august 5–18, 2019 | new york 31
around the block if she saw him getting out of a car in front of her.
When Ivanka would receive a call with his number on the caller ID,
she’d become very anxious. She’d have a momentary panic about
what he was going to say about her life and whether she was about
to be blindsided by his disapproval. “I think she knew,” the friend
says, “and at times resented, that she was a prisoner to the condition
of seeking his approval at all times.” When they’d talk, “she was very
careful. It was like listening to a person talking to her boss.”
But in her father’s presence, Ivanka never talked back or even
rolled her eyes. Friends I spoke with have not seen them fight. She
played the dutiful daughter on flights to Mar-a-Lago with her
friends when her father would do cringey things like put a VHS tape
of his recent media clips on the TV or ask them which female starsthey considered hot. Among the members of New York society in
the ’90s and early aughts, he was seen as a credit clown, a joke, but
never to Ivanka. His chauvinism frustrated her, however, and she
was repelled by the way he talked about women’s bodies—who was
fat, who was not. In 2003, when Paris Hilton’s sex tape was leaked
on the internet, Donald wouldn’t stop talking about it, saying, “Paris
is laughing all the way to the bank, she’s got the last laugh, she’s
marvelous.” Ivanka could not believe her father was not only idol-
izing an airhead heiress caught blowing a guy on a night-vision video
but encouraging her to follow Paris’s lead. (Speaking from the White
House, Grisham says, “This is untrue and is disgusting.”)
“The thing with Paris hurt Ivanka a lot,” says a friend. “He was
heartbreaking to her at times.” But as with so much of her father’s
behavior, she buried her feelings and moved on. She told herself that
the story of her father’s attitude toward women was, simply, compli-
cated, according to friends. Donald hired many women at the
Trump Organization, she knew, and these women weren’t univer-
sally pretty; he wanted to employ women with traditionally mascu-
line attitudes and almost enjoyed feeling discomfited by them, hav-
ing them boss him around. Her father may have had issues with
women, she felt, but he did not meet the textbook definition of a
misogynist—a belief she seems to hold to the present day.
Unlike Don Jr.—who enrolled at Donald’s alma mater, the Uni-
versity of Pennsylvania, after Donald had reportedly smoothed the
path—Ivanka went to Georgetown, a university without a connec-
tion to the Trump family, but transferred to Penn her junior year.
After graduating with a degree in finance and art history, she signed
up at real-estate developer Forest City Ratner but went to work for
her father a year later, like many heirs to the city’s real-estate for-
tunes. What was behind these decisions? “Ivanka always has to
prove to herself that she’s gotten ahead on her own without her
father,” says a friend. “She really has no idea she’s privileged. She
genuinely thinks she’s earned everything she has. She goes on and
on all the time about how hard she works.” Did she work hard?
“Sure, but she works hard the same way everyone works in New
York—she still goes to the gym and meets friends for dinner.”
In New York in her early 20s, Ivanka ran with a cool after-hours
cr owd even though she was transformingran around naked. Classmates who remained at home heard about
the trip in excruciating detail and felt horribly left out. But Ivanka
wasn’t trying to hurt anyone. There was simply a natural order to
things, and in that order she was at the top and others were at the
bottom, and she felt no need to exert herself to make anyone more
aware of this fact. They knew.
In her rebellious phase, she dyed her hair blue, listened to grunge
and country music, and cried over Kurt Cobain’s death, none of
which her parents were excited about. She also developed another
habit that friends say her father did not like—she became a prodi-
gious reader of great novels, burying her nose in Fitzgerald,
Hemingway, Austen, Morrison. In her 20s, she said her favorite
book was Ayn Rand’s Atlas Shrugged and she had modeled herself
on its capitalist heroine, Dagny Taggart.
“Her father hated that Ivanka was a major reader;
she’ll never admit this, but I think it threatened him,” says
an old friend. In truth, father and daughter kept to them-
selves. Ivanka mostly grabbed her father’s attention
either by flattering him or by appearing at the moment
he had someone important on speakerphone, when he’d
let loose a series of weird rhetorical questions for the VIP:
“Isn’t my daughter Ivanka the best? Isn’t she the great-
est?” When she began modeling at 15 in the late 1990s,
blossoming into a gorgeous girl with the oversize features
and blonde hair of ’60s Italian film star Monica Vitti,
muse of director Michelangelo Antonioni, he amped up
another question: “Isn’t she the most beautiful girl you’ve
ever seen?” When asked about the president complimenting
Iv anka, Stephanie Grisham, the White House press secretary, says,
“The president makes no secret of the fact that he is proud of his
daughter.” She adds, “To say her father was threatened by her in any
way—much less for reading—is not only false but laughable.”
