‘There’s no downside’

Trans Chicagoan looks at changes in the LGBTQ community.

John, who asked that his last name not be used, holding a picture of himself dressed as Karen about 1980, at a restaurant at 2901 W. Addison in Chicago on March 17, 2023.

John, who asked that his last name not be used, holds a picture of himself dressed as Karen, about 1980.

Neil Steinberg/Sun-Times

“Sometimes I look up and wonder, ‘What the hell happened?’” says John, sliding into a booth at Dapper’s East, a classic family-style restaurant on West Addison.

We order coffee, no food. John doesn’t want lunch, which strikes me as unusual.

“Do you not eat, as a practice?” I venture.

No, by necessity. Stomach cancer. Fifteen years ago.

“They took the whole thing out,” says John, who doesn’t want his last name used. “I beat the odds, but lost my appetite at some point.”

We last saw each other in 1992. I had been browsing the classifieds in the Reader, looking for story ideas, and noticed an ad for the store he owned on Elston Avenue, selling women’s clothing in large sizes to men.

“Now there’s a business you just don’t see in the paper much,” I thought, and headed over and met John, when he dressed as a man, and Karen, when she dressed as a woman.

Focusing just on the One to One Boutique seemed to miss the larger story. So I broadened my scope, attending a dance held by the Chicago Gender Society, also visiting a safe house — an empty apartment used to stash clothing and wigs and makeup away from prying eyes.

The store is long gone. When did that happen?

“The Yankees were just winning their first series in a long time” — says John, a baseball fan. “So it must have been ’96.”

The resultant story was written without any snickering or judgment: just a group of ordinary people who are unusual in a certain way, trying to comprehend what motivates them. It’s an approach I wish more Americans would embrace: to at least entertain the possibility that people different from themselves can be understood instead of simply condemned.

Cut to last fall, and a letter from a reader about the possibility of Texas secession. At the end, he mentions, “We met about 30 years ago. I’m the person on Elston ...”

This seemed an opportunity to better understand the connection, if any, between men who dress as women — called “transvestites” 30 years ago — and another, possibly related, group much in the news lately: trans men and women.

Even then, there were two distinct categories: transvestites, who were straight men, for the most part, dressing as women, and transsexuals, men who defined themselves as women, or women who defined themselves as men, and sometimes transitioned through hormones and surgery.

We begin at the beginning.

“My dirty dark secret is, I’m from Mount Greenwood,” says John. “I did not fit in well there.”

I’ll bet. John was about 5 when he realized he wasn’t like other boys. He spent two years at St. Jude’s, a Claretian boarding seminary in Momence, and then finished up at Brother Rice.

“It was a culture shock.”

Since nomenclature gets batted about so much, I cut to the chase.

“What do you consider yourself?”

“An old man,” says John, laughing. He’s 69. Then seriously. “I still consider myself to fall under the category of trans.”

You sometimes present yourself as a woman, but don’t consider yourself a woman?

“Mmm ... no,” he said, as if deciding.

I wondered how he viewed his once-secret world coming out into the light. Was it all positive? Or is there also a sense of loss, the way the Cubs finally winning the World Series ended their long-running lovable losers identity.

“It’s been all good, as far as I’m concerned,” John says. “The kids now are doing this in high school. I applaud them. Something you never would have thought of, the LGBTQ support in the schools. Gays and straights clubs in high schools. It was unthinkable. If somebody thought you were gay — and we’re all lumped together, still — you were going to be in trouble.”

There is still trouble today, pushback. But nowhere near as bad as before.

“There’s no downside,” John says. “The only downside is people are going to come after you. They cloak it in their religion, like with abortion — it was really about women having sex. They want all birth control made illegal. That tells you something right there.”

We talked for an hour, and I was reminded why we treat these issues with generalities, instead of focusing on individuals. Because everyone is so different, pursuing their hopes and dreams. The golden rule says, as we want ourselves to be respected, we should respect others, and not gin up imaginary harms attempting to justify our malice. That seems very simple. But it’s not.

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