An enormous crown encrusted with Swarovski crystals rested delicately in a glass case onstage. Dressed in T-shirts, ball gowns, and everything in between, about 100 audience members sat in anticipation waiting for the winner to be called. They’d all braved a tornado warning to attend Chicago’s Second Annual Trans Visibility Pageant.
This top prize went to the “mother of the House of Diamonds” — Alexandrea Diamond. In her acceptance speech, Diamond thanked her chosen family of “drag daughters.”
This fairytale moment of love and joy came as the very existence of transgender Americans is being challenged by conservative lawmakers across the nation. And that wasn’t lost on those gathered at the pageant, which was held recently in Chicago’s Austin neighborhood.
“We’re not here by coincidence,” said Zahara Bassett, CEO of Life Is Work, a resource center for transgender Chicagoans that organizes the pageant. “We’re here by thriving and striving and fighting continuously.”Even a solidly blue city like Chicago is not immune to transphobia. Hate crimes against people over their gender identity and/or sexual orientation have increased in recent years. And a bakery in nearby Lake in the Hills suburb recently announced it will move after months of harassment over brunches hosted by drag queens.
To get a better sense of what it means to be transgender in the Chicago area, WBEZ talked to performers and guests at this year’s pageant. Though they come from different generations, racial backgrounds and careers, all say the recent anti-trans attacks in the news are part of a much larger series of tribulations, and joys, that come with being transgender.
Here are four of their stories.
Passion Jackson, 52
Passion Jackson, a veteran pageant performer, divides her time between drag shows and pageants and assisting with makeup at a funeral home. At the inaugural Life Is Work pageant in 2022, she served as empress, crowning the first-ever winner, Keri Traid. This year Jackson returned to the pageant with royal flair, wowing the audience with a spirited lip-sync of Rose Royce’s 1976 hit “Car Wash.”
The audience rewarded her by mobbing the stage and tipping her handsomely in one-dollar bills.
As a child on Chicago’s West Side, Jackson’s love of makeup, performance and clothes started early. “I was kind of like the best-dressed in high school,” she says. “I always gave them fashion.” At the time, she identified publicly as a gay boy, but she was able to fit in despite her marginalized identity.
Jackson describes a supportive family. Her parents, she says, “knew I was going to be gay, but they didn’t know I was going to be trans. But either way, they accepted me.”
Still, when Jackson began her gender transition at the age of 17, her family did not have the money to pay for gender-affirming hormones or surgery, which were not covered by insurance for most trans individuals until the mid-2010s. She decided to drop out of high school and move out on her own to begin earning money, and to find support within Chicago’s trans community.
But she found that her career options were limited. She began styling hair, but quickly realized she could earn money much quicker through sex work. “Every day that I went out there, I made money. Hundreds of thousands of dollars.”
Though lucrative, spending time on the streets of Chicago as a trans woman could be dangerous. “[People] could be mean,” she says. “Calling me names, throwing rocks and bottles.”
Jackson frequented trans pageants, where she forged friendships with other trans women. She grew especially close with Christian Paige, a trans drag performer at Chicago’s Baton Lounge. The two moved in together, and Paige helped Jackson obtain her first hormone replacement therapy. But then tragedy struck. In what appeared to be a hate crime, Paige was brutally beaten and stabbed to death in their home. The murder has never been solved.
Jackson says Paige’s horrific murder made her question whether living openly as a trans woman was worth the danger. Ultimately, though, she decided that continuing with her transition would be best for her mental health. In 1997, another trans woman helped her to obtain her first gender-affirming surgery in Guadalajara, Mexico, during a time when it was common for transgender people to travel south of the border for more affordable procedures.
Since the 1990s, Jackson has completed her medical transition. She says she now feels safer moving around Chicago as a trans woman, and she notes that Obamacare has made it easier to receive gender-affirming healthcare paid for by insurance. And while she credits four trans women activists for constantly standing up for healthcare access for Chicago’s trans community – June LaTrobe, Joy Hightower Morris, Lois Bates and Lorrainne Sade Baskerville – she feels it can be difficult for young trans people to get necessary information when they first come out.
She urges people to find a trans mentor with lived experience. “Get up under the wing of somebody that’s been through it,” she says. “They’re gonna tell you the good and the bad, because there’s some good and some bad. I would love to mentor younger trans women.”
Mz. Mr., age undisclosed
Mz. Mr. has been a burlesque performer for more than a decade and has trained professionals in the Chicago area and around the world. But many days find her teaching at the Chicago Therapy Collective, a mental health and advocacy organization for trans people. There, she plans events like a variety show for trans performers at Andersonville’s Midsommarfest 2022 in Andersonville.
Mz. Mr. comes from nurturers. Growing up in New Mexico as part of an indigenous Tewa and Mexica family, she says she never had a coming out moment, since her femininity was always embraced by her relatives, especially the older women around her.
“I would dance around to music in a feminine way or a flamboyant way, and they would dance with me or applaud me, and celebrate that joy of life,” she says. She identifies as two-spirit, a term used in many indigenous cultures that encompasses various kinds of queer, trans and gender nonconforming identities. “In cultures of the Southwest, being gender variant is not an unusual or uncommon thing.”
It wasn’t until she became a teenager, moved to Albuquerque and attended school there, that she began to experience bullying from people who assumed she was a boy. “I became very suicidal and depressed,” she says. “I was called every terrible slur in the book.”
Mz. Mr. found solace within her family, and, when she became an adult, through burlesque performance. At the beginning of her career, she was often the only trans or gender nonconforming person in burlesque spaces, but performing allowed her to express her identity in its purest form: “A very high-femme, frilly, girly, glamorous, beautiful version of myself,” she says.