Though Ivana drank, Donald had been living clean after his
ol der brother died of alcoholism in 1981; that death is “absolutely”
th e reason Donald became so fixated on success, on overturning
th e failures of the past, says Nikki Haskell, an old family friend.
So when Ivanka started smoking, drinking, taking drugs, hanging
out at bars and nightclubs, and making out with guys on pool
ta bles at pre–voting age, she had to keep all of that secret from her
fa ther, and it does not seem he has ever known about it or wanted
to know. Even a decade ago, she was telling Oprah, “I’ve never been
very interested in being sort of a wild party girl—an ‘It’ girl. My
father is very strict ... No drugs, no drinking, no smoking.” Though
she was occasionally photographed smoking, friends say Ivanka
never developed a drinking problem, and when Don Jr. did, she
covered up for him as best she could.
She’s always “the same consistent friend,” says Maggie Cordish,
a friend and former adviser. “She hopped on a train to Baltimore
when I had a family issue. She was there four hours later.” She was
the protector of her brothers, and they remain close to this day.
She wasn’t a tomboy back then, but she was a girl’s girl—she was
into loyalty, she had her friends’ backs, she didn’t try to steal their
boyfriends even if she could. The issue, others say, was she thought
only about ... herself. That’s the No. 1 thing friends from her past
say about her: She isn’t a “mean person” or a “bad person” but is
simply aff licted with the same disease of narcissism as her father.
She is the movie projector and the screen.
But not when her father was involved. She operated in fear
around him, says a friend. Sometimes she would tell a taxi to drive(Continued on page 78)➨ A ten-part narrative podcast series,
TABLOID, produced by New York
and hosted by Vanessa Grigoriadis,
premieres August 5 on Luminary
(luminary.link/tabloid).“CLEOPATRA? DRUSILLA,sister of CALIGULA?DIANE DE POITIERS?Ivanka Trump would be in that mix.”Y ___ DD ___ AD ___ PD ___ EICTRANSMITTED________ COPY ___ DD ___ AD ___ PD ___ EIC1619FEA_Ivanka_lay [Print]_35541681.indd 31 8/2/19 5:51 PMaugust5–18, 2019 | newyork 31around the block if she saw him getting out of a car in front of her.
When Ivanka would receive a call with his number on the caller ID,
she’d become very anxious. She’d have a momentary panic about
what he was going to say about her life and whether she was about
to be blindsided by his disapproval. “I think she knew,” the friend
says, “and at times resented, that she was a prisoner to the condition
of seeking his approval at all times.” When they’d talk, “she was very
careful. It was like listening to a person talking to her boss.”
But in her father’s presence, Ivanka never talked back or even
rolled her eyes. Friends I spoke with have not seen them fight. She
played the dutiful daughter on flights to Mar-a-Lago with her
friends when her father would do cringey things like put a VHS tape
of his recent media clips on the TV or ask them which female starstheyconsideredhot.AmongthemembersofNewYorksocietyin
the’90sandearlyaughts,hewasseenasa creditclown,a joke,but
nevertoIvanka.His chauvinismfrustratedher, however,andshe
wasrepelledbythewayhetalkedaboutwomen’s bodies—whowas
fat,whowasnot.In 2003,whenParisHilton’ssex tapewasleaked
ontheinternet,Donaldwouldn’t stoptalkingaboutit, saying,“Paris
is laughingallthewaytothebank,she’s gotthelast laugh,she’s
marvelous.” Ivankacouldnotbelieveherfatherwasnotonlyidol-
izinganairheadheiresscaughtblowinga guyona night-visionvideo
butencouragingherto followParis’slead.(SpeakingfromtheWhite
House,Grishamsays,“Thisis untrueandis disgusting.”)
“ThethingwithParishurt Ivankaa lot,” saysa friend.“He was
heartbreaking to her at times.” But as with so much of her father’s
behavior, she buried her feelings and moved on. She told herself that
the story of her father’s attitude toward women was, simply, compli-
cated, according to friends. Donald hired many women at the
Trump Organization, she knew, and these women weren’t univer-
sally pretty; he wanted to employ women with traditionally mascu-
line attitudes and almost enjoyed feeling discomfited by them, hav-
ing them boss him around. Her father may have had issues with
women, she felt, but he did not meet the textbook definition of a
misogynist—a belief she seems to hold to the present day.
