Caitlyn Jenner was this close to being Bill Simmons’ first female guest.
The first four episodes of the Simmons-hosted Any Given Wednesday on HBO featured an all-male lineup of sports and pop culture guests that included a fired-up Ben Affleck and a giggly Bill Hader, among others. Last week, Simmons hosted a conversation about television that included Mad Men’s Christina Hendricks, but on the eve of the Rio Olympics, his most prominent guest to date might just be the former gold medalist-turned-reality TV star formerly known as Bruce Jenner.
And while Simmons missed an opportunity to land Mark Cuban’s endorsement of Hillary Clinton, preferring to focus instead on his day job running the Dallas Mavericks, the host did not hesitate to ask the openly-conservative Jenner about her latest foray into politics.
But first, they had to talk sports. “In 1976, not liking Bruce Jenner was like not liking Beyoncé in 2016. It was the single most un-American thing you could do,” Simmons said during his introduction. The interview began with Jenner extolling the virtues of the decathlon, calling it both the greatest and most difficult of all Olympic events simply because it requires so many different skills.
As for why she walked away from competition after those 1976 games, Jenner said, “I don’t think it’s a good lifestyle, when you’re that obsessed in one small area of your life called sports. There’s so much more to life.”
“I wanted to enjoy life,” she added, before referring to her eventual gender transition. “I had other issues that I was dealing with, obviously,” Jenner said, saying she used sports to “hide” and emphasize the “masculine” part of her identity.
However, asked by Simmons if the Olympics should be used as a “stage to make political statements,” Jenner replied, “Absolutely not.” Describing the Olympics as a force for “good” in the world, she said the games “have so much potential to bring people together.”
“For organizations to use it for their political advantage just bothers the heck out of me,” Jenner said. This led Simmons to bring up the episode of her E! reality show I Am Cait from earlier this year, during which she defended her Republican identity to some concerned friends. Is she still a conservative, Simmons wanted to know?
“Of course I am,” Jenner said, explaining that she thinks it’s “ridiculous” how much the federal government controls. “The Republican side, even though I’ve been very disappointed with them even over the last 10-20 years, has the best opportunity to bring this country back to what it was.”
But even if she seems to want someone to make America great again, Jenner said she has not “outwardly supported” Donald Trump or any other candidate, despite the fact that back in April, Jenner posted a video of herself using the ladies’ room at Trump Tower in Manhattan in which she thanked the candidate for his support in that area. She said she merely wants to “help the entire Republican Party do better when it comes to LGBT issues.”
Appearing in Cleveland last month during the Republican National Convention—though notably not on the Quicken Loans Arena stage—Jenner said she has no plans to “give up” on the GOP, despite years of disappointment, especially regarding the party’s position on LGBT issues. “It was easy to come out as trans,” she quipped. “It was harder coming out as a Republican.”
“The Republican Party has not been as good on LGBT issues and social issues,” Jenner admitted to Simmons, reiterating that she wants to educate conservatives about the “T” portion of that equation. So far, it isn’t working. The latest version of the GOP’s platform promotes only “natural marriage” and protects those who would discriminate against LGBT Americans under the protection of “religious liberty.”
Looking back on the past two years, Jenner said her “darkest moment” was about six or nine months before she came out, when she was getting “destroyed” in the tabloids, which aimed to out her themselves. She seriously considered taking the “easy way out” and shooting herself in the head. “That was probably the lowest I’d ever gotten,” she said. But then she realized, “I don’t want my story to end that way, on a negative note. I want my story to end on a positive note.”