Offline with Jon Favreau

220: Adam Friedland Just Wants to Understand

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. 

219: The Fight to Liberate Minnesota (and America)

Minneapolis isn’t just protesting ICE—it’s fully organizing against it. Lydia Polgreen, journalist and opinion columnist at The New York Times, joins Offline to explain the difference, share what she saw on the ground in the Twin Cities, and explain how it compares to other countries’ slides towards authoritarianism. As a former foreign correspondent in West Africa and India—and having grown up in Minnesota—Lydia breaks down this civil unrest and what it spells for the future of America.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.

218: The Enshittification of the Internet (with Cory Doctorow)

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. 

217: ICE Killings and the Death of Shared Reality

Does misinformation even matter if no one can agree on a shared reality? The New Yorker’s Jay Caspian Kang joins Offline to explain how the ICE shooting in Minnesota exposes Americans’ algorithm silos. Then, he and Jon explore the rise of a 23-year-old YouTuber who ignited the right’s fascination with fraud in Minnesota, and break down five media trends that will reshape the industry in 2026 and beyond.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. 

216: What Comes After Trump?

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.