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.)