The magazine editor and writer Tina Brown's new book, The Vanity Fair Diaries: 1983-1992, is full of glittery '80s gossip items like that time Warren Beatty propositioned her over a drink. But it also shines a light on some of that era's even murkier moments, like the evening in late 1991 when Brown attended a black-tie gala in New York with Donald Trump, who took the opportunity to pour a glass of wine down the back of a woman at the Tavern on the Green restaurant, in Central Park.
"She was sitting demurely in her black dinner suit at the Parks Commissioner Betsy Gotbaum’s table when she felt something cold and wet running down her back," Brown writes of the journalist Marie Brenner, who not so coincidentally had written a less than flattering profile of Trump and his then-wife Ivana in Vanity Fair the year before—which included mention of the fact that, according to Ivana, Donald kept a book of Adolf Hitler's collected speeches, My New Order, in a cabinet by his bed, which he would read "from time to time."
Brenner confronted Trump about the book, and transcribed their conversation about it in the story, which includes Trump attempting to clear things up by saying that "actually, it was my friend Marty Davis from Paramount who gave me a copy of Mein Kampf, and he’s a Jew." Davis then clarified to Brenner in the story that he gave Trump My New Order, not Mein Kampf, because he thought Trump would find it interesting, and that he is not in fact Jewish. (And earlier in the piece, Brenner shares another tidbit from Ivana—that Trump's cousin John Walter would click his heels and say "Heil Hitler" when he greeted Trump in his office, "possibly as a family joke.")
A few years later, Trump wrote in his book The Art of the Comeback that Brenner's story was, "in fact, one of the worst ever written about me," taking care to describe Brenner as an "unattractive reporter." Brenner finally got to respond in 2015, when the Daily Beast asked her about the incident; she cleared up that it was a glass and not a bottle of wine, which is what New York magazine had reported after Trump boasted about it to their reporter. "I didn’t even notice it was happening, because like everything with Donald, it was a stealth maneuver. It came from behind," she said, adding that she was still waiting for him to replace her jacket.
But around the same time, it looks like Trump actually was pouring entire bottles of wine down at least one woman's back—that of Leona Helmsley, the notorious real estate executive and so-called "Queen of Mean" whom Trump repeatedly disagreed with over several properties, including the Empire State Building. Their feud continued to play out through Playboy, where Trump called Helmsley "a disgrace to humanity" and a "vicious, horrible woman," to which she responded that he was "a sick, sick, sick, sick boy" and a "skunk."
In Trump's 1990 book Trump: Surviving at the Top, he helpfully explained what to him was clearly obvious—that Helmsley had taken a fancy to him and did not take kindly to being spurned, which apparently happened when Trump brought a model along to one of Helmsley's parties where he was "usually [seated] right near her."
And so, at some point around that time (in 2003, Trump told a New York Times reporter that he'd made the move more than 10 years earlier) he got his revenge on Helmsley at a gathering where he happened to be quite close to her back, and particularly to the hood hanging over her chair. "I took an entire bottle of red wine and poured it into the hood," Trump, who noted that he "left early that night," said. "I don't take it back and I hope Leona didn't get overly wet. I hope the dress she was wearing wasn't an expensive one, though that's not likely," he added, like a child.
The Times reporter took care to ask Trump if he had a choice between red and white, to which he replied, "Yes. White's not nearly as effective." Spoken just like you might expect from a man who exaggerated how much wine he poured down the back of another woman in a New York magazine story, the same one in which he shared his attitude towards women: "You have to treat 'em like s---."
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