Caitlyn Jenner was a vocal supporter of Donald Trump during the early days of his presidency. During Trump's campaign for president, Jenner expressed that, although she found his demeanor somewhat un-appealing, she believed that his future as policy maker was promising, and would prove beneficial to the women of America. "Um, I'm not a big fan because I think of his macho attitude," Caitlyn told a peer on her E! Entertainment show, I am Cait. "I think he would have a hard time with women when he doesn't even realize it, and it doesn't mean he wouldn't be good for women's issues, I think he would be very good for women's issues."

In a recent opinion editorial piece for The Washington Post, Jenner revealed that she no longer felt the same way the President. “Believing that I could work with Trump and his administration to support our community was a mistake,” she wrote, alluding to the Trump administration's efforts to narrow the definition of gender and thus threatening to dismantle federal civil rights laws protecting transgender people. “Trump was the first Republican presidential candidate to claim to support this valuable, vulnerable community, and I was encouraged by the applause he received when he said at the Republican National Convention in July 2016 that he would stand up for the LGBTQ community, she wrote. "But those have proven to be empty promises."