The Gray Area with Sean Illing

Masha Gessen debates the existence of a conspiracy between the US and Russian governments, explores the Trump-Russia investigation, discusses Trump's contradictory statements and poor response under pressure, delves into bullshitting and its role in authoritarian regimes, highlights the power of ideology, examines toxic politics and conspiracy theories, and offers book recommendations.

Kwame Anthony Appiah, philosopher and writer, discusses the challenges of living in a cosmopolitan world. They explore topics such as the implications of cosmopolitanism on immigration, responsibility and risks, appreciating differences, and the importance of emotional responses and solidarity.

Yascha Mounk, a Lecturer on Government at Harvard University, discusses the weakening consensus on democratic governance, Trump's illiberal instincts, the rise of right-wing populism, and the threat to American institutions. Mounk's international perspective and personal story of becoming an American citizen add depth to the conversation.

Bryan Stevenson is the founder and executive director of the Equal Justice Initiative. He and his staff have won reversals, relief, or release for more than 115 wrongly convicted prisoners on death row. He’s the author of the power book Just Mercy, and a winner of a MacArthur “Genius” grant. There are only a few people I’d say this about, but he’s a genuine American hero.This conversation begins with one of Stevenson’s most provocative arguments. “The opposite of poverty isn’t wealth,” he says. “It’s justice.” In this podcast, he explains what he means.We also talk at length about his argument — an argument I am now fully convinced by — that the question is not whether a criminal deserves to die but whether the state deserves to kill. We talk about America’s history, our justice system, our prejudices. We talk about what it’s like to be a black man in the South, driving down highways named for Robert E. Lee and attending high schools named for Jefferson Davis. We talk about the value of shame, and the way we honor it in the justice system even as we dismiss it in our national dialogue.The nature of writing these podcast descriptions is that they lend themselves to hype. I want you to listen, and I use this space to try to persuade you to listen. But that backfires a bit when it gets to a conversation like this one, which left me more changed than perhaps any of the discussions that came before it. This is worth listening to.Books:“The Brothers Karamazov," by Fyodor Dostoyevsky"Gilead," by Marilynne Robinson“Anna Karenina," by Leo Tolstoy Learn more about your ad choices. Visit podcastchoices.com/adchoices

There’s much talk of “empathy” in today’s politics, but it’s a cramped, weaponized form of empathy — an empathy designed to force us to grudgingly tolerate each other, or an empathy used to explain away the reasons we hurt each other.You can glimpse something better in the space Anna Sale creates on the WNYC podcast Death, Sex, and Money. Her show is, in this moment, powerful; the empathy she extends to her guests feels real and deep; the conversations she holds are bracingly difficult while still being honest and kind.Sale, it turns out, developed the idea for Death, Sex, and Money when she was a reporter covering politics, shouting questions at Anthony Weiner, crisscrossing the campaign trail. As we discuss in this podcast, that’s no accident.Sale and I talk about what she learned covering politics, as well as how she’d cover it if she were to do it again today. We dive into her interviewing technique — you’ll hear her turn it on me more than once — and the wonderful story behind her marriage, in which former Sen. Alan Simpson plays an unexpected but crucial role. We talk about death, about religion, and about what she learned from Bill Withers. Enjoy!Books:“Goodnight Moon," by Margaret Wise Brown"Everything in Its Path: Destruction of Community in the Buffalo Creek Flood," by Kai T. Erikson“Reviving Ophelia: Saving the Selves of Adolescent Girls," by Mary Pipher Learn more about your ad choices. Visit podcastchoices.com/adchoices

Senator Cory Booker is back! In this special live episode of The Ezra Klein Show — taped at Vox Conversations — Booker and I dig into America’s crisis of trust. Faith in both political figures and political institutions has plummeted in recent decades, and the product is, among other things, Trump’s presidency. So what does Booker think can be done about it?We also talk about: Whether Democrats need to be angry to fight Trump The $400,000 President Barack Obama recently accepted for a speech to a bond firm The lecture Booker’s mother gave him when he was sworn into the SenateBooker’s fight with the left over drug reimportation, and how he and Bernie Sanders came to agreementWhat Booker thinks of a universal basic income, single payer health care, political correctness on campus, artificial intelligence as a threat to humanity, and more.Speaking of which, when I asked Booker about a UBI — which he says his staff is aggressively exploring — he responded with an expansive, surprising riff that sure sounded a nascent presidential platform. So don’t miss that! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Washington has been gripped of late by the world’s most depressing, least imaginative, debate over health care. The question, as it stands, is whether Obamacare will survive (while being mildly, but persistently, sabotaged by the Trump administration), or whether it will be rolled back and replaced with a system that covers 24 million fewer people in order to fund tax cuts for the richest Americans. Huzzah!But a better conversation awaits. Bill Gurley is a partner at Benchmark Capital, and an early investor in Uber, Grubhub, Opentable, and more. In 2016, TechCrunch named him venture capitalist of the year. And for the last few years, he’s been studying the American health care system, trying to find an opening where technology can make a difference, and build a business. Now he thinks he’s found it.This is a conversation about what kinds of health care systems are, and aren’t, possible in this country. As you’ll hear in this discussion, I’m much more skeptical than Gurley is about both the need and the desirability for reforms that push costs onto consumers, but I agree with him that Obamacare has moved the system farther and faster in that direction than people realize. We talk about that, as well as why it’s been so hard for technology to cut costs in health care, the Singaporean health care system and the lessons American can learn from it, the way regulation protects incumbents, the government’s strangely structured investments in electronic medical records, and whether Silicon Valley’s move-fast-and-break-things culture can work for something as personal as medical care. We also discuss Gurley’s view that democracy and capitalism will, if given enough time, eat each other, and why he’s looking to China for the next great health innovations. This conversation won’t fix the American health care system, but it was, for me, a refreshing reminder that better, more productive discussions are possible. Books:“Catastrophic Care: Why Everything We Think We Know about Health Care Is Wrong," by David Goldhill"Startup: A Silicon Valley Adventure," by Jerry Kaplan“Myth or Magic - The Singapore Healthcare System," by Jeremy Lim"Shoe Dog: A Memoir by the Creator of Nike," by Phil Knight Learn more about your ad choices. Visit podcastchoices.com/adchoices

