The Esquire Decade
During a decade of war, assassination, and racial fear, Esquire editor Harold T. P. Hayes and his talented staff brought a revolutionary barrage of literary and visual firepower to America’s newsstands. Gay Talese, Tom Wolfe, and other stars of the
By Frank DiGiacomo. Vanity Fair, January 2007

Along with the heat, the summer of 1963 brought a palpable tension to the so-called United States. The May images of black demonstrators terrorized by fire hoses and police dogs in Birmingham still resonated on June 11, when President John F. Kennedy sent the National Guard to Tuscaloosa to thwart segregationist governor George Wallace’s attempt to block two black students from enrolling at the University of Alabama. That night, Kennedy appeared on national television to announce that he would introduce a civil-rights bill in Congress the following week, but the hope that his speech promised was undercut the very next day by the murder of N.A.A.C.P. field secretary Medgar Evers in the driveway of his Jackson, Mississippi, home.

By late June, race was Topic A in America. But up on the fourth floor of 488 Madison Avenue, in a corner office with a wraparound view of the Midtown Manhattan skyline, Harold Thomas Pace Hayes, the managing editor of Esquire magazine, was preoccupied with Christmas. At a time when typewriters, carbon paper, color transparencies, and hot type still constituted the primary tools of the publishing business, a single issue of a full-color monthly magazine took a minimum of three to four months to produce—“lead time” in industry parlance. This meant that, in order to get the December 1963 issue of Esquire onto the newsstands and into the hands of subscribers ahead of the post-Thanksgiving shopping rush, Hayes and his staff of editors and art directors needed to close the issue in the middle of August. There was one other factor to consider as well. The December Esquire was the parent company’s cash cow, carrying twice as many ads as a typical issue, and Hayes had been at the magazine long enough to know that the men who controlled the purse strings expected him to invoke the comforting spirit of Christmas on that year-end cover—the better to put the magazine’s readers in a receptive mood for the onslaught of liquor, fashion, and cologne pitches that awaited them inside.

So, with his ginger suede wing tips up on the desk and an inscrutable smile on his face, Hayes picked up the phone and placed a call to the man who did Esquire’s covers, a Runyonesque character named George Lois who swore like a longshoreman but exuded the confidence of a shipping magnate. Lois did not work at Esquire, or even in publishing. He ran one of the most sought-after advertising agencies in the business—Papert, Koenig, Lois, which he’d formed in 1960 after blazing trails as an art director at Doyle Dane Bernbach. But, back in 1962, after a lunch with Hayes at the Four Seasons Restaurant, Lois had taken on the job of designing Esquire’s covers in between servicing such agency clients as Xerox and Dutch Masters cigars.

To a magazine industry that, like the rest of the culture, was still throwing off the dull, mannered strictures of the 50s, Hayes’s arrangement with Lois was shocking. Admen sold soap, not magazines. But provocation, on many levels, was exactly what Hayes sought. Since taking the reins of Esquire two years earlier, he had pushed to make every column inch of the magazine sing with a brash authority that made news and upset the powers that be. In Lois, he had struck gold. Here was someone who could articulate that irreverence—in visual terms—on the most important page of the magazine. Once a month, Hayes provided Lois with the editorial lineup and his thoughts about what that issue’s cover story might be. And then Hayes did what he did with his writers: he stepped back and let Lois do his thing.

Given that December was the biggest issue of the year, however, Hayes exerted a little extra finesse once he got Lois on the phone. “George? Hey, buddy, I could really use a Christmasy cover for December,” he told Lois in his elegant North Carolinian accent. The ad-sales guys were putting his feet to the fire.

“You got it,” replied Lois, who, after some brainstorming, got on the phone with photographer Carl Fischer. According to the soft-spoken Fischer, the conversation began as it usually did when Lois called with one of his Esquire cover concepts: “I got a wild idea! Listen to this crazy idea!” the adman told the photographer in his staccato Bronx growl.

The idea required that Fischer and an assistant grab a plane to Las Vegas, where they turned a room at the Thunderbird Hotel into a makeshift studio. When the knock at the door finally came, world heavyweight boxing champion Sonny Liston stood in the doorway with a little girl, who Fischer guesses was eight, and another boxer, former heavyweight champ Joe Louis, the Brown Bomber.

Louis had been enlisted by George Lois to get Liston to the shoot and facilitate his cooperation, which began to evaporate around the time Fischer presented the hulking fighter with a Santa hat and suit to wear before the camera.

In 1963, Sonny Liston wasn’t just the heavyweight champ; he was, as Lois says, “the baddest motherfucker” ever kissed by fame. Frightening in and out of the ring, Liston—who had beaten the gallant Floyd Patterson in the fall of 1962—was an ex-con who had done time for armed robbery and assaulting a police officer. His ties to organized crime weren’t alleged; they were fact. The N.A.A.C.P. perceived his dark past to be a liability to the civil-rights movement.

Christmas would never be the same.

Liston didn’t exactly channel the spirit of Saint Nick when he learned what was expected of him. “[He] was very cranky,” Fischer says. “He was not going to put on any fucking hat”—let alone a velvety red tunic trimmed in white. But by the end of the shoot, using Louis and the little girl as a persuasive Greek chorus, Fischer had the image Lois wanted—and it landed like a stick of dynamite in Harold Hayes’s lap. Beneath the droopy Santa hat, Liston’s dead eyes stared sullenly at the reader. His festive apparel seemed only to accentuate his hostility. Writing about the incident years later, the editor recalled showing the cover to the executives who worked in Esquire’s business department. The magazine’s advertising director suggested that Esquire refrain from putting a black Santa on its cover until Saks Fifth Avenue put one in its stores. The magazine’s circulation director was stunned.

“Jesus Christ, Hayes,” he said. “You call that Christmasy? What the hell are you trying to do to us?”

“It is Christmasy,” Hayes told the executive. “Look at the Santa Claus hat.”

Ultimately, nobody at Esquire tried to stop Hayes from running the cover. After all, under his leadership, the magazine was clearly thriving and would hit an all-time high circulation of just under 900,000 that fall. More important, Hayes didn’t second-guess himself. “He had the exact thing that all of the great editors and producers and studio heads and politicians have, which is that he absolutely trusted his gut,” says Nora Ephron, who worked with Hayes when she was a columnist and feature writer for Esquire in the early 70s. “He knew what he wanted. He acted on it.”

Hayes lit the fuse, and Sonny Liston exploded a ragged hole in the country’s Norman Rockwell preconceptions of Christmas. Save for the magazine’s logo and dateline, the cover ran without any type, or even a caption identifying the fighter. None was necessary. Years later, Sports Illustrated recalled that Liston looked like “the last man on earth America wanted to see coming down its chimney.” An art-history professor at Hunter College proclaimed the cover “one of the greatest social statements of the plastic arts since Picasso’s Guernica.” The angry letters began to roll in, and stunned advertisers proceeded to pull out. Esquire’s advertising director would eventually estimate that the magazine lost $750,000 due to the cover.

