SEPTEMBER 2019 VANITY FAIR 121
still reside. “She’s still gorgeous!” Rautbord
says of Audrey, 90.)
After receiving a degree in history, Pritz-
ker returned to the Army, was commissioned
as a captain, and served in the 101st Airborne
Division, at Fort Campbell, Kentucky, and
the VII Corps in Germany. While promotions
came, “my family life was suffering,” she
says. Daughter Tal was born at Fort Camp-
bell in 1982, during Pritzker’s first marriage,
to Israeli-born Ayelet ben Mordechai, which
ended in divorce in 1987. She then married
Lisa Goren, an Illinois native, and they had
Andrew and William before the marriage
ended in 1997.
After transferring to the U.S. Army
Reserve and then the Illinois National Guard,
Pritzker retired at the rank of lieutenant colo-
nel and received an honorary promotion to
full colonel, along with more than 20 military
awards. “I did not have a particularly heroic
or distinguished career, but I did interesting
things,” she says.
As her military career ended, Pritzker
became increasingly active in Republican
Party affairs. Cousin J.B.’s recent gubernato-
rial run highlighted political divisions in the
family. Shortly before he entered the race,
J.B. tweeted, “As a protest against Trump’s
rescinding protections for trans kids, every-
one should use the other gender’s bathroom
today! #protecttranskids.” It backfired, with
all sides pouncing on him. One Democrat
accused him of playing “right into transpho-
bic rhetoric.”
Not long after that, at a groundbreaking
ceremony for one of her developments, a
Tribune reporter managed to ask Jennifer
if J.B. could expect her vote. “If he wants to
run, that’s his privilege.... I don’t know where
his current positions are, so...I can’t really
answer that now.”
“I think he was trying to be supportive,”
Jennifer told the same reporter about J.B.’s
tweet. “I don’t think he realized that informal
comments on social media become world
news quickly.”
J.B. issued a statement: “I have nothing
but love and respect for my cousin Jennifer.
While we belong to different political parties,
we share a deep respect for individual civil
rights. I have and always will support her.”
Did he get her vote in the end? “She’d like
to pass on this question,” says a communica-
tions aide, two of whom sat silently through
our interview.
Along with his wife, M.K., and their foun-
dation, J.B. was the third-largest contributor
to Hillary Clinton’s 2016 campaign, with
$12.6 million in donations. Jennifer, mean-
while, has ponied up “in excess of seven fig-
ures” over her lifetime, she says, to Republi-
can candidates.
“I think they’ve just accepted the fact that
I vote for who I vote for and write checks for
who I do, and they vote and write checks for
who they do,” she comments. After a slight
pause, Jennifer adds, wryly, “My mother
voted for Eisenhower.”
“She does stand out in that way,” cousin
Nick told me by phone from his home in San
Francisco, speaking of Jennifer’s political
leanings within the family. “She is a really
admirable person. I have one point of view
on a person and another of their political
views. I don’t conflate the two. I am not
offended by Republicanism per se. I am
offended by Republicanism as expressed by
this administration.”
The greater Pritzker clan has long dis-
liked Donald Trump for reasons nonpoliti-
cal too. In 1979, they became his partner in
developing the Grand Hyatt Hotel, in New
York—Trump’s first major project. It was a
rancorous and litigious relationship from
which the Pritzkers extricated themselves
in 1996, when they bought out Trump’s
half-interest.
As Trump began his candidacy, Jennifer
says, she supported him for various reasons:
“I did not want to see President Hillary
Clinton. I had a lot of problems with her,
and her husband. I took a rather optimis-
tic view of Trump. I thought that because
he wasn’t a politician he would be willing
to take some risks that professional poli-
ticians wouldn’t. I thought he would take
more favorable positions on taxes and gun
control. And I thought he would be at least
as LGBTQ-friendly as any Democratic can-
didate.” She was “disturbed” when Trump
referred to McCain as a loser but still hung
in: “I recognized he had a tendency to say
impulsive things, but I felt a lot of his posi-
tions were ones I could agree with.”
Cut to July 2017.
“Well, that tweet hit close to home,” she
says. “One ‘Aw, shit’ wipes out a thousand
attaboys.”
“It was his impulsiveness, his lack of
thought, that I resent most,” she continues.
“The military had done all kinds of surveys
and studies evaluating whether the policy
was feasible. Then he just arbitrarily said
transgenders couldn’t serve.
“I don’t know what he was really trying
to accomplish—to placate the extreme end
of his party, or create a bargaining chip for
the wall? Well, I don’t want to see my life
and the life of people like me become a
political poker chip. I felt he disrespected a
whole category of people in a really thought-
less way, and if he disrespects one category,
everybody is subject to that. Everybody has
the right to be considered on their own
merits.” Though she still considers herself
a Republican, she says the party will have to
work for any future largesse from her. “If I do
donate, it will be on a more selective basis,”
she says. “I’m going to want to see more of
a solid track record.”In recent years Pritzker, who also serves
on the board of the Chicago Symphony
Orchestra, has tapped into her vast coffers
to support trans rights. Her gifts include $6.5
million to the Program of Human Sexuality
at the University of Minnesota; $5.99 million
to Palm Center, an LGBTQ think tank, for a
study on trans people in the military; $2 mil-
lion for the world’s first chair of trans studies,
at the University of Victoria, British Colum-
bia; $1 million to Lurie Children’s Hospital of
Chicago for a Gender and Sex Development
Program; and $50,000 for the first trans-
study course at the University of Toronto.
“I don’t know what the solutions are, but I
think people with an M.D., such as the physi-
cians at Lurie Hospital, are more likely to find
the answers than politicians in Washington,”
she says. “Nobody is 100 percent male or
female. It’s difficult to make a precise science
out of it, but the emotions are real.”
And is she being received with open arms
by the LGBTQ establishment? “That the mil-
itary ban is the only thing about Trump that
has upset her is horrendous,” the director of
one of the leading national advocacy groups
tells me, fuming—the request for anonymity
was out of deference to the family at large.
But Sarah Kate Ellis, president and CEO
of GLAAD, the world’s largest LGBTQ
media advocacy organization, offered a
very positive assessment: “Colonel Pritz-
ker’s voice has been very critical to the
debate about transgender military service,
not just because she is a veteran who under-
stands what it means to prioritize military
readiness, unit cohesion, recruitment, and
retention, but also because she reminds us
that this is not—and never should be—a
partisan political issue. It’s simply doing
the right thing.”
On April 4—a week before the military ban
went into effect—the PMML and GLAAD
cosponsored a high-powered panel discus-
sion on transgender military service on
Capitol Hill. Speakers included Nancy Pelosi,
Congressman Joe Kennedy, and (via video
message) Pritzker. “It’s critical that we stand
together, in spite of party lines, to support our
transgender service members, as they have
stood for us,” she said.
On a grassroots level, Pritzker’s leader-
ship is appreciated, too. “The number-one
thing she has done for the trans commu-
nity is just being visible,” says Myles Brady
Davis, press secretary at Equality Illinois
(and a trans man). “Visibility is a luxury a
lot of trans people cannot afford. It can cost
them friends, jobs, housing—even their lives.
So her stepping up and saying, ‘This is who I
am’—that saves lives.”
Jennifer’s greatest admirers have known
her since she was a baby. “I always thought
she was the bravest person in our family,”
says John Pritzker, 66, another first cousin.
“She’s always been very much her own