Stephanie Winston Wolkoff Wrote the Book on Melania Trump

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This week, the latest Trump tell-all hit bookshelves. “Melania & Me” by Stephanie Winston Wolkoff is billed as an inside look at “the rise and fall” of a close friendship with the first lady, whose opaque mien, willingness to buck White House convention, and occasional startling sartorial choices have made her one of the most unknowable figures in the current administration.

The third of the big unauthorized Melania explainers, after “Free, Melania” by Kate Bennet in 2019 and “The Art of Her Deal” by Mary Jordan, which was published earlier this year, “Melania & Me” may also be the most revealing. Here’s why.

Credit…via Simon & Schuster

Who is Stephanie Winston Wolkoff?

She is the 49-year-old, 6-foot-1 former director of special events at Vogue (a.k.a., lord chief planner of the Met Gala), former fashion director of Mercedes-Benz New York Fashion Week at Lincoln Center, executive producer and chief creative officer for the Trump inauguration, and ex-Trusted Advisor to the first lady (among other things).

Ms. Winston Wolkoff grew up in the Catskills along with two brothers (one of whom is the actor Randall Batinkoff). Her mother, Barbara Batinkoff, was a homemaker, and her father, Barry Batinkoff, was a photographer from a line of chicken farmers.

Her parents got divorced when she was in high school, and Ms. Winston Wolkoff stopped speaking to her father. Her mother later married Bruce Winston, the son of the jeweler Harry Winston. He adopted Stephanie, and she took his name — which came with all of the related associations.

She is married to David Wolkoff, a real estate developer, has three children and lives on the Upper East Side. She is also a black belt in martial arts and active on the charity circuit.

She and Mrs. Trump became friends back in 2003, and she attended the Trump wedding and Mrs. Trump’s baby shower; Mrs. Trump came to her 40th birthday celebration. They used to have monthly lunches at places like the Mark Hotel in Manhattan. Sometimes, though a lot fewer times, they met up as couples.

ImageDavid Wolkoff, left, Ms. Winston Wolkoff, Mrs. Trump and Donald Trump at a benefit in New York in 2008.
Credit…Billy Farrell/Patrick McMullan, via Getty Images

So what does a Trusted Advisor do and what happened with the Trumps?

Shortly after the inauguration, which Ms. Winston Wolkoff helped organize, Ms. Winston Wolkoff joined Mrs. Trump’s office — the first hire made by the first lady, even before the more official roles of chief of staff and communications director were filled. Ms. Winston Wolkoff was, however, unpaid, and for a long time her actual title was nebulous.

It was a job that Ms. Winston Wolkoff portrays in the book as large part protector (the West Wing was full of plotters! Many of them against Melania!), part shadow chief of staff, and part friend and mentor.

According to Ms. Winston Wolkoff, she was instrumental in helping create Mrs. Trump’s child-focused Be Best campaign (though she disavows the name), and she tried hard to get Mrs. Trump to wear American designers, and to see that perhaps there was something hypocritical about adopting cyberbullying as a cause, though those efforts were largely unsuccessful.

This all ended in February 2018, when Ms. Winston Wolkoff resigned after revelations that her firm was paid nearly $26 million to plan the inauguration. She called the media’s coverage of the payout “completely unfair,” and in the book asserts that it was inaccurate and she left because she had been scapegoated and used by the administration.

“Was I fired? No,” Ms. Winston Wolkoff said more than a year later. “Did I personally receive $26 million or $1.6 million? No. Was I thrown under the bus? Yes.”

Why is her book such a big deal?

Although a number of former aides to President Trump have written tell-all books, this is the first insider look at Mrs. Trump’s life in the White House (and before). The first lady has maintained a tight control on her aides and social circle, and as a result, and because of the general mystique surrounding her, her choices, and her life, have remained an impenetrable puzzle to most of the world.

So what is going on behind the mask?

It’s not pretty. Ms. Winston Wolkoff goes from writing of the first lady, “Being with her was like having the sister I never had before — but a really confident, perfectly coiffed, ultimate older sister,” to writing, “Her selfishness is so deep, it enables her to keep her distance from the rest of the world.”

Ms. Winston Wolkoff writes that Mrs. Trump mostly shrugs about her reputation. Her attitude, according to Ms. Winston Wolkoff, is: “Pleasing anyone else is not my priority.” Mrs. Trump’s famous jacket that said, “I don’t really care. Do you?” on the back may have been a questionable thing to wear, but it fairly captured her attitude toward her detractors, Ms. Winston Wolkoff says.

