In May 1984, the cover of GQ featured a Richard Avedon portrait of a handsome thirty-eight-year-old in a suit, with bushy eyebrows and a mercurial, closed-lip smile. “SUCCESS,” read the headline. “How Sweet It Is.” The man in the photograph was Donald Trump.
The author of the accompanying article, a magazine writer named Graydon Carter, zeroed in on Trump’s outer-borough tells (“cuff links: huge mollusks of gold and stone the size of half-dollars”) and outsize vanity, like the Lucite-framed copy of a New York Times profile that he kept on the windowsill in his office. “Did you ever pass Trump Tower at night and see the way it glows?” Trump asks Graydon as they glide down Fifth Avenue in his stretch limo with “DJT” vanity plates. (Trump brags about the TV, radio, and wet bar he’s installed in the back seat.) This is the bombastic, barking, dissembling, self-mythologizing Trump that millions of Americans would soon come to know, captured by Graydon like a lepidopterist impaling a monarch. “I’m a first-class sort of person,” Trump says in closing. “I only go first class.”
Among the many readers who relished the article was Si Newhouse. And not just the writing: Si, who pored over circulation numbers, discovered that the Trump cover had sold much better on newsstands than comparable issues of GQ, an early example of the Trump Bump. As a celebrity, Trump was irresistible, and his unapologetic embrace of 1980s excess resonated with the younger yuppie readers, particularly men, who were flocking to GQ and other Condé publications. Si had acquired Random House, the prestige book publisher, in 1980, and the success of the Trump article prompted an idea. At a Random House sales conference in the Bahamas a few months later, Si instructed his team that securing a Trump book was a priority. “This Trump fellow was more than a comer,” Si told the group. “He had arrived.” Si soon took matters into his own hands: he rang up Trump himself. The whole thing, the book’s editor, Peter Osnos, recalled years later, “was very definitely, and almost uniquely, Si Newhouse’s idea.”
Trump agreed to take a meeting. Si asked Osnos and Howard Kaminsky, the Random House CEO, to join him at the pitch in the developer’s twenty-sixth-floor office at Trump Tower overlooking Central Park, a self-styled shrine to The Donald festooned with his press clippings and magazine covers. To help Trump envision the book’s possibilities, the men brought along a prop: a hefty Russian novel dummied up with a dust jacket featuring a photograph of Trump looking triumphant in the Trump Tower atrium, with his surname emblazoned in oversize gold typeface.
Trump’s only suggestion: “Please make my name much bigger.”
The Art of the Deal was in motion.
Si authorized a $500,000 advance, later split between Trump and his ghostwriter, a magazine journalist named Tony Schwartz. The book, released in November 1987, went on to be a smash hit that earned Random House millions and spent forty-eight weeks on the New York Times best-seller list. It was also a prime example of Si’s unseen hand in shaping American culture. The book catapulted Trump into bookstores and airport cafés across the country, morphing a provincial New York personality into a national pop culture product for the first time. He was interviewed by the Today show, Barbara Walters, David Letterman, Phil Donahue, People magazine, and a dozen local TV stations. Tina Brown ran an excerpt in Vanity Fair. Si, who rarely spoke publicly, accompanied Trump to a Memorial Day booksellers’ convention in Washington, where he declared he had made two great decisions in his publishing career: buying Random House, and convincing Trump to write a book. At Trump’s request, Si even ordered his warehouses to reopen over Christmas week so that a thousand copies could be flown to Aspen during Donald’s ski vacation.
Trump, the avatar of the arriviste eighties, whose obsession with wealth paralleled the driving impulse of Condé’s magazines, seemed both a byproduct of, and fuel for, Si’s personal ideal of American glamour. Like Si, Trump was an outer-borough scion who outperformed his old man, transcended déclassé roots, and remade himself as a Manhattan king. At the black-tie book party, held under the waterfall in the Trump Tower atrium, Trump greeted well-wishers with Si standing by his side.
THAT SI WAS THE INSTIGATOR of Trump’s first major media venture is a legacy that the Newhouse family isn’t eager to discuss. Si’s daughter, Pamela, cringed when I raised the subject with her. “I just don’t know whether Trump would have gotten that show”—The Apprentice—“but for the success of that book,” she said, ruefully. “So, my father, in a way, put Donald Trump on the map. It is a source of deep regret to everybody, to think that. But how would he have ever known?”
Perhaps Si had sensed the national fascination with Trump and made a shrewd business decision. But the reality was that he and Trump had a powerful friend in common: Roy Cohn, the pugnacious lawyer who had been Si’s confidant since Horace Mann. And the ties between Cohn and the Newhouses extended well beyond a childhood friendship.