For Hayes, the gains outweighed the losses. Liston-as-Santa was “the perfect magazine cover,” he wrote, looking back in a 1981 article in Adweek magazine, “a single, textless image that measured our lives and the time we lived them in quite precisely to the moment.” Published in a national climate “thick with racial fear,” he explained, “Lois’ angry icon insisted on several things: the split in our culture was showing; the notion of racial equality was a bad joke; the felicitations of this season—goodwill to all men, etc.—carried irony more than sentiment.”

With the December 1963 issue, Esquire’s metamorphosis was complete. Not only was it the first issue to carry Hayes’s new title, editor—he had been running the magazine since mid-1961 under the lesser honorific of managing editor—but it was also the first to display the full range of literary and visual firepower that would make Esquire the great American magazine of the 1960s, if not the great American magazine of the 20th century.

Certainly, Esquire did not begin in the 60s. By the time John Kennedy was exploring his New Frontier, the monthly was more than 25 years old and had published Ernest Hemingway’s “The Snows of Kilimanjaro” and F. Scott Fitzgerald’s “The Crack-Up” series, along with a formidable list of writers who need be identified by only their last names: Dos Passos, Salinger, Camus, Huxley, Steinbeck, Waugh, Mencken, and Pirandello, to name just a few. Still, by the 1950s, the magazine had grown as dull as the Eisenhower administration. Enter Hayes, who, after a brutal four-and-a-half-year contest for control of the magazine, emerged—hardened and battle-ready—to lead Esquire into a new era. And what an era it was.

The Magazine of the New

Hayes’s Esquire would identify, analyze, and define the new decade’s violent energies, ideas, morals, and conflicts—though always with an ironic and, occasionally, sardonic detachment that kept the magazine cool as the 60s grew increasingly hot. Esquire would become the magazine of the New: “The New Art of Success,” “The New Seven Deadly Sins,” “The New Sophistication,” and, ultimately, the New Journalism, the fancy term given to nonfiction that’s written like a novel.

Even a very short list of Esquire contributors in the 1960s reads like a roll call for the profession’s pantheon. James Baldwin dissected Norman Mailer in “The Black Boy Looks at the White Boy.” William Styron analyzed “My Generation.” Philip Roth visited “Iowa: A Very Far Country Indeed.” And Mailer twitted them all in “Some Children of the Goddess.” Bruce Jay Friedman asked model Jean Shrimpton if she had any fantasies and watched her rummage through her purse in “The Imposing Proportions of Jean Shrimpton.” Rex Reed braved the force of nature known as Ava Gardner in “Ava: Life in the Afternoon.” Susan Sontag took a “Trip to Hanoi.” Saul Bellow contributed “Literary Notes on Khrushchev.” Edmund Wilson published “The Rats of Rutland Grange.” Terry Southern juggled racism, majorettes, and moonshine in “Twirling at Ole Miss.” Dorothy Parker captured “New York at Six-Thirty P.M.” William F. Buckley Jr. explored the politics of Capote’s 1966 Black and White Ball. Kenneth Tynan explained why “Dirty Books Can Stay.” Anthony Lukas chronicled “The Life and Death of a Hippie.” Dan Wakefield and Thomas B. Morgan profiled, respectively, Robert F. Kennedy and his younger brother, Ted, for a package called “Bobby & Teddy.” Brock Brower examined “Mary McCarthyism.”

Measured against the streamlined, A.D.D.-friendly magazine writing of today, not all of Esquire’s 60s canon has aged well. Some of the prose is excessively woolly, some exceedingly self-important, and in a publication where articles in excess of 10,000 words were not uncommon, some stories come off as just plain interminable. There is also the sense that, toward the end of the decade, the magazine struggled with its own success—particularly when it came to finding new ideas and writers to top its previous achievements. For example, as smart as it may have sounded for the magazine to include author and political activist Jean Genet and macabre Beat author William Burroughs on the Esquire team that covered the 1968 Democratic convention in Chicago, their contributions, today, seem more wacky than worthy. Genet’s piece was titled “The Members of the Assembly” because he spent several sentences focusing on the crotches of Chicago’s police force.

But what’s really remarkable about Esquire’s coverage of the 60s is how much does still hold up. Get past the gooey wave of nostalgia that reading old magazines inevitably delivers and the writing, photography, and art still crackle with telling details, unexpected insights, and laugh-out-loud humor.

As Nora Ephron says, Esquire and the 60s were “the perfect moment of a magazine and a period coming together—not trying to say the period was something other than what it was, but telling us everything about it.” And though the decade climaxed in violence and hysteria that no monthly magazine could stay ahead of, Harold Hayes and his troops at Esquire not only cracked the code of the new culture but also engineered the genome for the modern magazine. Traces of its DNA can still be found in today’s magazines, including this one.

Harold Hayes died in 1989. Like the chapters of his unfinished book, Making a Modern Magazine, the clues he left behind about his life and his work at Esquire are frustratingly incomplete and, like the man himself, hard to fathom. They—the chapters and the clues—are filed, along with a career’s worth of correspondence, notes, and clippings, in the rare-manuscripts department of the Z. Smith Reynolds Library, at Hayes’s alma mater, Wake Forest University. (This trove of information is also featured at length in Carol Polsgrove’s 1995 book, It Wasn’t Pretty, Folks, but Didn’t We Have Fun: Esquire in the Sixties.) The files show that Hayes was born April 18, 1926, in Elkin, North Carolina, but spent roughly half his childhood in coal country, Beckley, West Virginia, before moving, at 11, to the considerably more cosmopolitan environs of Winston-Salem, North Carolina. The middle child of three, Hayes was the product of a nurturing, culture-loving mother—who, Hayes once said, wished her children “would be middle class gentility”—and a strict fundamentalist Baptist-minister father who insisted his offspring attend prayer meetings and revivals, and wouldn’t let Esquire magazine into the house during Harold’s childhood. This dogmatic upbringing left Hayes with what he called a lasting “moral hangover” that he resented by the time of his adolescence. He was somewhere between a hick and a naïf when he landed at Wake Forest—and as square as the trombone he had played in his high-school band.

He did not exactly catch fire at college. Hayes characterized himself as a “happy-go-lucky” C student whose education was interrupted by a stint in the navy reserve. He worked on student publications and after graduating, in 1948, headed for Atlanta, eventually landing at United Press, where he covered the Georgia legislature and re-wrote wire copy. When the Korean War flared in the summer of 1950, Hayes enlisted in the Marines, where he rose to the rank of first lieutenant but never saw action. Once his hitch was up, a mutual friend helped arrange his first audience with Arnold Gingrich, the founding editor of Esquire, who, after years away from the magazine, had just returned as its publisher. Gingrich, an impeccably dressed Renaissance man who collected rare violins and played them badly, didn’t have a position for Hayes and sent him on to a publisher developing a new magazine called Picture Week. Hayes was put in charge and nervously ran the show until, about two years into the job, he produced an end-of-the-year feature that foreshadowed the perverse point of view that would come to distinguish Esquire from its competition. While most editors used their year-end issues to recap the highlights of the last 12 months, Hayes had astutely sensed that there was much more entertainment value in looking at the low points and put together a piece that in an interview years later he called “The Hundred Bombs of the Year.” The publisher took one look at the layout and fired the entire editorial staff.

