The Gray Area with Sean Illing

Jon Favreau was President Obama’s chief speechwriter. In those days, he was a frequent critic of the political media, frustrated, as many in the Obama administration were, with its focus on conflict, on ephemera, on appearing even-handed even when reality was persistently skewed. Today, Favreau is changing the media from the inside. He’s a co-host on Pod Save America, and co-founder of Crooked Media, both of which have seen tremendous growth in 2017. In this conversation, we look back on 2017, talk through the first year of the Trump White House (“a day-to-day shitshow”); the Democrats he’s watching for 2020; the mechanics of building a podcast empire; Favreau’s concern about the left (“we need to take the time to persuade other people of what we believe”); and the rot in the Republican Party. To Favreau, the right-wing media is “the real center of gravity in that party; it’s not the Republicans in Congress, it’s not even really Donald Trump, although I guess you could say that he is, in some ways, a creation of that media machine.” Books: What Happened by Hillary Clinton The News: A User’s Manual by Alain de Botton All the Truth is Out by Matt Bai Learn more about your ad choices. Visit podcastchoices.com/adchoices

“The day before the Washington Post story came out, we were behind by one point, 46 to 45,” says Joe Trippi. “And the day before the election, we were ahead in our own survey by two points. We ended up winning by 1.8.” This, Trippi says, was the reality of the Alabama Senate election. It was a dead heat when it started. It was a dead heat on the day it ended. And a lot of what the media thinks they know about it is wrong. Trippi, who managed Howard Dean’s 2004 presidential campaign, was the chief media strategist on the Jones campaign. And in this conversation, he tells the inside story of that effort, and what people don’t know about it. The sexual abuse allegations against Roy Moore, for instance, played a more complex role than many realize — the Jones campaign found that they often re-tribalized a race that they were desperately trying de-tribalize, and would occasionally boost Roy Moore’s numbers. Trippi says the central insight of the Jones campaign was that many voters, including many Trump-friendly Republicans, are already exhausted by the chaos and hostility of Trump’s Washington, and they're open to alternatives. That was the opportunity Jones exploited, and it’s a lesson Trippi thinks other Democrats could learn in 2018. Here's how the Jones campaign did it. Books! What It Takes: The Way to the White House by Richard Ben Cramer Leonardo da Vinci by Walter Isaacson Grant by Ron Chernow Learn more about your ad choices. Visit podcastchoices.com/adchoices

The most important story in the world right now is how real the chance of war with North Korea is — and how cataclysmic such a war would be. Part of the reason the risk of war is so real is that our understanding of North Korea is so sparse. "The Hermit Kingdom" is a world unto itself; a land of deprivation, of lunacy, of tyranny, of delusion. We have no diplomatic relations, no trade, no cross-cultural exchanges. We don't understand Kim Jong Un, we don't understand his people, and they don't understand us. And so, ignorant, we lurch towards the possibility of nuclear war built atop mutual miscomprehension. The best view we have into life in North Korea is Barbara Demick's Nothing to Envy: The Ordinary Lives of North Koreans. Demick was the Los Angeles Times bureau chief in Seoul and Beijing, and she found herself obsessed with this country she couldn't cover and couldn't understand. So she began talking to the people who had left it, the refugees who escaped across the DMZ. She began asking them to reconstruct their lives, to tell her what it was like, to make everyday life in North Korea intelligible. And they did. They told her what it was like to grow up, and to fall in love, and to go to school, and to have dinner, and to flee. They told her what it was like to build new lives, to remember past friends, to know their family was in a place they could never visit again, to hear the rest of the world fear and pity the place they had once called home. This conversation is about North Korea, but it's also about North Koreans — about what it's like to live in the most closed society on earth, about what they know and don't know of the outside world, about how their existence can be both ordinary and extraordinary, about what would happen to them if there was a war. And this is a conversation about what we need to know about North Korea, about how the country's past informs its present, about what Demick would tell Trump if he would just listen. Learn more about your ad choices. Visit podcastchoices.com/adchoices

