COL. JENNIFER N. PRITZKER—The World’s ONLY Transgender Billionaire


CHICAGO—Ya gotta love Jennifer.  She’s got the kind of spunk and courage and let freedom reign spirit that positively IS America.  Forgot for a second that she is worth somewhere north of $2 billion—more bucks than 90% of third-world countries.  It’s not the money that drives this woman. She’s fighting mad, and she does not mind who knows it.

While it’s true she is a member of the Pritzker family, the seventh-richest in the country, there are many members of that clan (including JB Pritzker, the current governor of Illinois, and Penny Pritzker, the Secretary of Commerce under President Barack Obama). We’ve all rubbed elbows in some way or another with the Pritzkers, whether it was by staying in one of their Hyatt Hotels or buying from any number of their nuts-and-bolts manufacturing businesses.

But there was always something that made Jennifer stand apart from the rest of the family. She was its only Republican and a die-hard one at that, contributing millions of dollars over the years to the party that up until recently shared many of her moral and business values.

But all that was before Donald Trump was elected president and turned the party into an LGBTQ hate group that seemed determined to reverse every single gain the gay, lesbian and transgender community had gained either politically or legally under the Obama administration.

Born as James Nickolas Pritzker in 1950, Jennifer served in the Illinois Army National Guard from 1974-2001, plus the U.S. Army deployed during the Vietnam and Cold War eras, retiring as a Lieutenant Colonial. Two marriages, three children, and the creation of a multifaceted organization called TAWANI Enterprises Inc. later, Jennifer sent out a short memo to her staff that wasn’t meant to create a fuss or even become public for that matter.

While only three sentences long, it was a life-changer: “As of Aug. 16, 2013, J.N. Pritzker will undergo an official legal name change, and 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.”

For the Pritzkers, the announcement was not all that big of a deal. There had been talk among her siblings for years, and “whatever” was the common comment. The real confusion came with her political stance in this classically liberal dynasty where the word “Republican” was rarely uttered except as the punch line to a joke.

A lot has changed in Jennifer’s world since 2013, but nothing rattled it quite as much as the efforts by Donald Trump beginning in 2017 to make it illegal for transgenders to serve in the United States military.  At 9:08 am on July 26, 2017, the President began an unexpected series of tweets that rocked Jennifer’s world.

“After consultation with my Generals and military experts, please be advised that the United States Government will not accept or allow Transgender individuals to serve in any capacity in the U.S. Military,” Trump wrote.. “Our military must be focused on decisive and overwhelming victory and cannot be burdened with the tremendous medical costs and disruption that transgender in the military would entail.”

“Thank you,” he added.

Catching the Department of Defense completely off guard, as well as both Republicans and Democrats in Congress, there was an uproar over the attempt by the President to rule through Twitter that would affect the estimated 3,000 transgender soldiers currently serving in the military. Jennifer Pritzker was left shell-shocked.

Writing in the Chicago Sun-Times, Jennifer called Trump’s effort “a giant step backward.”

Being a transgender woman,” she wrote, “I had to hide who I was during my time in service… 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.”

If Trump thought that Jennifer would go quietly into the night, he quickly learned otherwise. In an opinion piece published right under his nose in the Washington Post several months later, Jennifer not only repeated her disdain for Trump’s transgender policies, this time she included the entire Republican Party.

“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?”

What Jennifer fails to mention is how she feels about Trump’s hard-line treatment of immigrants, though it is safe to say that she has a decidedly vivid one. It hasn’t actually been all that long since the first Pritzker emigrated to America. The year was 1881 when 10-year-old penniless Ukrainian immigrant Naphtali ben Yakov Pritzker arrived in Chicago.

While being given a medical examination, the rag-tag boy who went by the Americanized Nicholas, so impressed the examining doctor that the man arranged to give the boy a new set of clothes and a fresh start in America by investing $5.00 in his future. Nicholas used the money to buy some shoe polish, brushes and a wooden stand and set up his shoe-shining business outside of the First National Bank of Chicago building which had just moved into new headquarters at the corner of Dearborn and Monroe Streets.  Teaching himself English, and saving his cash in his socks, Nicolas made friends with the bankers and eventually opened his first bank account there.

