In 1881, Naphtali ben Yakov Pritzker arrived in Chicago, a 10-year-old penniless 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 investments, a conglomeration of nuts-and-bolts manufacturing businesses, and Hyatt hotels.

Several Pritzkers are currently well known. Jay Robert (known as “JB”) became governor of Illinois in January, and his sister, Penny, served as commerce secretary in the Obama White House. But the family has always closely guarded its privacy.

Thus there was some surprise in Chicago nine years ago, when the Naphtali 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 alteration was made on the tree, one which few people saw coming: “Jennifer Natalya Pritzker born as James Nicholas Pritzker.” The world’s only known transgender billionaire had, in fact, quietly announced herself a few months previously, in a private email sent to business 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 stature, 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 Crain’s called her “ever-private.”) And perhaps the country wasn’t ready for this conversation. It would be another two years before Caitlyn Jenner announced herself (in the July 2015 issue of Vanity Fair).

While Pritzker has remained press shy, 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 floor houses entities run by Pritzker under her umbrella company, TAWANI Enterprises: a private-wealth firm, which manages a diversified portfolio of business investments, including real estate development and management, hospitality assets, book publishing, 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 socially liberal and Democratic—the governor and the former commerce secretary are Jennifer’s first cousins—and Chicago 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 Jennifer’s personal life began to lift in July 2017, when President Trump tweeted his intention to ban transgender people in the military, reversing an Obama-era directive. The Chicago Sun-Times soon published an opinion piece, headlined “Col. Jennifer Pritzker: Trump’s transgender ban a ‘huge step backward.’” “Being a transgender woman, I had to hide who I was during my time in service,” Pritzker wrote. “I can’t express enough how strongly I disagree with Trump’s statement…[which] hurts our Armed Forces and shows a callous disregard for the rights of American citizens.”

In January she published another opinion piece, in The Washington Post. This time she expressed her disapproval of Trump and the Republican Party by issuing perhaps the only kind of warning they might heed: the threat to close her pocketbook. “I have hoped the Republican Party would reform from within and end its assault on the LGBTQ community. Yet the party continues to champion policies that marginalize me out of existence, define me as an eccentric character,” she wrote. “I ask Republicans to prioritize policies that improve our country for all Americans. When the GOP asks me to deliver six- or seven-figure contributions for the 2020 elections, my first response will be: why should I contribute to my own destruction?”

Shortly after the piece was published, I reached out to interview Colonel Pritzker. Two months later, on a brisk March morning, I found myself in her stately conference room, with its lovely views of the Frank Gehry–designed Jay Pritzker Pavilion in Millennium Park, Chicago’s civic hub, just across Michigan Avenue. (Jay, Jennifer’s uncle, founded the Pritzker Architecture Prize in 1979.)

Pritzker’s manner is no-nonsense but friendly. She wears a touch of light red lipstick, and her gray hair is gathered back into a bun, held fast with a gold clip. Black slacks are tucked into knee-high black leather boots. Over her light blue dress she wears a delicate printed shawl, fastened by a gold medallion.

Pritzker, who will turn 69 in August, is self-effacing. She jokes about not being able to fit into her old Army uniform. “It was issued to me a long time ago, in a previous life, many pounds ago. There’s more of me now,” she says. “I’m not going to be Miss America this week.”

Colonel Pritzker owns one of the biggest individual real estate portfolios in the Chicago region. In 2013, according to the Tribune, she owned some 35 properties, including a home in Evanston that was her primary residence (which she has reportedly sold). An avid cyclist, she often biked to and from the Loop, 24 miles round trip. Today she doesn’t specify where she lives, saying simply it’s “near here.” She still cycles quite a bit, just “kind of at old-lady speed.”

Pritzker has bought, restored, and redeveloped numerous historic buildings in and around Chicago, for which the prestigious Society of Architectural Historians bestowed her with its Award for Excellence in Architectural Stewardship. “The best buildings provide a sense of identity,” she says. Indeed her interest in historic preservation stems from memories of a large house at 340 Wellington Avenue, which was home to her grandparents Abram and Fanny Pritzker. When Jennifer was a child, it was knocked down and replaced by a glass tower. “If I had been an adult, I would have bought it. It was the house my parents got married in, and both my uncles. Many Pritzkers went into prototype at that location.”

