The Trans Woman Who Confronted Caitlyn Jenner Speaks: ‘Talking Softly Does Not Work’

Ashlee Marie Preston didn’t want to change Caitlyn Jenner’s mind. She wanted to make the reality star accountable.

Preston confronted Jenner at a Trans Chorus of Los Angeles event held on Aug. 27, calling the one-time Olympian a “f***ing fraud.” In a video of the altercation that subsequently went viral, the trans activist challenges Jenner for supporting President Trump despite his anti-LGBTQ policies. The conversation was filmed just days after the POTUS signed an executive order banning transgender people from serving openly in the military.

“It’s really fucked up that you continue to support somebody… that’s erasing our f***ing community,” Preston says in a passionate rebuke.

After coming out two years ago in a well-received Diane Sawyer special, Jenner’s continued defense of Donald Trump has made her trans community’s bête noire. During the 2016 election, she claimed the GOP nominee would be “very good for women’s issues” on her now-canceled reality show I Am Cait. The long-time Republican previously offered her services as a trans ambassador to Sen. Ted Cruz, were he to become president.

Preston tells INTO that she didn’t plan to call out Jenner at the event. If it were premeditated, Preston says she would have made sure she “wore a waist-trainer, had a sickening contour, and [her] hair was on right.” Instead 33-year-old claims that she was “born to call s**t out.”

“It was about letting people know that if you continue to support anti-LGBTQ interests, you will be checked for it,” she says.

Although many people who saw the video were learning Preston’s name for the first time, the former community organizer has been making waves in recent months. She was hired as the editor-in-chief at the feminist website Wear Your Voice in June, making Preston the first trans woman to lead a national publication.

But Preston says that shattering media’s highest glass ceiling was nothing new for her. She’s been fighting her entire life to create space for women like her, as well fighting to stay alive.


Preston always knew that she was different. Growing up in Louisville, Kentucky, she felt like Pat, the androgynous character played by Julia Sweeney on Saturday Night Live. The other kids at school thought Preston, who says that she always “had a very nonbinary nature,” was a lesbian. But she didn’t have a name for what she was feeling.

“We didn’t have a word for transgenderism,” Preston says. “I tried my best to conform the best way I knew how.”

Preston spent most of her childhood “feeling trapped.” She would move to Los Angeles in her late teens to begin living her journey authentically, even if she didn’t know what that meant yet. After meeting her first transgender person, an entire world opened to her. Preston learned for the first time that there were people who felt like she did and found a way to “express themselves to be in their own skin.”

“I didn’t think that was possible,” she adds.

If coming to the realization of her trans identity was difficult, the real struggle was being herself in a world that is often hostile to transgender people. After Preston began her transition at 19 years old, she faced frequent job discrimination. When she wasn’t able to afford rent, Preston says that she was forced onto the street. She couldn’t find housing at a women’s homeless shelter because she wasn’t “born a woman.” Preston claims that shelters felt she was a “liability.”

Many of the trans women Preston knew at the time were engaging in sex work, a concept that was initially alien to her. When Preston would see friends getting into strangers’ cars, she didn’t understand where they went. It wasn’t part of her reality.

But that would change.

Preston says the first time she got in someone’s car, she needed something to eat and a place to stay. She was a virgin.

Survival sex work gave Preston a front-row seat to how society treats its most marginalized. During her early 20s, she claims that a client drugged her and dropped her off on the side of the road. But Preston was one of the lucky ones. Friends would frequently disappear or turn up dead. Although the high murder rate of trans women has made headlines in recent years, she claims that these killings were a problem “long before the media got wind of it.”

“It’s just that our lives weren’t considered important enough for people to talk about it,” Preston says.

Preston got hooked on methamphetamines to help her stay awake at nightso she wouldn’t have to sleep on the street. But visiting a drop-in center in 2005 gave her the strength to get sober. The case workers there treated her like a “whole human being,” which Preston says she had never experienced before. They went with her to the courthouse when she got her name changed. Someone sat with Preston while she came out to her mother over the phone.