On October 24, 2016, in the final days of the presidential election, Paul Krugman, the Nobel-prize winning economist and New York Times columnist, tweeted, "When this election is finally over, I'm planning to celebrate with an orgy of...serious policy discussion.” Then, of course, Donald Trump won the election, and serious policy discussion took a backseat to alternative facts, at least for awhile. But now it’s time! In this podcast, Krugman and I cover a lot of ground. We talk taxes, net neutrality, universal basic incomes, job guarantees, antitrust, automation, productivity growth, health care, climate change, college costs, and more. Krugman explains why more information doesn’t make people better thinkers, the “kitchen test” for assessing how much technological progress a society is really making, and what the role of policy analysis is when the policymakers don’t care about evidence. Enjoy! Books: The Foundation novels by Isaac Asimov An Inquiry Concerning Human Understanding by David Hume Plagues and Peoples by William McNeil  Learn more about your ad choices. Visit podcastchoices.com/adchoices

I have grown obsessed with a seemingly simple question: Does the American political system have a remedy if we elect the wrong person to be president? There are clear answers if we elect a criminal or if the president falls into a coma. But what if we just make a hiring mistake, as companies do all the time? What if we elect someone who proves himself or herself unfit for office — impulsive, conspiratorial, undisciplined, destructive, cruel? I’ve spent the past few months reporting out a story on that question — a story that is about Donald Trump, sure, but also about the American political system more broadly — and so today, on the podcast, the tables are turned: Sean Rameswaram, the host of Vox's new, soon-to-be daily explainer podcast, interviewed me about “The case for normalizing impeachment.” The big question here is one that I've been weighing on the podcast in recent months (listen to my second episode with Chris Hayes and you'll hear an early version of it): Are the civic and political consequences of impeachment worse than the consequences of leaving a dangerously unfit president in office? I think I've come to an answer — but it's not the answer I started with. Enjoy! Suggested books on impeachment: Impeachment: A Handbook by Charles Black Jr. Impeachment: A Citizen's Guide by Cass Sunstein Young Radicals: In the War for American Ideals by Jeremy McCarter Constitutional Law Stories edited by Michael C. Dorf Learn more about your ad choices. Visit podcastchoices.com/adchoices

I wanted to take a post-Thanksgiving break from politics and current events this week to talk to Robert Wright. He's written some of the best books on religion and evolutionary psychology, including Non-Zero and The Evolution of God. His latest book is Why Buddhism is True, and it’s fantastic. I’m interested in mindfulness, and so have read a lot of books on the subject. This isn’t like those. It’s a not a how-to guide, or an argument for meditation’s health benefits. It’s a deep dive into theories of the mind, informed both by Wright’s scientific background and his study and practice of Buddhism. It’s about how our minds evolved to keep us alive, not to keep us happy or satisfied — and what can be done about it. There is practical advice in this podcast, too. Wright beautifully describes what happens when he reaches what he calls "meditative depths,” what it’s like to go on a 10-day silent meditation retreat, and why a mindful outlook doesn’t lead to complacency or neutrality. But whether you’re interested in meditation or not, you should be interested in how your mind works, and on that, Wright has a lot to say that’s worth hearing. Books: What is Life? / Mind and Matter by Erwin Schrödinger Mindfulness in Plain English by Bhante Gunaratan What the Buddha Taught by Walpola Rahula  Learn more about your ad choices. Visit podcastchoices.com/adchoices

We’re living through an upheaval. The #MeToo moment has engulfed some of the most powerful men in politics, entertainment, and media. It has also forced a national reckoning with the reality of America’s sexual and workplace cultures — how often they permitted harassment and assault to flourish, how routinely they protected perpetrators and blamed victims. But why is it happening now? And will it continue or be swept away in backlash? Rebecca Traister is a writer-at-large at New York magazine, as well as the author of Big Girls Don't Cry: The Election that Changed Everything for American Women. And she’s one of the most essential writers to read on the intersection of gender and politics. In this conversation, Traister traces this moment back to Anita Hill’s testimony against Clarence Thomas — a “turning point” that changed American politics. We talk about Bill Clinton’s complex legacy, and Traister’s view that there would be no #MeToo moment without Trump. We talk about why the Weinstein allegations were able to set off such a chain reaction — and also how this is a more fragile movement than many realize, and the various ways in which Traister fears it could collapse. Books: Strange Justice: The Selling of Clarence Thomas by Jill Abramson and Jane Meyer Eloquent Rage: A Black Feminist Discovers Her Superpower by Brittney Cooper One Woman One Vote: Rediscovering the Woman Suffrage Movement ed. Marjorie Spruill Wheeler Learn more about your ad choices. Visit podcastchoices.com/adchoices