Hayes was soon back on Esquire’s doorstep, and this time Gingrich took him on as his assistant—hardly an illustrious title, but Esquire’s publisher had plans for this new hire. Between 1933 and the end of that decade, Gingrich and a group of Chicago-based businessmen, led by a cunning hypochondriac named David Smart and his partner William Weintraub, had turned Esquire into one of the great magazine success stories of the early 20th century. (They also created Gentlemen’s Quarterly, now owned by Condé Nast.) Their Esquire was an innovative mix of high and low culture—akin to “having Thomas Mann or Ernest Hemingway read their work aloud at a burlesque house,” according to one critic of the time—delivered in a big, 13-inch-by-10-inch format and presided over by “Esky,” a pop-eyed dandy with a walrus mustache who appeared on every cover and bore more than a passing resemblance to Gingrich.

But Esquire’s original luster had long since faded by the early 50s, when the magazine moved from Chicago to New York to take advantage of the resurgent city’s new status as both the center of the advertising universe and the clearinghouse of American culture. The appearances in 1953 of Playboy—founded by former low-level Esquire employee Hugh Hefner—and, the following year, Sports Illustrated only worsened matters. Management eventually realized that the magazine’s future would have to be determined by someone younger and more in tune with the times. And so, in 1957, Gingrich began ushering Hayes and a handful of young, ambitious editors he called the “young Turks” into his cramped office, where he refereed one of the most vicious weekly story meetings in modern journalism. “I’m turning the magazine over to you,” Gingrich told the Turks at one of those first meetings, which really meant that he would preside over them as they battled one another to place their respective story ideas in Esquire. Though it wasn’t exactly stated that the last man standing would ascend to the top of the masthead, the combatants couldn’t help but notice that the corner office that had belonged to the magazine’s last editor—swept out in a purge of the previous regime—was being kept vacant. With this “beautiful red apple suspended way up at the top of the tree,” Hayes wrote, the editorial meetings quickly turned brutal, loud, and even personal. “They were very bloody,” said Ralph Ginzburg, another young Turk, who went on to start Eros magazine and push against the boundaries of the First Amendment. (Ginzburg, who spoke to Vanity Fair last spring, died in July.) “There was no predicting how nefarious, dirty, or low they would get.”

“The Big Change”

The contest ultimately boiled down to Hayes and a well-connected former Life-magazine editor named Clay Felker, a St. Louis native and Duke University graduate whose father was managing editor of The Sporting News and whose mother was also an editor. Felker stirred Hayes’s competitive instincts, but he intimidated him, too. In addition to possessing the more authentic-sounding title of features editor, Felker was known around the office as the “drinking editor,” because he attended so many parties. He was also a remarkably fertile source of good ideas. “He had the keenest distant-early-warning system of any editor I ever knew,” said Ginzburg. “He could spot something that was going to be a major trend six months before it happened.”

Felker could be forceful and engaging when pitching his own ideas and politically lethal when torpedoing somebody else’s. Hayes learned this early in the competition when, after he sold the idea of profiling the Communist Daily Worker newspaper, Felker embarked on a no-holds-barred (but ultimately unsuccessful) campaign to kill the story, and his tactics included a well-aimed swipe at Hayes’s feelings of intellectual inadequacy. “The trouble with you is, you just don’t know,” Felker told his rival. Years later, Hayes would admit, in a 1988 interview with University of Kansas student Joseph Rebello, that the remark was “the most damning and insulting thing anybody had said to me in a working relationship,” and it played a key role in his decision to apply for a Nieman Fellowship at Harvard. He was accepted, and, in 1958, left for Cambridge with Gingrich’s blessing. This time, the C student did A work and returned the following year a much more confident and connected man. (According to Felker, however, Hayes “still seemed threatened by me.”)

Hayes sometimes referred to the battle of the young Turks as “the Big Change,” and by the end of 1960 one of the last remaining vestiges of the old Esquire was the caricature of Esky that dotted the i in the magazine’s logo. A new Esquire had evolved, and it was a hybrid of Hayes’s and Felker’s respective editorial visions. Hayes wanted Esquire to be a magazine of ideas—politics, science, law, religion, sophistication. Felker saw power—and the powerful—as his unifying theme. Save for the fact that neither man wanted to share the reins, their worldviews weren’t incompatible. They were both outsider perspectives built on smart writing, strong reporting, provocative visuals, and bringing a new sensibility to old subjects. Gingrich’s mad plan had worked. Through all the infighting and backstabbing, Esquire had become a stronger magazine with an impressive roster of stars and newcomers. Felker had hired Gore Vidal as a political columnist and David Levine as an illustrator. He had also enticed Norman Mailer to cover the 1960 Democratic convention, from which the author of The Naked and the Dead produced an evocative and groundbreaking piece of literary nonfiction, “Superman Comes to the Supermarket,” which has since been heralded as one of the earliest examples of the New Journalism.

Hayes brought in William F. Buckley Jr. to write for the magazine. He was also instrumental in the production of Art Kane’s historic 1958 photo of jazz greats gathered on a Harlem stoop, and the first magazine editor to employ Diane Arbus. In the July 1960 issue, as part of a special package devoted to New York, Arbus made her first Esquire appearance, with a photo-essay of the city’s eccentrics called “The Vertical Journey,” as did another future Hayes favorite, New York Times reporter Gay Talese, whose pointillist portrait of the city, told through little-known facts and observations, was the backbone of the issue.

Had not fate—in the form of The Saturday Evening Post—intervened, Gingrich probably would have let Felker and Hayes battle it out until one quit or killed the other. (Those who worked with Esquire’s publisher often described his management style as “laissez-faire.”) But after Hayes received a series of increasingly enticing offers to join the Post as an editor, Gingrich finally appointed him managing editor in the summer of 1961, the promotion reflected on the masthead in Esquire’s September issue. Hayes moved into the coveted corner office. Felker began to look for a new job. “I was naïve,” Felker says curtly, more than 40 years after the decision. “Hayes cultivated Gingrich. I thought that all I had to do was keep coming up with good ideas.” Instead, in the fall of 1962, Felker moved on, and in 1963 resurfaced as a consultant at the New York Herald Tribune, where he eventually took over the newspaper’s Sunday magazine, which had been revamped and renamed, simply, New York. There, he would soon demonstrate that his rise at Esquire had been no fluke.

Hayes did not wait for Felker to leave before he consolidated his power and got down to the business of expanding his staff. In late 1961, he hired a preppish Harvard graduate named John Berendt as an associate editor. Around this time, fiction editor Rust Hills hired an assistant named Robert Brown, who came with a master’s in English literature from Yale (and would eventually succeed his boss). The following year, Hayes promoted Alice Glaser, a neurotic but brilliant Radcliffe-educated secretary, to the same station, and after Felker left, Hayes replaced him with former Time-Life Books editor Byron Dobell as his assistant managing editor. In 1963, Hayes hired a self-described North Carolina “hillbilly” named Robert Sherrill as an associate editor. Hayes and Sherrill had met at Wake Forest and become even closer friends when they both moved to Atlanta and lived in the same apartment complex. But when Sherrill arrived at Esquire, he found that his former schoolmate had changed.