Inside the restored Monroe Building, constructed in 1912, Pritzker is adding a new chapter to her family legacy. She leads me on a tour of the PMML, where admission to which is free for active servicemen and servicewomen, and just $5 for everybody else. (Supporting memberships are available too.) In addition to its 67,000 books, 120 defense serial and journal periodicals, there are exhibition areas, a sophisticated theater with a state-of-the-art production studio—three-time Pulitzer Prize winner Rick Atkinson recently spoke—and the Coleman T. Holt Oral History Room, where veterans are invited to tell their stories. First Lieutenant Holt was a Tuskegee Airman who became a lawyer and activist in Chicago. A plaque on the window notes that the history room was a gift of Karen Pritzker, one of Jennifer’s sisters.

In an anonymous storage room, Jennifer finds her old M8 bayonet, which she unsheathes and cheerfully passes to me, its lethal blade clearly still quite serviceable. She regales me with a tale of a Cold War–era mission she took part in while stationed near the Fulda Gap in Germany, which was thought to be a possible route for a Soviet invasion. “I think it’s declassified. I guess they won’t lock me up with Chelsea Manning for telling you,” she chuckles.

Down the hall in the Rare Book Room, there is a dog-eared volume of Naval Customs: Traditions and Usage. The copy is not particularly old or rare, but on the inside cover, “340 Wellington Avenue” is written in script. The book, says Pritzker, belonged to her uncle Jay when he enlisted in 1942—it “helped Ensign Pritzker not make a jerk of himself in the wardroom.” After the war, Jay gave the copy to Jennifer’s father, Robert, as a sort of managerial touchstone in his Elyria, Ohio, rocket-building factory.

“It’s kind of why we are here today. It’s indicative of the relationship between the military and civilian communities, with two brothers on either side, each one in their own way providing an essential service to the armed forces,” says Pritzker. “The purpose of this place is to explain how a democracy sustains a military force to carry out policy. This country spends $700 billion a year on defense. As a citizen you have a right, and an obligation, to understand where it goes.” The museum’s CEO, Rob Havers, later underscores that the PMML is “decidedly nonpartisan” in its efforts to “combine military history with contemporary thinking.”

Also in the records room are the discharge papers from Michael Reese Hospital for Naphtali, dated 1881. “One of the doctors took a liking to him, burned his suit, gave him new clothes and a dollar to launch his business career, which for him meant buying a stack of newspapers and a shoeshine kit,” Jennifer explains. “Eventually he taught himself English, studied pharmacy, graduated from law school. So I’m three generations away from a refugee charity patient with nothing but the clothes on his back, escaping a pogrom in the czar’s empire.”

Naphtali’s three sons joined his law firm. His middle son, Abram, known as “A.N.,” graduated from Harvard Law School and began to move the family into investing. A.N.’s three sons—Jay, Robert (Jennifer’s father), and Donald—ran with that. They bought up hundreds of companies under the umbrella of their holding company, the Marmon Group, which began to boom in the 1960s. By 2000, it was making $6 billion a year.

Most of the family wealth went into trusts. From time to time, money would be disbursed to family members “to meet their reasonable needs,” as Suzanna Andrews wrote for Vanity Fair in May 2003, recounting the epic family battle that erupted after Jay died in 1999, and some family members drafted a confidential plan to break up the fortune. According to that plan, 10 fourth-generation cousins would each receive $1.4 billion: Jay’s four surviving children; Donald’s three children; and Robert’s eldest three children (Jennifer, Linda, and Karen) from his first marriage, to Audrey, which ended in 1979. An 11th share would go to Nick, a third-generation nephew of A.N. An explosive challenge to this plan arose from Jennifer’s younger half-siblings, Liesel, now 35, and Matthew, 37, the offspring of Robert’s second marriage, to Irene Dryburgh, which ended in a bitter divorce in 1991. (Robert subsequently married Sao Mayari Sargent, with whom he had no children, before he died in 2011 at 85.) Liesel and Matthew were shortchanged in this distribution plan, which resulted in a lawsuit that dragged on for years, before a settlement was reached around 2005 by which they received about $500 million apiece. The others got their distributions as planned.

Today the cousins are all said to be back on amicable terms. Certainly they’re faring well financially. According to recent Forbes reports, Jennifer and Nick, for example, are each now worth around $2 billion, while JB’s fortune is pegged at $3.2 billion. (He was an early investor in Facebook.) The richest Pritzker of all is Jennifer’s Connecticut-based little sister, Karen, 61, with $5.1 billion. With her husband, Michael Vlock, she bought big into Apple, among other smart investments. (Vlock, with whom she has four children, died in 2017.)

