10 The Times Magazinegot burnt,” admits Stephanie Winston
Wolkoff, a glossy, groomed, Upper East
Side Icarus. “But I did it for all the right
reasons – it was an opportunity to make
a difference.” Unfortunately, the sun she
flew too close to was the gaudy, garish,
gold-plated glow of Donald Trump, his
glamorous, inscrutable wife, Melania,
and the hubris and hoopla of the court
that surrounds them. But, unlike that
of Greek mythology’s winged son, Winston
Wolkoff’s weakness wasn’t ambition, she
insists. “My Achilles’ heel is my loyalty,” she
says, with an earnest self-regard that only
Americans or people in fashion can ever truly
muster (Winston Wolkoff happens to be both).
“I am a pleaser,” she continues. “I’m
to blame for where I put myself. But my
relationship with Melania bankrupted
me. Not just financially, but emotionally,
psychologically, physically – she bankrupted
me to the core.”
But, bruised and “betrayed”, Winston
Wolkoff, 51, is “not backing down”. Instead,
she’s dishing the dirt on their 15-year
friendship in print: Melania and Me: The
Rise and Fall of My Friendship with the First
Lady is already a New York Times bestseller.
Trump’s Justice Department filed a lawsuit
in October claiming Winston Wolkoff violated
the terms of a nondisclosure agreement with
the book’s publication, and alleges the author’s
friendship with the now former first lady has
been “overstated”. Winston Wolkoff claims
that every allegation made in the book can
be backed up with documents – emails, texts,
recorded phone calls. “It’s not based on my
memory, so nothing can be refuted,” she says.
It is, of course, not the first bombshell book
to come out of the recently departed Trumps’
incendiary four years in the White House,
but it is possibly the most intimate, an account
of Winston Wolkoff’s relationship with the
former first lady, and, ultimately, its bitter
dissolution after, according to the former,
she was “used” then “thrown under the bus”,
“falsely framed” by the Trumps and their
stooges – the fall guy, she says, for serious
financial irregularities, cronyism and possible
serious corruption.
Furthermore, she believes she was specially
selected for that role from the start. “I know
it sounds a little crazy, but I was picked by
Donald. I was ‘approved’.” At 6ft 1in, with
model proportions, Trump’s approval of her is
not difficult to imagine at all. “I was an It girl
for him, so I was allowed in that circle. I could
make the calls. I had the access,” she says.
Certainly, her CV before she became
entangled with the Trumps was impressively
glitzy. After several years at Sotheby’s in New
York, where she worked on the auction of
Jackie Kennedy Onassis’ estate, she landed a
job at Vogue, first in public relations, then asdirector of special events, organising parties
and benefits for the magazine, and overseeing
the Metropolitan Museum of Art Costume
Institute Gala, aka the Met Gala, the most
high-profile event on the fashion calendar.
As befits a well-connected Manhattanite,
Winston Wolkoff is also heavily involved with
philanthropy, sitting on the boards of multiple
charities, supporting children’s mental health
initiatives and throwing regular fundraisers.
But she doesn’t, she stresses, hail from the
society pages. She was raised in the Catskills
in upstate New York, in upper middle-class
comfort – she and her brothers attended elite
east coast boarding schools – but was not, she
says, drily, “a diamond heiress”. That changed
somewhat after her parents divorced while she
was in high school, and her mother married
Bruce Winston, son of diamond jeweller
Harry Winston, who adopted Stephanie as
his legal daughter.
Her own wedding, at the age of 30, to
wealthy real estate agent David Wolkoff,
was in front of 300 guests, including Vogue’s
editor-in-chief, Anna Wintour, and its former
editor-at-large, André Leon Talley, at New
York’s historic Pierre hotel.
Winston Wolkoff is certainly a force to
contend with, even over Zoom. She speaks
at three times the pace of anyone I’ve ever
encountered, and ten minutes go by before she
pauses for long enough for me to interject an
actual question. She cries twice in the course
of our intense, two-hour conversation, forwhich she apologises. “I have major PTSD
[post-traumatic stress disorder],” she says.
“I know she cared about me, like I know
she cared about children,” she says of Melania.
“But then she wore that jacket [the notorious
Zara jacket with the words, “I really don’t care,
do u?” on the back as she boarded a plane to
visit immigrant children separated from their
parents at the Texas border]. It’s so confusing.
I wrote the book because I needed to put the
truth out there, but also to try to make sense
of what happened.”
I’m not sure that she has, entirely. Both
in the book and in person, Winston Wolkoff
ricochets between fangirling her former friend- “She exudes this warmth. She draws you
in,” she says. “Being with her was like having
the sister I never had before, but a really
confident, perfectly coiffed, ultimate older
sister” – and unvarnished attacks on her:
“She talks out of both sides of her mouth”;
“She has no moral compass”.
Winston Wolkoff is, perhaps, still a little
too close to the situation to make real sense of
it. And, after two hours, I am left wondering
to what extent she was always tightly wound
and somewhat paranoid, and to what extent a
deep and damaging immersion in the toxicity
of Trumpworld made her that way. At one
point, she mouths something silently at me,
repeatedly, that I can’t catch. Is Melania a
what? She scribbles frantically on a notepad
and holds it up to her camera. “A spy?”
The two statuesque brunettes first met
‘
I
With her husband, David Wolkoff, and the Trumps in 2008PREVIOUS SPREAD: BFA. THIS SPREAD: GETTY IMAGES