Welcome back to The Red Letter.
There was a time when President Donald Trump could charm young men on Twitch streams, meme his way through TikTok, and convince a generation drowning in student debt that he was on their side. That time is over.
In this week’s episode, I spoke with Harry Sisson, one of Gen Z’s loudest political voices and one of the first to be literally deep-faked by a sitting president. Trump used AI to generate a grotesque video of Sisson being defecated on. It was a humiliating attempt that says more about Trump’s state of mind than Sisson’s. But he may have found a worth target as Sisson, 23, represents a new class of digital activists who grew up online and are now rewriting how campaigns are run, how voters are reached, and how influence is built. He’s even considering suing Trump over the video — which, ironically, some might call a Trumpian move in itself.
But as piping hot as Trump’s videos are, he’s lost the imagination of the youth vote. According to the latest YouGov Economist poll, Trump’s approval rating among voters under 30 is –50. That’s not a typo.
“I despise Donald Trump with every fiber of my being,” Sisson told me. “But he won the social media battle [in 2024] after promising to eliminate inflation on day one, make it easy to buy a house — all of that has not happened. Inflation has only gone up. Prices have only gone up. And instead of focusing on these issues, he’s focused on a ballroom.”
Sisson said Gen Z expected those promises to be kept on Day One and as conditions stagnate, so does their loyalty.
Still, despite his focus on affordability, Sisson isn’t sold on NYC Mayoral candidate Zohran Mamdani’s Democratic socialism.
“I’m not a fan of the idea of socialism being a word associated with the Democratic Party,” he said. “We’ve got to run away from that as fast as we can.”
The self-described “Joe Biden liberal” — who stood by the 81-year-old president until the bitter end — sounded almost like a politician himself when I asked if he’d ever run for office.
“Can’t run for senator or president anytime soon, but I won’t rule anything out,” Sisson said. “We’ll see where the winds take me..”
I believe him. Because if this generation has proven anything, it’s that they don’t wait for permission they just log on and lead.
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