Using his self-taught English, he put himself through DePaul University College of Law and opened an office in downtown Chicago. After falling in love and marrying Annie Cohn, Nicolas and his wife gave birth to three sons–Harry, Abram, and Jack, all of whom became lawyers as well, and joined their father in Pritzker and Pritzker to transform Chicago, each in his own way. Harry concentrated on criminal law, Abram on business law, while Jack took on the legal challenges of real estate.

Abram, known as A.N. Pritzker, was the first to spread his wings and started to buy up property beginning in 1925. He was soon joined by his brother Jack, who set up trusts to own the real estate and placed the Pritzker family well on their way to a substantial fortune.

A.N. and his wife Fanny (ya gotta love it) had three sons of their own–Jay, Robert, and Donald. Jay turned out to be a prodigy of sorts in that he graduated from high school at age 14, and attended the University of Chicago, while still later getting his law degree from Northwestern University, right up the street.

Being the oldest, he was also the first to start reorganizing all those Pritzker investments, determined to diversify and flying around the world to do it. It was on a layover in Los Angeles that Jay checked out the coffee shop of a two-story, four-year-old motel called the Hyatt House across the street from the entrance to LAX. Jay had heard stories of the flamboyant owner of the place, a Los Angeles society type named Hyatt Robert von Dehn, who used his first name to give the place character.

While Jay wasn’t in the market for a hotel, he immediately saw the future in owning one by a large international airport, and put in an offer to purchase the place for $2.2 million that very day.  Von Dehn accepted the deal, and by September 1957, the Pritzker family found themselves in the hotel business. Or more specifically in the Hyatt Hotel business.

Jay put his youngest brother Donald in charge of expanding on the concept, and as with all things Pritzker, opportunity didn’t need to knock twice to get their attention. The Hyatt Hotel chain may have been born accidentally, but its growth was a careful mix of big bucks and luxury. While much of America was flocking to Holiday Inns for their family vacations, Don Pritzer developed the Hyatt name to be associated with deluxe high-rise five-star resort experiences, with multistory atriums as a signature.

For his part in the perpetual money machine, Robert Pritzker dipped his toe in the family legacy by buying the failing Colson Corporation, a conglomerate that made a variety of industrial transportation and building products. That company was renamed The Marmon Group and continued to prosper under Pritzker leadership providing half of the family’s income until it was sold to Warren Buffet’s Berkshire Hathaway Inc.

Robert Pritzker, who married three times, also created a family of five children–the oldest of whom is Jennifer. At the time of her birth in 1950, she was originally named James–a strapping boy with an intense interest in toy soldiers and all things military. He was sent to the private Francis W. Parker School, like many Pritzkers. The major difference with James was that he didn’t excel at his studies,  taking five years to get through high school–and then barely scraping by, graduating with a 1.9 GPA in 1968.

Unsettled and unsatisfied, James joined one of the Marmon Group companies as a truck driver in Arkansas, before quitting to hobo across the country on boxcars. Eventually, in 1973, he landed in Israel where he worked on several kibbutzes near Tel Aviv and felt motivated to fight with the Israelis during the October War against combined forces from Egypt and Syria.

Denied that opportunity, Pritzker returned to Chicago and enlisted in the U.S. Army, where he remained until 1978 when he enrolled in Loyola University through its ROTC program. Two years later, with a degree in history, Pritzker went right back to the Army, this time as commissioned as a Captain.

And there he remained before formally retiring with the rank of Lieutenant Colonial in 2001, and being awarded the honorary title of Colonial by the Illinois Army National Guard. In 2003, he founded the Pritzker Military Museum and Library dedicated to understanding and support of the “citizen soldier.”

Since announcing her decision to become a transgender woman, Jennifer has been moved to donate $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.

In 2016, Jennifer was presented with the Bonham Centre Award from The Mark S. Bonham Centre for Sexual Diversity Studies, University of Toronto, for her contributions to the advancement and education of issues around sexual identification.

Yet her real gift to the LGBTQ community is her visibility without regret or excuses. Sarah Kate Ellis, the president and CEO of GLAAD, told Vanity Fair that  “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.”

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