profile on him.

The Singing Grandson of a Shoemaker

In my meetings with the 25-year-old Nancy Sinatra, she proved to be as forthcoming as her father was evasive. Not only did she answer all my questions but she added information that I had not requested, such as how she felt about her father’s affair with the actress Mia Farrow, who was five years younger than herself.

“Mia and I have been guests at the same time in my father’s house in Palm Springs, and we get along very well,” Nancy said during our Friday lunch at the Paramount cafeteria. “My father has his private life, and I have mine, but he knows he can be himself with me. He knows that we can double-date and it doesn’t upset me. He has no reason to feel guilty. He is not married. He’s a single man, and yet a good family man.”

Sinatra and Mia Farrow on the set of Von Ryan’s Express.

Although he divorced her mother for Ava Gardner in 1951 after more than 10 years of marriage, he never left his family, Nancy pointed out; he created a loving and lifelong bond with his three children as well as a respectful and caring relationship with their mother, who never changed the locks after he left, nor did she limit visitation rights in an attempt to regulate his prerogatives as a parent.

When Ava Gardner divorced her father in 1957—Nancy was then 17—she hoped that her parents might re-marry. Her father, however, explained that her mother “could not live his life anymore,” but this did not diminish their continuing closeness as a couple, which was exemplified by the fact that her mother was overseeing Frank Sinatra’s forthcoming 50th birthday party at the Beverly Wilshire hotel.

Nancy said that she grew up “searching for a bit of her father in every eligible young man she met” but conceded it was difficult because he was a “perfectionist” with a strong personality, as well as being sensitive, intuitive, and introspective.

“He can completely take over a party, or he can be very quiet and listen and watch—and the entire mood of the party will change according to his behavior,” she said, adding: “In most ways he’s just like everybody else, but people don’t see it that way. They think that when they’re home watching television he’s out swinging somewhere. They forget that he likes to sit home and watch television too. I remember once being with him for two weeks and he didn’t have a woman the whole time. He also has qualities that most women would admire in any man, no matter what his last name might be—the way he dresses, that he always smells good, that he’s always on time, that he is very attentive, orderly, and remembers everything. Mention a book you’d like to read, and it is in the mail the next day. When you’re his guest in Palm Springs, you don’t have to bring a thing. Everything is there for you. There are clothes you can wear, the bathrooms are stocked with every drugstore item you can imagine, and, before you head back home, your car is washed and filled with gas.”

Sinatra with his daughter Nancy and Yul Brynner in Las Vegas, 1965.

She paused and continued: “He is fastidious and wants to know everything. When he does a television show, he knows what’s involved—the commercials, the lighting, the sound, the camera angles and blocking. He could probably do everything himself. Same with airplanes—he knows them inside and out. When he buys a car, it is not like other people buy a car. He knows everything about it. If he is going to tend bar, he knows about every kind of drink you can think of. He doesn’t do anything half-assed. He has a helicopter, and he doesn’t have a license, but he knows how to fly a helicopter.”

In addition to our long lunch at the Paramount cafeteria, Nancy Sinatra met with me briefly on two other occasions during the weekend, and on Monday she invited me to the United Western Studios in Hollywood to hear her sing a folk-rock song that would soon sell more than a million records and soar to the top of the Billboard Hot 100 chart. Written and produced by Lee Hazlewood, it was called “These Boots Are Made for Walkin’.”

This would prove to be the high point of her career, the first time that she was a star soloist instead of singing, acting, or otherwise appearing with her father or Elvis Presley or some other famous performer, or being a supporting actress in several movies. I could sense her satisfaction as we left the recording studio, and I also felt that she was fast becoming accustomed to being on her own in the aftermath of her recent divorce from the singer-actor Tommy Sands. She was now living alone in a new home in Beverly Hills that was furnished and decorated entirely to her own taste, and perhaps the fact that she was fully cooperating with me—doing what her father and so many of his followers had resisted doing—testified to her budding spirit of independence.

“In order to get to Sinatra the way you want, you have to be a friend. And if you’re going to be his friend, you’ll find you can’t write about him.”

I wondered, but did not ask, if her father knew that she was spending time with me. I assumed that he did, being so aware and conscientious, but maybe she herself decided (with her father and Mahoney later concurring) that it was a good idea for her to cooperate with Esquire’s writer in the hope of appeasing to some degree the magazine’s disgruntled editor, Harold Hayes. Or maybe she was making herself available to me because, like Brad Dexter, she believed that she might herself be the candidate for a full-length profile in Esquire.

But none of this really mattered to me because, after nearly a month of stress and disappointment while in Los Angeles, I was finally enjoying my work and was pleased not only to have attended Nancy Sinatra’s recording session but on the same day to accompany her, in her sporty green Ford Mustang, to the movie lot at Paramount to watch her father’s final scene in Assault on a Queen.