“It was sort of dramatic, because the last time I saw him, he’s one character, and the next time he’s another one,” Sherrill says, explaining that at Wake Forest Hayes was still “naïve, sweet, curious. He went wild over Tender Is the Night. He was almost a cheerleader.” Nearly 20 years later, Hayes was “the same person, but he’s tough,” Sherrill says. “You’ll have a hard time moving him.”

The triple-witching effect of the Marines, Gingrich’s boot camp, and Harvard had both hardened and emboldened Hayes, and the city had buffed him to a fine luster. An unconventionally handsome man with a full head of fair brown hair and bushy eyebrows that could look as untamed as the Manhattan skyline, he moved through Esquire’s offices at a forward tilt, the metal taps on his shoes heralding his arrival, his mood, and his utter confidence in the task at hand. “There was a specific Harold clickety-click,” says Kitty Krupat, who in the late 60s served as the magazine’s chief editorial researcher.

Hayes edited Esquire as if he were its most fervent reader. And he was. “He had an innate sense of the way a magazine should be—his magazine,” Sherrill says. “He loved structure and he loved the way people wrote. He could read something and almost immediately say ‘Good’ or ‘Bad’ and throw it over his shoulder.”

And as he tweaked Esquire to reflect his vision, Hayes also indoctrinated the staff. “We never wondered what he wanted. We absolutely knew,” says John Berendt. Though Hayes’s Esquire retained many of the hallmarks established during the young Turks’ turf war, its irreverent tone and sense of humor—“from black wit to custard-pie burlesque,” as the editor once put it—evolved, particularly with the debut of a franchise feature called the Dubious Achievement Awards that Hayes had asked his art director, Robert Benton, and an associate editor named David Newman to pull together for the January 1962 issue. Though inspired by a Harvard Lampoon staple that recognized the worst acting and movies of the year, Dubious Achievements was really just another run at the “Hundred Bombs of the Year” piece that had gotten Hayes fired from Picture Week. A wry look at the Bay of Pigs fiasco and other low points of Kennedy’s first year in office, Dubious Achievements was built around a recurring photo of the usually glowering Richard Nixon laughing maniacally. The caption beneath the photo read: “Why is this man laughing?” Benton says the juxtaposition of image and text was simply a reference to the turmoil of Kennedy’s first year. “[Nixon] was laughing because he wasn’t president,” he says. And yet, the joke still seemed to be on the former vice president.

By using Nixon—an embodiment of the Eisenhower era—as the highbrow equivalent of Mad magazine’s Alfred E. Neuman, Esquire had declared itself a brash corrective to the square sobriety of the 50s, and Hayes had taken a significant step forward in defining his magazine.

Ultimately, he wanted every column inch of Esquire’s editorial content to reflect that tone. So, on Fridays, Hayes broke out the liquor and presided over a casual brainstorming session disguised as a cocktail party that would be attended by the staff and any contributors who happened to be in the building. When Berendt had started, Hayes used a copy of the day’s New York Times to show him and Glaser how to convert daily news and feature stories into Esquire ideas by, Berendt says, “giving articles a special slant, by getting a principal in the story to write the piece, or by assigning a well-chosen writer with a specialty that fit the story.” Not long after that, the editors were having Friday drinks in Hayes’s office when, Berendt says, “Harold brought up the Times thing again and said, ‘It’s child’s play. Anyone can do it.’ ” This prompted one of the staffers to devise a challenge: pages of the Times were affixed to corkboard that covered part of the wall in Hayes’s office, and darts were flung at them. The goal was to come up with an Esquire-worthy story wherever the dart landed. “It became very competitive,” Berendt says. “People shouted out ideas and were very clever and hilarious about it, but Harold was absolutely ingenious.”

“Point of view,” “tone,” “perspective,” and “irreverence” were terms that got thrown around a lot on the fourth floor of 488 Madison. “Great P.O.V.,” Hayes might scrawl on an idea memo when he came across something he liked. Or, after hearing a story idea, he might raise his hand in front of his face and rotate it, which meant that the editor needed to do the same with his idea. These qualities distinguished Esquire from the jaunty suburban earnestness of The New Yorker, or its duller competitors Harper’s and The Atlantic. They also gave the magazine an urgency and a timeliness that monthlies didn’t ordinarily have.

And with the July 1963 issue, Esquire made news with a feature called “The Structure of the American Literary Establishment,” which was pure point of view. The focus of the feature was a two-page spread that looked like a cross between a chart and a lava lamp. Onto these pages, fiction editor Rust Hills had grouped dozens of writers, agents, playwrights, and critics into such categories as “Writers Who Get in Columns” and “The Cool World.” The pinnacle was “The Hot Center,” which spanned the centerfold of the magazine under a splash of red-orange ink. The chart was satirical and keenly observed—for one thing, a writer’s heat seemed to have more to do with his agent than his writing—and it threw the thin-skinned literary world into a tizzy, particularly The New York Times Book Review, which had been relegated to “Squaresville” (and which then published a squarely earnest rebuttal that seemed to miss the humor of the piece). In addition to being the first of many Establishment charts to come—covering various industries and hierarchies—the feature “was an important turning point for Esquire,” Berendt says. “It was Esquire taking charge and calling the shots.”

Bracing as the Sonny Liston cover was in a country that had gone to the barricades over racism, it was swiftly eclipsed by the shock and grief produced by another national tragedy. On November 22, 1963, about a week after the December issue of Esquire reached newsstands, President Kennedy was assassinated in Dallas. For the first time since Hayes had taken over the magazine, Esquire’s three-month lead time looked like it might become a liability. The January issue was at the printers, which meant that photos and text made inaccurate or tasteless by the assassination had to be literally blacked out of copies that hadn’t already shipped. It was too late, however, to remove Kennedy’s picture from the Dubious Achievement–themed montage cover. Worst of all, the magazine would not be able to weigh in on Kennedy’s death until 1964. Its coverage would have to be original.

But as Hayes watched news reports of Kennedy’s death and its aftermath, he sussed out the direction he needed to take. He had noticed that the excessively moist media coverage of Kennedy’s life had all but deified the man. So, in the waning days of 1963, he wrote to New York Times correspondent Tom Wicker and asked him to write about “Kennedy without tears.” In a letter dated December 22, 1963, Wicker responded, “Some of those myths are going to take a hell of a lot of unsentimentalizing,” but he agreed to the assignment and produced a memorably clear-eyed assessment of Kennedy’s political life for the June 1964 issue.

