PSJ Special Segment: The First AI-Assisted Election | The Pirate Street Journal

The midterm elections wrapped up yesterday, and plenty of people are still sorting through the results. But the hosts of the Pirate Street Journal came away with a different kind of takeaway. This may have been the first AI-assisted election at any real scale, and each of them used the technology in a very different way. One built a voting framework with Claude, one cross-checked three chatbots on California propositions, and one skipped AI entirely and tested what campaign marketing does to a voter’s head. What they found was useful, a little uncomfortable, and in one case very funny.

You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.

Building a Voting Plan With a Chatbot

Eddie went into this cycle with a problem most of us share. Beyond the two or three names at the top of the ballot, he had no idea who half the candidates were. So he gave Claude his address, asked it to pull up his ballot, and had it interview him about what he cares about. The result was a personal framework: a sensible economy, a reflective stance on AI, leaders who look forward, and measurable outcomes over speeches. He voted ahead of time, so the booth held no pressure.

The tool had gaps. It missed a few races, and judges and forest preserve candidates were beyond its reach because no information existed. Eddie filled the holes with a loose belief in checks and balances, voting against incumbents in a heavily Democratic Illinois and tossing a few random votes to Republicans for the sake of competition. When he had nothing at all, he confessed he voted for Asian candidates, a bit of what he called positive racism borrowed from a Ronny Chang comedy routine.

Cross-Checking Props and Local Races

Christopher faced a different headache in California. Many ballot propositions are worded so confusingly that even when you know what you want, you can’t tell whether to vote yes or no. He ran the props through ChatGPT, Perplexity, and Grok, and argued with each of them, since he figures a single chatbot is too eager to please. Gemini, he said, shut down any political conversation almost immediately. About two thirds of his props turned out to involve raising taxes or making it easier to raise them.

He was also surprised by how much the models knew about hyper-local races. ChatGPT had details on a city council contest in Capitola, a town of roug