122 VANITY FAIR SEPTEMBER 2019
person. My feeling about her transition
was, thank God, because it gave her the
freedom to be exactly who she is. It makes
us a more interesting family, too! As a kid,
she had all these toy soldiers,” John adds.
“But she wasn’t just playing around. She
would re-create Napoleonic battle scenes.
Intellectually, she is maybe the smartest
person in our family.”
“She is incredibly courageous,” says Nick
Pritzker, 73. “I am very happy she is able to
be who she is. I am confident that represents
the view of all of my generation and below.
I can’t speak for the last generations. But I
know my cousins well enough to know that
they are all very supportive of her.”
Even for a billionaire with a loyal family,
transitioning is arduous. “I’ve had troubles
and woes being transgender. Anyone who
is does,” she says. “Anyone who’s transgen-
der, I think, has, like, this inner compass.
Whenever it is used, it will point to true
north. Femininity is my true north. I think
I had these feelings going all the way back
to when I was a child. I had a dual current.
I had a male body, but I would gravitate to
feminine things, like wanting to dress. In my
youth, in a lot of places, it was against the law.
And forget about going in the Army.”
For years, Pritzker cross-dressed in pri-
vate. “It was a vehicle, a tool, to take you to
another state. I discovered that I really do
think of myself inwardly as a female. I don’t
deny biological reality. I was born with a male
body. But the whole point of being transgen-
der is that human beings are complex and
multidimensional. It is possible to have a
person who has the physical characteristics
of one sex but the emotions and psychologi-
cal makeup of the other.”
Now that she is out, she says dressing has
become a little more “complicated.” “I like to
wear dresses or skirts, but I want stuff that’s
functional, that I can move in. I don’t like
pantyhose. I have found that a way to accom-
plish that mission is with bike shorts. I tend
to gravitate to classical clothing. I wear a lot
of things that could have been worn 50 years
ago. I have impressions in my mind of things
people wore when I was a child. The hard-
est thing for me is finding shoes. By women’s
standards I’ve got gunboats, though by male
standards my feet are pretty average.”
At large in Chicago society, Jennifer is
admired for her increasing activism and
visibility. A man-about-town remarked of
the “frisson” that fills a room when Jen-
nifer walks in. “It’s like, forget Abra—Jen-
nifer’s here!” he said, referring to Abra
Rockefeller Prentice Wilkin, the longtime
queen of Chicago society. “I love Jennifer!”
says Rautbord. “She’s one of the best people
on the planet.”
Such supportive community members
eased Pritzker’s transition, though it was
not her choice to make it public so quickly.
“The media didn’t really give me an oppor-
tunity to come out in a more orderly fash-
ion,” says Pritzker. “I wanted to release it on
terms that would be least stressful for my
family and the people I work with. They had
a right to know and needed to know. Unfor-
tunately, the letter I wrote to the folks in my
organization got leaked.”
Though Pritzker says there were some
“tough times” with her sons, now 24 and27, in her transition process, she now enjoys
good relationships with them, as well as with
her daughter, 38, a married mother of three.
“There’s still a little bit of ambiguity. I’m still
their grandfather, regardless of the exterior,”
Pritzker says. “So, they refer to me as Grand-
pa Jen. But they use the female pronoun.”
Some people in her life occasionally slip
up and use the old name and pronoun, she
says: “I just sort of smile. If they are having
a little trouble, I just say, ‘Pronouns,’ that’s
all. I know that when people do it, they are
not intending to be demeaning or derogatory.
Things just take a while to sink in. I mean,
I still refer to where the White Sox play as
Comiskey Park.”
When I ask Jennifer if she has a romantic
partner, both press aides speak up: “We’re
not commenting on that.”“I had reached the point where I was tired
of fighting it out within myself. The world
had become a more tolerant place. At least
I wouldn’t get arrested. And my children
were grown,” says Pritzker of her decision
to transition. “Now I feel a lot calmer. I find
I am able to think more clearly, because I
don’t have those inner conflicts anymore.
I have come to accept who I am and try
to make the best of it. Overall, I would say
it’s a net gain.”
Throughout the interview, I had been
admiring the lovely gold medallion on her
neck. As we wrap up, I ask about it. “It’s a
golden dollar issued by the U.S. Mint—the
head of Sacagawea,” she says. “I wore it today
because I figured, if she could get Lewis and
Clark halfway across the continent, from the
Mississippi to the Pacific, well, maybe she’ll
get me through this interview.”of the figures’
resemblance to the racist caricatures in the
1899 children’s book Little Black Sambo. “His-
tory cannot continue to repeat itself,” Ezie
wrote. “Black America deserves better. And
we demand better.” Prada (the company)
pulled the figurines and issued a blanket
apology which read, in part, “Prada Group
never had the intention of offending anyone
and we abhor all forms of racism and racist
imagery.” It’s a familiar refrain, a version of
which was delivered by Dolce and Gabbana
earlier that month, following a set of ads
showcasing Chinese model Zuo Ye attempt-
ing to eat Italian food with chopsticks, and
another issued by Gucci two months later,
after its release of a sweater with a balaclava
collar that evoked blackface.
In most of these cases, the product is
pulled, the apology is issued. But in the
wake of what Prada herself soberly refers
to as “this mistake,” she had a conversation
with Theaster Gates. “What can we do to use
this occasion to make things even better,” he
says he asked her, “to check our designers
and say, ‘Even with good intentions, some-
times racist images spew out’? How do we
deal with that?” Last February, Prada Group
launched a Diversity and Inclusion Advisory
Council, cochaired by Gates and Duvernay
and advised by Harvard professor Sarah
Lewis. The council, in its early stages at press
time, is focused on educational efforts and
broadening internal conversations, bothwithin Prada and the industry at large. (Two
days after Prada’s announcement, Gucci
released a set of initiatives aimed at upping
awareness, diversity, and inclusion.) “What
is your practice? What has been comfort-
able in the past?” Duvernay says she has put
to Prada’s team. “What I really talked with
them about is not being performative in this
process. I don’t feel like there needs to be a
public presentation of what they plan to do.
They just need to do it.”
Prada seems motivated by the challenge.
“The whole world is full of so many different
cultures and religions and races,” she says.
“We should start embracing diversity of any
kind. The fact seems that it’s happening more
or less the opposite.” Nationalism is growing,
she says. I think of the U.S.-Mexico border
wall; she mentions Europe.
Other concerns are being addressed
within the brand. This summer, after years
of research and experimentation, the com-
pany released its first pieces made fromMiuccia Prada
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Pritzker’s Politics