From the start, Tina Brown deemed Donald Trump to be “an entertaining con man, and I suspect the American public would like nothing better.” | Evan Agostini/Invision/AP Tina Brown on Trump: 'I came to think he was very silly' The legendary former Vanity Fair editor, whose recently published diaries contain a surprising amount of Trump lore, has been watching the Donald Show for decades.

Donald Trump was once a comical figure to Tina Brown, a big personality who made her chuckle when he bragged to her over breakfast at the Four Seasons about the results he was seeing from the Atkins diet.

Now, decades later, the legendary former magazine editor views the man inhabiting the Oval Office as someone totally transformed from the likable con artist she first encountered in the 1980s, when she was a rising star in the Conde Nast media empire. Back then, Trump and his gold-plated tower were also establishing themselves as icons of New York, and he was eager to win her approval.


For a period of time, he did. “There’s something authentic about Trump’s bullshit,” Brown writes in “The Vanity Fair Diaries,” the recently published collection of daily observations she kept during her time as Vanity Fair’s editor-in-chief, between 1983 and 1992.

Brown, the British-born magazine editor who made her name on the New York scene during the same gaudy decade as Trump made his, is one of the earliest and most scathing chroniclers of the Trump phenomenon. She was the first to publish an excerpt from Trump’s ghost-written memoir “The Art of the Deal,” and she chose to feature him in Vanity Fair’s annual “Hall of Fame.”

From the start, Brown deemed Trump to be “an entertaining con man, and I suspect the American public would like nothing better.”

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Today, Brown is out of the business of covering Trump. But she’s still watching — from the unique vantage point of someone who knew him when — and still critiquing what she sees from the president she has known for decades, as well as his inner circle. In an interview this week, she expanded on the Trump impressions jotted down in her diaries decades ago, updating her views of the president and his family.

“The most unwise thing for Ivanka Trump to do was move to Washington and go into the White House,” Brown said of Trump’s eldest daughter, echoing a sentiment that is now widely held, but rarely vocalized, inside the West Wing. “If she had stayed in New York and positioned herself as the one who thinks differently but supports her dad, she would have been the most powerful woman. Even just waiting two years to go in would have been smarter. Anyone in the daily thrust is doomed.”

Brown has a kinder read of how the first lady has positioned herself. “Melania is underestimated,” she said. “She’s doing as good a job as a lot of other first ladies have done of just being decorative, not doing anything embarrassing, being dignified and pleasant. She probably enjoys just sitting beside the pool and never said she didn’t. I think she’s an authentic person, and I quite like her.”

Her assessment of Trump’s third wife fits with how she has long viewed the women in Trump’s life — as important boosters for the man at the center of it.

“Ivana was a real driving force in his success and persona,” Brown recalled of Trump’s first wife, who Brown said was as interesting to her, journalistically, in the 1980s as The Donald himself. “She doesn’t get enough credit for making him relevant. In terms of his perception, it never went right for him after he kicked her to the curb. Before the divorce, he was seen as a somewhat appealing con man — a big mouth but a big figure. After, with the divorce and the bankruptcies, he seemed like a more tawdry person.”

And post-divorce, without Ivana Trump scheduling their regular dinners at Le Cirque, Trump disappeared from society for a decade. “I think he stayed in his bathrobe in the gold tower, taking the elevator down one floor,” recalled Brown, a staple of the social scene herself. “I honestly never saw him again.”

Brown said she forgot how much Trump figured in her early chronicling of Manhattan society, until she revisited the diaries to gather material for her book. “I was delighted to find him there; I forgot he was,” she said. “There’s nothing more truthful than the impression at the time. I did get it right.”

Throughout Brown’s diary entries, Trump pops up at dinner parties she attends and in pitch meetings she presides over. Most of the time, he is presented as an amusing bullshit artist for whom Brown seems to have a soft spot — even as she sees right through him.