Credit…Mandel Ngan/Agence France-Presse — Getty Images

Ms. Winston Wolkoff also writes that Mrs. Trump seemed pretty unbothered when an “Access Hollywood” tape of Mr. Trump saying he liked to “grab” women “by the pussy” went public. “I know who I married,” the first lady is quoted as saying.

And the book provides corroboration to claims that the first lady has a strained relationship with her stepdaughter Ivanka Trump, which Ms. Winston Wolkoff calls a “cold war.” Mrs. Trump was said to alternate between calling Ivanka Trump “Princess” and saying that she and other family members working in the Trump administration were “snakes.”

The book also suggests that Mrs. Trump is as interested in image as her husband is, and kept insisting on being called “first lady-elect” in inauguration materials, despite the fact she had not actually been elected.

So how did the friendship come to be?

According to her book, Ms. Winston Wolkoff met Mrs. Trump in 2003 at Vogue when Mrs. Trump was still Melania Knauss. Both women were 32, and Mr. Trump was trying to engineer a splashy debut in New York society for Melania, then his girlfriend; he thought Anna Wintour could help. (Mr. Trump and Ms. Wintour were “friendly,” the book says, and Ivanka had been offered a job at Vogue.)

André Leon Talley, Vogue’s editor-at-large at the time, took Melania under his wing and engineered a makeover, which, Ms. Winston Wolkoff writes, transformed her from “a brunette Marilyn Monroe” to “editorial worthy.”

The 2004 Met Gala was deemed to be the right context for an unveiling, even though, according to Ms. Winston Wolkoff, Mr. Trump always bought the cheapest tickets: the individual ones, for a mere $1,500 each.

Melania wore Versace, and a giant engagement ring, since Mr. Trump had just proposed. She then attended the couture shows with Mr. Talley in order to pick a wedding gown, and appeared on the cover of Vogue in her Dior by John Galliano dress in February 2005.

Credit…Evan Agostini/Getty Images

So they really were good friends.

Depends who you talk to. A long trail of emoji-filled texts in the book indicates they were — at least to the degree the Trumps have good friends outside the family.

Sure, maybe Mrs. Trump repeatedly referred to one of Ms. Winston Wolkoff’s sons by the wrong name, Ms. Winston Wolkoff writes, and was always asking for favors. But before the election — a time when most of the fashion world and New York society was distancing itself from the Trumps — Ms. Winston Wolkoff strongly defended her friend, warning people to not underestimate the future first lady.

Even after Inauguration-gate, Ms. Winston Wolkoff was quoted in The Washington Post calling Mrs. Trump “dignified” (referring, in particular, to the first lady’s habit of dodging the president’s public displays of affection).

Mrs. Trump’s chief of staff, Stephanie Grisham (whom Ms. Winston Wolkoff calls an “underminer and all-around bad apple” in the book), told reporters the friendship had been “overstated.”

Ms. Grisham also said, in response to reports that Ms. Winston Wolkoff used secretly recorded conversations with Mrs. Trump for the book, that “it’s really unfortunate to take advantage of somebody’s trust like that while being a friend.”

What do the author’s other friends say about her?

”She’s everything you want to hate in a girl,” her friend Kim Gardner told The New York Times for Ms. Winston Wolkoff’s wedding announcement in 2000. ‘’She’s tall, she’s accomplished, she’s athletic, she’s thin, she’s in, she’s hip, she works at Vogue. But she’s a sweetheart. You can’t hate her. You have to love her.’‘

Over the years there have been snipes about her use of the name Winston, with suggestions that Ms. Winston Wolkoff was trying to erase her past to upgrade her résumé. “I am who I am,” she said to The Times in 2017, adding that the reason she doesn’t describe Mr. Batinkoff as her father is “because I’ve seen him twice in 20 years and because Bruce adopted me.”

At Vogue, Ms. Winston Wolkoff was respected for her ability to hustle and get things done. Ms. Wintour, her former boss, referred to her as “General Winston.” When she worked on the Met Gala, she reportedly told people who wanted to go to the after-parties that admission wasn’t free: “no money, no come-y.”

So why open this can of worms? What does Ms. Winston Wolkoff get out of it?

Besides what was probably a pretty good advance? A chance to tell her own story her way, defend her actions, re-emerge in the public sphere via news and talk shows, and salvage her reputation, both in general and in New York society, where a toxic antipathy prevails toward the Trumps and anyone who works with them.

In the meantime, Ms. Winston Wolkoff and Ms. Trump no longer speak.

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