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Meet Melania Trump’s former best friend, Stephanie Winston Wolkoff: the former Vogue PR and Met Gala organiser wrote an exposé about Donald Trump’s wife in 2020, but what’s happened since?

Her former pal Winston Wolkoff isn’t afraid to offer her views, claiming, for instance, that the Trump marriage was all a sham created by TV execs for The Apprentice.

Here’s how the Met Gala organiser got to know the Trump family.

Stephanie Winston Wolkoff is Melania Trump’s ex-bestie

David Wolkoff, Stephanie Winston Wolkoff, Melania Trump and Donald Trump in 2008 – the two families were once close. Photo: Getty Images

So how did the friendship begin, anyway?

Per The New York Times, Winston Wolkoff and Melania became friends in 2003 after Donald asked Vogue’s Anna Wintour to help him introduce Melania to New York society. Melania was “presented” at the 2004 Met Gala, wearing a Versace dress and flaunting an engagement ring, as Donald had just proposed. Winston Wolkoff and Melania connected, and the two women went on to attend milestone events in each other’s lives like baby showers and birthday celebrations.

What is Stephanie Winston Wolkoff’s background?

Stephanie Winston Wolkoff in 2017. Photo: Getty Images
Winston Wolkoff’s parents, Barbara and Barry Batinkoff, got divorced when she was in high school, per The New York Times. Her mother married Bruce Winston, son of famous jeweller Harry Winston. Bruce adopted Stephanie and she took his name.
According to The Times, she married property mogul David Wolkoff in 2000 at The Pierre in Manhattan. Wintour attended the wedding and told the publication that the bride, who wore a Michelle Roth gown, looked like Audrey Hepburn: “She’s immaculate. She makes everyone else feel like a complete mess.”

Stephanie Winston Wolkoff used to work at Vogue

Anna Wintour and Stephanie Winston Wolkoff – the latter worked at Vogue for over a decade. Photo: Getty Images
Winston Wolkoff’s name is synonymous with Vogue, as she worked at the publication for more than a decade. According to Town and Country magazine, Wintour first hired her to be Vogue’s PR manager. She eventually became the director of special events at the iconic fashion publication, and was known for her role in arranging the Met Gala. The New York Times even gave her the informal title “lord chief planner of the Met Gala”.
Stephanie Winston Wolkoff later published the book Melania and Me. Photo: AFP

But Winston Wolkoff left Vogue in 2009 for the role of fashion director at the Lincoln Center, and later started her own agency, SWW Creative. It was during this period that she tried to strengthen her own brand, and articles about her luxury wardrobe and the galleries of her Upper East Side New York flat abounded in lifestyle publications.

She was senior adviser to the former first lady

Donald Trump and Melania Trump in 2021. Photo: AFP

Just after Donald’s inauguration in 2016, Winston Wolkoff joined Melania’s office as a senior adviser to the first lady – Melania’s first official appointment, according to The Washington Post. The move was seen as the first step to help Melania in her new role as first lady of the United States.

But it ultimately ended the pair’s friendship. The New York Times reported in 2018 that Donald’s inaugural committee paid US$26 million to Winston Wolkoff’s firm, as she had been hired as the executive producer and chief creative officer for the event. The firm, WIS Media Partners, was created just a month before the 2016 inauguration. After a public fallout, Winston Wolkoff resigned from her position, writing in her book that she believed she was “thrown under the bus”.

Her Melania Trump exposé

Melania and Me: The Rise and Fall of My Friendship with the First Lady was published in 2020. Photo: @SWinstonWolkoff/X

In September 2020, Winston Wolkoff released her book, Melania and Me: The Rise and Fall of My Friendship with the First Lady. The New York Times dubbed it the first “inside” look from someone in Melania’s inner circle.

Winston Wolkoff wrote that Melania doesn’t care about pleasing other people. She also claimed that Melania had an “operation block Ivanka” at Donald’s 2016 inauguration to ensure that his daughter did not steal the spotlight. If the friendship wasn’t already over before, the book was the final nail in the coffin.

She claims Donald Trump and Melania Trump’s marriage is a sham

Winston Wolkoff has not shied away from commentary around her former pal, Melania and her relationship with her husband, the former US president. Commenting on a book by Ramin Setoodeh, Apprentice in Wonderland, Winston Wolkoff alleged the narrative around Melania and Donald’s relationship was created by TV execs for The Apprentice.

Per Newsweek, Winston Wolkoff shared a video from The Apprentice depicting Donald as a family man with his doting wife waiting for him to arrive home. “Millions of Americans watched The Apprentice. Donald was a household name. He needed a woman who looked and played the part and let him be the star,” she claimed on X (formerly Twitter) in June.

As Donald’s legal battles continue in tandem with his presidential campaign, Melania has reportedly remained out of the public eye during his court battles – for the most part. Of course, Winston Wolkoff had comments to make about that, too. In an op-ed published on The Daily Beast, she called Melania a master at avoiding exposure, adding, “she’s a ruthless survivor and opportunist – willing to do whatever it takes to resort to any means necessary for self-preservation”.

However, in the aftermath of Donald’s shooting, Melania released a statement about her husband on X, praising “his laughter, ingenuity, love of music and inspiration”.


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