“Trump, apparently, picks up every call very quickly but cuts you off mid-sentence as soon as his secretary brings a piece of paper announcing someone else,” she writes in one entry. “The trick is to call him back three minutes later just as he’s got bored with whoever replaced you.”

As editor-in-chief of The New Yorker, in 1996, she convinced The Donald to participate in a damning profile, this time by journalist Mark Singer, who concluded in his piece that Trump was a man “who had aspired to and achieved the ultimate luxury, an existence unmolested by the rumbling of a soul.”

But she said in his high-flying days with Ivana by his side, Brown didn’t see what she calls “the darkness” that she believes defines him now. “I didn’t think he was an evil force,” she said. “I thought he was a funny, irreverent, anti-establishment voice.”

“I think he has gotten increasingly darker,” she added. “But we could sense that he wanted to be more than he was. There was an abiding resentment toward the money establishment of New York. You’d never see him at the establishment homes, with the Kravises, or Leon Black, or the Blankfeins.”

Brown happened to be seated directly behind Trump at the now infamous 2011 White House Correspondents' Dinner, where Trump was the brunt of President Barack Obama’s taunts from the dais. “He went from the color of pale shrimp to beet red,” Brown recalled of the public humiliation that many credit with motivating him to run for president. “I do think that night was absolutely critical to making him run, and that’s when he went absolutely dark.”

While Trump has changed to someone she now finds virtually unrecognizable, there are a few Trumpian attributes that have remained unchanged. Trump is still obsessed with his media coverage. And Brown thinks that inside the president, there still resides the winking imp that is often taken too seriously by both his political foes and the journalists who cover him today. “There are times when he’s just being the carnival barker,” she said, pointing to Trump’s labeling of Democrats who didn’t applaud his State of the Union address as “treasonous” and “un-American.”

Watching the West Wing from the sidelines — today Brown, who founded the Women in the World summits, is the CEO of Tina Brown Live media — she said she feels little responsibility for her part in Trump’s creation story, even though her coverage helped make him famous. “Trump was a great New York story,” she said. “He was an icon. That tower is a symbol of the ‘80s to me. He was very much a part of that. We were publishing then. If I was publishing now, I would cover him differently.”

Her coverage of Trump had already started to shift by the time she became editor of The New Yorker and persuaded him — over the breakfast where she recalls that he bragged about his success with the Atkins diet for 20 minutes — to participate in the Singer story. Trump has said that Brown deceived him, promising a flattering profile that turned into a scathing portrait of a man with no soul.

It was the second time Brown pulled a fast one on Trump, after publishing an infamous 1990 story in Vanity Fair, by journalist Marie Brenner, about Trump’s divorce from Ivana — which included the damning detail that he kept a book of Adolf Hitler’s speeches on his bedside table. (To exact his revenge against Brenner, Trump famously poured a glass of red wine down her back during a dinner gala at the Tavern on the Green — and then ran away.)

But Brown admits she may have been purposefully misleading in her efforts to pin down his cooperation for a second go-round. “I charmed him to do this piece, knowing exactly what I was looking for,” she said. “He was so angry when it came out. He probably thought, ‘She did it to me again.’ But it was my job to get the piece in The New Yorker. Who knows, he could have charmed Mark [Singer]. But he didn’t.”

Trump trashed Brown in his “Art of the Comeback” as “totally overrated ... third-rate at best.” These days, there isn’t much of a relationship left between Trump and Brown. When she sat near Trump during the fateful night at the Correspondents' Dinner, she said they didn’t even exchange pleasantries. “We ignored each other,” she said. “I don’t go up to him, I don’t want to go to talk to him. I never really did. I came to think he was very silly.”

If she thought he was silly then, a thin-skinned buffoon fuming about Obama’s taunts, it’s less amusing to her now. “Power makes him much, much worse — it feeds his narcissism,” Brown said. “He’s such a needy man. Every despot in history has been a very needy person.”



CORRECTION: An earlier version of this story described Brown's Women in the World as a speaker series, rather than as a summit.