Sinatra at his home in Palm Springs, 1961.

There she knew nearly all the cast members and spectators on the set, introducing me to some of them, and while I was at her side I felt more credentialed and less an intruder. Perhaps this is why, after the director Jack Donohue had called a break in the action, and I noticed Frank Sinatra sitting alone in a canvas chair chatting with a cameraman, I had the confidence to take the initiative and approach him. When I had last seen him four days before, prior to his departure to Palm Springs for the weekend, he suggested that he might speak to me when he returned; and since I was tired of waiting, I thought it was now or never.

“Excuse me, Mr. Sinatra,” I began, kneeling in front of him. He turned away from the cameraman and smiled as I went on: “I’m hoping that we can finally schedule an interview once you’re done with this film.”

“I’m sorry,” he said quickly, “but I just don’t have the time. When I finish here today, and a recording tonight, I’m getting on a plane and going to Mexico. I want to get away, I need to get away.” He paused before continuing: “It’s all been too much. It’s reached a saturation point. When I was younger I was always aware of saturating the market, and now that’s what happened.”

“I understand,” I said—and I did understand. What he was saying I myself had been saying a month before to Harold Hayes in my failed attempt to avoid this assignment. All year long there had been a nationwide overdose of publicity about Frank Sinatra as he approached his 50th birthday, and now he was overwhelmed by it, and I was also. On this very day Look magazine was on the newsstands with yet another cover story, and from it I learned nothing that I had not already read in other magazines or newspapers or had heard during television or radio interviews.

When the director Donohue came over and interrupted us, saying that filming was about to resume, Sinatra quickly got up to shake hands, say good-bye, and walk away. I would never speak to him again. I was disappointed by the suddenness of his departure but also resigned to the fact that my quest for his attention was finally over. I had done my best to reach out to him and now there was no reason to delay my return to New York.

Sinatra at the Sands, one table away from Count Basie, 1965.

In my typed notes I had enough material for the Esquire article, nearly all of it drawn from my observations along the sidelines, or from my interviews with those who associated with Sinatra in the film or record business, or who worked for his company or him personally, or who accompanied him socially during his off-hours—in other words: friends, relatives, retainers, hangers-on, and various other relatively obscure individuals who, as I have repeatedly said, have always been my main sources for information and insights.

With very few exceptions, none of these individuals would have been considered newsworthy by an obituary editor were it not for their connections to Sinatra, and yet collectively they helped me write about him without my relating to him personally. On reflection, however, this was not entirely true because, in another context, I had been relating to him personally since my boyhood, and this is what I wish I had mentioned to him before he said good-bye.

As an Italian American who grew up in South Jersey listening to him on the radio and reading about him in the press during the 1940s, I was inspired by his life, by the way he lived it, and by the way other people responded to it. He was admired by most of my female classmates in high school as well as the matrons who patronized my mother’s dress shop in my white-bread Protestant-dominated hometown of Ocean City, an island resort about 12 miles south of Atlantic City.

In the movies he romanced beautiful actresses in light comedies, co-starred in musicals along with Duke Ellington, Count Basie, and Tommy Dorsey’s band, and, in an era when most Italian names in the news referred to Mafia members, he avoided gangster roles and instead presented himself as a lawful leading man, a repudiator of racism and anti-Semitism, and always an engaging performer who was generous and patriotic: dancing in a sailor suit with Gene Kelly in Anchors Aweigh, presenting flowers to a swooning scullery maid in Higher and Higher, or preaching tolerance to a gang of bigoted boys in “The House I Live In.”

In this last film he spoke about being a descendant of Italian immigrants, tracing his origins, as I did, back to the underprivileged masses of alien opportunists who, after existing for a time near the bottom of the social pecking order in America, gradually improved their lives through their own initiative, the flexibility and growth of the New World’s economy, and no doubt a bit of luck.

Sinatra in 1965.

Among the immigrants who arrived on American shores a century or more ago were people with such names as DiMaggio, Cuomo, Scalia, Iacocca, Coppola, Giamatti, DeLillo, Stella, Scorsese, De Niro, Pelosi, and Germanotta (the latter being the ancestors of Lady Gaga)—but it is likely true that none of the progeny of these traveling Italians surpassed the worldwide fame and long-lasting popularity of the singing grandson of a shoemaker from Sicily named Francesco Sinatra.

Francesco Sinatra, born in 1857 in a sulfur-mining town about 30 miles southeast of Palermo where child labor was the norm, arrived alone in America in the late 1890s. After working in a pencil factory because there were then in New York too many shoemakers from Italy, he finally saved enough money to arrange for his wife and their four children to join him in 1903.

