Conversations with Bill Kristol

“This branding binge [Trump] has been on: with everything he’s trying to have put his name on. To build the White House ballroom, the arch in front of Arlington Cemetery. And the war and military adventurism. It’s a way of trying to cement his state permanently as a dominant figure in history, because he knows he’s going to die.” So argues veteran political reporter A.B. Stoddard in a bracing analysis of President Trump’s character and conduct during his second term. Reflecting on the last ten years, Stoddard argues that Trump’s aspirations to cement his role as a dominant figure in history have increased dramatically—and the acceleration of his actions must be taken seriously. For Stoddard, above all, this requires us to confront questions about the 2028 elections, including the possibility that Trump might refuse to leave office or try to keep the presidency in the family. Stoddard warns against the assumption that normalcy will return after 2028: “People just want to hope that we’re going to keep with term-limited presidents.... I don’t think we know what’s coming.”

“What is human happiness? What is political excellence? What is speech, and rhetoric? It’s always important to remind ourselves of that. But especially when you have artificial intelligence, and all of these vast possible changes in human affairs, it’s important to remind ourselves of what’s basic…. And Aristotle uncovers 80%, 90%, 95% of what really one could say, I think, reasonably, and intelligently about lots of political, and ethical matters.” So argues the distinguished scholar of political philosophy Mark Blitz, author of the newly published Aristotle’s Political Philosophy. In this profound yet accessible Conversation, Blitz distills insights from Aristotle’s works on politics and ethics, covering topics such as the character of human excellence, the centrality of political regimes, the nature of justice, and the relationship between speech and deed. This is a must-see introduction to Aristotle’s reflection on the permanent human problems.

“It’s hard for me to see how [the war] ends in a way that enhances our position in the world generally—and, in particular, enhances our position with relation to the country that I still think is our principal strategic challenge, namely China. And that’s what really worries me.” So argues Princeton professor and Aaron Friedberg in an incisive and sober conversation on the war in Iran and its broader geopolitical implications. Noting that there are a wide range of possible outcomes to the war, ranging from the positive to the very negative, Friedberg warns that China may see the American war in Iran as “working in their favor.” He also points to the damage to relationships with allies in Europe and Southeast Asia, who were not informed about US war plans—and the erosion of US credibility to lead a coalition of free countries to counter China and Russia.

“Whatever happens in 2026, I think no one should take any interpretation of that as a precursor to what’s going to happen in 2028.” So argues Doug Sosnik, former political director for Bill Clinton and one of the shrewdest and most imaginative analysts of American politics. Sosnik considers possible scenarios in 2026 including a wave election year for Democrats driven by higher turnout of college-educated voters—but their prospects in a presidential election year are threatened by "atrophied support amongst all working-class voters…. that is a barrier for winning the White House in ‘28 if we can’t do better.” In his deeply perceptive and often surprising account of the state of our politics, Sosnik shares his perspective on the challenges facing both parties in the lead up to 2028—which may prove to be one of the most significant elections in American history.

“The US government wants to arrest, detain, and deport one in every 24 people in the country—4% of the US population. That cannot be done without fundamentally transforming who we are as a people and our relationship to law enforcement.” So argues Aaron Reichlin-Melnick, a leading expert on immigration and Senior Fellow at the American Immigration Council, in a bracing Conversation on the scale and scope of the Trump administration's mass deportation mission. Reichlin-Melnick shares his perspective on the administration’s massive political and financial investment in deportation and detentions, which already have reached record levels. Kristol and Reichlin-Melnick also consider the implications of these policies for legal immigration, civil liberties, the nature of American law enforcement, and the character of American society.

“The Europeans have been in this alliance [NATO] to protect themselves, largely from Russia and other aggressors. And now it has an aggressor within the gates, so to speak. And that’s quite an extraordinary situation.” So argues the eminent political thinker Francis Fukuyama, who begins with his assessment of Trump’s bullying of Denmark and Western Europe in recent days. In a thought-provoking tour d’horizon Conversation, Fukuyama shares his perspective not only on Greenland but on a world in crisis more generally, covering Ukraine, Europe, China, Japan, as well as developments in the United States. As he puts it, in bracing terms: “Trump is doing the same thing domestically that he’s doing internationally. He’s trying to erode all the existing constraints on his ability to use power.”

Where do things stand in American politics as we head into a midterm election year? To discuss these questions we are joined again by Ron Brownstein, a Bloomberg Opinion columnist and senior CNN political analyst. Brownstein points to President Trump’s approval rating as perhaps the most significant indicator in the 2026 midterm elections—and potentially still a major factor in 2028. As he puts it, "Amid all of the swirling currents that you get whenever Trump is in the White House… the real message of '25 was ‘the fundamental things apply.’” Brownstein shares his in-depth analysis of the current demographic and partisan fault lines in American politics, and the challenges both parties face as we look ahead to the midterms and presidential elections.

“We take for granted the degree of peace that we’ve enjoyed over the past eight plus decades. And we think that’s the norm. The norm is actually a lot more like what the world looked like before 1945. Certainly, the previous 100 years were one of constant great power warfare. And I don’t think people are ready for that—the world that we’re now moving into.” As the distinguished historian Robert Kagan puts it in this provocative Conversation, Trump’s foreign policy may be a decisive break from the past that will not be followed by a return to the status quo. According to Kagan, we are at risk of returning to a multipolar world of shifting alliance structures and transactional foreign policy that would greatly endanger American security. Kagan’s bracing account considers the stakes of current foreign policy challenges in Asia, the Middle East, Latin America, and Europe—as well as the contest over liberal democracy at home.

Dick Cheney (1941-2025) is widely regarded as one of the most consequential vice presidents in American history. To discus his life and legacy, we are joined by Steve Hayes, CEO and editor of The Dispatch and author of Cheney (2007), who had extraordinary access to Cheney during his time as vice president. In this Conversation, Hayes shares his personal reflections on Cheney’s character, views, and decades of public service, which spanned from the Ford through the George W. Bush administrations. Hayes reflects on the ways in which Cheney was understood—and misunderstood—by the media and public, and what the story of Cheney's life can teach us about the last half century of American political history.

How has the second Trump presidency differed from the first? How did Trump’s experiences during his time out of office and on the campaign trail in 2024—including his trial in New York and the assassination attempts—shape him? What can we expect in the months and years ahead? In this Conversation, Jonathan Karl, a leading chronicler of Donald Trump and author of Retribution: Donald Trump and the Campaign that Shaped America, argues for the centrality of retribution in understanding Donald Trump’s second presidency. Drawing on his extraordinary access to the president over many years, Karl reflects on how we got here and considers where we might be going.