When we talk about the future of work, we usually focus on artificial intelligence, robotics, driverless cars. The future of work, we’re told, is a future where humans cease to be necessary. Ai-jen Poo wants to refocus that conversation. When we think about the future of work, she says, we need to think about care workers. Home care work — caring for the elderly and for children — is the fastest-growing occupation in the entire workforce, expanding at five times the rate of any other job. By the year 2030, child care and elder care jobs will be our economy's single largest occupation. If you’re talking about the future of work and you’re not talking about care work, you’re doing it wrong. Poo is a MacArthur "genius" grant-winning activist and organizer. She began her career in New York City, organizing domestic workers, and eventually lobbied New York state to pass the Domestic Workers Bill of Rights. Thanks to her efforts, seven other states have now passed similar legislation. Today, Poo is the executive director of the National Domestic Workers Alliance, the co-director of Caring Across Generations, and the author of The Age of Dignity: Preparing for the Elder Boom in a Changing America. In this episode, we talk about how she managed to organize a population of workers that spend most of their lives behind closed doors, why she calls herself a "futurist," and the central paradox of care work in America — that the folks who care for those we love are often the most undervalued and least protected. Books: Being Mortal: Medicine and What Matters in the End by Atul Gawande Year of Yes by Shonda Rimes, My Life on the Road by Gloria Steinem Learn more about your ad choices. Visit podcastchoices.com/adchoices

Evan Osnos is the author of the National Book Award-winning The Age of Ambition: Chasing Fortune, Truth, and Faith in the New China, as well as a staff writer at the New Yorker. And he’s recently back from a trip to North Korea, where he learned how Trump’s threats are playing in one of the strangest and most sealed-off regimes on earth. “To go between Washington and Pyongyang at this nuclear moment is to be struck, most of all, by how little the two understand each other,” he wrote. “In eighteen years of reporting, I’ve never felt as much uncertainty at the end of a project, a feeling that nobody—not the diplomats, the strategists, or the scholars who have devoted their lives to the subject—is able to describe with confidence how the other side thinks.” In this discussion, Osnos and I talk about that trip: about what North Korea is like, what they think about us, and what war with them would actually mean. We also talk about China — they literally can’t believe their luck with Donald Trump, he says — and whether the widespread rumors that Trump is facing some kind of mental deterioration are true. Osnos, who dove deep into the subject for a New Yorker article on the 25th Amendment, fears they are. And that’s not all: We dig into the pressures for war in Washington, the tendency toward survivalism in Silicon Valley, and why Osnos finds his best article subjects by looking at some of the worst things that could possibly happen to the human race. I enjoyed this conversation immensely. I think you will, too. Books Citizen-Protectors by Jennifer Carlson The Vegetarian by Han Kang The China Fantasy by James Mann  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Here’s a counterintuitive thought: maybe Congress in particular, and politics in general, has too little conflict, not too much. That’s James Wallner’s argument, and it’s more persuasive than you might think. Wallner is a political scientist who became a top Republican Senate aide, working as legislative director for Senators Jeff Sessions and Pat Toomey, as well as executive director of the Senate Steering Committee under Toomey and Lee. He’s now a senior fellow at the R Street Institute, and the author of “The Death of Deliberation: Partisanship and Polarization in the United States Senate.” Wallner is immersed in congressional history and procedure, and one of his conclusions after years of both study and experience is that the leadership in both parties are using the rules to stymie disagreement and suppress chaos — and well-intentioned though this might be, it’s making everything worse. Congress, Wallner believes, is an institution designed to surface conflict so that positions can be made clear, compromises can be tested, and a way forward can be found. That’s not happening now, and the results are disastrous. The Republican Party is particularly bad on this score, he says. “They pretend like they all agree on everything...But if you never deal with your problems, what do you think happens? A break-up! And that's literally what you're seeing right now.” The first few times I hard Wallner’s arguments, I was skeptical. In some ways, I’m still skeptical, as you’ll hear in this conversation. But I’m also convinced he’s onto something important. Books: The Professor's House by Willa Cather Democracy and Leadership by Irving Babbitt Notes of Debates in the Federal Convention of 1787 by James Madison Learn more about your ad choices. Visit podcastchoices.com/adchoices