I Wonder What Caitlyn Jenner Is Thinking These Days?

In the spring of 2015, the landscape for the transgender community was irrevocably altered by a single, seismic event: Caitlyn Jenner’s interview with Diane Sawyer. I remember it vividly, not just as a viewer, but as someone in the room, having served as an advisor to Diane Sawyer, her 20/20 production team, and the ABC executives. We knew we were creating something that had the potential to be a watershed moment—a high-profile, sensitive, and deeply personal portrayal of one transwoman’s journey to her authentic self. For me, and for so many others, it was a profoundly validating experience. It was the first time that a person of such immense public stature had so vulnerably shared a story that, in its essence, mirrored our own—minus the Olympic medals, of course.

The interview was a masterclass in humanizing a community that had long been relegated to the margins of public discourse. It was a moment of hope, a powerful narrative that transcended the tabloid frenzy and spoke to the universal human desire to live an honest life. We hoped it would open hearts and minds, proving that our struggle was not a choice or a curiosity, but a fundamental part of the human condition.

But in the decade since, much has happened. Caitlyn Jenner’s political journey has diverged sharply from that of the trans community she once helped illuminate. She has embraced conservative politics, aligning herself with a party that has actively championed the very laws and policies that threaten the rights of trans people across the country. Her public statements have at times been viewed as dismissive of the struggles of a community facing relentless attacks on everything from healthcare access to the right to simply exist in public spaces. The woman who once told the world, “I am a woman,” now often seems to live in a political world that seeks to deny that truth to others.

And so, the question that haunts me today is not a political one, but a deeply personal one: I wonder what Caitlyn Jenner is thinking these days? Her immense wealth and celebrity undoubtedly afford her a level of protection that most trans people can only dream of. Does her privilege shield her from the daily assault? Does she have to worry about which state’s bathroom she can safely use, or if her family will lose their health insurance because of a new anti-trans law? Does she, like so many of us, feel the knot in her stomach every time a new bill is proposed, wondering what aspect of our lives will be legislated away next?

In spite of her political affiliations, Caitlyn Jenner is still a member of our community. She carries the knowledge of our shared struggle, the pain of being unseen, and the courage it takes to live authentically. As the attacks on our right to exist escalate, I can only hope that, on some level, she worries too. I hope that the immense vulnerability she showed in 2015 is still a part of who she is, and that it allows her to feel the weight of what is happening to her trans siblings.

For all the division, the core truth of that watershed moment remains: we are all human, we are all seeking our authentic selves, and no amount of privilege can ever fully erase the shared reality of what it means to be transgender in a world that is still learning to, or simply would rather not, see us.