‘Everything is Possible’: Puerto Rico’s First Trans Beauty Queen Inspires Hope for Progress

Lead Photo: Art by Stephany Torres for Remezcla
Art by Stephany Torres for Remezcla
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Anti-trans violence weighs heavier in the air than humidity for trans Puerto Ricans. In the stretch of a single year, seven of their brothers and sisters have been killed.

But just this month, Paolys Reyes became the first-ever trans woman to win one of the island’s beauty pageants, Miss Piel Canela Puerto Rico.

Another trans woman, Joanna Cifredo, hopes to boost her community organizing and human rights work by winning the 17th annual Miss Queen International–the world’s biggest pageant for transgender women–later this year. She’s been officially selected to represent the island.

There are positives for trans people in Puerto Rico: It’s a place where a trans person can amend their birth certificate and other government paperwork to reflect their lived name. Protections against gender identity discrimination in the workplace exist, although they’re not always adhered to-this problem exists globally. Grassroots activism among and for LGBTQIA+ people is strong, albeit limited primarily to leftist circles. And while there certainly needs to be more, especially in rural areas, multiple federally funded LGBTQIA+ organizations provide resources in the island’s major municipalities.

Still, mandatory gender equity education in public schools was banned two administrations ago and has yet to be reinstated. Another issue is the lack of separation of church and state in Puerto Rico’s government: Catholicism of the variety that does not accept LGBTQIA+ people, especially not trans people, is rampant among its politicians. For years now, religious liberty bills have come into its legislature like clockwork, though fortunately, none have been made law.

And some of Puerto Rico’s most prominent LGBTQIA+ oganizations don’t recognize or talk about non-binary people. Maybe the higher-ups fear they’ll alienate cisgender people, but regardless, the result reads as not taking seriously the many genders that exist outside the binary.

Yet Sunday (Jan. 24), after years of feminist activists’ pleading and protesting to previous administrations, newly inaugurated Governor Pedro Pierluisi declared a state of emergency due to high rates of gender-based violence. Surprisingly, Pierluisi stated specifically—when asked—that yes, this order and all the work that will follow it does include trans women.

But again: In Puerto Rico, seven trans people have been killed in the span of a single year. And several of those people were initially misgendered by police and the press—another slap of trauma—and later criticized, belittled, and demeaned via transphobic social media commentary.

What could beauty pageants do to shift progress forward? A lot, actually.

Pageantry in Puerto Rico is a cultural institution. Local, national and international competitions are followed closely by many. When Angela Ponce became the first trans woman to win Miss España–and she would go on to compete in Miss Universe–in 2018, reactions on Puerto Rican social media were markedly transphobic. Some complained that trans women shouldn’t be allowed to compete alongside cisgender women, that they should stick to their own pageants. Others just spewed hate for trans people, period.

“I took the challenge, because I’m a very brave woman,” says Reyes, who entered the pageant as the representative of Bayamón, a municipality just outside San Juan.

Reyes, an actress, model, and makeup artist who runs her own salon, has heaps of experience in LGTBQIA+ beauty pageants. Best known as Paolys Wonder in this realm, and on social media, she holds various titles both in Puerto Rico and the U.S. Once Ponce paved the way, Reyes says, she finally gave in to all the friends who urged her to compete in in pageants traditionally restricted to cisgender women. She says she worried she wasn’t thin or “perfect-looking” enough.

“But everything is possible,” Reyes says. “So I took the challenge, because I’m a very brave woman.”

Her qualifying interview, conducted by video, went something like this: The president tells her she’s beautiful. Reyes expresses her gratitude for Angela Ponce, who pried open those once-sealed doors. The president asks: but what does that have to do with her? Reyes realizes the president doesn’t know she’s of trans experience, and so she tells her. The president says she’ll have to speak with her lawyers and others involved in the competition before making a decision. She’ll get back to her within a week.

But Reyes gets a callback the following day: She’s been accepted.

“I represented what it is to be a woman, because we, trans women, we are women,” Reyes says of her time in the competition. “I won the title and I was so emotional, so happy, that I’d earned this.”

Reyes also won best talent for a performance imitating Beyoncé, who she names as one of her favorite divas.

Days after earning the title, Reyes was interviewed by Molusco, a famous Puerto Rican radio, podcast, and YouTube host. He’s notoriously ungentlemanly, Reyes points out. But with her, he’s mostly respectful. She says she felt comfortable throughout the nearly one-hour-long show, which aired on YouTube.

