Stephanie Winston Wolkoff was one of the key planners of Donald Trump's inauguration events in January 2017, and went to work with First Lady Melania Trump in the East Wing at the very beginning of the administration.
A longtime friend of Melania's with deep ties to the world of fashion and New York society, Wolkoff left the First Lady's office after a New York Times story detailed controversies about inauguration spending.
Winston Wolkoff tells her side of the story with a new book, Melania and Me: The Rise and Fall of My Friendship with the First Lady, which came out September 1. Among the revelations in the book are tensions between Melania and her stepdaughter Ivanka. She and Winston Wolkoff planned what they jokingly referred to as "Operation Block Ivanka," an effort to keep Donald Trump's daughter and White House aid from being positioned visibly close to her father during the inauguration's swearing-in ceremony. Read an excerpt of the book, here.
In October, Wolkoff appeared on CNN, and shared tapes of the First Lady speaking about children being separated at the border as well as her disdain for decorating the White House at Christmas. Listen to the recorded conversation here.
This story was originally published in March, 2018.
Just a week after the January 20, 2017 inauguration of President Donald Trump, America’s new First Lady, Melania Trump, announced her first hire. Stephanie Winston Wolkoff, a New York social fixture, event planner, and former Vogue staffer, was brought on as an unpaid advisor to Mrs. Trump, a role which took precedence over traditionally crucial team members such as a chief of staff or social secretary.
The January 26 news of Wolkoff’s hiring was covered breathlessly in the press, in part because of the mystery and speculation around how Mrs. Trump—who many saw as a reluctant, immensely secluded figure—would step into her new role as First Lady.
But over the first few months working with FLOTUS, Wolkoff often led the charge around positioning the First Lady as a serious figure, confirming Mrs. Trump’s plans to move into the White House and clarifying her intention to keep Michelle Obama’s kitchen garden in tact.
In those crucial early days, Wolkoff, 47, the same age as the First Lady, played a key role in the East Wing, handling a variety of duties, including responding to press inquiries, planning events, and positioning Mrs. Trump as someone who contrasted sharply with the President’s loud, boastful image.
“Don’t underestimate her just because she is quiet and reserved,” Ms. Wolkoff had told DuJour magazine in a profile of Mrs. Trump that was published during the 2016 campaign. “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.”
Almost always described as a “longtime friend of the First Lady,” Wolkoff was also one of the key planners for Donald Trump’s 2017 inauguration, and her responsibilities included securing venues and subcontracting out to New York society event planner David Monn. Her involvement in the inauguration, however, ultimately landed her in hot water.
In late February of this year, The New York Times revealed that WIS Media Partners, a company Wolkoff had started about six weeks before the inauguration, was paid $25.8 million by the president's inaugural committee for its role in planning the event; they were the largest single vendor. These numbers made headlines because the Trump committee had raised $106.8 million, roughly twice as much as Barack Obama's 2009 committee, and IRS filings showed it spent most of the money on events that were scaled back significantly from past years.
A source told the Times that Wolkoff personally received $1.62 million for her work. Wolkoff told the paper her firm earned that amount "for all of its consulting and creative services, which was divided among our staff of 15 members (including myself).”
In the wake of the Times story, the First Lady's office publicly announced that it would no longer be working with Wolkoff. While multiple sources told the paper that the move was specifically prompted by displeasure from the Trumps over the news that Wolkoff’s firm took such a hefty payday, Wolkoff herself rebuts this.
“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 said via email when Town & Country reached out to her for comment. "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."
The “unpaid” advisor’s departure from the White House is a particularly harsh blow for Wolkoff, who, despite warnings from her high-powered (mostly liberal) New York pals, aligned herself with the Trump administration. Sources within fashion and society circles agree that Wolkoff’s lost connection to Melania Trump will cut deeply for someone whose standing in the fashion industry has slipped in recent years. “This was front page news,” a friend of Wolkoff's told Town & Country. “She will be out with the Trumps.”
All this might come as something of a shock to anyone who knew Wolkoff in 2000. That was the year Stephanie Winston married real estate mogul David Wolkoff at the Pierre Hotel. The couple was featured in a Times "Vows" column that quoted Anna Wintour, a guest at the festivities. “I thought she looked like Audrey Hepburn,'' said the Vogue editor in chief. ''She's immaculate. She makes everyone else feel like a complete mess.''
Wintour had first hired Wolkoff in 1998 to be Vogue’s PR manager. She was promoted a handful of times during her 11 year run at the magazine, and was ultimately given the title of director of special events. Until she left in 2010, Wolkoff worked closely with Wintour, planning events for Vogue including the Metropolitan Museum's Costume Institute Gala, which became, over the years, the most important social event of the season—not just for New Yorkers, but for many in Hollywood too.