“Kennedy Without Tears” served as both headline and cover line for the story, and George Lois provided a sly riff on that thesis. A full-page, sepia-toned photograph of Kennedy stared straight out at the reader while, from the bottom of the page, a man’s hand holding a white handkerchief—both depicted in full color—dabbed at a spot beneath the president’s left eye. Above the handkerchief, spilled tears beaded up on the photograph. Was the man attached to the hand weeping? Or was the slain president crying for his lost legacy? Soon after the issue went on sale, the New York Herald Tribune, a newspaper known for its own brand of insouciance, threw a third question into the mix: “Has Esquire magazine leaped off the bridge of good taste?”

Actually, it had moved so far ahead of the curve that the laggards could not see it, and in the July 1964 issue Hayes published what proved to be a profoundly prescient feature by Benton and Newman. “The New Sentimentality” proposed that a new sensibility had quietly but firmly taken hold in America—an ironic, unsentimental, self-interested sensibility that had roots both in the Kennedy administration and in the French New Wave films of Godard and Truffaut. Eisenhower was “the last bloom of Old Sentimentality.” Lyndon Johnson, Jackson Pollock, Frank Sinatra’s Rat Pack, and the children’s-book character Stuart Little were other symbols of the Old Sentimentality. English model Jean Shrimpton, artist Roy Lichtenstein, the Beatles, Sonny Liston, and Charlie Brown signified the New. Marilyn Monroe and Humphrey Bogart were among the few who were relevant in both categories.

Benton and Newman did not reference Esquire in the piece, but like Monroe and Bogart, the magazine moved in both worlds without really embracing either. Esquire dwelled in the conflict between the new world that was rushing in and the old ways that were shuffling out. “With Harold, I think, it was just one big carnival,” says Tom Wolfe. “I don’t think he ever cared for a second who won an election, any of that stuff. I think it all seemed amusing. It all offered such great journalism. And I think that’s really the only form of objectivity in journalism: that you are either having so much fun with the material, or you feel what you’re doing is so important that you don’t care about any political gains.”

On paper, Norman Mailer sounded like Esquire’s literary soul mate: the Great American Novelist who had switched to great American nonfiction in the 60s, a man who challenged political correctness with every angry breath, as well as a writer who could give perspective to a paper clip. But his relationship with the magazine was star-crossed at virtually every turn. In 1960, after writing “Superman Comes to the Supermarket,” he had a public falling-out with the magazine, in part because Gingrich had altered Mailer’s headline to “Supermart.” After Esquire apologized to the writer within its own pages in 1962, Mailer returned to write a regular column, “The Big Bite,” and, beginning in January 1964, a serialized novel, An American Dream. Esquire ran the book over eight issues, with Mailer writing on deadline, and the two parties drove each other nuts. Mailer’s attempts to bull through the limits of sexual and scatological language in a commercial magazine brought out the Marine in Hayes and the prude in Gingrich, who had not forgotten Esquire’s bruising—though eventually successful—landmark Supreme Court battle in the 1940s; the nation’s staunchly Catholic postmaster general, Frank Walker, had attempted to revoke the magazine’s precious second-class mailing permit because, he claimed, Esquire was publishing obscene material. Exhausting bargaining sessions involving Hayes, Mailer, and the magazine’s lawyers ensued, and Sherrill recalls the day that managing editor Byron Dobell appeared at his cubicle with a smile on his face and jerked his head toward Hayes’s office. Sherrill got up from his desk and quietly joined the other editorial staffers eavesdropping outside Hayes’s office as their leader haggled by phone with Mailer over expletives contained in his latest installment. When Hayes saw his staff lurking, Sherrill says, he smiled and rolled his eyes before presenting his latest offer to the novelist on the other end of the line. “Norman,” Hayes said, “I’ll trade you two ‘shits’ for a ‘fuck.’ ”

The breaking point came that same year when Mailer wrote about the Republican convention in San Francisco. Again, he wrangled with Esquire’s lawyers. Mailer wanted to call the piece “Cannibals and Christians,” but the lawyers worried that the Republicans might claim malice. Mailer settled for “In the Red Light,” but split again with the magazine. In later years, he seemed to carry a grudge. Hayes’s son, Tom Hayes, remembers Mailer once refusing to get on an elevator with his father, and when associate editor Tom Hedley tried to get the writer to profile Fidel Castro, Hedley says, Mailer told him, “It probably could be one of the best pieces I’ve ever written, [but] I’ll never do it for Harold Hayes. You know why? Because he’ll put my asshole over Castro’s eyebrow on the cover.” (Mailer declined to be interviewed for this piece.)

If Esquire was a magazine where novelists could apply their literary talents to nonfiction, it was also a place where a handful of journalists wrote articles that read like short stories. The writer most identified with that legacy is Gay Talese, a man whose Calabrian profile is as sharp as his tailored clothing. Having made his bones in journalism at the stylistically restrictive Times, Talese found the freedom that Esquire gave its writers “narcotic,” he says, and he particularly excelled at profiling achievers who had fallen a little—or a lot—from the pinnacle. Thus, in November 1965, at Hayes’s behest, Talese embarked on the long, harrowing trip that would lead him to produce the greatest literary-nonfiction story of the 20th century. Talese flew to Los Angeles and checked into the Beverly Wilshire Hotel to prepare for an interview the following day with Frank Sinatra.

“A Kind of Psychosomatic Nasal Drip”

Sinatra—in the second decade of a comeback that had begun with the 1953 film From Here to Eternity—was Talese’s kind of subject, but not long after the writer had settled into his hotel room, a call came telling him the interview was off and that in order to reschedule it Talese would have to agree to submit his profile to Sinatra’s handlers prior to publication. This was unacceptable, of course, but Hayes told Talese to keep working. As the days turned into weeks, Talese relayed his progress, or lack thereof, in a series of letters to Hayes that are filed at Wake Forest. They show a writer bouncing from hope to despair to paranoia and back as he works furiously to deliver the goods by shadowing the notoriously controlling Sinatra and talking to everyone who might be able to shed light on the entertainer without setting off any alarms. “I may not get the piece we’d hoped for—the real Frank Sinatra,” Talese wrote in one letter, “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.”

That last sentence provides the key to “Frank Sinatra Has a Cold,” the piece that Talese published in the April 1966 issue of Esquire, after three months of writing and research. Talese built his story on the conceit that Sinatra’s attempts to record a song for an NBC television special had been thwarted because he had a head cold. “Sinatra with a cold is Picasso without paint, Ferrari without fuel,” Talese wrote. It “affects not only his own psyche but also seems to cause a kind of psychosomatic nasal drip within dozens of people who … depend on him for their own welfare and stability.”

Talese’s story doesn’t just capture the essence of Sinatra, it reveals the inner workings of the climate-controlled biosphere the singer had constructed around himself—and the inhospitable atmosphere coalescing outside its shell. It is clear in the reading that by late 1965 the hat-suit-and-tie culture that enabled Sinatra’s 50s comeback was fast being replaced by something closer to a Nehru jacket. “In a sense, he was battling The Beatles,” Talese wrote of the purpose behind the NBC special, but the Fab Four were just a part of the problem. Having already fallen once from the public’s favor, Sinatra was fighting like hell to remain relevant, and beneath his sometimes obnoxious swagger, Talese divined the pathos of an increasingly vulnerable entertainer.