Elizabeth Warren is the founder of the Consumer Financial Protection Bureau, the senior senator from Massachusetts, and the author of the new book, “This Fight Is Our Fight: The Battle to Save America's Middle Class.”You might have heard of her.Warren is also one of the Democrats most capable of defining the Democratic Party’s soul and message in a post-Trump era. In her book, she says she had at least one big disagreement with President Obama — a disagreement that speaks to the direction she wants to lead the party. Obama told Americans, “the system isn’t as rigged as you think.”"No, President Obama,” Warren replies, "the system is as rigged as we think. In fact, it’s worse than most Americans realize.”In this interview, we go deep into Warren’s view on how, where, and why the system is rigged — as well as what can be done about it. We also talk about whether fighting Trump requires matching his tone and tactics, how complex policies and processes create space for special interests to take over, and why Trump’s abandonment of economic populism hasn’t affected his support among his voters.Warren is an able, thoughtful advocate for one of the Democratic Party’s possible futures: becoming a party that represents the economic populism Trump claimed to champion, but quickly abandoned. But as she’s the first to admit, that won’t be easy.Books:“Evicted," by Matthew Desmond"Two Dollars a Day," by Kathryn Edin “The Little Engine that Could," by Watty Piper Learn more about your ad choices. Visit podcastchoices.com/adchoices

I was asked recently to name a book that changed my life. The book I chose was Cal Newport’s “Deep Work,” and for the most literal of reasons: it’s changed how I lived my life. Particularly, it’s led me to stop scheduling morning meetings, and to preserve that time for more sustained, creative work.Which is all to say that I’m a bit obsessed with Newport’s work right now, and especially his account of how the digital environment we inhabit is training us out of concentration and into distraction in ways that are bad for us, bad for our work, and ultimately bad for the world. Most of the conversations on this podcast are how to think about things differently. This one is too, but it’s more importantly about how to do things differently, and why you should do them differently. We discuss:-How Newport defines depth when it comes to work-Why the information revolution boosted productivity up until the 2000s, but then stagnated-What he thinks is problematic about the constant accessibility of technologies like email, Slack, and other communication tools-His perspective about how we’re still in an early age of the internet, and what looking back at periods like the Industrial Revolution can teach us about using new technology to work smarter-How to take productive breaks, rather than flicking through email and Facebook and Twitter-How “flow work” and deep work overlap, and how they’re distinct from each other-Why he consumes and produces information more slowly and more traditionally—through newspapers and radio, and why that might benefit people who work in the knowledge economy-His vision of the workplace of the futureI hope you get as much out of Newport’s ideas as I have.Books:-Jaron Lanier, “You Are Not A Gadget” and “Who Will Own The Future"-Douglas Rushkoff’s “Throwing Rocks at the Google Bus” Learn more about your ad choices. Visit podcastchoices.com/adchoices

This is a podcast about topics we don’t always cover on this show. Religion. Spirituality. Gender roles. Traditionalist societies. Comic books.G. Willow Wilson is the author of The Butterfly Mosque, Alif the Unseen, and the Hugo award winning comic book, Ms. Marvel. She’s also lived a fascinating, unusual life: she’s an American who converted to Islam and then moved to Egypt, where she met her now-husband. The hallmark of her work is an empathy and appreciation for societies that are often caricatured or even reviled by Americans. This conversation went in some wonderful, weird directions. We talk about Richard Dawkins’ “God gene,” and why Wilson feels she has it, and I don’t. We talk about how sickness can strengthen faith, what happens to spirituality when it’s decoupled from beauty, and why being in Egypt made Wilson feel less free, but more appreciated.We also talk about writing and comics, about the ways in which superheroes have become modern myths, and how her character, Ms. Marvel, became an surprise commercial success as well as an unexpected protest icon. We touch on Gamergate, representation in comic books, and Mike Pence’s rules for interacting with women who aren’t his wife.Wilson has a quality you find in the very best writers: an ability to look at the same world you see every day, but somehow discover much more behind it. Books:Anya’s Ghost, by Vera BrosgolThe Color of Earth, by Dong Hwa KimFun Home, by Alison Bechdel“A Revolution Undone,” by H.A. Hellyer“Throne of the Crescent Moon,” by Saladin Ahmed“The Meccan Revelations,” by Ibn al'Arabi Learn more about your ad choices. Visit podcastchoices.com/adchoices