Offline with Jon Favreau

Progressives are highly critical of America, and for good reason. But we are losing more than problematic idols and ideals when we abandon patriotism. Jerusalem Demsas, founder and editor of “The Argument,” argues that if we’re going to save America, we’ll have to start loving it first. She joins Offline to explain how liberals have ceded patriotism to the right, why No Kings is starting to fix this, and how to talk about our country’s issues without undermining hope that America still holds promise.For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast, episode title, and episode date.

AI company Anthropic has a new, values-oriented “constitution” that they’re feeding their chatbot, Claude. Amanda Askell, the company’s in-house philosopher, joins Offline to talk about what it means to teach ethics to an LLM, whether the AI skews more human or more robot, and how she is training Claude to make its own judgements. Breaking with other AI models—and social media’s attention obsession—Amanda is trying to teach Claude not to be sycophantic or engagement-driven, but a kind soul who may, one day, be considered sentient.For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.

Adam Friedland sits down with Jon to make sense of his unlikely rise from the self deprecating (and self defecating) cohost of Cum Town to…a public intellectual? "The Adam Friedland Show" has a knack for jolting politicians and celebrities out of their canned talking points, and its host shares what he thinks of the format he initially set out to skewer, the questions we need to be asking about the ICE crackdown, and his issues with Republicans and Democrats alike. For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.

Journalist, blogger, and science fiction writer Cory Doctorow stops by the studio to talk to Jon about “enshittification,” his theory that explains how, sometime over the last decade, everything online became substantially worse. The two discuss how tech companies lure in, trap, and then extract as much capital as possible from users; how that process played out at Facebook and Amazon; and what it would take — from a Democratic-led FTC and Congress — to reverse the trend before it’s supercharged by AI.For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.

What does 21st century authoritarianism look like in the United States? Author and Atlantic staff writer George Packer joins Offline to talk about America’s zombie democracy, who could be the most dangerous MAGA heir, and how Democrats should be fighting for the country. For our last episode of 2025, George and Jon connect the dots between Trump, polarization, oligarchs, AI, social media, Charlie Kirk and more. For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.