After the Army-McCarthy hearings in 1954 left his career in disarray, Cohn started his comeback by securing a general counsel position with Henry Garfinkle, one of the country’s most powerful newsstand magnates and a close family friend of the Newhouses. In 1959, after Sam Newhouse purchased Condé Nast, Cohn and Garfinkle helped ensure that Vogue, Glamour, Mademoiselle, and other Condé titles were placed in prime positions at tens of thousands of newsstands across the country, enticing a new group of readers. The magazine arm of the Newhouse empire succeeded in no small part thanks to Si’s old pal. Cohn went on to represent the Newhouse family across a variety of legal matters, from union disputes at the family’s local papers to individual divorces. A master at manipulating older, powerful men, Cohn cultivated his friendship with Sam Newhouse, even claiming that Sam bailed him out when he had money troubles. “He reached into his drawer and got out his checkbook and he wrote me a check for half a million dollars,” Cohn said. “He told me not to worry about repaying him.”
As young men, Si and Cohn vacationed together in Havana, Acapulco, and Palm Beach. After Si’s divorce, Cohn’s friends claimed that Sam, concerned his son could become involved with a socially unsuitable woman, paid Cohn a retainer to keep an eye on Si’s dating life; Cohn supposedly once steered Si away from a potential marriage match that Sam deemed ill-considered. When Cohn was thrice tried—and thrice acquitted—in federal court on charges ranging from fraud to blackmail to perjury, Si sat vigil in a Manhattan courthouse for every day of the trials. Just as Alex Liberman had introduced Si to the world of high culture, Roy Cohn was his mentor in the dark arts, explaining how to navigate the corridors of political and corporate power.
And there is little doubt that Cohn and Si discussed The Art of the Deal. Cohn, who was Trump’s lawyer and Pygmalion, was almost certainly the conduit by which Trump and Si first met; both men attended Cohn’s raucous birthday parties at Studio 54. Cohn saw the potential boost that a best-selling book could provide for Trump, and the opportunities that Si’s empire offered for mythmaking. (Random House later offered Cohn a hefty sum for his memoir; “I didn’t see how we could not do it, given how close he was to Newhouse,” recalled Robert L. Bernstein, the president of the publishing company at the time.) Si, self-conscious about his reputation in the insular publishing world—and aware of the Random House old guard’s skepticism about their nouveau owner—was eager to show he could deliver a hit.
“There’s no question the Trump thing was Roy’s idea to Si,” recalled Peter Osnos. “Si says, ‘Roy Cohn says he’s an amazing guy, the magazine sold like hot cakes. We gotta go see him.’ ” To use a corporate term that the litterateurs of Condé might have sneered at: it was synergy.
THE SUCCESS OF THE ART OF THE DEAL permanently yoked Trump and Si, and by extension the editors of Condé Nast, together. In the years that followed, Trump turned up regularly in the pages of Condé magazines. The flashy developer was only the latest in a long line of parvenus who sought Condé’s status-bestowing power, but few others had the kind of leverage that his friend Cohn held over Si—and the entire Condé universe knew it.
Tina Brown once received a call from Si, who relayed that Trump was upset about an upcoming item in Vanity Fair revealing that knobs had been falling off the doors inside Trump Tower. Si expressed concern that Trump might cease advertising in his magazines. The story was killed. Only as Trump’s businesses began to unravel did Tina publish a probing piece by the investigative journalist Marie Brenner, which plumbed Trump’s mendaciousness and his collapsing marriage to Ivana. Among other revelations, Brenner reported that Trump kept a volume of Hitler’s speeches in his bedroom. (“If I had these speeches, and I am not saying that I do, I would never read them,” Trump told Brenner.) The article also included a prescient quote from a Trump lawyer: “Donald is a believer in the big-lie theory. If you say something again and again, people will believe you.”
Graydon Carter, who unwittingly set the groundwork for The Art of the Deal with his original GQ profile, had gone on to fillet Trump in Spy magazine as a “short-fingered vulgarian,” solidifying Donald’s image as a poster child of stomach-churning eighties excess. But after Si hired Graydon in 1992 to take over Vanity Fair, the editor displayed a newfound graciousness toward his former foil. In 1993, Graydon took Trump as his guest to Vanity Fair’s table at the White House Correspondents’ Association Dinner. “We buried the hatchet over lunch months ago,” Graydon breezily told The New York Observer at the time. “Donald and I have a healthy, ironic relationship.” Trump returned the hosannas, with an edge: “I’ve called him one of the most upwardly mobile people I know,” he said of Graydon, “and I mean that.” Later that year, Trump invited Graydon to his blowout wedding at the Plaza to Marla Maples.