In an era when most Italian names in the news referred to Mafia members, he avoided gangster roles and instead presented himself as a lawful leading man.

Among them was his nine-year-old son and the future father of Frank Sinatra: Antonio Martino Sinatra, who as a teenager would work as a boilermaker on the dry docks of North Jersey and then take up prizefighting under the name “Marty O’Brien,” in deference to boxing’s many Irish fans and promoters as well as to the fact that in those days the foreign names and customs of Italians stigmatized such newcomers as Antonio and rendered them unmarketable on the billboards of even this low-caste and barbaric sport.

The prejudice against Italians in America would continue for decades, as I myself can attest from the insults—“dago,” “wop,” “guinea”—that I regularly received from some of the young Irish bullies who were classmates in parochial school. The wartime 1940s were a particularly troubling time for me. Not only was Italy then affiliated with Nazi Germany but two of my Italian-born father’s younger brothers, my uncles Nicola and Domenico, who had chosen not to immigrate to America, were now serving as infantrymen in Mussolini’s army opposing the Allied invasion of their ancestral area of Calabria, a mountainous region situated within the toe of Italy’s boot-shaped peninsula, separated by a narrow strait from the eastern tip of Sicily. My uncles’ military involvement would promptly prove to be a losing cause and result in their battlefield injuries and then their surrender and confinement to a British P.O.W. camp in North Africa.

On a chest of drawers in our living quarters, across from the radio where I would listen to Frank Sinatra singing on Saturday nights, were framed photos of my uncles taken earlier in the war, showing them smiling while wearing their uniforms adorned with unfamiliar epaulets; and late at night, following the news of their imprisonment, I would often overhear my father praying for their survival and well-being; and at Sunday Mass I would watch as he approached the altar to light votive candles with no doubt his captured brothers in mind.

But otherwise, while conversing with customers in his tailor shop, or having lunch across the street at the corner café, my father, Joseph Francesco Talese, was outspokenly pro-American; and once in a speech at the local Rotary Club he declared that were he younger he would proudly serve in the United States Army and participate in the destruction of his native country.

The author in 1985.

His remarks made the front page in our weekly Ocean City Sentinel-Ledger, accompanied by a photo of my smartly attired father; but though his sentiments were very well received they were not surprising because he had long been highly regarded within this flag-waving Republican community as a loyal and compatible token American, which was attributable at least in part to his tailoring talent in cutting and shaping any form to fit.

It also helped that he had been a citizen of the United States since 1928, and a resident of Ocean City since 1922, having traveled alone two years earlier at age 17 from his Calabrian village, after the premature death of his father, to help support his widowed mother and siblings while advancing his craft as an apprentice tailor under the temporary tutelage of an older debonair cousin in Paris, Antonio Cristiani, who had first arrived there in 1911 and now operated a successful men’s shop on the Rue de la Paix.

Seven months later, in the spring of 1921, my father continued his journey to America from the port of Cherbourg in northern France to Ellis Island in New York Harbor, settling first in Philadelphia—where he found work in a department store altering and measuring suits and trousers—and a year later obtained a bank loan to take over a small vacant tailor shop in Ocean City, about 60 miles southeast of Philadelphia, a popular summer resort for many of the prominent families of that city.

Many men from such families, plus the local gentry who set standards for the island’s year-round population of 3,000, became in time my father’s customers, being impressed with his workmanship and later as well with his slender and attractive fashion-conscious partner, my mother, who had previously sold dresses in Brooklyn’s leading department store, Abraham & Straus. After meeting my father at an Italian wedding in that borough, and marrying him months later in the early summer of 1929, she and my father bought a larger building on the main street of Ocean City and expanded the tailoring enterprise to include a boutique catering to the island’s leading ladies.

Like practitioners of journalism, who regularly associate with influential and noteworthy individuals, merchants of fashion who devote themselves to selling fine suits and dresses to the prominent are engaged in careers offering social-climbing possibilities. Certainly in my parents’ case this applied, as evidenced by their success in first befriending their decorous clientele and eventually being invited by them to bridge parties and membership at the country club across the bay, where, removed from the dry law that reigned in Ocean City, liquor was available.

But whatever elevated status had been bestowed upon my parents by their patrons, it brought me no relief from the sons of the working-class Irish who berated me almost daily and sometimes tossed dirt at my custom-made clothing in the schoolyard during recess.

Throughout my pre-teen years I sensed myself as fractionized, native-born but feeling foreign, a juvenile minority member in a land where Italian names were associated with Fascists abroad and gangsters at home, and not even the pre-war presence of the fan favorite Joe DiMaggio was much help. DiMaggio was a solitary man, an introverted self-centered superstar who communicated through his bat and did not socialize even with his Yankee teammates.

