When I met Caitlyn back at her home on Saturday, she had just returned from a lengthy hike on the surrounding mountain paths. She was dressed down in sandals and a T-shirt, headed to pick up a set of clubs from her private golf club.Sherwood Country Club sits in another upscale neighborhood about 30 minutes from Malibu, nestled in the shadows of the Santa Monica Mountains. The course was designed by Jack Nicklaus, and Tiger Woods used to host a tournament there every year. Caitlyn has been a member for more than 15 years, and she walked the sprawling property like it was a second home. While golf courses have a reputation as the natural habitat of rich, straight, white men, for Caitlyn they have been a sanctuary. Before her transition, it was one of the few places where she could exist. “I would take my little bras up there,” she told me, “in this very quiet golf course, and [see] what it was like playing with boobies.”Today, Caitlyn can comfortably inhabit spaces here and elsewhere in Malibu as herself—as a wealthy, famous white woman. And while she has faced some harassment because of her gender expression, it tends to be online. But that’s not life for most transgender people, for whom every day can be a struggle for survival, let alone luxury. Transgender people, especially people of color, encounter discrimination, harassment, and violence while seeking employment, housing, and healthcare. When the National Center for Transgender Equality conducted the US Transgender Survey (USTS), the largest survey of its kind, in 2015, nearly 30 percent of respondents were living in poverty, compared to 12 percent of the overall population; the unemployment rate among respondents (15 percent) was triple the national rate at the time of the survey. The disparity is even larger for trans people of color.
“I think it’s good that I’m on the Republican side because the Republicans know that, and I have an immediate in with them to change their minds,” Caitlyn told me, and would mention at various points the meetings she’s taken with conservative lawmakers and administration officials like Betsy DeVos and Nikki Haley. “The Republicans need the most work when it comes to our issues, I get that. I would rather work from the inside. I’m not the type of person who is going to stand on a street corner with a sign and jump up and down. No, I’m going to go have dinner with these people.”That’s why she flew to the Capitol for Trump’s swearing-in. “I went to the inauguration just because I wanted to meet people. I wanted to be there,” Caitlyn said. One of the people she met was Vice President Mike Pence. “I had a great conversation with him.”With political divisions as vast as they have become in the US, many Americans might not be so eager to talk with Pence, who has opposed expanding rights and protections for the LGBTQ community throughout his career. Caitlyn, however, saw an opportunity to convince a powerful conservative to rethink some of his views.“He did some really anti-LGBT community stuff,” she told me. “I know that. He’s also very Christian. He’s kinda like, from our standpoint, the real enemy. But that’s OK, I can handle that.”
“The Republicans need the most work when it comes to our issues, I get that. I would rather work from the inside."
Her story is also emblematic of the push and pull in our divided nation. A transgender celebrity who voted for Trump and continues to associate with the Republican Party, she does not easily fit into one ideological box for conservatives or liberals. Caitlyn Jenner makes people uncomfortable. She is also a human being, a product of her generation, who is trying her best to do the right thing for her community, and for herself.As the sun set on Sunday evening, Caitlyn and I walked the grounds outside her home, following a dirt path lined by tall grasses. Standing there in the approaching twilight, Caitlyn told me about how she piloted a small plane out of Los Angeles earlier that week. She likes to fly, to be alone among the clouds.Years ago, when Bruce was at his lowest, Caitlyn would materialize in the sky, coming into being on lonely flights to nowhere. She says she kept a wig and set of women’s clothing in her plane so that she could go somewhere to be herself, even if it couldn’t be on Earth. “I would be up there in my little lonesome, free as can be,” Caitlyn said. Maybe she felt closer to God.Sometimes, Caitlyn told me, she would turn her plane vertically, hurtling at hundreds of miles per hour straight up into the sky before she would stop, float briefly in the air, and fall back down.
“We come and we go and at the end, when it’s all said and done, hopefully your family is going to be there.”