The Gray Area with Sean Illing

The Supreme Court is aggressive on almost everything. Except the internet.

Sean talks with Vox’s Ian Millhiser about a surprising pattern at the Court. While the Court has been eager to reshape schools, healthcare, and civil rights law, it has consistently taken a cautious, almost hands-off approach to regulating the internet. They unpack a recent case involving music piracy, the broader legal fight over who’s responsible for what happens online, and why even a highly ideological Court seems wary of breaking the digital world.

Host: Sean Illing (@seanilling) 

Guest: Ian Millhiser (@imillhiser)

We would love to hear from you. To tell us what you thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.

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The Pentagon has spent years building AI tools to help identify targets, speed up battlefield decisions, and make war more “efficient.” What started as an effort to analyze drone footage has grown into something bigger and much more unsettling.

Sean talks with Bloomberg’s Katrina Manson about Project Maven, the Defense Department’s long-running push to bring AI into warfighting. They discuss how these systems actually work, what “human in the loop” really means, why autonomy is no longer some far-off sci-fi scenario, and what happens when the speed and scale of machine decision-making collide with the fog of war. 

Host: Sean Illing (@seanilling) 

Guest: Katrina Manson (@KatrinaManson)

We would love to hear from you. To tell us what you thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.

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Back in 2015, before President Donald Trump, before January 6, before all the craziness of the last decade, Matt Yglesias made a blunt prediction: American democracy is doomed.

Guest host Zack Beauchamp talks with Matt about what that argument got right, what it missed, and why the real problem might not be any one politician but the structure of the system itself. They get into presidential power, partisan loyalty, why Congress keeps folding, and how the two-party system might be quietly making everything worse. They also discuss what it would actually take to fix it — or whether things have to completely break first.

Host: Zack Beauchamp (@zackbeauchamp)

Guest: Matt Yglesias (@mattyglesias)

We would love to hear from you. To tell us what you thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.

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What does it mean to be “woke”? It's become a catch-all term to smear or dismiss anything that has any vague association with progressive politics. So anytime you venture into an argument about “wokeness,” it becomes hopelessly entangled in a broader cultural battle.

Today’s guest, journalist and professor Musa al-Gharbi, helps us untangle “wokeness” from its fraught political context. The author of the book, We Have Never Been Woke: The Cultural Contradictions of a New Elite, al-Gharbi discusses what effects the movement is and isn’t having on our society.

This episode originally aired in November 2024.

Host: Sean Illing (@seanilling) 

Guest: Musa al-Gharbi (@Musa_alGharbi)

We would love to hear from you. To tell us what you thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. 

And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. 

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It’s easy to forgive other people because you don’t have to live inside their head. Forgiving yourself is different and much, much harder.

Sean Illing is joined by philosopher Myisha Cherry to talk about what it actually means to forgive yourself without letting yourself off the hook. They discuss the difference between guilt and shame (one can push you to repair, while the other just makes you want to hide), why even small screwups can leave a lingering moral aftertaste, and how regret can either trap you in self-reproach or become fuel for doing better.

Host: Sean Illing (@SeanIlling)

Guest: Myisha Cherry (@myishacherry)

We would love to hear from you. To tell us what you thought of this episode, email us at [email protected] or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. New episodes drop every Monday and Friday.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members.
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