In 1881, Naphtali ben Yakov Pritzker
arrived in Chicago, a 10-year-old pen-
niless Jewish immigrant from Ukraine.
Nicholas, as he later was known, taught
himself English, worked his way through
law school, and opened a law firm, which
thrived. Today, his descendants rank as
America’s seventh-richest family, with
a $29 billion fortune derived from in-
vestments, a conglomeration of nuts-
and-bolts manufacturing businesses,
and Hyatt Hotels.
Several Pritzkers are currently well-
known. Jay Robert (known as J.B.) be-
came governor of Illinois in January, and
his sister, Penny, served as commerce
secretary in the Obama White House.
But the family has always closely guard-
ed their privacy.
Thus, there was some surprise in
Chicago nine years ago when the Naph-
tali ben Yakov Pritzker American History
Wing was inaugurated at the venerable
Chicago History Museum. In addition
to its lead show, Facing Freedom in
America, the wing featured a permanent
Pritzker family history exhibition, which
included a family tree. Here, one could
scroll down and see the name of James
Nicholas Pritzker—a great-grandchild of
Naphtali and the lead benefactor of the
new wing—annotated by birth (1950),
marriages (two), children (three), and
career (colonel, Illinois National Guard;
lieutenant colonel, U.S. Army, retired;
Cold War era, Vietnam era, Antarctica,
U.S. Army; U.S. Army Reserve, Illinois
Army National Guard, 1974–2001).
But around the end of 2013, an altera-
tion was made on the tree, one that few
people saw coming: “Jennifer Natalya
Pritzker born as James Nicholas Pritz-
ker.” The world’s only known trans-
gender billionaire had, in fact, quietly
announced herself a few months previ-
ously, in a private email sent to business
THOMAS (TOM)
PRITZKER
Chairman and CEO
of the Pritzker
Organization.
JOHN PRITZKER
Avid art collector;
funded the
Pritzker Center
for Photography
at SFMoMA.
DAN PRITZKER
Director/
musician; spent
over a decade
and more than
$50 million
producing and
directing a Buddy
Bolden biopic.
GIGI PRITZKER
Cofounded
Madison
Wells Media,
MWM, where
she produces
big-budget
Hollywood films.
NANCY
PRITZKER
(1948–1972)
ABRAM NICHOLAS (A.N.) PRITZKER
(1896–1986)
JAY PRITZKER
(1922–1999)
I
associates: “As of Aug. 16, 2013, J.N.
Pritzker will undergo an official legal
name change, will now be known as
Jennifer Natalya Pritzker. This change
will reflect the beliefs of her true identity
that she has privately held and will now
share publicly. Pritzker now identifies
herself as a woman for all business and
personal undertakings.”
A week later, Crain’s Chicago Business
broke the story. For all the family’s stat-
ure, the story stayed curiously below the
radar nationally, perhaps because Colonel
Pritzker was so little known—by choice.
(The Chicago Tribune described her as
“exceptionally private,” while Crai n’s
called her “ever-private.”) And perhaps
the country wasn’t ready for this conver-
sation. It would be another two years be-
fore Caitlyn Jenner announced herself (in
the July 2015 issue of Vanity Fair).
P
ritzker has remained press shy,
but she has been anything but
idle. In 2003, two years after
retiring from the military, the colonel
founded the Pritzker Military Museum
& Library (PMML), which expanded in
2011 when it moved into the landmark
16-story Monroe Building in the Loop,
which she purchased for $31.2 million,
then meticulously restored.
While the PMML occupies three
floors, another houses entities run by
Pritzker under her umbrella company,
TAWANI Enterprises: a private-wealth
firm, which manages a diversified port-
folio of business investments, including
real-estate development and manage-
ment, hospitality assets, book publish-
ing, and a precious-metals trading firm.
Under the same roof are the Pritzker
Military Foundation and the TAWANI
Foundation, which dispensed about
$28 million in grants in the past two
years. TAWANI is an amalgam of the
names of Jennifer’s three children: Tal,
37, Andrew, 27, and William, 24. All three
sit on the foundation’s board.
Pritzker has also been highly active in
politics. In the view of some, the startling
thing about her is her choice of party. The
Pritzker clan has long been decidedly so-
cially liberal and Democratic—the gover-
nor and the former commerce secretary
are Jennifer’s first cousins—and Chi-
cago itself is deep blue. But the colonel
is blood red. A top Republican donor,
she has written big checks to the likes of
John McCain, Jeb Bush, Mitt Romney,
and Donald Trump, for whom she voted.
“For the Pritzkers, her transitioning
wasn’t that eventful. They’re all cool with
it. It’s like, ‘Pass the salt,’ ” says a family
friend. “Her Republicanism—that’s more
difficult for them.”
The curtain over Pritzker’s personal
life began to lift in July 2017, when Pres-
ident Trump tweeted his intention to
ban transgender people from the mili-
tary, reversing an Obama-era directive.
The Chicago Sun-Times soon published
104 VANITY FAIR SEPTEMBER 2019