That experience also ignited her non-profit work, Preston says. She wanted to give other trans women of color the space to “feel the same amount of love, compassion, and humanity” that she found at the center.

Preston’s record of working for change in her community is nothing if not remarkable. In her decade as a community advocate, she has served as a board member for groups like Trans Can Work, which furthers LGBTQ inclusion in the workplace; Christopher Street West, the L.A. Pride group; and Mirror Memoirs, a trans oral history project. Her extensive resume also includes the Stonewall Democratic Club and the local Human Rights Campaign.

But her work with at-risk homeless youth showed Preston that she has something many organizations lack: experience.

“I knew the struggle it took for me to get to where I was,” Preston says. “Every step it took to get there, I knew how painful it was. That’s what gave me the strength to go forward, accomplish my goals, and do all the things people said I wouldn’t.”


Being asked to serve as the editor-in-chief of Wear Your Voice, Preston says, is merely an extension of her previous advocacy.

The feminist website, founded in 2014 by Ravneet Vohra, tells stories through an intersectional lens. Operated out by a “core team of five people” of a WeWork on Sunset and La Brea, Wear Your Voice often challenges media representation of the LGBTQ community and people of color. Recent stories have focused on the “overwhelmingly” white cast of David Lynch’s Twin Peaks reboot, Tina Fey’s comments about Charlottesville, and racism in the tattoo industry.

One of the site’s most widely circulated stories interrogated Orange Is the Black’s depiction of black suffering, calling it “trauma porn written for white people.”

The reason that Wear Your Voice’s mission to “give a voice to people who traditionally aren’t represented in mainstream media” resonated with Preston is because she knew what it was like to not see herself reflected in the world around her. She says that having a website like Wear Your Voice when she was growing up, one dedicated to telling the stories of her community, would have given her a greater “sense of pride and belonging.”

“If I saw myself reflected, I wouldn’t have tried to find myself through drugs or through other people,” Preston says. “I wouldn’t have had to go through the pain of trying to conform to a society that was never meant to include me.”

But according to Preston, the work of building a better world for trans people isn’t just about inclusion. It’s also about rejecting oppression.

When Preston confronted Caitlyn Jenner two weeks ago, she says that she was inspired by the activists who challenged Anita Bryant in the 1970s. Bryant, a former singer and orange juice spokesperson, was an outspoken opponent of the emergent gay liberation movement. She fought for the right to discriminate against LGBTQ people in the workplace and housing. Bryant also compared same-sex relationships to “people who sleep with St. Bernards.”

A group of activists responded to Bryant’s platform by smashing a pie in her face during a 1977 appearance in Des Moines, Iowa.

Preston says that people who stand in the way of equality, whether it’s an anti-gay activist or a famous reality star, need to be shown that their politics have consequences. When Jenner is tweeting at her own audience or appearing on television, it’s easy for her to take shelter inside her silo of privilege. But it’s harder to hide when someone pops up at a concert Jenner is attending and speaks truth to power.

“Talking softly does not work,” Preston claims. “No group of people has ever become liberated by asking kindly.”

A majority of the responses to her video thanked Preston for voicing the concerns about Jenner shared by many other members of the LGBTQ community. Out celebrities like Scandal’s Guillermo Diaz and Angelica Ross of Her Story stood by her. But Preston says that not all the feedback was positive. Some critics questioned her approach: Did she have to get in Jenner’s face? Couldn’t they have hashed things out privately?

But Preston says that these responses miss the point. She’s not interested in respectability politics. She wanted to voice her truth loudly enough that all of America could hear it.

“I unfriended so many people after that,” Preston says. “I’m no longer interested in people who are passive, neutral, or espouse messages that have no teeth. It’s important for people to truly stand for what they believe and do so unapologetically. If you do not stand for people of color, transgender people, and women, you are standing on the wrong side.”

“Anyone who gets in my way,” she adds, “it’s like standing in front of a moving train.”


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