It is an irony worthy of Spy that in March 1994, the same month the satirical magazine announced it would shut down, Donald Trump appeared, with his new bride and baby, on the cover of Graydon’s Vanity Fair. “I sort of admire him after all this time,” Graydon told a reporter, “in the way that former enemies can have a grudging admiration for each other.”
At Vogue, emblem of elegance, Anna Wintour had also made room for The Donald, for the same reason that enticed Si in the first place: Trump moved product. In May 1990, Wintour was looking to reprise the enormous success of her Madonna cover from a year earlier. Ivana Trump came to mind. She and Donald were in the midst of a not-so-conscious uncoupling that had turned into a national soap opera. Anna had her doubts, asking a colleague if an Ivana cover would be “too tacky.” But she cast those misgivings aside, tasking André Leon Talley and the photographer Patrick Demarchelier with turning Mrs. Trump into a vision worthy of Vogue. “The Real Ivana” was a rah-rah feature that congratulated its subject on “coming out of her nightmare.” The cover sold 750,000 copies, a massive hit; it meant so much to Ivana that she hoarded hundreds of copies of the issue, which were later discovered in her town house after her death.
Anna had no illusions about the calculation she had made. “Ivana was thrilled with the cover and the article. As she should be,” Anna said at the time. “It sort of gave her a whole new lease on life.” Then she laughed. “Gave Vogue a boost, too.”
For his part, Alex Liberman was appalled. “I should turn in my grave, if that’s the correct expression,” he confided to his biographers, referring to the feature as “Anna’s idea.” Alex, the old lion, still believed in his bones that Vogue carried something of a sacred mission, to expose its readers to the superlatively attractive in life and culture. “It had to be the best,” he said. “Well, I can’t say that Mrs. Trump is the best.”
That Anna could override Alex’s hesitation spoke to the changing dynamic inside 350 Madison as the 1990s dawned. Then in his late seventies, Alex retained the editorial director title and, crucially, the ear of Si. (His vanity was also intact: asked by a colleague which actor might play him in a movie, the aging Alex replied, “Tom Cruise.”) But he was deferring to the younger generation more than he used to. At the urging of a young Vogue editor, James Truman, Alex had begun occasionally exchanging his suit-and-knit-tie uniform for Yohji Yamamoto jeans and sneakers. Visitors to his Connecticut weekend home recalled him listening to Milli Vanilli and Madonna as he painted; another Condé bright young thing, Linda Wells, brought him CDs by the hip-hop artists MC Hammer and Bobby Brown. In a sense, Alex’s effort to keep up with pop culture was a testament to his aesthetic antennae: in the highly volatile world of glossy magazines, where editors and publications could be equally disposable, he grasped that the only formula for long-term success was change.
ANNA MAY HAVE HAD THE Ivana bump in mind when she decided to feature Trump’s third wife, Melania Knauss, on her cover in February 2005. (Marla Maples never made a Vogue cover, but the magazine did showcase her in an obsequious 1996 feature about the spa at Mar-a-Lago.) In 2004, Trump had proposed to Melania at the 2004 Met Gala—theme: “Dangerous Liaisons”—piggybacking on the Vogue publicity machine surrounding the event. He then tapped a former Vogue publicist to represent Melania in her discussions with Anna about a potential cover story. Once again, Talley was tasked with the class-up work, posing Melania in a John Galliano gown; the accompanying article, “How to Marry a Billionaire,” included fawning quotes from designers like Manolo Blahnik, who cooed, “She is a true beauty. She has it.” An editor’s note from Anna insisted that Donald had a “good-natured, kindhearted side.” Readers were being indoctrinated in the idea that the Trumps represented the pinnacle of wealth, success, and glamour—that they deserved the discerning imprimatur of Vogue.
Anna and André attended Donald’s wedding to Melania at Mar-a-Lago—as did Bill and Hillary Clinton. At one point, Anna offered Trump’s daughter Ivanka a plummy position at Vogue, traditionally reserved for the children of the high-born. Ivanka politely declined, telling Anna that she wanted to focus on real estate. But Donald’s reaction was telling. He repeatedly asked his daughter to reconsider, to the degree that Ivanka found herself taken aback. “It was a bit disconcerting to me why he was pressuring me to take the job at Vogue,” she said. “I was a little bit upset about it.”