Unlike Don Jr.—who enrolled at Donald’s alma mater, the Uni-
versity of Pennsylvania, after Donald had reportedly smoothed the
path—Ivanka went to Georgetown, a university without a connec-
tion to the Trump family, but transferred to Penn her junior year.
After graduating with a degree in finance and art history, she signed
up at real-estate developer Forest City Ratner but went to work for
her father a year later, like many heirs to the city’s real-estate for-
tunes. What was behind these decisions? “Ivanka always has to
prove to herself that she’s gotten ahead on her own without her
father,” says a friend. “She really has no idea she’s privileged. She
genuinely thinks she’s earned everything she has. She goes on and
on all the time about how hard she works.” Did she work hard?
“Sure, but she works hard the same way everyone works in New
York—she still goes to the gym and meets friends for dinner.”
In New York in her early 20s,Ivankaranwitha coolafter-hours
cr owd even though she was transformingran around naked. Classmates who remained at home heard about
the trip in excruciating detail and felt horribly left out. But Ivanka
wasn’t trying to hurt anyone. There was simply a natural order to
things, and in that order she was at the top and others were at the
bottom, and she felt no need to exert herself to make anyone more
aware of this fact. They knew.
In her rebellious phase, she dyed her hair blue, listened to grunge
and country music, and cried over Kurt Cobain’s death, none of
which her parents were excited about. She also developed another
habit that friends say her father did not like—she became a prodi-
gious reader of great novels, burying her nose in Fitzgerald,
Hemingway, Austen, Morrison. In her 20s, she said her favorite
book was Ayn Rand’s Atlas Shrugged and she had modeled herself
on its capitalist heroine, Dagny Taggart.
“Her father hated that Ivanka was a major reader;
she’ll never admit this, but I think it threatened him,” says
an old friend. In truth, father and daughter kept to them-
selves. Ivanka mostly grabbed her father’s attention
either by flattering him or by appearing at the moment
he had someone important on speakerphone, when he’d
let loose a series of weird rhetorical questions for the VIP:
“Isn’t my daughter Ivanka the best? Isn’t she the great-
est?” When she began modeling at 15 in the late 1990s,
blossoming into a gorgeous girl with the oversize features
and blonde hair of ’60s Italian film star Monica Vitti,
muse of director Michelangelo Antonioni, he ampedup
another question: “Isn’t she the most beautiful girl you’ve
ever seen?” When asked about the president complimenting
Iv anka, Stephanie Grisham, the White House press secretary,says,
“The president makes no secret of the fact that he isproudofhis
daughter.” She adds, “To say her father was threatenedbyherinany
way—much less for reading—is not only false but laughable.”
Though Ivana drank, Donald had been living cleanafterhis
ol der brother died of alcoholism in 1981; that death is“absolutely”
th e reason Donald became so fixated on success, onoverturning
th e failures of the past, says Nikki Haskell, an old familyfriend.
So when Ivanka started smoking, drinking, taking drugs,hanging
out at bars and nightclubs, and making out withguyson pool
ta bles at pre–voting age, she had to keep all of that secretfromher
fa ther, and it does not seem he has ever known about it or wanted
to know. Even a decade ago, she was telling Oprah, “I’ve never been
very interested in being sort of a wild party girl—an ‘It’girl. My
father is very strict ... No drugs, no drinking, no smoking.”Though
she was occasionally photographed smoking, friends say Ivanka
never developed a drinking problem, and when Don Jr.did, she
covered up for him as best she could.
She’s always “the same consistent friend,” says Maggie Cordish,
a friend and former adviser. “She hopped on a train to Baltimore
when I had a family issue. She was there four hours later.”She was
the protector of her brothers, and they remain close to this day.
She wasn’t a tomboy back then, but she was a girl’s girl—she was
into loyalty, she had her friends’ backs, she didn’t try to steal their
boyfriends even if she could. The issue, others say, was shethought
only about ... herself. That’s the No. 1 thing friends from her past
say about her: She isn’t a “mean person” or a “bad person” but is
simply aff licted with the same disease of narcissism as her father.
She is the movie projector and the screen.
But not when her father was involved. She operated in fear
around him, says a friend.Sometimesshewouldtella taxitodrive
(Continued on page 78)➨ A ten-part narrative podcast series,
TABLOID, produced by New York
and hosted by Vanessa Grigoriadis,
premieres August 5 on Luminary
(luminary.link/tabloid).“CLEOPATRA? DRUSILLA,sister of CALIGULA?DIANE DE POITIERS?Ivanka Trump would be in that mix.”