Perhaps the most controversial aspect of Caitlyn Jenner is her political identity: Jenner's a staunch conservative Republican — a detail that surprised many during her conversation with Diane Sawyer, and has only created more consternation over time. During the second season of I Am Cait, she got into a number of tense discussions with her newly formed cohort, including the author Jennifer Finney Boylan. “Every conservative guy out there believes in everybody’s rights,” Jenner told them. "That is a lie!" returned Boylan, who even swatted at her with a rolled-up newspaper. “It got heated!" Jenner told The Advocate afterward. "Especially with poor little me, who’s the lone Republican conservative against all the liberal Democrats.” More damning was what she said next: “I like Ted Cruz. I think he’s very conservative and a great constitutionalist and a very articulate man."
Since then, Jenner, a savvy press strategist, has struck a considerably more measured tone. Most recently, she discussed her politics with Bill Simmons on Any Given Wednesday, but kept it fairly neutral. When he asked her if she supported Donald Trump, she responded, “Honestly, no — I haven’t. I have not outwardly supported anybody.” On her show, however, she was vehemently anti-Hillary. Jenner said that Trump "would be very good for women's issues," whereas Clinton "couldn't care less about women." She later said, "I would never, ever, ever vote for Hillary. We're done, if Hillary becomes president, the country is over." In a later episode however, Jenner met Clinton saying she was "very sweet" and tweeted out a photo with her with the hashtag #willingtolisten.
Increasingly, Jenner has positioned herself as an advocate for trans rights within the Republican party. While she tells Simmons that she has been "very disappointed" with the Republican party over the past couple of decades, she says she believes in conservative principles. Jenner then wisely moved to discussing issues that affect the trans community, like a significantly higher suicide rate, murder rate, and bullying. “Maybe I can help the Republican party do a better job when it comes to these types of issues," said Jenner. Caitlyn 2020?