What’s not evident from reading the piece is the conflicted relationship that Talese had with his editor while he was writing it. On one hand, he says, the backbone that Hayes showed during the reporting process was reassuring. “I was really worried about how much money I was wasting” while waiting and waiting at the top-shelf Beverly Wilshire, Talese says, but Hayes told him to keep his eye on the prize. “If you needed any support, he was tough,” the writer says. “He would back you up. I loved that about Hayes.”

On the other hand, Talese saw his boss’s smile as a “tricky” one, especially after a blowup he’d had with him over a 1962 piece entitled “Harlem for Fun.” Hayes had originally assigned the story to the novelist James Baldwin, asking him to build it around illustrations by artist Tommy Keogh. But when Baldwin turned in his manuscript, his narrative had nothing to do with the art, which was already at the printer. Hayes turned to Talese, who checked into a Harlem hotel and banged out a piece to his editor’s specifications. “You know that term ‘Take one for the team’?” Talese says. “Well, I got hit in the head.” Sometime later, when the two men were haggling over Talese’s contract, Hayes told him, “Look, we published that ‘Harlem for Fun,’ which was not your best piece.” Talese was furious. “I said, ‘Listen, you fuckhead. I did that as a favor to you. It wasn’t my assignment. You only gave it to me because Baldwin screwed up.’ ”

From that point on, Talese says, he never trusted Hayes, and he secretly vented some of his anger over that mistrust in the issue in which “Frank Sinatra Has a Cold” appeared. That month, a small item about Talese ran in the “Backstage with Esquire” column, a behind-the-scenes look at the stories and writers in the issue. The “Backstage” piece was illustrated with a photo of the two shirt boards on which Talese had written the final outline for his Sinatra piece, and while it’s not visible to the naked eye, a magnifying glass placed over the left shirt board reveals the words, scrawled in Talese’s handwriting, “Fuck Hayes.”

Talese says the complexity of his relationship with his editor is best described by something his Italian great-grandfather used to say: “Those who love you make you cry.” Despite their skirmishes, Hayes “was the editor who had the most meaning in my life,” Talese says. “I never had another relationship like that. Never.”

Tom Wolfe’s relationship with Hayes was not as intense, but it did have its memorable moments, particularly the cunning way in which Hayes brokered the first piece that Wolfe published in Esquire, in the October 1963 issue—a profile of the boxer Cassius Clay called “The Marvelous Mouth.”

Clay was still months away from his February 1964 heavyweight-championship upset of Sonny Liston, immediately after which he would change his name to Muhammad Ali, but, again exhibiting his prescience, Hayes wanted Clay in the magazine. So, Wolfe says, the editor personally got the fighter on the phone, and found that Clay expected to be paid for his cooperation. He was coming to New York to make a spoken-word recording, but his backers weren’t going to give him much spending money to enjoy his stay. Hayes explained that he didn’t pay for stories, that it was “an honor” to appear in Esquire, but Clay wouldn’t budge. “Get this,” says Wolfe, who was working full-time as a reporter at the New York Herald Tribune when the assignment came through. “Harold says [to Clay], ‘O.K., I’ll give you $150. I’ll give you $50 when you first meet our man on Monday, $50 on Wednesday, $50 on Friday when he finishes up.’ ”

Clay took the bait, the first $50 installment was forked over, and “off we went,” Wolfe says. “He’d made a deal, and he was going to tolerate me,” but just barely. On Tuesday, however, the two men were in a taxi crossing Central Park when, out of the blue, Clay “gets real chummy.” As the pair were walking through Central Park, Clay “puts his arm around me and he says, ‘This is a great day. It feels like Wednesday, doesn’t it?’ I didn’t catch on at first,” Wolfe says with a laugh. “He wanted his next $50. So, I said, ‘I’m sorry. They don’t give it to me until the day I give it to you.’ ” Even more astute than Hayes’s deal with Clay was the editor’s decision to use his most flamboyantly nimble writer to nail down the giddy, kinetic outlandishness of boxing’s most flamboyantly nimble fighter. In that sense, “The Marvelous Mouth” has a nice cosmic symmetry to it. It marks the Esquire debuts of two men who would bring an unmatched level of showmanship to their respective professions.

When Wolfe became a sensation at Esquire—where he would meet his wife, the former Sheila Berger, in the art department—he was already working hard for both the Herald Tribune’s daily paper and its Sunday magazine, New York, where Clay Felker had taken over as editor. So, when Esquire began vying for Wolfe’s byline as well, Felker reportedly was not happy. But if the ingredients were there for Hayes and Felker’s earlier rivalry to turn into something more public, and ugly, that’s not what happened. Though the two editors’ paths would continue to cross in odd and ironic ways, any lingering tensions between them tended to be expressed—at least for public consumption—under the guise of friendly competition or blithe ignorance. For his part, Felker says, he never read Esquire much after he left the magazine. And though Wolfe doesn’t recall this episode, Hayes wrote in one of the chapters of his unfinished book that, once, when Wolfe owed assignments to both Esquire and New York, “and was ducking us both,” he sent the writer “a wire suggesting the pressure had eased up on his New York deadline” and that the writer should go ahead and finish his Esquire assignment. “I signed it ‘Felker,’ ” Hayes wrote, adding, “He still turned his piece in late.”

By the end of 1966, Harold Hayes had watched approvingly as a number of his star writers established footholds in longer forms. Gay Talese was working on his fourth book, an opus about The New York Times called The Kingdom and the Power that had begun as a 1966 Esquire piece. Tom Wolfe had put out his first collection of articles, The Kandy-Kolored Tangerine-Flake Streamline Baby, and was working on a book about Merry Prankster Ken Kesey. And Peter Bogdanovich had moved to Los Angeles to work in the very medium he covered for Esquire: film. Bogdanovich had charmed his way into the magazine four years earlier after getting into a spirited argument with Hayes over motion pictures at the 1962 premiere of Howard Hawks’s Hatari. “I said, ‘God, you have bad taste in movies,’ ” Bogdanovich recalls. “I was very flippant with him.” But Hayes remembered his tormentor when Bogdanovich called days later to sell a piece he’d written on Hollywood. The story, “Talkies,” ran in the August 1962 issue. “It was one of the great, exciting moments of my life,” Bogdanovich says.

As he became a regular presence in Esquire, Bogdanovich and his then wife, Polly Platt, became close friends with Hayes and his first wife, the actress Suzette Meredith. The Bogdanoviches lived near the Hayeses’ apartment, which was on Riverside Drive and West 100th Street, and often the couples would meet for dinner. “I remember one time when we went over. He had just seen Hello, Dolly! [which premiered on Broadway in January 1964], and he had the original-cast album,” Bogdanovich recalls. “He said, ‘Listen to this! This is terrific.’ And he played me that tune, the title song. He played it three times. ‘Isn’t that great!’ ” Bogdanovich laughs, as if he still can’t quite believe that Harold Hayes, the man who loved to puncture pomposity in Esquire, could fall for such an overinflated musical. “I said, ‘It’s O.K., Harold.’ But he just loved it.”