However, much had changed by the time I entered high school in 1945: The war over, the Allied armies were triumphant, Mussolini was dead, my P.O.W. uncles were released, and the fabulously famous young Frank Sinatra, thanks to his talent and his outward-reaching public persona that touched both minority groups and the mainstream, had emerged as the first fully assimilated United States citizen of Italian origin—one who also paved the way for people like me to finally feel at home in America.

I mentioned this to Nancy Sinatra during my final conversation with her in Los Angeles. She said she understood my wanting to send a farewell note to her father, and after she promised to relay it to him, I wrote:

Saturday, December 4, 1965

Dear Mr. Sinatra:

This afternoon I called to say goodbye to your lovely and gentle daughter Nancy, and in the course of our talk I expressed disappointment at not having gotten close to you in the month I spent here. If I had been allowed to share your informal company, I told Nancy, if I had been permitted to travel with you and your friends and to gain glimpses into the warmth of your inner world, there is no doubt that I would have produced a classic profile on you, one that would have fulfilled all the unfulfilled promises of the television documentaries and magazine articles of the past.

Like yourself, I want all the advantages when I work. Regrettably I had few of them this past month—there was your illness, your incredibly busy schedule, and other things that kept me a distant observer. Even so, I hope to do justice to you in this Esquire profile, to present an exciting portrait of Sinatra the Man and the effect you have on your friends, your enemies, your era.

I came as a friend. I leave as one. I took you very seriously as a living force before I met you, and now I take you even more seriously. May the very best continue to happen—I wish you the luck to match your matchless talent.

—Gay Talese

Slices of Shirtboard

I never received a reply to my Sinatra letter, nor did I ever learn from him, or Nancy, or anyone else who might know, what he later thought of my Esquire article, if indeed he even read it.

Published in the April 1966 issue and titled “Frank Sinatra Has a Cold,” it began with when I first saw him in Los Angeles: him sitting between two blondes on a lonely night at the bar of the Daisy, smoking a cigarette, sipping bourbon, and on the verge of taunting Harlan Ellison in the poolroom. It ended more tranquilly with a description of Sinatra sitting pleasantly behind the steering wheel of his Ghia coupe, driving alone on a sunny day in Beverly Hills as the traffic light is about to change:

“Frank Sinatra stopped his car. The light was red. Pedestrians passed quickly across his windshield but, as usual, one did not. It was a girl in her twenties. She remained at the curb staring at him. Through the corner of his left eye he could see her, and he knew, because it happens almost every day, that she was thinking, It looks like him, but is it?

“Just before the light turned green, Sinatra turned toward her, looked directly into her eyes waiting for the reaction he knew would come. It came and he smiled. She smiled and he was gone.”

This street scene was related to me not only by some of the involved young women “pedestrians” whom I met during my research, but Sinatra himself corroborated it in conversations he had with such intimates as his daughter Nancy. The rest of my 14,000-word article, which covered 53 manuscript pages, was drawn from my observing Sinatra on the movie set, in the recording studio, during his trip to Las Vegas, and from my personal comments and complaints that I scribbled daily with a ballpoint pen on the slices of shirtboard that fit into my jacket pocket and accompanied me everywhere.

I later reviewed these working notes, eliminated what I no longer considered relevant, and, in an attempt to bring some aesthetic flair to this boring process, I used multicolored Sharpie fine-point pens to reprint the rest of my selected material across two uncut 14-by-8-inch pieces of cardboard, producing a rather flamboyant graphic chart that served as my outline—one that presented, in summary form and with directional arrows, a scene-by-scene word picture of the entire piece along with references to some of the frustrations I experienced while researching and writing it.

The Edward Sorel–illustrated April 1966 cover of Esquire.

One day shortly after I had finished the article but two months before it appeared in print, I was in Esquire’s office cooperating with the fact-checkers when someone from the promotion department, apparently charmed by the outline that I had brought along, insisted that it be photographed and later printed in the front section of the April issue, near the index and editor’s page, as a gimmick calling attention to my Sinatra article that followed.

Unfortunately, the person from promotion and the fact-checkers failed to carefully read all of my tiny handwritten words that appeared in various places within the graphic chart—words in which I complained about the Sinatra assignment or referred very disrespectfully to the magazine’s editor:

“I did not want to fly out here. But the magazine “Esquire” had for years wanted a cover story on Sinatra—and I was unable to talk Harold Hayes out of it. I did not fully trust him … and if I failed, he would not be interested in my foolish excuse about F.S.’s cold—Fuck Hayes … ”

Excerpted from Gay Talese’s new book, Bartleby and Me: Reflections of an Old Scrivener, to be published on September 19 by Mariner