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In 2024, I was working with Olivia Troye, whom I met three years earlier at the Renew America Movement, where I worked on the comms team. Our Executive Director, Miles Taylor, brought her in as Chief of Strategy, and we became fast friends. Though our backgrounds and experiences were very different, we had much in common. Olivia became something of a confidant and was also generous enough to help me find some contract work in the pro-democracy space.
In the fall of 2024, Olivia was heavily involved in Republicans for Harris, and she was publishing pieces on Substack focused on what she lived through as part of Donald Trump’s first administration. It was intended as a reminder to voters with short memories—and as a warning to those who weren’t listening to what Trump was clearly saying on the campaign trail about his plans for a second term.
While Olivia is a very competent writer in her own right, she was on the road for the Harris campaign constantly. So I was doing research, drafting op-eds, and writing video scripts for her in the leadup to the election. We talked daily, often multiple times a day, and by October, we were getting nervous. Kamala Harris had lost some of her momentum, despite a killer debate performance and a convention speech for the ages.
I saw Harris in person twice, including when she introduced Tim Walz as her running mate in my hometown of Philadelphia. What I saw didn’t remotely match the right-wing podcast and social media characterization of her as a woman “who couldn’t string two sentences together.” Quite the opposite.
So I pitched Olivia a different sort of idea for a script: let’s send a letter to Americans from two years in the future. Let’s show them what a vote for Donald Trump could really mean, and how it would vastly overshadow concerns about policy differences, how Harris became the nominee, or any other perceived flaws Harris might have. Olivia loved the idea, so I got to work.
I turned over a script within a day. It was forming in the back of my mind for a while, so it practically wrote itself. This was good, because my mother’s 80th birthday happened to fall in the same week, and we were busy planning a dinner party. Such a strange juxtaposition of joy and fear. Olivia didn’t make a single change, which was unusual for her. She recorded it sans makeup, without her hair done, and with a look of pure dread on her face. It was jarring, as Olivia always looks top-notch—the epitome of a happy warrior.
Ultimately, on October 24, 2024, we published the text as well, which I’m reprinting here. It’s a fraction of the length of some of the deep dives I’ve written, but I’m still quite proud of it. At the same time, I would much prefer that I had been wrong. That I had been exaggerating. That fear had caused me to hyperbolize hysterically. I don’t think that’s the case. You can judge for yourself.
Whether we can turn the tide before October 24, 2026, remains to be seen.
October 24, 2026
Dear Friend,
I hope all is well where you are. I’m managing. As difficult as my situation is, at least I have friends here. It helps make the long, anxious days a little easier. None of us knows exactly what to expect next...

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