She recalls that audience members would sometimes react negatively to seeing a gender nonconforming burlesque artist. But Mz. Mr. says she was able to win over many people in the burlesque community, including what she calls her “burlesque babies,” fellow performers who admired her style and became her mentees. As a mentor and teacher, she says, “I’ve had students come out following a session with me, and realize that the gender presentation that they’ve had was not accurate to how they want to live their truth.”
Mz. Mr. tries not to let the recent anti-trans news keep her from living her life to the fullest, but she sometimes wears extra-feminine clothing and thicker makeup to protect her safety in trans-unfriendly or otherwise unfamiliar spaces, such as on a recent trip to India with her partner. “This is a really common thing for trans people,” she says.
Theo Zelkind, 22
Theo Zelkind has lived in Chicago for two years, and works at a family-owned clothing and alterations shop. A lucky Instagram post recently led him to the Trans Visibility Pageant.
Zelkind says seeing attacks on the trans community in the news can make him feel resentful. But seeing the contestants’ performances at the recent pageant turned that resentment into pride. He says the colorful performances and bold looks felt “radical,” adding, “My face was twitching from my jaw hanging open the whole time.”
Growing up in San Diego, Zelkind says he lived in a supportive bubble of family and friends. After some mental health issues unrelated to gender in his early teens, his mom had a hunch her son might be trans and found him a therapist who specialized in gender. “I wasn’t a particularly subtle child,” he says. “I wore trunks and no t-shirt when I swam until way after it was appropriate.”
Zelkind says he felt supported when he came out in middle school, but the process was still a complicated one for logistical reasons. “I was one of the first trans kids to come out in my district, so I was a bit of a guinea pig.” He was, he says, “the subject of many a district meeting” regarding which bathroom to use. In the end, the district allowed him to use the boys’ bathroom and gave him permission to have a school security officer escort him there if he felt unsafe.
Still, Zelkind says his mother did a lot of work to inform district officials about trans kids’ needs.
Two years ago, Zelkind moved to Chicago, where he says he’s found a community of trans and queer friends. “It’s been really interesting to see how much we are everywhere,” he says. “I’ve been pleasantly surprised by how much I find happy queer people all around me.”
Since he feels surrounded by a loving community, he says the recent wave of anti-trans legislation elsewhere in the country has made him more willing to openly identify as trans in public.
“I have a lot of privilege,” he says. “I’m white and I pass [as male] really well. I’ve built myself a space that’s safe, so I think it would be a shame if I didn’t use it to its full potential.” On the International Transgender Day of Visibility, that meant attending a march for trans youth, and later the pageant, wearing a trans pride flag as a cape.
DaVon Anderson, 60
DaVon Anderson won one of this year’s Lois Bates Lifetime Achievement Awards for advocating for the trans community and for her career as a healthcare professional. Anderson is the associate director of practice management at Howard Brown Health, an LGBTQ-affirming health clinic with several locations around Chicago.
Anderson was primarily raised by her father and paternal grandmother, who loved and supported her trans identity. Her grandmother even opened her mind to the possibility of working in healthcare. “When [I was] little, she would go to relatives’ and friends’ houses and take care of those who were sick or dying, and I would always be with her,” she says. “Being around people who were sick or dying wasn’t anything that was strange to me.”
Realizing she was a girl at around age 8, Anderson says she never tried to conceal her identity, though she has many trans friends who did. Her teenage years weren’t easy. “I fought all the time,” she says, with kids who attacked her for not acting like a boy. “I was not masculine at all.”
As a young adult, Anderson first decided to study cosmetology, but switched to healthcare because she needed the money. Her boyfriend at the time “came home one day and told me I had to get a job because he was tired of taking care of me.” Though she was not relying on her boyfriend financially, his harsh words made her realize she wanted more financial stability than beauty school could offer.
She immediately found work at a nursing home, which paid for her to take a six-week certified nursing assistant course and assigned her night shifts so she could attend class during the day.
Anderson credits this busy time as the beginning of a prosperous career in healthcare, but also wonders if it provided her with one of the reasons she’s happily single today. “I’ve kissed a lot of frogs, and I’m here to tell you they stay frogs,” she says, laughing.
Working as a nursing assistant, Anderson was often the only trans employee on her team. Transphobia – the kind that alienated many trans people from professional environments – was a common occurrence, but she developed a thick skin and a sharp wit. Once, when a colleague implied she thought Anderson looked masculine, Anderson replied, “That’s OK, because the gender marker on my driver’s license is the same as your mother’s,” and returned to work.
Her poise and empathy made her an ideal healthcare professional during the AIDS crisis in the late 1980s, when she was assigned to the HIV ward at St. Joseph Hospital, and later served HIV-positive patients as a home health aide. At the time, an HIV diagnosis was often a death sentence. “The unit was more like a hospice,” she says.
“There were many times when people were there alone — they had separated from their families and friends,” she recalls. “There were many times where I was with someone during their [passing] so I could comfort them. A lot of the women I worked with were older and less educated, and they would refuse to go to those patients, so I would go.” After a while, Anderson began managing clinics, leading to her current management role at Howard Brown Health.
In addition to her healthcare career, Anderson has also volunteered to provide free food and discussion groups for LGBTQ youth at Gay Horizons, now the Center on Halsted. In her acceptance speech for the lifetime achievement award at the 2023 Trans Visibility Day Pageant, she thanked the many people she’s worked with in her career, including trans advocate Lois Bates, the award’s namesake.
“The running joke at Howard Brown is that I’ve worked with everybody,” she said. Reacting to recent anti-trans legislation, she told the crowd, “I’ve seen that we’ve come a long way and we still have a longer way to go. I’m here for the fight.”
Char Daston is a freelancer who covers education, arts and culture for WBEZ. Follow him @behindthissky.