Because Hayes’s talent as an editor seemed to come from such an instinctual place—a realm defined and colored by his personal tastes and experiences—he had some definite blind spots. “There was nobody smarter than Harold on certain things and nobody dumber than him on certain things,” says Robert Benton. “What Harold was comfortable with, he was brilliant at. And what he wasn’t comfortable with made him uneasy.” Hello, Dolly! was something that the jazz-loving, trombone-playing husband of a stage actress could understand. Rock ‘n’ roll was another story. And so Esquire devoted comparatively little space to it. Hedley recalls the time Hayes “embarrassed me in a meeting when I said Bob Dylan was one of the most important poets, musical writers, of any time.” “How old are you, again?” Hayes asked him after a good laugh.

Hayes may not have grasped the cultural influence of Bob Dylan, the Beatles, or even Sonny and Cher, but in 1965 his instincts as an editor, and, perhaps, as a former Marine, established Esquire as an authority on the escalating war in Vietnam. By 1965 the U.S. had committed 200,000 troops and begun Operation Rolling Thunder, a three-year bombing campaign against the Vietcong. Esquire had run some coverage of the conflict, but nothing like the story that John Sack, a former CBS News bureau chief in Madrid, pitched in a letter to Hayes. Sack, who had been a soldier in the Korean War, proposed to follow an infantry company through boot camp and into its first battle in Vietnam and write about it for Esquire.

His story led the October 1966 issue, and, like the best Esquire stories, it was suffused with humor. But as the soldiers of M Company traded the jitters of basic training for the insanity of real, live war, Sack’s tone grew progressively darker, before finally going black when a grenade thrown, on orders, into a hut killed a seven-year-old Vietnamese girl.

From the cold horror of this scene came Esquire’s starkest cover. Against a black background, the words of the soldier who discovered the child’s body were printed in white:

“Oh my God
—we hit
a little girl.”

It was a knockout combination of art direction and literary journalism that brought the horror and the humanity of a distant war home in a way that no three-minute TV report could.

Nineteen sixty-six was a very good year for Esquire. According to Carol Polsgrove’s It Wasn’t Pretty, Folks, but Didn’t We Have Fun?, The Sunday Times of London named Esquire one of “the world’s great magazines,” circulation topped one million, and advertising revenue jumped 25 percent to $10.5 million—still a far cry from the $17 million that Playboy raked in, but remarkably good for a magazine aimed for its readers’ heads without the added value of a centerfold.

The following year, Bond girl Ursula Andress appeared on July’s cover with a Band-Aid slapped over her brow for a special issue on violence, an increasing and troubling feature of American life. The package included a photo-essay about violence in the arts called “Now Let the Festivities Proceed,” by then contributing editors Robert Benton and David Newman, who were just weeks away from seeing the premiere of their own groundbreaking contribution to the topic. The duo had written the script for Bonnie and Clyde, which was released to U.S. audiences in August 1967. Directed by Arthur Penn and starring Warren Beatty and a radiant Faye Dunaway, Bonnie and Clyde was more than just a violent movie.

It was an Esquire movie—its characters, dialogue, and detachment all expressions of the New Sentimentality that Benton and Newman had diagnosed three years earlier. “We had written the treatment for Bonnie and Clyde when we did ‘The New Sentimentality,’ ” Benton says. “One was an expression of what we felt about the other.” The film contained no traditional heroes. Its main characters were a couple of beautiful but inept criminals who became celebrity revolutionaries by robbing banks—The Man, in the jargon of the times—then succumbed in a blood-soaked, bullet-riddled, balletic climax. Along the way, people died gruesomely to the madcap bluegrass sounds of Flatt and Scruggs’s “Foggy Mountain Breakdown.” Sex was depicted with a perverse frankness. It was the seminal statement of a new, unsentimental era of moviemaking. Says Benton, “One of the reasons I think Bonnie and Clyde worked is that we came out of a magazine culture. We came out of the urgency and the irreverence of that specific Esquire world.”

The Chinese Curse

After witnessing the carnage of the Tet offensive, in January 1968, a gifted young writer named Michael Herr wrote Hayes from the city of Hue on February 5 to plead that Esquire scrap two stories he’d written on the war—including one on the Vietnam Establishment—and let him crash a new one. “Before the Tet offensive, the war had a kind of easy sameness to it, and writing against [Esquire’s] lead time was no problem,” Herr explained to his editor. “Now, all the terms have changed, all the old assumptions about the war, about our chances for even the most ignoble kind of ‘victory’ in it, have been turned around.” The year had just begun and the U.S. seemed caught in a frightening tailspin—but not Esquire. For spring, Lois had come up with two classic covers. April depicted Muhammad Ali, photographed by Carl Fischer, as the arrow-pierced Saint Sebastian, martyred for refusing to fight in the Vietnam War. For May, Lois had taken a stock picture of Nixon asleep on Air Force One during his vice-presidential years and merged it with a custom photo of a cluster of hands wielding makeup tools, including a tube of lipstick. “Nixon’s Last Chance. (This time he’d better look right!)” read the cover line, a nod to his sweaty performance during the 1960 debates with Kennedy.

But reality quickly became more shocking and unpredictable than any story or cover image that Esquire’s brain trust could produce. On March 31, faced with the escalating disaster of Vietnam and the prospect of a drawn-out and divisive battle for the Democratic nomination, Lyndon Johnson announced that he would not seek re-election. On April 4, while the Ali cover was still on the stands, Martin Luther King Jr. was truly martyred in Memphis. And in the early morning of June 5, presidential candidate Robert F. Kennedy was shot and mortally wounded at the Ambassador Hotel in Los Angeles.

America was coming unmoored, and Esquire’s lead time made it look slow, even callous. “What can you do when the coverage of one assassination comes out after the next one?” Hayes asked the writer Garry Wills. Though a number of staffers and writers who worked with Hayes in 1968 don’t recall seeing him unnerved by these events, Hayes began to invoke a traditional Chinese proverb—a curse, actually: May you live in the most interesting of times. “He would say that all the time, and shake his head, [as if asking] ‘What is going on?’ ” Hedley remembers.

In the ensuing months, Esquire muted some of its wilder satirical impulses. “The best we could provide was a bleak grin,” Hayes wrote in the introduction to the magazine’s aptly named anthology of 60s articles, Smiling Through the Apocalypse (which was prefaced by the Chinese curse). For the October 1968 issue—Esquire’s 35th anniversary—the magazine displayed a cover depicting John and Robert Kennedy and Martin Luther King Jr. standing together at Arlington National Cemetery. The casualties of a decade condensed into one solemn image, without tears, but also without Esquire’s trademark irreverence.