Outside of finance and politics, the Pritzkers have distinguished themselves in other fields. Jean (“Gigi”), 57, has produced films, including Drive and The Way Way Back. Karen and Jennifer’s sister, Linda, 66, is a Jungian psychotherapist and an ordained lama in the Tibetan Buddhist tradition, who also goes by the name Lama Tsomo. A divorced mother of three, she speaks fluent Tibetan and is an author, teacher, and co-founder of the Namchak Foundation, based on her ranch in Missoula, Montana.

“There’s one rule in the Pritzker family: whatever you do, do it well,” says Chicago socialite and novelist Sugar Rautbord, who has been a family friend for decades. “So it’s a hard family to be happy in. The expectations are high—Olympian.” At the same time, the Pritzkers have eschewed conspicuous consumption. “Jay used to say, ‘We’re rich socialists.’ They don’t run around in jewels and sables,” says Rautbord. “They hate being on the Forbes list.”

One aspect of being on that list rankles Jennifer particularly. “Forbes gave me a ‘self-made rating’ of 1,” she scoffs. (“A 1 indicat[es] the fortune was completely inherited, while a 10 [is] for a Horatio Alger–esque journey,” says the magazine.) “I don’t know anybody else listed in Forbes who went from private to lieutenant colonel. Army promotion boards could care less what your net worth is. You have to perform to certain standards to get in and to stay in.”

Clearly military service helped Pritzker forge her sense of self-worth.

“In my youth I had some trouble finding myself,” Colonel Pritzker continues. “It took me five years to get through high school, with a 1.9 GPA.” After attending Francis W. Parker, one of Chicago’s elite private schools, class of 1968, she wandered around for six years, driving trucks in Arkansas for one of her father’s companies, riding the rails out West like a Dust Bowl hobo, before spending nine months working on a kibbutz in two different locations in Israel. Being there during the outbreak of the 1973 Yom Kippur War was enlightening. “Within 72 hours, 80% of the men of military age had gone into combat. I wanted to fight.”

Pritzker returned home and enlisted in the Army as a private in February 1974, serving with the 82nd Airborne Division. Wanting to become an officer, she took a leave in 1978 to obtain the required bachelor’s degree, enrolling in Loyola University in Chicago through the ROTC program, and sailed through in two years with a 3.6 GPA. Jennifer’s mother, Audrey, was a fellow student, finally getting a degree after being “a busy mom,” Jennifer explained last year, while announcing a $10 million donation to Loyola in Audrey’s honor. (Two years after her divorce from Robert, Audrey married Albert B. Ratner, a prominent real estate developer, and moved with him to Cleveland, where they still reside. “She’s still gorgeous!” Rautbord says of Audrey, 90.)

After receiving a degree in history, Jennifer 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,” Pritzker says. Daughter Tal was born at Fort Campbell in 1982, during her 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, she retired with the rank of lieutenant colonel 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 JB’s recent gubernatorial run highlighted political divisions in the family. Shortly before he entered the race, JB tweeted, “As a protest against Trump’s rescinding protections for trans kids, everyone 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 transphobic rhetoric.”

Not long after that, at a groundbreaking ceremony for one of her developments, a Tribune reporter managed to ask Jennifer if JB 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 JB’s tweet. “I don’t think he realized that informal comments on social media become world news quickly.”

JB 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 communications aide, two of whom sat silently through our interview.

Along with his wife, M.K., and their foundation, JB was the third-largest contributor to Hillary Clinton’s 2016 campaign, with $12,600,000 in donations. Jennifer, meanwhile, has ponied up “in excess of seven figures” over her lifetime, she says, to Republican 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 disliked Donald Trump for reasons nonpolitical 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 optimistic view of Trump. I thought that because he wasn’t a politician, he would be willing to take some risks that professional politicians 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 candidate.” 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 positions 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 thoughtless 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 in 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 million for the world’s first chair of trans studies, at the University of Victoria, British Columbia; $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 physicians at Lurie Hospital, are more likely to find the answers than politicians in Washington,” she says. “Nobody is 100% 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 military 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 Pritzker’s voice has been very critical to the debate about transgender military service, not just because she is a veteran who understands 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-power panel discussion on transgender military service, on Capitol Hill. Speakers included Nancy Pelosi, Congressman Joe Kennedy, and (via video message) Colonel 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 leadership is appreciated too. “The number one thing she has done for the trans community 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 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 transgender 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 private. “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 transgender 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 psychological 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 accomplish 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 hardest 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 visibility. A man about town remarked of the “frisson” that fills a room when Jennifer walks in. “It’s like, forget Abra—Jennifer’s here!” he said, referring to Abra 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 opportunity to come out in a more orderly fashion,” 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. Unfortunately 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 and 27, 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 Grandpa 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.”

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