During her tenure, according to insiders, Wolkoff primarily oversaw selling tables to high-profile celebrities, socialites, and designers for the event. “It was an incredibly complicated process and [Wolkoff] was adept at moving and managing the process. But Anna ultimately had the final say,” explained a fashion industry source with knowledge of Wolkoff’s time at Vogue.
Her role at Vogue is also how Wolkoff developed what would become a very close friendship with Mrs. Trump. Over the years, the women were often snapped together at parties, including Wolkoff’s glittery 40th birthday in 2011.
Reports leading up to the election noted Mrs. Trump and Wolkoff had lunch together at least once a month and traveled together to the Trumps’ Mar-a-Lago estate in Florida. “They were very friendly and talked often,” the Wolkoff acquaintance says. “Melania was always on her list for events.”
The close relationship between Mrs. Trump and Wolkoff remained, even after the event planner left Vogue in 2009 for a position as the founding fashion director at Lincoln Center. It was one of the few close contacts Wolkoff held on to, according to multiple sources, who paint a picture of Wolkoff’s stint at Lincoln Center—where she worked to bring fashion and celebrity events to the venue and oversaw the move of Mercedes-Benz Fashion Week from Bryant Park to Damrosch Park—as the start of a rockier time.
The fashion source notes that after Wolkoff left Vogue, she struggled to replicate her success with the Met Ball. “When she went to Lincoln Center her experience was dealing with people—not production,” said the source who explained that once she was out from under Wintour’s wing, the people Wolkoff relied on to buy pricey tables at her events became harder to secure. “When you are calling on behalf of Anna Wintour, people pick up the phone for you.”
In 2012, Wolkoff left her role as fashion director at Lincoln Center to launch her own agency, SWW Creative, to “provide creative collaboration within the spheres of fashion, beauty and entertainment” for clients such as IMG, CFDA, and Lincoln Center. (It is unclear what the current status of SWW is; the firm has no apparent website or phone number.) In the years that followed, Wolkoff worked to raise her own personal profile, offering herself up to lifestyle publications which featured everything from her home to her wardrobe to her favorite places to eat and shop.
Still, maintains the fashion source, Wolkoff had another side to her. The social powerhouse was known for throwing her influence behind causes she cared about. “She was always focused on charities,” the source says of Wolkoff, who worked with the Sean N. Parker Center for Allergy Research at Stanford University, New Yorkers for Children, and the UN Women for Peace Association. “She was always involved with her kids, very focused on them. She could be a very giving person, and, when she shined her light on you, it was incredible.”
But as she drifted further from her Vogue-established social and professional circles, Wolkoff’s light became more laser-focused on Mrs. Trump. The friendship between the women, who both happen to be strikingly tall (Mrs. Trump is 5’11, Wolkoff is 6’1) endured, even as Wolkoff’s friends encouraged her to steer clear of the Trumps when they began their bid for the White House. “All of [Wolkoff’s] friends told her that working with the Trumps was a bad idea. Everyone told her it would ruin her career,” added the former friend.
The advantages for the Trumps, on the other hand, were clear. For the future First Lady, having someone high-profile like Wolkoff in her corner was a boost, particularly in contrast to her controversial husband. While Trump boasted often on the campaign trail that he would surround himself with “the best people,” when it came time to plan his inauguration, he had trouble attracting any celebrities as either guests or entertainment. When Wolkoff joined Mrs. Trump’s team, it signaled a rare stamp of approval from a high-profile, well-connected person in the fashion industry—and at a time when many designers making public announcements, in the wake of the election, about their unwillingness to style her.
Wolkoff clearly hoped the negative press would blow over—and that she could play a role in building Melania Trump’s profile as First Lady, traditionally a position that commands great respect and deference from the fashion world. “[Wolkoff] went to work for the Trumps because she wanted to stay relevant. She really saw working with Melania as an opportunity to get back with top designers,” adds the former friend. “[Wolkoff] probably did think Melania could help her get back into the fashion circles,” confirms another insider. “But why would she think that? Most of the fashion world was pro-Hillary.”
Though a spokeswoman for Mrs. Trump did not return our request for comment for this story, Wolkoff told us, “I expect to remain a trusted source for advice and support on an informal basis.”
The former pal, however, considers this outcome unlikely. "Melania really can’t be seen as supporting [Wolkoff] publicly after this," said the friend. “It’s doubtful they will remain as close as they were before.”
In this respect, at least, Wolkoff has plenty of company. She is certainly not the first Trump insider to find herself in the crosshairs of bad press once the Trumps no longer find her friendship—or high profile connections—useful.
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