Meet the Former Melania Trump Friend & Adviser About to Release a Behind-the-Scenes Memoir

A friend of the first lady for years before a falling out, Stephanie Winston Wolkoff decided to write a memoir about the "rise and fall" of their bond

Stephanie Winston Wolkoff, Melania Trump
Stephanie Winston Wolkoff (left) and First Lady Melania Trump in 2017. Photo: Clint Spaulding/WWD/Shutterstock

There have been many books about the Trump family since Donald Trump took office in 2017, but few promise to be as intimate as the upcoming Melania and Me, written by a former friend and adviser to First Lady Melania Trump.

The memoir's reported details — including the friction between Mrs. Trump and stepdaughter Ivanka Trump epitomized by "Operation Block Ivanka" — started circulating days ahead of the publication date.

Here's what to know about the author, the socialite and noted New York City event planner Stephanie Winston Wolkoff.

Who is she?

The author of the new tell-all book about Mrs. Trump, 50, has long been a friend of the first lady after first meeting in 2003.

Their bond dates back to N.Y.C., where they reportedly met through their fashion industry social circles while Wolkoff was a special events planner at Vogue and helped organize a number of other prominent events, including the Metropolitan Museum of Art's Costume Institute Gala.

As a former events planner for Anna Wintour, Wolkoff, also 50, climbed through the ranks of the fashion magazine before joining the Lincoln Center as a fashion director, according to The Washington Post. She was also featured in a 2005 New York piece.

Stephanie Winston Wolkoff, Melania Trump
Stephanie Winston Wolkoff (left) and Melania Trump in 2008. BILLY FARRELL/Patrick McMullan via Getty

According to reports, Wolkoff was frequently seen at events with prominent socialites — including the future first lady.

Wolkoff was one of the first White House staff members that Mrs. Trump hired, bringing her on in an advisory role before the first lady had even hired a communications director or a social secretary.

In the early days of President's Trump's tumultuous time in office, Wolkoff had multiple duties including interview requests and events, according to Town & Country.

"Event planning" is where Wolkoff's tenure at the White House took a turn in 2018.

What caused the falling out?

Though Wolkoff disputes that she was forced out of her White House role, she left the East Wing in early 2018 after and eyebrow-raising New York Times report that her firm was paid about $26 million from the president's inauguration committee for her role in planning the January 2017 events.

“Although it’s not nearly as exciting as the phony story that broke, the real reason I’m no longer working at the White House is because all gratuitous volunteer contracts were ended,” Wolkoff told Town & Country. "Every dollar of the money that my company was responsible for was pre-approved, fully accounted for and submitted to the presidential inaugural committee over a year ago."

“Was I fired? No,” she told the Times in 2019. “Did I personally receive $26 million or $1.6 million? No. Was I thrown under the bus? Yes.”

Stephanie Winston Wolkoff
Stephanie Winston Wolkoff. Andrew Toth/Getty

What has she said about the first lady?

Wolkoff has spoken highly of her longtime friend and one-time employer, once telling DuJour not to "underestimate" the notoriously private first lady.

“Don’t underestimate her just because she is quiet and reserved," Wolkoff said before the 2016 election. "There is virtue in the fact that she appears to be quiet and isn’t on the front lines constantly saying, Hear me, see me. But she’s very confident in her viewpoint."

Wolkoff added then: "She does not agree with everything that [Donald] says or everything that’s being done, but she believes in the greater good. They are a power couple. They are each other’s teammate," before noting, “He’s out there. He has so much going on. It isn’t about her yet. She has always said, when and if the time comes, she will step up. She’s a wife and a mother until that day comes.”

But in the lead-up to the Tuesday release of her new book about their relationship, Wolkoff is telling other stories: According to journalist Yashar Ali, she taped Mrs. Trump making "disparaging" comments about her husband and her stepchildren and those recordings were also used to backup quotes in the tell-all.

(The White House did not respond to repeated requests for comment about Wolkoff's book of the reported tapes.)

Both New York and Washington, D.C., where the Trumps have spent much of their time, have "one-party" recording laws that mean Wolkoff could have taped her conversations without telling anyone.

“I’ve heard a little bit about this book; I don’t know much about it," Mrs. Trump's spokeswoman Stephanie Grisham told MSNBC. "It sounds like it’s just another one of those books that unfortunately people are writing. And you know, if there were any recordings taken, it’s really unfortunate to take advantage of somebody’s trust like that while being a friend.”

Melania Trump and Stephanie Winston Wolkoff
Melania Trump (left) and Stephanie Winston Wolkoff in 2006. Joe Schildhorn/Patrick McMullan via Getty
Stephanie Winston Wolkoff, Donald Trump, Melania Trump
From left: Melania and Donald Trump with Stephanie Winston Wolkoff. Billy Farrell/ BFA

What do we know about Wolkoff's book?

The book's description says she "takes you into Trump Tower and the White House to tell the funny, thrilling, and heartbreaking story of her intimate friendship with one of the most famous women in the world, a woman few people truly understand."

An excerpt of the book in New York details what the author calls a "petty" mission she carried out with the first lady on Inauguration Day in 2017 in attempt to limit first daughter Ivanka Trump's role.

Wolkoff wrote in the excerpt that she and the first lady put together an effort they called "Operation Block Ivanka" that aimed to keep Ivanka out of the best photo ops that day.

"It was Donald's inauguration, not Ivanka's," Wolkoff wrote, according to New York. "But no one was brave enough to tell her that. Melania was not thrilled about Ivanka's steering the schedule and would not allow it."

Wolkoff said that she now feels "abandoned" and "betrayed" by Mrs. Trump, according to New York reporter Olivia Nuzzi. Though perhaps it was instructive.

“A Trump," Wolkoff writes, "is a Trump is a Trump."

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