He does, however, point out what he believes are “masculine features” in Reyes’ appearance. He asks personal questions about her sexual relationships. Molusco precedes all this by saying he doesn’t know a lot about trans people, and he needs Reyes to educate him.

Joanna Cifredo, a community organizer and human rights activist, says having to explain yourself as a trans person is an unfortunate reality that “comes with the territory.”

“I say this as a trans woman who’s done a lot of media interviews: You’re going to be confronted with people like that,” Cifredo says. “In a perfect world, that the reporter or whoever, they would do their research-and some of them do, most of the time it’s female interviewers who do research-but the reality is that you can’t walk into it expecting that they’re going to have a Trans 101 understanding of gender. You need to quickly understand, within the first few minutes of talking to a person, OK, this person is not going to ask me the more in-depth questions; this is Trans 101. And then you have to switch into educator mode. And it sucks, but that’s part of being trans, you know?”

Cifredo will compete in a pageant this year, too. She’ll represent Puerto Rico at Miss International Queen, a competition for trans women that’s based in Thailand. The island hasn’t been represented there since 2009. This will be Cifredo’s inauguration into the world pageantry.

“I love pageants, I live for the girls. I grew up watching pageants because it’s cultural. But I’ve never competed. I’ve never done shows,” she says.

Her stage experience is limited to a stint in New York during which she did stand-up comedy. She worked for GLSEN at the time, supporting LGBTQ students from kindergarten to high school graduation.

This was after years of work in Central Florida, then D.C., during which she helped shape area university’s response to sexual violence, administered cultural competency training, helped reform healthcare policies to be affirming and accessible to trans people. At one point she worked at the National Center for Trans Equality as a racial and economic justice policy analyst. Advocating for sex worker rights, prisoner’s rights, and lobbying on the Hill for the Equality Act-which included testifying before Congress, the first trans Boricua ever to do so-are also on her resume.

When Hurricane Maria wrecked Puerto Rico in September of 2017, though, she immediately felt the need to return home.

Currently she’s in the final phases of launching Camp Albizu, a summer program for young Puerto Ricans, both island-based and hailing from the diaspora. She hopes the Miss International Queen platform will help her fundraising efforts for Arianna’s Center, the organization that will facilitate Cifredo’s endeavor.

Cifredo says she’s not concerned as much with how the minds of transphobic cisgender people might be changed as she is with how her reign, should she win Miss International Queen, could empower trans youth.

In the late ‘90s or early 2000s, a barely teenaged Cifredo saw Erica Andrews, the iconic Mexican trans woman, on The Maury Povich Show. Seeing the woman—so elegant, so gorgeous, Cifredo recalls—changed her life.

The host and audience treated Andrews and the other women despicably, but what Cifredo saw was their courage, their beauty. Andrews showed her what the possibilities of life could be. (Andrews passed in 2013. Before that, however, she won Miss International Queen in 2006. She earned a lot of other pageant titles, too.)

“I know it’s not easy growing up in a world being inundated with so much hate and violence, but we have to be bold, and we have to be brave, and we have to be authentic,” she says. “[Legendary trans activist] Sylvia Rivera told us that we must be visible. That we shouldn’t be ashamed for being who we are. So that’s what I’m trying to do. Hopefully, the young trans people will see me and they’ll get what i got when I saw Erika Andrews for the first time.”

It’s because of Andrews that Cifredo became the human rights activist she is today.

“Not a lot of girls like me have gone through the things I’ve gone through and have lived to tell the story,” Cifredo says of her personal life. “So I feel a responsibility to my community, to the trans women who came before me, because the only reason Joanna is even able to be, and the only reason I’m able to exist as the woman I am, is because there were women who came before me who were unapologetic in their transness and who fought and many times killed so that I can live my life authentically.”

Reyes, for her part, plans to continue performing as a drag queen while simultaneously holding her Miss Piel Canela title. Considering the abominable exclusion of trans women from drag—it was trans women at the helm of the artform since the beginning—and the exclusion of trans women from womanhood, her decision speaks volumes.

“Of course, I’m in another stage of my life,” she says. “But if you told me when I was signing the contract that I couldn’t entertain my public? I’m sorry. I’m representing women in this pageant, but I’m representing trans women too. Paolys Reyes is the queen of Miss Piel Canela, but Paolys Wonder is still the queen of the people.”