Why Trump’s Got A Big AI Problem

The Trump Administration has gone all in on artificial intelligence. It doesn’t hurt that AI’s biggest backers also happen to run the biggest companies on earth . Oh, and they also happen to have donated millions of dollars to Trump’s presidential campaign, inaugural committee, and even his fancy new ballroom. But it turns out that while Trump and his billionaire friends love AI, a lot of Republicans don’t — a fact that’s preventing him from getting rid of what little AI regulation exists. To talk more about Trump, AI, and why Republicans aren’t yet sold on the wonders of chatbots, we spoke to Gerrit De Vynck , a tech reporter for the Washington Post. And in headlines, lawmakers share what they saw in a video of the infamous “second strike” on an alleged drug trafficking boat, a longstanding newborn vaccine recommendation is in jeopardy, and the Supreme Court agrees to hear arguments for ending birthright citizenship. Show Notes: Check out Gerrit's piece – https://www.washingtonpost.com/technology/2025/11/23/trump-maga-division-tech-ai/ Call Congress – 202-224-3121 Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8 What A Day – YouTube – https://www.youtube.com/@whatadaypodcast Follow us on Instagram – https://www.instagram.com/crookedmedia/ For a transcript of this episode, please visit crooked.com/whataday