At the end of 1968, Hayes had sent a memo to the staff in which he’d written, “I’m scared.” Newsstand sales were down 20,000 from 1967, the magazine was hiring too many “hacks,” and the competition was not. Willie Morris’s Harper’s—which had scored big that year with Norman Mailer’s “On the Steps of the Pentagon”—was surging. So was New York, which Felker had spun off into a stand-alone magazine in April 1968 shortly after the Herald Tribune folded. With Wolfe on board, as well as Gloria Steinem and a provocative new writer named Gail Sheehy, New York was poised to become one of the great magazines of the 70s, and the blueprint for every other city magazine that would follow it. (It would also take on a number of former Esquire employees, including managing editor Byron Dobell, assistant art director Walter Bernard, and editor-writer Aaron Latham.) And though Hayes didn’t mention it in his memo, there was also an upstart out of San Francisco called Rolling Stone that was using New Journalism techniques to explain the burgeoning rock ‘n’ roll culture.

But Hayes rallied the troops once more, and by 1969, Esquire was showing signs of its old self. Michael Herr’s fever-dream dispatches from Vietnam were the best writing on the subject. A Hayes discovery named Jean-Paul Goude had arrived from Paris with his Bentley and was shaking up the magazine’s look as its new art director. An unorthodox new fiction editor, Gordon Lish, who signed his office memos “Captain Fiction,” was doing the same with Esquire’s literary pages. And a sardonic writer named Nora Ephron debuted in the February 1970 issue with a profile of Helen Gurley Brown. At one point, Hayes would even assign his new associate editor, Lee Eisenberg, the impossible task of wooing New York’s hot women writers—such as Sheehy (whom Felker would marry in 1984)—over to Esquire.

Esquire’s resurgence could not last, of course. The economy was slumping, and Hayes would soon lose a distracting battle against the business side’s move to shrink the publication to the smaller size that had become standard for magazines. August 1971 was the last oversize issue and featured a solemn, elegant sepia-toned photo of Mafia kingpin Joe Bonanno, dressed to the nines. The cover story was an excerpt from Gay Talese’s new book, Honor Thy Father. Talese had become a best-selling book writer, as had Tom Wolfe. And though they still kept in touch, both had moved on, as had John Berendt, Tom Hedley, and Hayes’s friend Robert Sherrill. Berendt would edit New York magazine and become a best-selling author, too, with the publication of Midnight in the Garden of Good and Evil, in 1994. (His most recent book, City of Falling Angels, is dedicated to Hayes and Felker.) Tom Hedley would conceive the story and co-write the script for Flashdance. Benton and Newman had embarked on a successful career in Hollywood, which would include the original Superman movies, and so had Bogdanovich, who in 1971 would release his masterpiece, The Last Picture Show. All three would collaborate on the 1972 film What’s Up, Doc? In 1973, Hayes moved on, too, forced out of Esquire after management sought to bump him upstairs with the title of publisher and he insisted on retaining editorial control. George Lois broke with the magazine soon afterward.

Some of the materials found in the Wake Forest archives suggest that the 70s must have been humbling for Hayes as he attempted to get back into the red-hot center of the magazine world. Though in later writings Hayes professed a begrudging admiration for Clay Felker, he didn’t shy away from his former rival’s old turf. There is a typed, undated one-paragraph memorandum addressed to “Rupert,” presumably Rupert Murdoch, whose 1976 purchase of New York magazine and The Village Voice led to Felker’s unplanned departure as the editor of the former. In the memo Hayes writes: “I don’t know how you feel about New York at the moment, but it looks weak to me.” Give him two years and a free hand, he adds, and “I could make it into a very strong magazine for you.” It’s unclear if Hayes even sent his letter; at any rate, he never got the opportunity to prove his assertion. (In 1978, Felker returned to his old stomping grounds to edit the short-lived Esquire Fort Nightly, which was published every two weeks instead of monthly.) A foray into television met with mixed results: Hayes was well received as host of an interview show that ran on New York’s local PBS station in the 70s, but his and art critic Robert Hughes’s debut as the original co-hosts of ABC’s 20/20 newsmagazine, on June 6, 1978, would go down as one of the great disasters of network television. The New York Times’s TV critic branded the show “dizzyingly absurd,” ABC News chief Roone Arledge went on record saying he “hated the program,” and Hayes and Hughes were replaced the following week by Hugh Downs. In the 80s, Hayes would move to Los Angeles to take a stab at editing another of Clay Felker’s creations: California magazine, which Felker had founded as New West.

But Hayes’s second act would not come from editing, it would come from writing about a subject as impenetrable as he was: Africa. Hayes had ventured to the continent in late 1969 at the urging of longtime Esquire photographer Pete Turner and “fell in love with it,” says his second wife, Judy Kessler. “He had to know everything about it.” Beginning in 1977, he wrote three books on the subject. The last, which was finished and published after his death from a brain tumor in 1989, dealt with Dian Fossey, the subject of Gorillas in the Mist, a movie adapted from a Life-magazine article Hayes wrote about her murder. Africa would also become his final resting place. Late in the summer of 1989, Tom Hayes took his father’s cremated remains up in a helicopter and released them over the Masai Mara game park, on the border of Tanzania and Kenya.

Hayes always had “a keen eye for the mood changes,” as Arnold Gingrich once wrote, so maybe he foresaw some of the curves ahead. But back in the summer of 1970 he was still very focused on his one true ambition: editing his magazine. And the November 1970 issue was going to be a Molotov cocktail. Hayes had brokered a deal for exclusive rights to the story of Lieutenant William L. Calley Jr., the soldier facing trial for the My Lai massacre, in which he stood accused of murdering more than 100 villagers, some of them children. Hayes had paid Calley a lot more than the $150 he’d given to Cassius Clay—$20,000 for his participation with three exclusive articles written by M Company’s John Sack; the first would run as the cover story. The cover, by the way, was a masterpiece. It made the Sonny Liston cover look like a Disney cartoon. The image showed Calley in uniform, surrounded by Vietnamese children. He was the nation’s Frankenstein monster. And in the photo, he was smiling.

For Harold Hayes, Christmas had come early.


articles from Vanity Fair by Frank DiGiacomo

The Game Has Changed
March 2008

John Mellencamp: One from the Heartland
February 2007

The Esquire Decade
January 2007

The Gossip Behind the Gossip
December 2004

articles from The New York Observer by Frank DiGiacomo

Puff Daddy’s Black and White Ball ’98
December 3, 2006

The Bling of Comedy
February 8, 2004

Baldwin Aroused
November 30, 2003

Triumph Sniffs a Hit
October 19, 2003

Jack Carter Smothers Brothers at Rip-Roaring Friars Roast
October 12, 2003

» See all posted articles


Me and Mr. Johnson
Here’s a link to my latest feature in Vanity…

And Featuring Scarlett Johansson in the Role of…Angelina Jolie
Following last night’s screening of Gomorra, an invitation-only crowd…

See Naples and Die of Heartbreak
If you have any connection to Italy, be it…

P.S. Elliott
This past summer, I wrote a profile of comic…

If You See Something, Say Something (to the Girl in the Hot Chiffon Top)
The police presence at my local subway stop was…


VF Daily
Shipment of Fail
TV Barn
Andrew Sullivan
The Huffington Post
Geeks of Doom
Big Apple Music Scene
WFMU’s Beware of the Blog
Funny or Die
Drew Friedman
Comedy Smack
The New York Observer
Dead Frog