Meet the Trans Woman Challenging Caitlyn Jenner on Her Conservatism

'I Am Cait' cast member Jenny Boylan is trying to help Jenner ease into the role of very public trans figure

The second season of Caitlyn Jenner's reality show 'I Am Cait' premiered on E! Sunday.
Meet the Trans Woman Challenging Caitlyn Jenner on Her Conservatism

Author and activist Jenny Boylan was on a bus full of trans women, barreling down a highway in the Southwest, when she learned that a high-profile trans rights measure on the November ballot, the Houston Equal Rights Ordinance, or HERO, had been voted down.

In Houston and nationwide, the religious right had campaigned fiercely against the anti-discrimination measure, claiming it would allow men to use women's restrooms. The argument, ludicrous as it may sound, resonated with voters, and 62 percent of them voted against it.

Boylan was on that bus as a cast member of Caitlyn Jenner's reality show I Am Cait, which in its second season takes the form of a cross-country road trip. In the first episode, which aired Sunday on E!, the cast members have a contentious conversation about HERO, in which Jenner declares — to the horror of the other trans women onboard — that Republicans aren't standing in the way of gay and trans rights.

Boylan, a board co-chair for GLAAD and a consultant on I Am Cait and Transparent, acts as a kind of a spirit guide for Jenner as she eases into the role of very publicly bringing awareness to the trans community. In this case, perhaps Jenner is bringing awareness to the fact that not all trans people share the same political beliefs.

Boylan tells Rolling Stone she sees Jenner's political views as frustrating, but not really surprising. "There are people in this country who don't see their own civil rights as the most important issue on the ballot. For me, it's pretty important. It's a matter of life and death," she says.

As for Jenner's claim that "every conservative guy out there believes in everybody's rights," Boylan says, "I just think that's delusional.

"To pretend that Republicans and Democrats have been equally supportive of LGBTQ rights, this or any other election year — it's just plain false."

So-called bathroom bills like HERO are a prime example. "Some Republicans have demonized us at every turn, and now we're facing this slew of bathroom panic bills just to scare people to the polls using this false narrative that there are going to be predators in dresses in the ladies' room," she says.

This season of I Am Cait will feature several other politically charged debates among its cast members — who also include trans artists and activists Candis Cayne, Zackary Drucker and Kate Bornstein. For instance, viewers will see the genesis of Jenner's recent declaration that she'd like to be Ted Cruz's "trans ambassador."

By any measure, Cruz is not a friend to the trans community. He supported anti-HERO pastors and has condemned the military's decision to lift a ban on transgender servicemen and women. At an Iowa rally in January, the Republican candidate said it would be better for trans students to use a faculty restroom than to "inflict" them on other children. But to Jenner, Cruz's thoughts on trans rights are secondary to his positions on things like the federal budget and the economy.

Boylan isn't surprised that Jenner's political views have caused an uproar among trans individuals. "I like to say if you've met one transgender person, you've met one transgender person," Boylan says. "It's also the problem in terms of assembling a political agenda, because the trans community is diverse, it's contentious, we have not come to any agreement on the discourse."

As an example, she cites a "very vigorous discussion" about the word "tranny," which, she says, "some people in our community — most of the women on the bus, in fact — claim as a word of celebration and joy.

"Someone like me, I see that word as a slur — as a word that was used while I was being beaten by someone who didn't see any joy in my existence," she says.

Creating space to debate those issues is in many ways the point of the show. Much of the time on the bus was spent "wrangling over: What does it mean to be trans in this country right now? As it turns out, there are a lot of different answers, and they are all valid," Boylan says. "We're not going to come to consensus, but what I hope is that people will realize all of these embodiments are cool and deserve to be celebrated."

When asked if she would volunteer to be Ted Cruz's "trans ambassador," Boylan takes a deep breath and shares an anecdote from her time filming I Am Cait that tells us something about how she might approach a figure like Cruz. "There is this right-wing minister who is just about one of our most vocal enemies. He's one of the people who was behind the repeal of HERO," she says. "We went to his church, and I prayed with him, and I prayed, 'Dear Lord, please open the heart of this son of a bitch.'"