In March 2011, Trump began publicly espousing racist “birther” conspiracy theories about President Barack Obama. He and Melania attended that year’s Met Gala in May; they were invited back for the 2012 fete, too. Trump appeared, for the final time, at Vanity Fair’s Oscar party in February 2011. By then, however, his old feud with Graydon Carter was on the verge of being revived. The next month, Vanity Fair’s website published an item mocking his White House aspirations, under the headline, “Donald Trump Still Really into the Donald-Trump-is-Running-for-President Story.” Trump fired off a furious reply, written in gold Sharpie, that invoked their old eighties rivalry, even needling Graydon about the collapse of Spy. “Graydon—I know far more about you than you know about me,” Trump wrote. “You never got the ‘Trump thing.’ ” Graydon gleefully published the letter on Vanity Fair’s website. He then requested that his web team mock up “a proclamation call for Trump to prove his hair is real.”
“Trump must present a notarized certificate from his barber and/or dermatologist that it’s real to soothe concerned citizens of the ‘hairers’ or whatever we want to call the movement,” a VF editor wrote to colleagues, relaying Graydon’s instructions under the subject line “Urgent project.”
A couple days later, Graydon commissioned a blog post making fun of Trump’s stone-faced look at that year’s White House Correspondents’ Dinner. The article carried a Spy-style headline—“Every C-SPAN Shot of Donald Trump Looking Angry About Seth Meyers’s Donald Trump Jokes”—and asked “whether The Washington Post brought a life-size marble bust of Trump to the dinner instead of The Apprentice impresario himself.”
Trump in turn began regularly mocking Graydon and Vanity Fair on his Twitter account, even invoking his Art of the Deal publisher: “If the great Si Newhouse were still running @CondeNastCorp, he would fire Graydon Carter immediately—circulation tanking.” (In 2013, when the tweet was sent, Si was eighty-five and had stepped away from day-to-day management.) Graydon dutifully framed each tweet and hung it outside his office, quipping, “This is the only wall Trump’s built.” In late 2013, after Vanity Fair published an article about fraud charges levied against Trump University, Trump lashed out at “dopey Graydon Carter” and a restaurant that he owned, the Waverly Inn, tweeting that it served the “worst food in city.” The quote has appeared at the top of the Waverly menu since.
As ever, this was a mutually rewarding pas de deux. Graydon buttressed his political bona fides and silenced critics who had accused him of going soft since his Spy days. Donald had Vanity Fair, a big, juicy symbol of the elite liberal media, as a convenient piñata. In a sense, the men were Bizarro World versions of each other: status-conscious, thrice-married masters of the Manhattan universe with singular hairdos. Both found fame in the 1980s; both owed their success, at least in part, to Si Newhouse. Again and again, Condé Nast had brought them together. It had one more extraordinary summit in store.
SHORTLY AFTER HE SECURED THE presidency in November 2016, Donald Trump made the rounds of the Manhattan media institutions he revered. He jousted with editors and reporters at The New York Times, where I witnessed his glee at commanding the undivided attention of the newspaper of record. He taped an interview with Lesley Stahl for 60 Minutes. And then, two weeks before his inauguration, he visited the Condé Nast headquarters at 1 World Trade Center to sit with the most famous magazine editors in the world.
The meeting was Anna Wintour’s idea.
Even as Trump traded blows with one star Condé editor, he had kept up relations with another. In December 2012, at the height of his Graydon-bashing era, Trump extended some rare praise when rumors emerged that Anna was under consideration for an ambassadorship to Britain or France. “I am happy to hear that Pres. Obama is considering giving Anna Wintour @voguemagazine an ambassadorship,” Trump tweeted. “She is a winner & really smart!”
In 2016, however, Anna took the unprecedented step of issuing Vogue’s first-ever political endorsement: of Hillary Clinton. The decision made sense given the women’s long-standing ties: Anna had helped dress Hillary since her days as First Lady, hosted fundraisers for her, and frequently served as a financial and social connector. Anna had taken Huma Abedin, Hillary’s longtime aide, under her wing after the implosion of her husband, Anthony Weiner, in a sexting scandal; Abedin spent long stretches at Anna’s country estate in Long Island. (When Abedin wrote a memoir, Anna proposed the title Truth Hurts, but the publisher opted for the more cryptic Both/And. Anna later recycled “Truth Hurts” as the cover line when Vogue ran an excerpt.) Rumors again flew that Anna was eyeing an ambassadorship, maybe to the United Kingdom, in a prospective Hillary Clinton administration. When Anna gathered her stunned staff to acknowledge Trump’s victory, her voice quavered and she cried.
