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The Gray Area with Sean Illing
The Great Enshittening
The Gray Area with Sean Illing
Oct 20, 2025 • 48 min
America chose violence. Now what?
The Gray Area with Sean Illing
Oct 13, 2025 • 58 min
What's worth remembering?
The Gray Area with Sean Illing
Oct 6, 2025 • 59 min
Why TikTok matters
The Gray Area with Sean Illing
Sep 29, 2025 • 1 h 04 min
The sun will save us
The Gray Area with Sean Illing
Sep 22, 2025 • 47 min
How much free speech is too much?
The Gray Area with Sean Illing
Sep 15, 2025 • 54 min
Imagine there's no billionaires
The Gray Area with Sean Illing
Sep 1, 2025 • 54 min
America's lawyers vs. China's engineers
The Gray Area with Sean Illing
Aug 25, 2025 • 52 min
So, what exactly is the “New Right?”
The Gray Area with Sean Illing
Aug 18, 2025 • 52 min
America is losing big on sports betting
The Gray Area with Sean Illing
Aug 11, 2025 • 54 min
It’s time to get weird
The Gray Area with Sean Illing
Aug 4, 2025 • 1 h 01 min
What if humans went extinct next Friday?
The Gray Area with Sean Illing
Jul 28, 2025 • 1 h 00 min
Can college survive Trump?
The Gray Area with Sean Illing
Jul 21, 2025 • 58 min
Hopeful pessimism
The Gray Area with Sean Illing
Jul 14, 2025 • 52 min
If AI can do your classwork, why go to college?
The Gray Area with Sean Illing
Jun 30, 2025 • 55 min
Is Trump winning?
The Gray Area with Sean Illing
Jun 16, 2025 • 49 min
A right-wing economist makes his case
The Gray Area with Sean Illing
Jun 9, 2025 • 1 h 04 min
What "near death" feels like
The Gray Area with Sean Illing
Jun 2, 2025 • 52 min
Machiavelli on how democracies die
The Gray Area with Sean Illing
May 26, 2025 • 48 min
Do you have moral ambition?
The Gray Area with Sean Illing
May 12, 2025 • 57 min
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