Col. Jennifer Pritzker is someone who firmly believes in giving.
There's the transgender activist who has been supportive of many LGBTQ+-related causes. And, of course, there's the Jennifer Pritzker who spent almost three decades in the U.S. Army, Army Reserve and Illinois Army National Guard, and who is extremely supportive of the military to this day. In 2017, she created the Pritzker Military Foundation, which serves as the Pritzker Military Museum & Library's grantmaking arm.
Pritzker—a cousin of Illinois Gov. JB Pritzker—also created the TAWANI Foundation (named after her children) in 1995. TAWANI is about philanthropy in the areas of education, gender and human sexuality, cultural institutions, environmental initiatives, and health and human services.
And she also believes in giving her opinions. In a recent interview, Pritzker offered her thoughts on everything from philanthropy to her Republican background—and why she severed ties with former Donald Trump's administration after voting for him in 2016.
Note: This conversation was edited for clarity and length.
Windy City Times: I wanted to start with something recent: The Chicago LGBT Hall of Fame. What did the induction ceremony feel like for you, and what would you have said if you could give a speech?
Col. Jennifer Pritzker: I actually have a lot of different views about that.
On one hand, it's always nice to be appreciated. I certainly couldn't have wanted a better venue; the Chicago History Museum is one of my favorite places in Chicago. My father started taking me there back as long as I can remember. I've seen a lot of changes; back then, it was the Chicago Historical Society.
Right now, in this country, anything having to do with LGBT+—I'm using four out of the 26 letters in the alphabet, no disrespect—is very controversial. It's a double-edged sword—to some people, if you're in the LGBT Hall of Fame, you're a hero; to others, you're an agent of Satan. So I'm already somewhat on the [borderline] because I come from a well-known family, I've got a few bucks and I have cousins who are prominent in politics—one who's been in Obama's Cabinet, Penny Pritzker; and, of course, the governor, JB. Some people think I'm his sister; some people think I'm his wife. That's why I have the Pritzker family exhibit in the historical museum; it lays out who's who.
If I may get a little risque, in addition to being a public figure, I'm also something of a PUBIC figure. It's like I'm a novelty figure, a sideshow exhibit: "Is it a he?" "Is it a she?" "Does it stand to sit and pee?" Why should being LGBT be a bigger factor than having blue or green eyes, or if you're 28 or 58? Certain things are what they are, and you can do good or not-so-good things with them—but that's not all of what you are.
No matter what I do or say, some people's notions of me will not change—and they're as unchangeable as the Rocky Mountains. But, you see, mountains change. They have volcanic eruptions, and they're influenced by wind and water. So the Earth doesn't remain stable; it's always in a state of change.
I am what I am. I'm a 73-year-old transgender woman who's been endowed with prosperity. I'm of European Caucasian descent. I'm Jewish. I'm a veteran. I am a father and a grandfather even though I live as a woman. I spent 27 years in the Army—eight-and-a-half years on duty and the rest in the National Guard reserves. I've had some kind of business of my own since 1987. Some days are good, some are not so good and some days I've avoided disaster by the skin of my teeth. So you have ups and downs; that has nothing to do with what gender I'm living in or what my physical state is.
I've been engaged in many different kinds of philanthropy. Now there are people, like [journalist] Jennifer Bilek, who think that my cousin and I, and other people like me, are on a conspiracy to screw up the world, to rob everyone of their identity—but it's quite the contrary. Most of the philanthropy I've done has been for scientific research and medical treatment. I've only become involved in advocacy because I've had to.
And while I'm not that wild about voting for Democrats, there's no way that me or someone like me—or, for that matter, any rational person—can vote for Donald Trump. I made the grave mistake of voting for him in 2016. I should've followed the advice of my youngest son, William, who said, "If you don't like Hillary Clinton, then vote libertarian," which I did in 2004. I voted against Bush the younger for two reasons: I thought it was a mistake to invade Iraq and he wanted a constitutional amendment to ban same-sex marriage. But we have freedom OF religion and freedom FROM religion.
WCT: So would you vote for someone like Liz Cheney, who was not ruled out running in 2024?
JP: Probably—but I don't know if she can do it as a Republican because the Republican Party has gotten so [mixed] up. To be a little vulgar, the Republican Party is like constipation; they can't even pass gas. I hate saying that because I voted Republican for a long time. I started voting in 1972 and I didn't vote Republican twice—in 2004, when I voted Libertarian; and in 2020, when I voted Democrat because I wanted to make sure Trump didn't get back to the White House.
[Biden] wasn't my favorite choice but he was a plausible one; he's a lot more rational than Mr. Trump and he looks like he has his weight under control—and that's no small feat. What really turned me against Trump was when he said there was no place for transgender people in the military. Naturally, I had a very negative reaction to that. Also, he's said some extremely disparaging remarks about people like John McCain. The Department of Defense went through a hell of a lot of trouble to change that policy [regarding transgender inclusion in the military]; they didn't do it on a Twitter whim.
Right now, the Republican Party is reactionary, spiteful and totally unproductive. You have state legislatures competing with each other to see who can pass the most repressive laws the quickest.
I've contributed a lot to LGBT+ causes but I've also contributed a lot more to things like military history and military affairs. If we're going to have a democracy in which the military is controlled by the civilian population, how can they do it if they don't know anything about the military? With a voluntary and non-governmental organization, I can do things that I could never do in uniform.
[At this point, TAWANI Marketing and Communications Director Theadora Gerber said, "I think one point you make really well is that [neither] side is contributing to finding solutions. If there's a hysteria going on, they should look for solutions.]
I would agree that both [main political parties] have taken extreme views. We've seemed to have lost the ability to have true bipartisan, nonpartisan approaches to common problems.
Now no matter what your views, there is climate change. Now how much is attributable to humans, I don't know but we have to deal with it. And what about the war in Ukraine? We can't just sit by and do nothing—but what do we do? The current war in Israel—what do we do about that? We've got some serious economic problems in this country. We have a serious problem about paying for healthcare.
WCT: With October [when this interview was conducted] being National Coming Out Month, who was the first person you came out to?
JP: I don't know. It's hard to say because, for years, I thought of myself mainly as a transvestite. That's a term you don't hear much anymore; that shows how old I am.
I didn't really have the opportunity to explore who I was. In those days, a male could get arrested for appearing in public in women's clothing. But after the age of 10 or 12, my parents sent me to a psychiatrist; I'd say things like, "I could see myself in dual current." It was hard to find a way to "resolve" the issue for a long, long time. Going into the Army was not a great place to do it—although a lot of transgender people join the military to find resolution. You can function with the suppression but, after a while, you just can't do it anymore.
It's hard to say who the very first person was. It took me a long time to realize that the clothing was just a tool. It's so subjective about what's considered men's and women's clothing. I'm at the point where I've taken an interest in a lot of women's issues; I identify as a woman so these issues are a lot more relevant to me.
Maybe another way of coming out is trying to find out who you are so you can be at peace with yourself—so that you can function.