But it was unlike Anna, ever meticulous in her social chess moves, to leave herself so exposed to an adverse outcome. (Presumably, she genuinely saw no possibility that Trump might win.) Access to the White House mattered for Vogue, which had always considered the First Lady important to cover. Compounding Anna’s problems, she had been overheard by a British tabloid musing that Trump had only sought the presidency for personal financial gain. She quickly apologized, and days later, made a covert visit to Trump Tower to pay her respects face-to-face, slipping in through the building’s residential entrance to avoid detection by the photographers staking out the main lobby.
Trump figured Anna wanted to grovel for an ambassadorship. Instead, she invited him to 1 World Trade to clear the air. Notably, Trump agreed without insisting that the editors come to him; the only other media institution Trump deigned to visit while president-elect was The New York Times. “It just shows that it was a priority for him,” Hope Hicks, Trump’s 2016 campaign press secretary, told me, of his mindset at the time. “Vogue is Vogue and The New York Times is The New York Times. We can tweet that they’re failing, all of that stuff, but it still has a certain prestige to it, and he recognized that.”
When Anna met with Graydon in her office to break the news of the upcoming summit, it did not go over well.
“There’s a meeting I would like you to come to…” Anna began.
“Okay, sure.”
“… with Donald Trump.”
Graydon’s face dropped. “You’ve got to be kidding me.”
Besides his objection to Trump, Graydon was also dismayed that Anna had agreed for the meeting to be off the record, which he believed made the conversation journalistically useless. (When Trump visited The New York Times, the newspaper insisted that the discussion be on the record, to the extent that I was invited to attend as the media reporter and report the proceedings on Twitter in real time.) Anna pressed her case, and Graydon eventually relented.
Early on January 6, 2017, as an icy wind vexed Manhattan, Anna greeted the president-elect and his entourage—which included Hicks and Kellyanne Conway—in the 1 World Trade Center lobby. It all seemed like an amusing anachronism. Condé Nast was struggling to persuade readers and advertisers of the relevance of print magazines in a digital age. Yet here was the president-elect, ascending in a high-speed elevator to the forty-second floor, where he entered an executive conference room with floor-to-ceiling glass windows overlooking the Hudson River and the Jersey City skyline. From his Trump Tower condo that morning, Donald had proudly informed the public via Twitter that Anna had personally invited him. In a subtle nod to the Roy Cohn years, he added a shout-out to Si’s nephew, by then a top family executive: “Steven Newhouse, a friend.” Ringing the conference table were the company’s editors in chief, including his old nemesis-turned-friend-turned-nemesis Graydon, and David Remnick, whose post–Election Day essay for The New Yorker’s website had been titled “An American Tragedy.” These were the gatekeepers whose respect Trump, for the moment at least, still desired.
The discussion covered Putin, feminism, climate change, hate crimes, race, and abortion. Things were mostly cordial. Spotting Graydon, Trump joked, “I can’t even believe we’re sitting near each other in a room like this.” (On this isolated point, Graydon agreed.) An uncomfortable moment came when one editor said Trump’s campaign was the reason that swastikas were spray-painted on her children’s playground; Trump angrily rejected this notion, invoking his daughter Ivanka, who had converted to Judaism before her marriage to Jared Kushner.
For the most part, though, Trump appeared to be on his best behavior. This was Condé Nast, after all. “He left feeling like, ‘I didn’t come out of that any worse than when I went in,’ ” Hicks said.
In hindsight, the meeting was something of a final stand between Trump and the company that had done so much to boost his profile. In October 2017, after his chaotic first nine months as president, Anna appeared on the late-night show of James Corden and declared that President Trump would not be invited back to the Met Gala. An attempt by Vogue to photograph Melania Trump for the magazine earlier that year had fallen through when the First Lady declined, apparently because Anna would not guarantee her the cover. “They’re biased, and they have likes and dislikes,” Melania said later of the magazine that seventeen years earlier had paid for her bridal shopping spree in Paris. “It’s so obvious, and I think American people and everyone sees it.” Vanity Fair’s website resurfaced the magazine’s most famous Trump-bashing features and published tough reporting on his messy personal life and finances. The #Resist readership rewarded VF.com with record traffic. After Trump responded on Twitter by rebuking “the really poor numbers of @VanityFair,” the magazine plastered the insult on its next cover, verbatim.
In his scathing tweet, Trump also included a prediction about the career of the man who had penned the GQ profile that, three decades earlier, and unbeknownst to all involved at the time, had set in motion the journey that would take Donald Trump, improbably, all the way to the apex of American life: “Graydon Carter, no talent, will be out!”
Twenty-four hours later, Condé Nast announced that subscriptions to Vanity Fair had soared.